85PathwaySteroid BiosynthesisThe steroid biosynthesis (or cholesterol biosynthesis) pathway is an anabolic metabolic pathway that produces steroids from simple precursors. It starts with the mevalonate pathway, where acetyl-CoA and acetoacetyl-CoA are the first two building blocks. These compounds are joined together via the enzyme hydroxy-3-methylgutaryl (HMG)-CoA synthase to produce the compound known as hydroxy-3-methylgutaryl-CoA (HMG-CoA). This compound is then reduced to mevalonic acid via the enzyme HMG-CoA reductase. It is important to note that HMG-CoA reductase is the protein target of many cholesterol-lowering drugs called statins (PMID: 12602122). The resulting mevalonic acid (or mevalonate) is then phosphorylated by the enzyme known as mevalonate kinase to form mevalonate-5-phosphate, which is then phosphorylated again by phosphomevalonate kinase to form mevolonate-5-pyrophsophate. This pyrophosphorylated compound is subsequently decarboxylated via the enzyme mevolonate-5-pyrophsophate decarboxylase to form isopentylpyrophosphate (IPP). IPP can also be isomerized (via isopentenyl-PP-isomerase) to form dimethylallylpyrophosphate (DMAPP). IPP and DMAPP can both donate isoprene units, which can then be joined together to make farnesyl and geranylgeranyl intermediates. Specifically, three molecules of IPP condense to form farnesyl pyrophosphate through the action of the enzyme known as geranyl transferase. Two molecules of farnesyl pyrophosphate then condense to form a molecule known as squalene by the action of the enzyme known as squalene synthase in the cell’s endoplasmic reticulum. The enzyme oxidosqualene cyclase then cyclizes squalene to form lanosterol. Lanosterol is a tetracyclic triterpenoid, and serves as the framework from which all steroids are derived. 14-Demethylation of lanosterol by a cytochrome P450 enzyme known as CYP51 eventually yields cholesterol. Cholesterol is the central steroid in human biology. It can be obtained from animal fats consumed in the diet or synthesized de novo (as described above). Cholesterol is an essential constituent of lipid bilayer membranes (where it forms cholesterol esters) and is the starting point for the biosynthesis of steroid hormones, bile acids and bile salts, and vitamin D. Steroid hormones are mostly synthesized in the adrenal gland and gonads. They regulate energy metabolism and stress responses (via glucocorticoids such as cortisol), salt balance (mineralocorticoids such as aldosterone), and sexual development and function (via androgens such as testosterone and estrogens such as estradiol). Bile acids and bile salts (such as taurocholate) are mostly synthesized in the liver. They are released into the intestine and function as detergents to solubilize dietary fats. Cholesterol is the main constituent of atheromas. These are the fatty lumps found in the walls of arteries that occur in atherosclerosis and, when ruptured, can cause heart attacks.MetabolicPW000050CenterPathwayVisualizationContext5041504550#000099PathwayVisualization6085Steroid BiosynthesisThe steroid biosynthesis (or cholesterol biosynthesis) pathway is an anabolic metabolic pathway that produces steroids from simple precursors. It starts with the mevalonate pathway, where acetyl-CoA and acetoacetyl-CoA are the first two building blocks. These compounds are joined together via the enzyme hydroxy-3-methylgutaryl (HMG)-CoA synthase to produce the compound known as hydroxy-3-methylgutaryl-CoA (HMG-CoA). This compound is then reduced to mevalonic acid via the enzyme HMG-CoA reductase. It is important to note that HMG-CoA reductase is the protein target of many cholesterol-lowering drugs called statins (PMID: 12602122). The resulting mevalonic acid (or mevalonate) is then phosphorylated by the enzyme known as mevalonate kinase to form mevalonate-5-phosphate, which is then phosphorylated again by phosphomevalonate kinase to form mevolonate-5-pyrophsophate. This pyrophosphorylated compound is subsequently decarboxylated via the enzyme mevolonate-5-pyrophsophate decarboxylase to form isopentylpyrophosphate (IPP). IPP can also be isomerized (via isopentenyl-PP-isomerase) to form dimethylallylpyrophosphate (DMAPP). IPP and DMAPP can both donate isoprene units, which can then be joined together to make farnesyl and geranylgeranyl intermediates. Specifically, three molecules of IPP condense to form farnesyl pyrophosphate through the action of the enzyme known as geranyl transferase. Two molecules of farnesyl pyrophosphate then condense to form a molecule known as squalene by the action of the enzyme known as squalene synthase in the cell’s endoplasmic reticulum. The enzyme oxidosqualene cyclase then cyclizes squalene to form lanosterol. Lanosterol is a tetracyclic triterpenoid, and serves as the framework from which all steroids are derived. 14-Demethylation of lanosterol by a cytochrome P450 enzyme known as CYP51 eventually yields cholesterol. Cholesterol is the central steroid in human biology. It can be obtained from animal fats consumed in the diet or synthesized de novo (as described above). Cholesterol is an essential constituent of lipid bilayer membranes (where it forms cholesterol esters) and is the starting point for the biosynthesis of steroid hormones, bile acids and bile salts, and vitamin D. Steroid hormones are mostly synthesized in the adrenal gland and gonads. They regulate energy metabolism and stress responses (via glucocorticoids such as cortisol), salt balance (mineralocorticoids such as aldosterone), and sexual development and function (via androgens such as testosterone and estrogens such as estradiol). Bile acids and bile salts (such as taurocholate) are mostly synthesized in the liver. They are released into the intestine and function as detergents to solubilize dietary fats. Cholesterol is the main constituent of atheromas. These are the fatty lumps found in the walls of arteries that occur in atherosclerosis and, when ruptured, can cause heart attacks.Metabolic19122SubPathway1611142Compound89284SubPathway1621142Compound89386SubPathway163940Compound89489SubPathway164940Compound89584SubPathway165940Compound89610SubPathway166940Compound89790SubPathway16747Compound89888SubPathway16847Compound860Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.85Pathway61Norman, A.W, and Litwack, G. Hormones (2nd ed.) (1997) San Diego : Academic Press.85Pathway62Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.85Pathway63Vance, D.E., and Vance, J.E. Biochemistry of lipids, lipoproteins, and membranes (4th ed.) (2002) Amsterdam; Boston: Elsevier.85Pathway28029212602122Simons J: The $10 billion pill. Fortune. 2003 Jan 20;147(1):58-62, 66, 68.85Pathway1CellCL:00000005HepatocyteCL:00001824CardiomyocyteCL:00007463NeuronCL:00005407Epithelial CellCL:00000662Platelet CL:00002338Beta cellCL:00006391Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote5Bos taurus9913EukaryoteCattle24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog4Arabidopsis thaliana3702EukaryoteThale cress10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse60Nitzschia sp.0001EukaryoteNitzschia417Rattus norvegicus10116EukaryoteRat6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast51Picea sitchensis3332EukaryoteSitka spruce282Sus Scrofa9823EukaryotePig3Mitochondrial MatrixGO:00057595CytoplasmGO:00057372MitochondrionGO:00057391CytosolGO:00058294PeroxisomeGO:000577712Mitochondrial Inner MembraneGO:00057438Smooth Endoplasmic Reticulum GO:000579010Cell MembraneGO:000588613Endoplasmic ReticulumGO:000578314Mitochondrial Outer MembraneGO:000574127Peroxisome MembraneGO:00057787Endoplasmic Reticulum MembraneGO:00057896LysosomeGO:000576411Extracellular SpaceGO:000561516Lysosomal LumenGO:004320218Melanosome MembraneGO:003316225Golgi ApparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563431Periplasmic SpaceGO:000562035ChloroplastGO:000950736MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259732Inner MembraneGO:007025819Sarcoplasmic ReticulumGO:001652926Golgi Apparatus MembraneGO:000013924Mitochondrial Intermembrane SpaceGO:000575839Mitochondrial membraneGO:00319661LiverBTO:00007597294Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273106KidneyBTO:00006717182Endothelium BTO:000039318PancreasBTO:00009885cardiocyteBTO:000153915BoneBTO:000014016SkinBTO:0001253154254311PW_BS0000048511PW_BS0000083211PW_BS0000032111PW_BS0000025411PW_BS000005171211PW_BS000017111811PW_BS00001114101PW_BS000014103331PW_BS000103124151PW_BS00012410813PW_BS0001081553241PW_BS0001551613181PW_BS00016111PW_BS0000011783211PW_BS0001781601181PW_BS0001601632181PW_BS0001631985181PW_BS000024222341PW_BS000024151141PW_BS00015121013181PW_BS000024226441PW_BS0000242991101PW_BS000024315123PW_BS0000241333121PW_BS0001331115121PW_BS0001111122121PW_BS0001121321121PW_BS0001321151012PW_BS00011513412121PW_BS0001343344121PW_BS0000283683601PW_BS0000281192171PW_BS0001193761017PW_BS00005317018PW_BS000170406351PW_BS000115405105PW_BS000115122551PW_BS000122407251PW_BS000115408451PW_BS0001153841251PW_BS0001001203171PW_BS0001201355171PW_BS0001351181171PW_BS0001183744171PW_BS00005312112171PW_BS0001214793101PW_BS0001154781010PW_BS0001152975101PW_BS0000244824101PW_BS0001154812101PW_BS00011548012101PW_BS000115501361PW_BS000115209106PW_BS000024205561PW_BS000024388161PW_BS000112502461PW_BS000115206261PW_BS0000243911261PW_BS000112185321PW_BS000024221411PW_BS000022592711PW_BS00005929111PW_BS000029311511PW_BS000031181311PW_BS000018101711PW_BS0000105811411PW_BS000058541315PW_BS0000546131PW_BS0000061021231PW_BS0001021041431PW_BS000104101531PW_BS00010116212181PW_BS00016219914181PW_BS000024188118PW_BS000024224241PW_BS0000241951318PW_BS0000242491341PW_BS00002449711PW_BS00004929341PW_BS00002432914121PW_BS0000283361121PW_BS00002812915121PW_BS00012933217121PW_BS000028350114121PW_BS00002833527121PW_BS00002813013121PW_BS0001303331212PW_BS0000283317121PW_BS0000283821451PW_BS000100383751PW_BS0001002881441PW_BS0000243891461PW_BS000112390761PW_BS00011239914171PW_BS0001133987171PW_BS000113117131PW_BS0001171231751PW_BS00012343311451PW_BS0001151251351PW_BS000125429151PW_BS0001154141551PW_BS0001154222751PW_BS00011544717171PW_BS000115468114171PW_BS00011513613171PW_BS0001364641171PW_BS00011545015171PW_BS00011537527171PW_BS00005348414101PW_BS00011549127101PW_BS00011530013101PW_BS0000245082761PW_BS0001153951361PW_BS0001131861221PW_BS0000248911421PW_BS0005529611PW_BS00000913121PW_BS00001315111PW_BS0000152811611PW_BS000028204111PW_BS000020331811PW_BS000033432511PW_BS0000432441011PW_BS00002460251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097100521PW_BS000100943PW_BS000094105113PW_BS0001051136121PW_BS000113110231PW_BS000110126651PW_BS00012612711651PW_BS0001271141112PW_BS000114140103PW_BS00014014315191PW_BS0001431465191PW_BS000146107313PW_BS000107951721PW_BS0000951471241PW_BS0001471572241PW_BS00015715924PW_BS00015916611PW_BS0001661802211PW_BS00018015284PW_BS000152207661PW_BS0000242111018PW_BS0000242137181PW_BS00002421425181PW_BS0000242156181PW_BS0000242164181PW_BS00002421217181PW_BS0000241901118PW_BS0000242253541PW_BS000024261115PW_BS0000262771218PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS00002465111PW_BS0000652905491PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS0000243016101PW_BS000024302116101PW_BS0000242231241PW_BS0000242941141PW_BS0000243081011PW_BS0000243183123PW_BS0000243221231PW_BS000024253541PW_BS000024337116121PW_BS00002834141121PW_BS00002834318121PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115409115PW_BS0001154151851PW_BS0001154251355PW_BS0001154192551PW_BS00011543441051PW_BS000115436255PW_BS0001154436171PW_BS0001154461217PW_BS0001151371117PW_BS000137448116171PW_BS00011545118171PW_BS00011546013175PW_BS00011545525171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS0001154831110PW_BS00011548718101PW_BS00011549025101PW_BS0001154957101PW_BS000115208116PW_BS0000245041861PW_BS0001155072561PW_BS00011551541061PW_BS0001155131761PW_BS0001157906111PW_BS0005248346111PW_BS00054916212PW_BS0000163211515PW_BS000032397113PW_BS0000396618518PW_BS0000665181PW_BS000051231511PW_BS000023918511PW_BS000091892PW_BS0000892171518PW_BS00002421815181PW_BS00002412815121PW_BS0001283511512PW_BS000028184121PW_BS000024109323PW_BS0001094101551PW_BS000115435155PW_BS00011544415171PW_BS0001154701517PW_BS00011548515101PW_BS0001154991510PW_BS0001155161561PW_BS000115517156PW_BS000115471914PW_BS00004731323PW_BS000024241529PW_BS00002425715291PW_BS00002430412PW_BS000024215114PW_BS000021562611PW_BS000056372102PW_BS00002830635511PW_BS0000243551914PW_BS000035168321PW_BS000168422411PW_BS00004234524121PW_BS0000284182451PW_BS00011545424171PW_BS00011548924101PW_BS0001155062461PW_BS00011515612241PW_BS00015617912211PW_BS0001793583912PW_BS00002836912601PW_BS00002814117191PW_BS00014178811PW_BS0000787841511PW_BS000522693741PW_BS00051278615131PW_BS000522104716711PW_BS0005779731715PW_BS0005695311015PW_BS000053112125717PW_BS00058011251615PW_BS000581118912821PW_BS000588940Acetyl-CoAHMDB0001206The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.72-89-9C0002444449315351ACETYL-COA392413CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC23H38N7O17P3SInChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1ZSLZBFCDCINBPY-ZSJPKINUSA-N809.571809.125773051FDB022491Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme aPW_C000940Ac-CoA21343858842324162244652896173340114840145278103547612457331086025155607716163861647017869231607106163729119874602228245151827721012582226130122994261531577121133772911117756211277706132779941157835513478433334800073688063411980663376901241701199534061201454051203041221206324071224174081226263841227431201229591351231371181249863741252001211253434791255074781256332971265644821265724811267784801268865011270442091273942051276653881281375021281452061283743911407621851142Acetoacetyl-CoAHMDB0001484Acetoacetyl-CoA is an intermediate in the metabolism of Butanoate. It is a substrate for Succinyl-CoA:3-ketoacid-coenzyme A transferase 1 (mitochondrial), Hydroxymethylglutaryl-CoA synthase (mitochondrial), Short chain 3-hydroxyacyl-CoA dehydrogenase (mitochondrial), Trifunctional enzyme beta subunit (mitochondrial), Hydroxymethylglutaryl-CoA synthase (cytoplasmic), Peroxisomal bifunctional enzyme, Acetyl-CoA acetyltransferase (cytosolic), Acetyl-CoA acetyltransferase (mitochondrial), 3-hydroxyacyl-CoA dehydrogenase type II, Succinyl-CoA:3-ketoacid-coenzyme A transferase 2 (mitochondrial), 3-ketoacyl-CoA thiolase (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal) and Trifunctional enzyme alpha subunit (mitochondrial).1420-36-6C0033243921415345ACETOACETYL-COA388353CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC25H40N7O18P3SInChI=1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1OJFDKHTZOUZBOS-CITAKDKDSA-N851.607851.136337737FDB0226483-acetoacetyl-coa;3-acetoacetyl-coenzyme a;3-oxobutyryl-coa;3-oxobutyryl-coenzyme a;Acetoacetyl coa;Acetoacetyl coenzyme a;Acetoacetyl-coa;Acetoacetyl-coenzyme a;S-acetoacetylcoenzyme aPW_C001142ActaCoA5924792810493527910370021617292198735716375981608242226830621015239151772581337822411278914111901261701202834061207634071214651221229481201233591191240231351256224791260854811271495011275412061407961851099Coenzyme AHMDB0001423Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).85-61-0C0001068161146900CO-A6557CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC21H36N7O16P3SInChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1RGJOEKWQDUBAIZ-IBOSZNHHSA-N767.534767.115208365FDB022614Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphatePW_C001099CoA21143868845387922892172407592414224595281329286231334211335118461810462958484214486554487965232102524710452801035477124573410857771016023155607516163841646817869301606961162697319970831887108163729319873472107458222822915190812269090224912417092151951301329915318249254884942616315769072937711913377222134772303297729211177550132775553347756311277633336776721297799611578047332780563507841333578567130792593337997433180005368806201188062737480635119806653769382838293834383986742881105553891105613901158423991158473981199514061201474051202313841203051221206344071207621171214061231214214331215211251216664291216824081217144141224044221227411201229041211229601351239654471239794681240791361242204641242654501249743751253414791255094781255794801255924841256342971260844811265494911265604821267463001268845011270462091271093911273012051275402061276673881281215081281335021283403951407511861407631851407678911420WaterHMDB0002111Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-N18.015318.010564686FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O558949109513941513162144811352615624286521069120770338231883821094311377491465541590432018242532222678602727462778172805293143703164723634614598364727374941935030275156751959752141005227945236103529710553191115343113535511254021105470123548312554921265507127553413055371145541129559113556081185622108569165759140577810158411435853146587710758909559101475940151603215560591576087161612316361331596215162181666477178650718066001526713117684018868881607162205718120771932067211211722821372382147243215729519873502167388210740121274672227492224750019075881708201225823722684141629265261185027711922164120112811221328512250286122642871232724912520227126326512693290127052911271529213007298130193001302530113037302132612231332729415340308423273154269531843691322769142937701925377102132771311337721513477378331773973327747133377516115775363347762833677722337777593417781634377982347780713297823535278242353782703567911336080014368800393708059122880656119938303839479438411055739011063939111584439811987923211991512211996340612000840712004640812011312412036541212043040512043840912060641512079441412115842512124042912135112112138141912160743412211838212238443612275312012279737412280444312301244612306437612307213712313144712314213612316244812323145112338445012373046012381046412394045512416546912467039912493847112494547212530529712535347912538648112542448212548029912568248312570747812574548712605449012623849512627348412676448012689650112696350212701738812717720812719920912722750412750650712757651512783638912808239512817651314067479014067583414075518510633-Hydroxy-3-methylglutaryl-CoAHMDB00013753-hydroxy-3-methylglutaryl CoA (HMG-CoA) is formed when Acetyl-CoA condenses with acetoacetyl-CoA in a reaction that is catalyzed by the enzyme HMG-CoA synthase in the mevalonate pathway or mevalonate-dependent (MAD) route, an important cellular metabolic pathway present in virtually all organisms. HMG-CoA reductase (EC 1.1.1.34) inhibitors, more commonly known as statins, are cholesterol-lowering drugs that have been widely used for many years to reduce the incidence of adverse cardiovascular events. HMG-CoA reductase catalyzes the rate-limiting step in the mevalonate pathway and these agents lower cholesterol by inhibiting its synthesis in the liver and in peripheral tissues. Androgen also stimulates lipogenesis in human prostate cancer cells directly by increasing transcription of the fatty acid synthase and HMG-CoA-reductase genes. (PMID: 14689582).1553-55-5C00356439218154673-HYDROXY-3-METHYL-GLUTARYL-COA388357C[C@](O)(CC(O)=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC27H44N7O20P3SInChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1CABVTRNMFUVUDM-VRHQGPGLSA-N911.659911.157467109FDB022587(s)-3-hydroxy-3-methylglutaryl-coa;(s)-3-hydroxy-3-methylglutaryl-coenzyme a;3-hydroxy-3-methyl-glutaryl-coa;3-hydroxy-3-methyl-glutaryl-coenzyme a;3-hydroxy-3-methylglutaryl-coa;3-hydroxy-3-methylglutaryl-coenzyme a;Hmg-coa;Hmg-coenzyme a;Hydroxymethylglutaroyl coenzyme a;Hydroxymethylglutaryl-coa;Hydroxymethylglutaryl-coenzyme a;S-(hydrogen 3-hydroxy-3-methylglutaryl)coenzyme a;S-(hydrogen 3-hydroxy-3-methylpentanedioate;S-(hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme a;S-(hydrogen 3-hydroxy-3-methylpentanedioic acidPW_C001063HMG-CoA5954794210513152087296198735816382782101524015115241222776931337822511278916111120509406120765407121467122123115120123361119124025135152Mevalonic acidHMDB0000227Mevalonic acid is a key organic compound in biochemistry. It is a precursor in the biosynthetic pathway, known as the HMG-CoA reductase pathway, that produces terpenes and steroids. Mevalonate is produced by NADPH from 3-hydroxy-3-methylglutaryl CoA via reduction. This reaction occurs in the cytosol. It is the committed step in cholesterol synthesis, -- Wikipedia The production of mevalonic acid (MVA) by the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, is the rate-limiting step in the biosynthesis of cholesterol. (Jemal et. al, Rapid Communications in Mass Spectrometry, 2003, 17:1715) Plasma concentrations and urinary excretion of MVA are decreased by HMG-CoA reductase inhibitor drugs such as pravastatin, simvastatin and atorvastatin. Naoumova RP, Marais AD, Mountney J, Firth JC, Rendell NB, Taylor GW, Thompson GR. Atherosclerosis 1996; 119: 203.150-97-0C0041844925351MEVALONATE436CC(O)(CCO)CC(O)=OC6H12O4InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)KJTLQQUUPVSXIM-UHFFFAOYSA-N148.1571148.073558872FDB005126(3rs)-mevalonate;(3rs)-mevalonic acid;2,4-dideoxy-3-c-methylpentonate;2,4-dideoxy-3-c-methylpentonic acid;3,5-dihydroxy-3-methyl-valerate;3,5-dihydroxy-3-methyl-valeric acid;3,5-dihydroxy-3-methylpentanoate;3,5-dihydroxy-3-methylpentanoic acid;3,5-dihydroxy-3-methylvalerate;3,5-dihydroxy-3-methylvaleric acid;Dl-mevalonate;Dl-mevalonic acid;Hiochic acid;Mk 91;Mva;Mvs;Mevalonate;Mevalonic acid;Rs-mevalonate;Rs-mevalonic acid;B,d-dihydroxy-b-methylvalerate;B,d-dihydroxy-b-methylvaleric acid;B,d-dihydroxy-beta-methylvalerate;B,d-dihydroxy-beta-methylvaleric acidPW_C000152Mva79751523872971987600160831821078917111121468122124026135414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N507.181506.995745159FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171407708911036Mevalonic acid-5PHMDB0001343Mevalonic acid-5P, also known as mevalonate-5P or phosphomevalonate, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Mevalonic acid-5P is soluble (in water) and a moderately acidic compound (based on its pKa). Mevalonic acid-5P has been found throughout most human tissues. Within the cell, mevalonic acid-5P is primarily located in the peroxisome. In humans, mevalonic acid-5P is involved in the pamidronate action pathway, the fluvastatin action pathway, the simvastatin action pathway, and steroid biosynthesis pathway. Mevalonic acid-5P is also involved in several metabolic disorders, some of which include the smith-lemli-opitz syndrome (slos) pathway, the hypercholesterolemia pathway, the wolman disease pathway, and the child syndrome pathway. Outside of the human body, mevalonic acid-5P can be found in a number of food items such as elderberry, persian lime, purple laver, and apple. This makes mevalonic acid-5P a potential biomarker for the consumption of these food products. 5-Phosphomevalonate is a metabolic intermediate in the mevalonate pathway, catalyzed by the enzyme mevalonate kinase from Mevalonate. (wikipedia).73566-35-5C0110743940017436CPD-499388517C[C@@](O)(CCOP(O)(O)=O)CC(O)=OC6H13O7PInChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1OKZYCXHTTZZYSK-ZCFIWIBFSA-N228.137228.039889282FDB022566(r)-5-phosphomevalonate;(r)-5-phosphomevalonic acid;(r)-5-phosphomevaloonate;(r)-5-phosphomevaloonic acid;(r)-mevalonic acid 5-phosphate;5-phosphomevalonate;Mevalonate-5-p;Mevalonate-5-phosphate;Mevalonate-5p;Mevalonate-p;P-mevalonate;(r)-mevalonate 5-phosphate;(r)-mevalonic acid 5-phosphoric acidPW_C001036Mvn-5P800515378729919876041608279210789181111214691221240271351034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N427.2011427.029414749FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP234134841522482138015963159783106114151821901492104182113102161582408592435272728472736462855293165723635614400234476314770915036265157752089752171005315111534911253921035446120554412955721335624108574111757641015849143585614658781075899147592615160501556111161623116664951786700946841188687216071592057187206720821072262137231211730019873032167391217741021874331637483222818722511851277119051701201328112180285132622231532930842328315423983134262232242696318770292537708713277216134773063297747233377663336780393327804335078170128782153517824435378414335784951157870533178849130789203348003036880622118806511358067611994827124113283388116204109119944122119994406120156407120318382120366412121248429121394123121399433121472408121899383121976410122064125122085405122405422122445435122973399123013446123818464123953447123958468124030374124452398124529444124615136124636376124947472124975375125012470125334297125373479125492299125517481125645484126125485126219300126235495126242478126550491126597499126915501127733516127780395127797390127803209128122508128168517128313389857(R)-5-Diphosphomevalonic acidHMDB0001090(S)-5-Diphosphomevalonic acid, also known as mevalonate 5-diphosphate or (S)-mevalonic acid-5-pyrophosphate, belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O (S)-5-Diphosphomevalonic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, (S)-5-diphosphomevalonic acid is primarily located in the peroxisome. In humans, (S)-5-diphosphomevalonic acid is involved in the risedronate action pathway, the ibandronate action pathway, steroid biosynthesis pathway, and the lovastatin action pathway (S)-5-Diphosphomevalonic acid is also involved in several metabolic disorders, some of which include the mevalonic aciduria pathway, the cholesteryl ester storage disease pathway, lysosomal acid lipase deficiency (wolman disease), and the hypercholesterolemia pathway. Outside of the human body, (S)-5-diphosphomevalonic acid can be found in a number of food items such as peanut, rowanberry, buffalo currant, and garden rhubarb. This makes (S)-5-diphosphomevalonic acid a potential biomarker for the consumption of these food products. 5-pyrophosphomevalonate is a metabolic intermediate in the mevalonate pathway, catalyzed by the enzyme phosphomevalonate kinase from 5-phosphomevalonate. (wikipedia).C0114343941815899CPD-641388531C[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=OC6H14O10P2InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m1/s1SIGQQUBJQXSAMW-ZCFIWIBFSA-N308.1169308.006219692FDB0224201,1,3,7-tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-oate;1,1,3,7-tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-oic acid;1,1,3,7-tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-oic acid ion(1-)1,3-dioxide;5-diphosphomevalonate;5-diphosphomevalonic acid;Mevalonate 5-diphosphate;Mevalonate pyrophosphate;Mevalonate-diphosphate;(s)-mevalonic acid-5-pyrophosphate;(r)-5-diphosphomevalonatePW_C000857R-5DPMA1542573042168280210789213341214734081240313741104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032OP(O)(O)=OH3O4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)NBIIXXVUZAFLBC-UHFFFAOYSA-N97.995297.976895096DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi24484881458181883129803176314176749250010272947273746312929316672363661385123424922447531503127515875207975216100531711153511125381103544712055431295573133560513556251085693658481435855146591114759411516040155610016162941076487178669110167141176842188688916071612057189206721221173061987389210740221274361637475222819622582582271011824110134257117481321176111511773213119041701192716412014281127282901326322334819174225530442350315424353184369232277018253771942937721713477940336779661307804833278057329782453537866933180022368892793089383138394796384110558390110640391113235941158453981162061091199824061200691221206994071210571241212161251212684291213521211214091231214233821218524051233041191236211181237861361238384641239684471239813991244053761249484721253624791254462971257744811259542991262214781265943001266042981267234841269045011274133881277832091281663951281775131283153891039Isopentenyl pyrophosphateHMDB0001347Isopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia).358-71-4C001291195165841158DB04714CC(=C)CCOP(O)(=O)OP(O)(O)=OC5H12O7P2InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)NUHSROFQTUXZQQ-UHFFFAOYSA-N246.0921246.005825762FDB022569Isopentenyl diphosphatePW_C001039IsopPyr80558302154987307198760616082812101231022512352249789231111214751221240331351316Carbon dioxideHMDB0001967Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.124-38-9C0001128016526274O=C=OCO2InChI=1S/CO2/c2-1-3CURLTUGMZLYLDI-UHFFFAOYSA-N44.009543.989829244DBMET00423FDB014084Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744PW_C001316CO25081211204448013503186403677316952080651133431638491745225511731447052831035320111575010857711015968100602615560781616471178663710769221907017160703516370611887163205730819873332137461222753021082152258223151915824911849277119081701246422612688290426263154352331876994293771221337717013277470333777391127775012977763341780771347840535678427334789413317922713080008368806751198071713594836384113291391115549121119954406120089122120155407120364412120556414120833419120922124120991408121284125121505383122744120123011446123190450123418455123489118123556374123855136124063398125344479125460297125516481125824490125870299125931482126280480126887501127052206127277507127331388127390502140798185874DimethylallylpyrophosphateHMDB0001120Dimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphate, belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Dimethylallylpyrophosphate exists as a solid, slightly soluble (in water), and a moderately acidic compound (based on its pKa). Dimethylallylpyrophosphate has been found in human muscle tissue. Within the cell, dimethylallylpyrophosphate is primarily located in the peroxisome, cytoplasm and mitochondria. Dimethylallylpyrophosphate exists in all living organisms, ranging from bacteria to humans. In humans, dimethylallylpyrophosphate is involved in the lovastatin action pathway, the desmosterolosis pathway, the risedronate action pathway, and the ibandronate action pathway. Dimethylallylpyrophosphate is also involved in several metabolic disorders, some of which include the wolman disease pathway, the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the mevalonic aciduria pathway, and the child syndrome pathway. Outside of the human body, dimethylallylpyrophosphate can be found in a number of food items such as ucuhuba, yellow wax bean, white cabbage, and european plum. This makes dimethylallylpyrophosphate a potential biomarker for the consumption of these food products. Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. (wikipedia).358-72-5C0023564716057CPD-4211627DB01785CC(C)=CCO[P@](O)(=O)OP(O)(O)=OC5H12O7P2InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)CBIDRCWHNCKSTO-UHFFFAOYSA-N246.0921246.005825762FDB0224341,1-dimethyl-4-phenylpiperazinium iodide;2-isopentenyl diphosphate;3,3-dimethylallyl pyrophosphate;3-methyl-2-buten-1-ol pyrophosphate;3-methyl-2-buten-1-ol trihydrogen pyrophosphate;3-methyl-2-butenyl pyrophosphate;3-methylbut-2-enyl pyrophosphate;Dmapp;Dmpp;Delta2-isopentenyl diphosphate;Delta2-isopentenyl-diphosphate;Dimethylallyl diphosphate;Dimethylallyl pyrophosphate;Dimethylallyl-pp;Dimethylallyl-ppi;Dimethylallyl-diphosphate;Dimethylallyl-pyrophosphate;Dimethylallylpyrophosphate;Diphosphoric acid mono(3-methyl-2-butenyl) ester;Ipe;Prenyl diphosphate;Prenyl-diphosphate;Delta-prenyl diphosphate;Monoprenyl diphosphate;2-isopentenyl diphosphoric acid;Dimethylallylpyrophosphoric acid;Delta2-isopentenyl diphosphoric acid;δ2-isopentenyl diphosphate;δ2-isopentenyl diphosphoric acid;Dimethylallyl pyrophosphoric acid;Monoprenyl diphosphoric acid;Prenyl diphosphoric acidPW_C000874Ipe81057309216123112251248815178924334121477408124035374423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-N24.30523.985041898FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+86822742681647627272681158191888322936399833992211167461483491529431764142124102411592942233126293373745403147749148695449745652531045329111535611253761035906147593415160381556094161625016664841786594164688116069791997170205719420672272137233211725021473102167313198747322211763132118432101231222512324249125132881258122612729290152752851533730877137133772363297793733678393334784173357848911578522331785363567857413080020368800451848004837280623118806541358086515809652538184151938323839490027108596223110559390115687398119974406120070122120247382120702407120981408121181124121265429121319419121924125122086405122408422122759120122921399123307119123546374123835464123889455124477136124637376124978375125447297125598484125669479125777481125921482125947299125973495126000490126243478126553491126753300127125389127164501127380502127407388127451507127804209128125508128347395140773891993Geranyl-PPHMDB0001285Geranyl diphosphate is the precursor of monoterpenes, a large family of natural occurring C10 compounds predominately found in plants and animals. Geranyl diphosphate is regarded as a key intermediate in the steroid, isoprene and terpene biosynthesis pathways and is used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids. (wikipedia). In humans, geranyl diphosphate synthase (GPPS) catalyzes the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl diphosphate. Animals produce IPP through the mevalonate (MVA) pathway. Isoprenoid compounds have been implicated in several human disease states including coronary heart disease, blindness, infectious hepatitis and cancer. Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.763-10-0C0034144599517211GERANYL-PP393471DB02552CC(C)=CCC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)OC10H20O7P2InChI=1S/C10H20O7P2/c1-9(2)5-4-6-10(3)7-8-16-19(14,15)17-18(11,12)13/h5,7H,4,6,8H2,1-3H3,(H,14,15)(H2,11,12,13)/b10-7+GVVPGTZRZFNKDS-JXMROGBWSA-N314.2091314.068426018FDB001463(2e)-3,7-dimethylocta-2,6-dien-1-yl trihydrogen diphosphate;Geranyl diphosphate;Geranyl-pp;Geranyl-diphosphate;Geranyl-pyrophosphate;Monoterpenyl diphosphate;Neryl diphosphate;Trans-geranyl pyrophosphate;Polyisopentenylpyrophosphate;Polyisopentenyldiphosphate;Trans-polyisopentenyldiphosphate;Polyprenyl diphosphate;Polyisopentenylpyrophosphoric acid;Polyisopentenyldiphosphoric acid;Trans-polyisopentenyldiphosphoric acid;Polyprenyl diphosphoric acidPW_C000993Gryl-PP808515988731119876091608282210123142251521830678925111121479122124037135170PyrophosphateHMDB0000250The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.14000-31-8C0001364410218361PPI559142DB04160OP(O)(=O)OP(O)(O)=OH4O7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)XPPKVPWEQAFLFU-UHFFFAOYSA-N177.9751177.943225506FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170Ppi122354638429237353288222121731620492410592815294175144868545034895252104529410154091175424103543311854581205548111555913255841335606135565510858791076239166697819970731887134163727216073121987318213827515182832101186916112002222120411641231522512323249125122881257922612695290152193061537518347601742561315426973187723532977317128776353367841633578928331791531127995013479958130800473728041717085630194786384948141259481938298678223110634391113270395113275389115527136115532399119934122120017124120032406120330410120936407121261429121341121121486383122407422122985444123502119123831464124044398124977375125324297125395299125410479125597484125656485125876481126552491126869205126935388126950501127337206128124508140772891768Farnesyl pyrophosphateHMDB0000961Farnesyl pyrophosphate, also known as farnesyl diphosphoric acid or farnesyl-PP, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesyl pyrophosphate is considered to be a practically insoluble (in water) and relatively neutral molecule. Farnesyl pyrophosphate has been found in human testicle tissue, and has also been primarily detected in blood. Farnesyl pyrophosphate can be found anywhere throughout the human cell, such as in membrane (predicted from logP), peroxisome, mitochondria, and endoplasmic reticulum. Farnesyl pyrophosphate exists in all living organisms, ranging from bacteria to humans. Farnesyl pyrophosphate participates in a number of enzymatic reactions. In particular, Ferroheme b and farnesyl pyrophosphate can be converted into heme O; which is mediated by the enzyme heme O synthase. Furthermore, Farnesyl pyrophosphate and isopentenyl pyrophosphate can be converted into octaprenyl diphosphate through the action of the enzyme octaprenyl diphosphate synthase. Furthermore, Farnesyl pyrophosphate can be biosynthesized from geranyl-PP and isopentenyl pyrophosphate through its interaction with the enzyme geranyl diphosphate synthase / farnesyl diphosphate synthase. Finally, Farnesyl pyrophosphate and isopentenyl pyrophosphate can be converted into di-trans,octa-cis-undecaprenyl diphosphate; which is catalyzed by the enzyme undecaprenyl diphosphate synthase. In humans, farnesyl pyrophosphate is involved in the simvastatin action pathway, the risedronate action pathway, the alendronate action pathway, and the ibandronate action pathway. Farnesyl pyrophosphate is also involved in several metabolic disorders, some of which include the hyper-igd syndrome pathway, the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the porphyria variegata (PV) pathway, and lysosomal acid lipase deficiency (wolman disease). Outside of the human body, farnesyl pyrophosphate can be found in a number of food items such as sweet basil, apple, spearmint, and nuts. This makes farnesyl pyrophosphate a potential biomarker for the consumption of these food products. Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. -- Wikipedia.372-97-4C0044844571317407FARNESYL-PP393270DB07780CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=OC15H28O7P2InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+VWFJDQUYCIWHTN-YFVJMOTDSA-N382.33382.131027238FDB022339(2e,6e)-farnesyl diphosphate;(2e,6e)-farnesyl pyrophosphate;(e,e)-farnesyl diphosphate;(e,e)-farnesyl pyrophosphate;(all-e)-farnesyl diphosphate;2-trans,6-trans-farnesyl diphosphate;2-trans,6-trans-farnesyl pyrophosphate;All-trans-farnesyl pyrophosphate;Farnesyl diphosphate;Farnesyl pyrophosphate;Farnesyl-pp;Trans-farnesyl pyrophosphate;Trans-trans-farnesyl diphosphate;Trans-trans-farnesyl pyrophosphate;(2e,6e)-farnesol diphosphate;Trans,trans-farnesyl diphosphate;(2e,6e)-farnesol diphosphoric acid;2-trans,6-trans-farnesyl diphosphoric acid;(2e,6e)-farnesyl diphosphoric acid;(2e,6e)-farnesyl pyrophosphoric acid;(all-e)-farnesyl diphosphoric acid;(e,e)-farnesyl pyrophosphoric acid;2-trans,6-trans-farnesyl pyrophosphoric acid;All-trans-farnesyl pyrophosphoric acid;Farnesyl diphosphoric acid;Farnesyl pyrophosphoric acid;Trans,trans-farnesyl diphosphoric acid;Trans-trans-farnesyl diphosphoric acidPW_C000768FarPP8135161483744270471607314198828421012316225123191517860513278926111809683121482122122039407124040135124593119126191481146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1ACFIXJIJDZMPPO-NNYOXOHSSA-N745.4209745.091102105FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH18581903778107965821188372160929161549468731479314479714531011157891085972147612815962713567791177068188710316371542057205160731521373452107559212759117081942258219151842122411812198118932111200622212150164122452861259622612648249423433154374632276911293771661327738533177394332774601307750411277511115776233368071211911316494120105407120425405120452122120616123121141125121275429121402124121483383123059376123086135123241447123712136123846464123961118124041398125472481125696297126214299126529495127009206127572388128101390140706168175SqualeneHMDB0000256Squalene is a natural raw material found in human sebum (5%) and in shark-liver oil. An unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds. (Hawley's Condensed Chemical Reference) Biological Source: Found in fish liver oils, yeast lipids and many vegetable oils, e.g. palm oil, cottonseed oil, rapeseed oil. Volatile component of scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey). Component of adult human sebum principally responsible for the fixing of fingerprints (ChemNetBase) Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. -- Wikipedia; Squalene is the biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. -- Wikipedia; Squalene is a low density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the shark's liver, is lighter than water with a specific gravity of 0.855. -- Wikipedia Uses: Bactericide. Intermediate in the manufacture of pharmaceuticals, rubber chemicals and coloring materials (Physical Constants of Chemical Substances).111-02-4C007511197527315440SQUALENE10148626CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC=C(C)CC30H50InChI=1S/C30H50/c1-25(2)15-11-19-29(7)23-13-21-27(5)17-9-10-18-28(6)22-14-24-30(8)20-12-16-26(3)4/h15-18,23-24H,9-14,19-22H2,1-8H3/b27-17+,28-18+,29-23+,30-24+YYGNTYWPHWGJRM-AAJYLUCBSA-N410.73410.39125161FDB015781(e,e,e,e)-squalene;(all-e)-2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene;2,6,10,15,19,23-hexamethyl-2,6,10,14,18,22-tetracosahexaene;All-trans-squalene;Nikko squalane ex;Spinacen;Spinacene;Squalen;Squalene;Trans-squalenePW_C000175Squalen817181619497316213761116082852101232124978927331121484383124042398143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-N743.405743.075452041FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP18381913768578010824188392161129161749468531479614480114530811157901086017147613215962733567781177069188710516371522057206160731721373462107562212758917081972258220151841922411811198118972111200822212152164122492861259722612650249423443154374532276913293771641327738433177396332774611307751511577624336778143347787011280713119113165941201064071204294051204501221206044081206181231211421251212774291214011241214853831230633761230841351232293741232434471237131361238484641239601181240433981254734811256942971257434821262152991265284951270102061272255021275703881281003901407091681065OxygenHMDB0001377Oxygen is the third most abundant element in the universe after hydrogen and helium and the most abundant element by mass in the Earth's crust. Diatomic oxygen gas constitutes 20.9% of the volume of air. All major classes of structural molecules in living organisms, such as proteins, carbohydrates, and fats, contain oxygen, as do the major inorganic compounds that comprise animal shells, teeth, and bone. Oxygen in the form of O2 is produced from water by cyanobacteria, algae and plants during photosynthesis and is used in cellular respiration for all living organisms. Green algae and cyanobacteria in marine environments provide about 70% of the free oxygen produced on earth and the rest is produced by terrestrial plants. Oxygen is used in mitochondria to help generate adenosine triphosphate (ATP) during oxidative phosphorylation. For animals, a constant supply of oxygen is indispensable for cardiac viability and function. To meet this demand, an adult human, at rest, inhales 1.8 to 2.4 grams of oxygen per minute. This amounts to more than 6 billion tonnes of oxygen inhaled by humanity per year. At a resting pulse rate, the heart consumes approximately 8-15 ml O2/min/100 g tissue. This is significantly more than that consumed by the brain (approximately 3 ml O2/min/100 g tissue) and can increase to more than 70 ml O2/min/100 g myocardial tissue during vigorous exercise. As a general rule, mammalian heart muscle cannot produce enough energy under anaerobic conditions to maintain essential cellular processes; thus, a constant supply of oxygen is indispensable to sustain cardiac function and viability. However, the role of oxygen and oxygen-associated processes in living systems is complex, and they and can be either beneficial or contribute to cardiac dysfunction and death (through reactive oxygen species). Reactive oxygen species (ROS) are a family of oxygen-derived free radicals that are produced in mammalian cells under normal and pathologic conditions. Many ROS, such as the superoxide anion (O2-)and hydrogen peroxide (H2O2), act within blood vessels, altering mechanisms mediating mechanical signal transduction and autoregulation of cerebral blood flow. Reactive oxygen species are believed to be involved in cellular signaling in blood vessels in both normal and pathologic states. The major pathway for the production of ROS is by way of the one-electron reduction of molecular oxygen to form an oxygen radical, the superoxide anion (O2-). Within the vasculature there are several enzymatic sources of O2-, including xanthine oxidase, the mitochondrial electron transport chain, and nitric oxide (NO) synthases. Studies in recent years, however, suggest that the major contributor to O2- levels in vascular cells is the membrane-bound enzyme NADPH-oxidase. Produced O2- can react with other radicals, such as NO, or spontaneously dismutate to produce hydrogen peroxide (H2O2). In cells, the latter reaction is an important pathway for normal O2- breakdown and is usually catalyzed by the enzyme superoxide dismutase (SOD). Once formed, H2O2 can undergo various reactions, both enzymatic and nonenzymatic. The antioxidant enzymes catalase and glutathione peroxidase act to limit ROS accumulation within cells by breaking down H2O2 to H2O. Metabolism of H2O2 can also produce other, more damaging ROS. For example, the endogenous enzyme myeloperoxidase uses H2O2 as a substrate to form the highly reactive compound hypochlorous acid. Alternatively, H2O2 can undergo Fenton or Haber-Weiss chemistry, reacting with Fe2+/Fe3+ ions to form toxic hydroxyl radicals (-.OH). (PMID: 17027622, 15765131).7782-44-7C0000797715379CPD-6641952O=OO2InChI=1S/O2/c1-2MYMOFIZGZYHOMD-UHFFFAOYSA-N31.998831.989829244FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391924(S)-2,3-EpoxysqualeneHMDB0001188(S)-2,3-Epoxysqualene, also known as (S)-squalene-2,3-epoxide, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units (S)-2,3-Epoxysqualene is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, (S)-2,3-epoxysqualene is primarily located in the membrane (predicted from logP), endoplasmic reticulum and cytoplasm. In humans, (S)-2,3-epoxysqualene is involved in the desmosterolosis pathway, the alendronate action pathway, the pamidronate action pathway, and the simvastatin action pathway (S)-2,3-Epoxysqualene is also involved in several metabolic disorders, some of which include the smith-lemli-opitz syndrome (slos) pathway, the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the child syndrome pathway, and lysosomal acid lipase deficiency (wolman disease). Outside of the human body, (S)-2,3-epoxysqualene can be found in a number of food items such as roman camomile, loquat, pistachio, and pepper (c. baccatum). This makes (S)-2,3-epoxysqualene a potential biomarker for the consumption of these food products. (S)-2,3-Epoxysqualene is an intermediate in the biosynthesis of Terpenoid. It is a substrate for Squalene monooxygenase and Lanosterol synthase.9029-62-3C010545347772315441EPOXYSQUALENE30776536CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CC[C@@H]1OC1(C)CC30H50OInChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+/t29-/m0/s1QYIMSPSDBYKPPY-RSKUXYSASA-N426.7174426.386166222FDB022476(s)-2,3-epoxysqualene;(s)-squalene-2,3-epoxide;Squalene 2,3-epoxide;Squalene 2,3-oxidePW_C000924S23O8221816214973202131232624978929331121488383124046398964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N785.5497785.157134455FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD9991145186819232164253176282882518840211881414894216122916224921335825362237232646023646883147411347581048816526810352851025335111549612655111275613118603015560541566082161611616263901647517864991796666107703916371752057321213746522274872239076224118182161188721511899211122962251232824912443151125192271259522612710291127202921302930113041302436233187708029377126133771521347750111377507112775181157754133477615132777263377805432978375345789303317922233679272358800123688003436980714119119958406119999384120051408120107407120432405120453122120490124121278429121298418121417382121489383122748120122776121122802374122823443123066376123087135123166448123849464123868454123976399124047398125348479125378480125429482125474481125697297125979489126107299126277484126891501126920391126968502126987207127011206127310209127432506127602388127840389140790185140799186966LanosterolHMDB0001251Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. Lanosterol is biochemically synthesized starting from acetyl-CoA by the HMG-CoA reductase pathway. The critical step is the enzymatic conversion of the acyclic terpene squalene to the polycylic lanosterol via 2,3-squalene oxide.(wikipedia).79-63-0C0172424698316521LANOSTEROL216175[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3)[C@H](C)CCC=C(C)CC30H50OInChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1CAHGCLMLTWQZNJ-BQNIITSRSA-N426.7174426.386166222FDB013802(3 beta)-lanosta-8,24-dien-3-ol;(3alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-ol;(3beta)-lanosta-8,24-dien-3-ol;(3beta,5alpha)-4,4,14-trimethyl-cholesta-8,24-dien-3-ol;4,4',14alpha-trimethyl-5alpha-cholesta-8,24-dien-3beta-ol;Botalan base 138;Lanosta-8,24-dien-3-ol;Lanosta-8,24-dien-3beta-ol;Lanosta-8,24-dienol;Lanosterin;Lanosterol;Lanster;(3beta,5alpha)-4,4,14-trimethylcholesta-8,24-dien-3-ol;(3b)-lanosta-8,24-dien-3-ol;(3β)-lanosta-8,24-dien-3-olPW_C000966Lastrol82718162487322198761416082862107893111112149112212404913514070049296224,25-DihydrolanosterolHMDB000683924,25-Dihydrolanosterol, also known as lanostenol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, 24,25-dihydrolanosterol is considered to be a sterol lipid molecule. 24,25-Dihydrolanosterol is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 24,25-dihydrolanosterol is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 24,25-dihydrolanosterol is involved in the simvastatin action pathway, the atorvastatin action pathway, the alendronate action pathway, and the ibandronate action pathway. 24,25-Dihydrolanosterol is also involved in several metabolic disorders, some of which include the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the cholesteryl ester storage disease pathway, the mevalonic aciduria pathway, and lysosomal acid lipase deficiency (wolman disease). Outside of the human body, 24,25-dihydrolanosterol can be found in a number of food items such as yellow bell pepper, orange bell pepper, green bell pepper, and red bell pepper. This makes 24,25-dihydrolanosterol a potential biomarker for the consumption of these food products. 24,25-Dihydrolanosterol is involved in the biosynthesis of steriods. 24,25-Dihydrolanosterol is reversibly converted to lanosterol by delta24-sterol reductase [EC:1.3.1.72].79-62-9C0510944056028113CPD-8606389460[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3C30H52OInChI=1S/C30H52O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h20-22,25-26,31H,9-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1MBZYKEVPFYHDOH-BQNIITSRSA-N428.7333428.401816286FDB004614LanostenolPW_C0029622425Di1626497323213789323311214933831240513988094,4-Dimethylcholesta-8,14,24-trienolHMDB00010234,4-Dimethylcholesta-8,14,24-trienol is a product of the enzyme delta14-sterol reductase [EC 1.3.1.70] (KEGG). It is involved in the biosynthesis of steroids and is involved in the conversion of lanosterol to zymosterol. In particular, lanosterol 14-alpha-demethylase, catalyzes the C-14 demethylation of lanosterol to form 4,4-Dimethylcholesta-8,14,24-trienol in the ergosterol biosynthesis pathway. It is thought to be a meiosis activating sterol.64284-64-6C114554432121781344-DIMETHYL-CHOLESTA-812-24-TRIENOL391478C[C@H](CCC=C(C)C)[C@H]1CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3C29H46OInChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1LFQXEZVYNCBVDO-PBJLWWPKSA-N410.6749410.354866094FDB022376(3beta,5alpha)-4,4-dimethylcholesta-8,14,24-trien-3-ol;(3beta,5alpha)-4,4-dimethyl-cholesta-8,14,24-trien-3-ol;4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol;4,4-dimechol-8,14,24-trienol;4,4-dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol;4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3-ol;4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol;4,4-dimethyl-cholesta-8,14,24-trienol;4,4-dimethylcholesta-8,14,24-trienol;Ff-mas;Follicular fluid meiosis activating sterol;4,4-dimethylcholesta-8(9),14,24-trien-3beta-olPW_C000809FF-Mas162849732421383192107893333112149538312405339892Formic acidHMDB0000142Formic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer.64-18-6C000581897100230751FORMATE278DB01942OC=OCH2O2InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)BDAGIHXWWSANSR-UHFFFAOYSA-N46.025446.005479308DBMET00489FDB012804Add-f;Ameisensaure;Aminate;Aminic acid;Bilorin;Collo-bueglatt;Collo-didax;Formate;Formira;Formisoton;Formylate;Formylic acid;Hydrogen carboxylate;Hydrogen carboxylic acid;Methanoate;Methanoic acid;Methanoic acid monomer;Myrmicyl;Sodium formate;Sybest;Wonderbond hardener m 600lPW_C000092Formate94689773162949194325314111534811266361077158205718620673252137616160828721011982151435223187696322578652132789343311206701221206974071214963831217511241232841351233021191240543981243021181257532971257724811264782991268214951276373881284263901799HemeHMDB0003178Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.14875-96-8C0003217627HEME_A24604415DB02577CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=OC34H32FeN4O4InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;KABFMIBPWCXCRK-RGGAHWMASA-L616.487616.177297665FDB016272(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematinPW_C001799Heme2471630810324860827665124431354491413361963182806292938932381133672634211437344404331482328517095547212354851255517129583014162467862831659715170441607060161732621311835198118982111206516413009298130213004227817769152937693124977351111773641307736733177398332775171157762933677813334783801337860213278963112799321341204314051206034081209554071210853831216584291217461241219101221225704061226913841230653761231334471231441361232283741235211191236503981242164641242971181244631351251421201252771211257424821258964811261962991264992971265124951267184791268274801272245021273572061276323881280702051280833951280863901283095011284343919944,4-Dimethyl-5a-cholesta-8,24-dien-3-b-olHMDB00012864,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol (14-demethyllanosterol) is an intermediate in sterol biosynthesis. In particular, it is an intermediate in the conversion of lanosterol to zymosterol. 4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol is a substrate for C-4 methyl sterol oxidase, NAD(P)-dependent steroid dehydrogenase, Cytochrome P450 51A1 and Delta(14)-sterol reductase.7448-02-4C05108509900811836444-DIMETHYL-5ALPHA-CHOLEST-7-EN-3BET25994967[H][C@@]12CCC([C@H](C)CCC=C(C)C)[C@@]1(C)CCC1=C2CC[C@@]2([H])C(C)(C)[C@@H](O)CC[C@]12CC29H48OInChI=1S/C29H48O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,20,22-23,25-26,30H,8,10-18H2,1-7H3/t20-,22?,23+,25+,26+,28-,29-/m1/s1CHGIKSSZNBCNDW-GKBRUXRCSA-N412.6908412.370516158FDB022534(3beta,5alpha)-4,4-dimethylcholesta-8,24-dien-3-ol;14-demethyllanosterol;4,4-dimethyl-5 alpha -cholesta-8,24-dien-3 beta -ol;4,4-dimethyl-5-alpha-cholesta-(8,24)-dien-3-beta-ol;4,4-dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol;4,4-dimethyl-5a-cholesta-8,24-dien-3b-ol;4,4-dimethyl-5alpha -cholesta-8,24-dien-3-beta -ol;4,4-dimethyl-5alpha-cholest-7-en-3beta-ol;4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol;4,4-dimethyl-8,24-cholestadienol;4,4-dimethylzymosterolPW_C00099444Dcdol1631497327213761816082882107893533112149838312405639814070816829634,4-Dimethyl-5a-cholesta-8-en-3b-olHMDB00068404,4-Dimethyl-5a-cholesta-8-en-3b-ol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4,4-Dimethyl-5a-cholesta-8-en-3b-ol is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 4,4-dimethyl-5a-cholesta-8-en-3b-ol is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 4,4-dimethyl-5a-cholesta-8-en-3b-ol is involved in steroid biosynthesis pathway, the alendronate action pathway, the risedronate action pathway, and the simvastatin action pathway. 4,4-Dimethyl-5a-cholesta-8-en-3b-ol is also involved in several metabolic disorders, some of which include the hypercholesterolemia pathway, the wolman disease pathway, lysosomal acid lipase deficiency (wolman disease), and the smith-lemli-opitz syndrome (slos) pathway. 4,4-Dimethyl-5alpha-cholesta-8-en-3beta-ol is involved in the biosynthesis of steriods. 4,4-Dimethyl-5alpha-cholesta-8-en-3beta-ol is reversibly converted into 14-Demethyllanosterol by delta24-sterol reductase [EC:1.3.1.72].C159152372460430792004[H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3C29H50OInChI=1S/C29H50O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h19-20,22-23,25-26,30H,8-18H2,1-7H3/t20-,22-,23?,25+,26+,28-,29-/m1/s1FYHRVINOXYETMN-HFPXORMNSA-N414.7067414.386166222FDB0241133beta-hydroxy-4,4-dimethyl-8(9)-cholestene;3beta-hydroxy-4,4-dimethylcholest-8(9)-ene;4,4-dimethyl-3beta-hydroxy-8(9)-cholestene;4,4-dimethyl-3beta-hydroxycholest-8(9)-ene;4,4-dimethyl-5alpha-cholesta-8-en-3beta-ol;4,4-dimethylcholest-8(9)-en-3beta-ol;4,4-dimethylcholesta-8(9)-en-3beta-olPW_C00296344DCBol16334973282137893633112150038312405839830094a-Methylzymosterol-4-carboxylic acidHMDB00069274a-Methylzymosterol-4-carboxylic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 4a-Methylzymosterol-4-carboxylic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, 4a-methylzymosterol-4-carboxylic acid is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 4a-methylzymosterol-4-carboxylic acid is involved in the desmosterolosis pathway, the rosuvastatin action pathway, the atorvastatin action pathway, and the alendronate action pathway. 4a-Methylzymosterol-4-carboxylic acid is also involved in several metabolic disorders, some of which include the cholesteryl ester storage disease pathway, the chondrodysplasia punctata II, X linked dominant (CDPX2) pathway, the hypercholesterolemia pathway, and the mevalonic aciduria pathway. 4alpha-Methylzymosterol-4-carboxylic acid is a steroid derivative involved in steroid biosynthesis. It is generated from 14-demethyl-lanosterol via the enzyme methylsterol monooxygenase (EC 1.14.13.72).C1580853477909C[C@@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@](C)(C1CC3)C(O)=OC29H46O3InChI=1S/C29H46O3/c1-18(2)8-7-9-19(3)21-11-12-22-20-10-13-24-28(5,23(20)14-16-27(21,22)4)17-15-25(30)29(24,6)26(31)32/h8,19,21-22,24-25,30H,7,9-17H2,1-6H3,(H,31,32)/t19-,21?,22?,24?,25-,27+,28+,29-/m0/s1MYWAIWDQTCHPTH-IUGQOUSLSA-N442.6737442.344695338FDB0241544alpha-carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol;4alpha-methylzymosterol-4-carboxylic acidPW_C0030094M4CA16344973292138308210789373311215013831240593989794IronHMDB0015531Iron is a metallic element found in certain minerals, in nearly all soils, and in mineral waters. Iron is required for life. It exists in all living species, ranging from bacteria to humans. It can be found primarily in blood and it is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. In humans, iron is involved in several metabolic pathways, some of which include the rofecoxib pathway, magnesium salicylate action pathway, etodolac pathway, and diclofenac pathway. Iron is also involved in several metabolic disorders, some of which include adenine phosphoribosyltransferase deficiency (APRT), porphyria variegata (PV), adenylosuccinate lyase deficiency, and AICA-ribosiduria. The major activity of supplemental iron is in the prevention and treatment of iron-deficiency anemia. Iron has putative immune-enhancing, anticarcinogenic, and cognition-enhancing activities. Iron can be found in a number of food items such as chinese water chestnut, hyssop, daikon radish, and peppermint, which makes it a potential biomarker for the consumption of these food products.7439-89-6C00023239251824822368DB01592[Fe++]FeInChI=1S/Fe/q+2CWYNVVGOOAEACU-UHFFFAOYSA-N55.84555.934942133C0002326fe;Eisen;Fe;Fer;Ferrum;HierroPW_C009794Iron11388126651533216354931192943411873302131205622577683130779283367826113278409111784283347893833112083812212099240812125642912137112412150238312172712512342313512355737412382646412393011812406039812427813612582929712593248212604429912728220512739150212749638829613-Keto-4-methylzymosterolHMDB00068383-Keto-4-methylzymosterol is an intermediate in the biosynthesis of steroids (KEGG:C15816). It is the 8th to last step in the synthesis of vitamin D2 and is converted from 4-methtylzymosterol-carboxylate via the enzyme sterol-4alpha-carboxylate 3-dehydrogenase (decarboxylating) (EC:1.1.1.170). It is then converted to 4-methylzymosterol via the enzyme 3-keto steroid reductase (EC:1.1.1.270).C1581653477900505093CPD-4578C[C@H](CCC=C(C)C)C1CCC2C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)C1CC3C28H44OInChI=1S/C28H44O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24H,7,9-17H2,1-6H3/t19-,20?,22?,23?,24?,27-,28+/m1/s1DBPZYKHQDWKORQ-JQDPPCHWSA-N396.6484396.33921603FDB024112(5a)-4-methylcholesta-8,24-dien-3-one;(5alpha)-4-methylcholesta-8,24-dien-3-one;3-dehydro-4-methylzymosterol;3-keto-4-methylzymosterol;4-methyl-5a-cholesta-8,24-dien-3-one;4-methyl-5alpha-cholesta-8,24-dien-3-onePW_C0029613K4Mzol163749733221375292107623160789403311215043831240623989464a-MethylzymosterolHMDB00012174a-Methylzymosterol is an intermediate in the biosynthesis of steroids (KEGG ID C05103). It is the 7th to last step in the synthesis of vitamin D2 and is converted from 3-keto-4-methtylzymosterol via the enzyme 3-keto steroid reductase [EC:1.1.1.270]. It is then converted to zymosterol. (KEGG).7448-03-5C051032221249519494-METHYL-824-CHOLESTADIENOL20036827[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)CC28H46OInChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24,26,29H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1FOUJWBXBKVVHCJ-YIJYGBTNSA-N398.6642398.354866094FDB022496(3b,4a,5a)-4-methylcholesta-8,24-dien-3-ol;(3beta,4alpha,5alpha)-4-methylcholesta-8,24-dien-3-ol;(4s,5s)-4,10,13-trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol;4a-methyl-5a-cholesta-8,24-dien-3b-ol;4a-methylzymosterol;4alpha-methylzymosterol;4alpha-methyl-5alpha-cholesta-8,24-dien-3beta-ol;(3β,4α,5α)-4-methylcholesta-8,24-dien-3-olPW_C0009464aMzmol16404973342137625160829121078943331121507383124065398140714142697Zymosterol intermediate 2HMDB0006271Zymosterol is the precursor of cholesterol and is found in the plasma membrane. zymosterol circulates within the cells. The structural features of zymosterol provided optimal substrate acceptability. In human fibroblasts, zymosterol is converted to cholesterol solely in the rough ER. Little or no zymosterol or cholesterol accumulates in the rough ER in vivo. Newly synthesized zymosterol moves to the plasma membrane without a detectable lag and with a half-time of 9 min, about twice as fast as cholesterol. The pool of radiolabeled zymosterol in the plasma membrane turns over rapidly, faster than does intracellular cholesterol. Thus, plasma membrane zymosterol is not stagnant. [3H]Zymosterol pulsed into intact cells is initially found in the plasma membrane. (PMID: 1939176).128-33-6C05437927461825283724[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3C27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,19-21,23-24,28H,6,8-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1CGSJXLIKVBJVRY-XTGBIJOFSA-N384.6377384.33921603FDB023869(3b,5a)- cholesta-8,24-dien-3-ol;5alpha-cholesta-8,24-dien-3beta-ol;Cholest-8,24-dien-3b-ol;Cholesta-8,24-dien-3-ol;Delta8,24-cholestadien-3beta-ol;Zymosterol;Zymostrol;5a-cholesta-8,24-dien-3b-ol;5α-cholesta-8,24-dien-3β-ol;Delta8,24-cholestadien-3b-ol;δ8,24-cholestadien-3β-ol;δ8,24-cholestadien-3b-olPW_C002697ZymolI21642873351987894511112150912212406713529655a-Cholesta-7,24-dien-3b-olHMDB00068425alpha-Cholesta-7,24-dien-3beta-ol is involved in the biosynthesis of steroids. 5alpha-Cholesta-7,24-dien-3beta-ol is reversibly converted to 5alpha-Cholest-7-en-3beta-ol by delta24-sterol reductase [EC:1.3.1.72]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to zymosterol by cholestenol delta-isomerase [EC:5.3.3.5]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to 7-Dehydrodesmosterol. 5a-Cholesta-7,24-dien-3b-ol is a substrate for 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase.651-54-7C05439440670162905-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL389550[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)C3CC[C@]12CC27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,10,19-21,23-25,28H,6,8-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25?,26+,27-/m1/s1PKEPPDGGTSZLBL-FZAJRYLSSA-N384.6377384.33921603FDB0241155 alpha-cholesta-7,24-dien-3beta-ol;5alpha-cholesta-7,24-dien-3beta-olPW_C0029655CDBol16434973362137894633112151038312406839829645a-Cholest-8-en-3b-olHMDB00068415a-Cholest-8-en-3b-ol is a normal human metabolite and an intermediate of cholesterol synthesis. The concentrations of zymostenol are higher, both in serum and bile of patients with cerebrotendinous xanthomatosis, compared to controls or in patients with cerebrotendinous xanthomatosis treated with chenodeoxycholic acid. Kidney transplant recipients had lower serum zymostenol when compared to controls. During consumption of plant stanol ester spread by hypercholesterolemic children, plant sterols in the plasma decrease and cholesterol precursor sterols such as zymostenol increase. (PMID: 15736111, 16709621, 16477216, 12756385).566-97-2C0384510177016608CPD-862191952[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1QETLKNDKQOXZRP-XTGBIJOFSA-N386.6535386.354866094FDB024114(3beta,5alpha)cholestenol;3beta-hydroxy-8(9)-cholestene;3beta-hydroxycholest-8(9)-ene;5alpha-cholest-8(9)-en-3beta-ol;5alpha-cholest-8-en-3beta-ol;Cholest-8(9)-en-3beta-ol;Cholesta-8(9)-en-3beta-ol;Delta(8)-cholestenol;5-alpha-cholest-8-en-3-beta-ol;Cholestenol;Zymostenol;5a-cholest-8-en-3b-ol;5α-cholest-8-en-3β-olPW_C0029645aChlol164549733721378947331121512383124070398908LathosterolHMDB0001170Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID: 8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O.80-99-9C011896572817168CPD-418659151[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1IZVFFXVYBHFIHY-SKCNUYALSA-N386.6535386.354866094FDB022463(3beta)-cholest-7-en-3-ol;(3beta,5alpha)-cholest-7-en-3-ol;(3beta,alpha)-cholest-7-en-3-ol;(7)-cholestenol;3b-hydroxy-5-cholestene;3beta-hydroxy-5alpha-cholest-7-ene;5-a-cholest-7-en-3-beta-ol;5-alpha-cholest-7-en-3-beta-ol;5alpha-cholest-7-en-3beta-ol;7-cholesten-3-beta-ol;7-cholestenol;7-cholesterol;Cholest-7-en-3-ol;Cholest-7-en-3beta-ol;Cholest-7-en-ol;Cholesterol - synthetic;Cholesterol pharma;Cholesterol extra pure;Cholesterol gr;Cholesterol,nf grade;Delta7-cholesten-3beta-ol;Delta7-cholestenol;Lathosterol;Delta(7)-cholestenol;Gamma-cholestenol;Gamma-cholesterol;G-cholesterol;γ-cholesterolPW_C000908Lathost16484973382137894833112151338312407139819897-DehydrodesmosterolHMDB00038967-Dehydrodesmosterol is a sterol intermediate in the biosynthesis of steroids. 7-Dehydrodesmosterol is a substrate of the enzyme 24-dehydrocholesterol reductase (EC:1.3.1.72), an important enzyme in the biosynthesis of Cholesterol. Cholesterol is synthesized from either Lathosterol, 7-Dehydrocholesterol, Desmosterol or Cholestenol by the enzyme 3beta-hydroxysterol delta7 reductase (EC 1.3.1.21, Dhcr7). The Smith-Lemli-Opitz syndrome (SLOS, OMIM 270400) is caused by a genetic defect in cholesterol biosynthesis; mutations in the enzyme 3beta-hydroxysterol delta7 reductase lead to a failure of cholesterol synthesis, with an accumulation of precursor sterols, such as 7-Dehydrodesmosterol. SLOS results in craniofacial, limb as well as major organ defects, including the brain. In individuals with this syndrome, mental retardation, as well as other CNS dysfunction, is almost 100% prevalent. (PMID: 15862627, 17197219).1715-86-2C0510744055827910389458[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)CC27H42OInChI=1S/C27H42O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9-10,19,21,23-25,28H,6,8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1RUSSPKPUXDSHNC-DDPQNLDTSA-N382.6218382.323565966FDB01278124-dehydroprovitamin d3;Cholesta-5,7,24-trien-3beta-ol;Cholesta-5,7,24-triene-3beta-ol;Cholesta-5,7,24-trien-3b-ol;Cholesta-5,7,24-trien-3β-ol;Cholesta-5,7,24-triene-3b-ol;Cholesta-5,7,24-triene-3β-olPW_C0019897-DHMOL1649873391987565213764716082982107894911112151412212407213514072349227-DehydrocholesterolHMDB00000327-Dehydrocholesterol is a zoosterol (a sterol produced by animals rather than plants). It is a provitamin-D. The presence of this compound in skin enables humans to manufacture vitamin D3 from ultraviolet rays via an intermediate isomer provitamin D3. It is also found in breast milk.434-16-2C01164439423177597-DEHYDRO-CHOLESTEROL388534[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1UCTLRSWJYQTBFZ-DDPQNLDTSA-N384.6377384.33921603FDB021882(-)-7-dehydrocholesterol;(3b)-cholesta-5,7-dien-3-ol;(3beta)-cholesta-5,7-dien-3-ol;10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-3-ol;17-(1,5-dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-ol;5,7-cholestadien-3-beta-ol;5,7-cholestandien-3-ol;5,7-cholestandien-3beta-ol;7,8-dehydro-cholesterol;7,8-didehydrocholesterol;7-dehydro-cholesterol;7-dehydrocholesterin;7-dehydrocholesterol;7dhc;Cholesta-5,7-dien-3 beta -ol;Cholesta-5,7-dien-3-beta-ol;Cholesta-5,7-dien-3-ol;Cholesta-5,7-dien-3b-ol;Cholesta-5,7-dien-3beta-ol;Dehydrocholesterin;Dehydrocholesterol;Delta5,7-cholestadien-3beta-ol;Delta5,7-cholesterol;Delta7-cholesterol;Provitamin d3;Provitamin-d3;5,7-cholestadien-3beta-ol;(3β)-cholesta-5,7-dien-3-olPW_C0000227DHC16554973402137895033112151538312407339847CholesterolHMDB0000067Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50% of the lipid in the membrane or 60-80% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with cholesterol has always been specifically with cholesterol transport patterns, not total cholesterol per se. For example, total cholesterol can be low, yet made up primarily of small LDL and small HDL particles and atheroma growth rates are high. In contrast, however, if LDL particle number is low (mostly large particles) and a large percentage of the HDL particles are large (HDL is actively reverse transporting cholesterol), then atheroma growth rates are usually low, even negative, for any given total cholesterol concentration. These effects are further complicated by the relative concentration of asymmetric dimethylarginine (ADMA) in the endothelium since ADMA down-regulates production of nitric oxide, a relaxant of the endothelium. Thus, high levels of ADMA, associated with highly oxidized levels of LDL, pose a heightened risk factor for vascular disease. Chronically high levels of cholesterol are associated with at least five inborn errors of metabolism, including cerebrotendinous xanthomatosis, cholesteryl ester storage disease, congenital lipoid adrenal hyperplasia, hypercholesterolemia, and Zellweger syndrome. In chronically high levels, cholesterol can function as an atherogen (causes atherosclerosis and cardiovascular disease). Specifically, chronically high levels (from diet or from genetic predisposition or from diseases such as hyperlipidemia) of cholesterol and cholesterol esters lead to an excess of low-density lipoprotein (LDL) particles. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. Resistin, a protein secreted by fat tissue, has been shown to increase the production of LDL in human liver cells and also degrades LDL receptors in the liver. As a result, the liver is less able to clear cholesterol from the bloodstream. Resistin accelerates the accumulation of LDL in arteries, increasing the risk of heart disease.57-88-5C00187599716113CHOLESTEROL5775DB04540[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)CC27H46OInChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1HVYWMOMLDIMFJA-DPAQBDIFSA-N386.6535386.354866094FDB013269(+)-ent-cholesterol;(-)-cholesterol;(20bfh)-cholest-5-en-3b-ol;(3b)-cholest-5-en-3-ol;(3beta)-cholest-5-en-3-ol;20-epi-cholesterol;20-iso-cholesterol;20bfh-cholest-5-en-3b-ol;3beta-hydroxycholest-5-ene;5-cholesten-3b-ol;5-cholesten-3beta-ol;5:6-cholesten-3-ol;5:6-cholesten-3beta-ol;Cholest-5-en-3-ol;Cholest-5-en-3b-ol;Cholest-5-en-3beta-ol;Cholesterin;Cholesterine;Cholesterol;Cholesterol base h;Cholesteryl alcohol;Cholestrin;Cholestrol;Cordulan;Dastar;Dusoline;Dusoran;Dythol;Epicholesterin;Epicholesterol;Fancol ch;Hydrocerin;Kathro;Lanol;Liquid crystal cn/9;Nimco cholesterol base h;Nimco cholesterol base no. 712;Super hartolan;TegolanPW_C000047Lanol829216584923303284029284515734121375672107649160776533367768511478951331789881121215163831216974291217314091218314071240743981242464641242821371243841191690DesmosterolHMDB0002719Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursor's 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203).313-04-2C0180243957717737CPD-4141388662[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC=C(C)CC27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1AVSXSVCZWQODGV-DPAQBDIFSA-N384.6377384.33921603FDB00537424-dehydrocholesterol;3beta-cholesta-5,24-dien-3-ol;Cholest-5,24-dien-3beta-ol;Cholesta-5,24-dien-3-ol;Cholesta-5,24-dien-3b-ol;Cholesta-5,24-dien-3beta-ol;Desmosterol;3b-cholesta-5,24-dien-3-ol;3β-cholesta-5,24-dien-3-ol;Cholesta-5,24-dien-3β-olPW_C001690Desmost165987342198756621076481607895211112151712212407513514072449699Vitamin D3HMDB0000876Vitamin D3, also called cholecalciferol, is one of the forms of vitamin D. Vitamin D3 is a steroid hormone that has long been known for its important role in regulating body levels of calcium and phosphorus, in mineralization of bone, and for the assimilation of Vitamin A. It is structurally similar to steroids such as testosterone, cholesterol, and cortisol (although vitamin D3, itself, is a secosteroid). Vitamin D3 is a derivative of 7-dehydroxycholesterol formed by ultraviolet rays breaking the C9-C10 bond. It differs from ergocalciferol in having a single bond between C22 and C23 and lacking a methyl group at C24. Vitamin D3 can also come from dietary sources, such as beef liver, cheese, egg yolks, and fatty fish (PubChem). The first step involved in the activation of vitamin D3 is a 25-hydroxylation catalyzed by 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyzes the first reaction in the oxidation of the side chain of sterol intermediates. The active form of vitamin D3 (calcitriol) binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by (1) increasing GI absorption of phosphorus and calcium, (2) increasing osteoclastic resorption, and (3) increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through the formation of a calcium-binding protein.67-97-0C054435280795289404444353DB00169[H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C)[C@H](C)CCCC(C)CC27H44OInChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1QYSXJUFSXHHAJI-YRZJJWOYSA-N384.6377384.33921603FDB012732(+)-vitamin d3;(3beta,z,7e)-9,10-secocholesta-5,7,10(19)-trien-3-ol;(5e,7e)-9,10-secocholesta-5,7,10-trien-3-ol;3-beta,z,7e-9,10-secocholestr-5,7,10(19)-trien-3-ol;9,10-secocholesta-5,7,10(19)-trien-3-beta-ol;9,10-secocholesta-5,7,10(19)-trien-3-ol;9,10-secocholesta-5,7,10-trien-3-ol;Arachitol;Cc;Calciol;Cholecalciferol;Cholecalciferol d3;Colecalciferol;D3-vigantol;Delsterol;Deparal;Devaron;Ebivit;Feracol;Granuvit d3;Micro-dee;Oleovitamin d3;Provitina;Quintox;Ricketon;Trivitan;Vi-de3;Vidde-3-hydrosol;Videkhol;Vigantol;Vigorsan;Vitinc dan-dee-3PW_C000699VitD31664873431987895311112151912212407713513608-DehydrocholesterolHMDB00020278-Dehydrocholesterol (8-DHC) elevated concentration is one of the diagnostic biochemical hallmarks of classical Smith-Lemli-Opitz syndrome (SLOS). Plasma 8-DHC could be only marginally elevated. (PMID: 16435228). Smith-Lemli-Opitz syndrome (SLOS) is an autosomal recessive condition caused by a defect in cholesterol synthesis (caused by a deficit of 3beta-hydroxysterol-Delta7 reductase). Affected children often have malformations and mental retardation. Autistic behaviors also are evident. In children, the baseline cholesterol, 8-DHC levels, and cholesterol levels following supplementation does not correlate with the presence or severity of autistic symptoms. (PMID: 16761297). Accumulation of 8-dehydrocholesterol in Amniotic fluid is diagnostic for SLOS. (PMID 16231320).70741-38-7129846114943[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3)[C@H](C)CCCC(C)CC27H44OInChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1VUKORTMHZDZZFR-BXAZICILSA-N384.6377384.33921603FDB0228053b-cholesta-5,8-dien-3-ol;8-dehydrocholesterolPW_C0013608Dhchol1665873441987895411112152012212407813540705Fatty acidHMDB0061373Palmitic acid, also known as C16 or palmitate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Palmitic acid exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Palmitic acid has been found throughout most human tissues, and has also been detected in most biofluids, including sweat, blood, urine, and cerebrospinal fluid. Palmitic acid can be found anywhere throughout the human cell, such as in peroxisome, adiposome, membrane (predicted from logP), and endoplasmic reticulum. Palmitic acid exists in all living organisms, ranging from bacteria to humans. Palmitic acid can be converted into palmityl-CoA through its interaction with the enzyme short chain acyl-CoA synthetase. Outside of the human body, palmitic acid can be found in a number of food items such as japanese persimmon, rye, fireweed, and scarlet bean. This makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid is a potentially toxic compound.57-10-3C0024998515756960DB03796CCCCCCCCCCCCCCCC(O)=OC16H32O2InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)IPCSVZSSVZVIGE-UHFFFAOYSA-N256.4241256.240230268C002491-hexyldecanoic acid;1-pentadecanecarboxylic acid;C16 fatty acid;C16:0;Cetylic acid;Ch3-[ch2]14-cooh;Hexadecanoate;Hexadecoic acid;Hexadecylic acid;Hexaectylic acid;N-hexadecanoic acid;N-hexadecoic acid;Palmitate;Palmitinic acid;Palmitinsaeure;Pentadecanecarboxylic acid;1-hexyldecanoate;1-pentadecanecarboxylate;Cetylate;Hexadecanoic acid;Hexadecoate;Hexadecylate;Hexaectylate;N-hexadecanoate;N-hexadecoate;Palmitinate;Pentadecanecarboxylate;Edenor c16;Emersol 140;Emersol 143;Glycon p-45;Hexadecanoate (n-c16:0);Hexadecanoic acid palmitic acid;Hydrofol;Hydrofol acid 1690;Hystrene 8016;Hystrene 9016;Industrene 4516;Kortacid 1698;Loxiol ep 278;Lunac p 95;Lunac p 95kc;Lunac p 98;Palmitoate;Palmitoic acid;Pam;Plm;Prifac 2960;Prifrac 2960;Pristerene 4934;Univol u332PW_C040705FA469654699973482167351215789553347895811312152340812152612612408137412408444340704Cholesterol EsterHMDB0061374Ce(18:0), also known as ce(18:0/0:0), belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Ce(18:0) is considered to be a practically insoluble (in water) and relatively neutral molecule. Ce(18:0) has been found throughout all human tissues, and has also been detected in multiple biofluids, such as blood and urine. Within the cell, ce(18:0) is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, ce(18:0) is involved in the pamidronate action pathway, the rosuvastatin action pathway, the pravastatin action pathway, and the zoledronate action pathway. Ce(18:0) is also involved in several metabolic disorders, some of which include lysosomal acid lipase deficiency (wolman disease), the smith-lemli-opitz syndrome (slos) pathway, the cholesteryl ester storage disease pathway, and the hypercholesterolemia pathway.[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])C2=CC=C2C[C@H](CC[C@]12C)OC(=O)CCCCCCCCCCCCCCCC43H74O2InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h24-25,33-34,36,38-40H,7-23,26-32H2,1-6H3/t34-,36+,38-,39+,40+,42+,43-/m1/s1NLSCQUMWOFPZDA-GERPYZGRSA-N623.0465622.568881612PW_C040704ChoEst4697573492167895633412152440812408237413Acetyl-CoA acetyltransferase, cytosolicQ9BWD1HMDBP00013ACAT26q25.3BC00040812.3.1.9793892691351Hydroxymethylglutaryl-CoA synthase, cytoplasmicQ01581This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
HMDBP00053HMGCS15p14-p13CH47111912.3.3.1079521521813965078414098313990Mevalonate kinaseQ03426May be a regulatory site in cholesterol biosynthetic pathway.
HMDBP01053MVK12q24M8846812.7.1.36802515388139613784955Phosphomevalonate kinaseQ15126HMDBP01017PMVK1q22L7721312.7.4.28045830721013577316613961578414637718954Diphosphomevalonate decarboxylaseP53602Performs the first committed step in the biosynthesis of isoprenes.
HMDBP01016MVD16q24.3BC00001114.1.1.338075155081357741661396167841429Isopentenyl-diphosphate Delta-isomerase 1Q13907Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP).
HMDBP01541IDI110p15.3AF27172315.3.3.215765875Farnesyl pyrophosphate synthaseP14324Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
HMDBP00932FDPS1q22AK29108412.5.1.10; 2.5.1.1809583521599862511666281186595164139618784874Geranylgeranyl pyrophosphate synthaseO95749Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
HMDBP00931GGPS11q43AB01903612.5.1.-; 2.5.1.1; 2.5.1.29; 2.5.1.10833216038139623784254Squalene synthaseP37268HMDBP00260FDFT18p23.1-p22BC02964112.5.1.21816582018161849137000693139619784139620786142758104714277031148Squalene monooxygenaseQ14534Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
HMDBP00153SQLE8q24.1BX64740011.14.13.1328261884121623491427571047142769973421Lanosterol synthaseP48449Catalyzes the cyclization of (S)-2,3 oxidosqualene to lanosterol, a reaction that forms the sterol nucleus.
HMDBP00430LSS21q22.3AJ23902715.4.99.782818162581357754914275910471688Delta(24)-sterol reductaseQ15392Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
HMDBP01935DHCR241p32.3AF39833711.3.1.7216274913578518259Lanosterol 14-alpha demethylaseQ16850Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
HMDBP00265CYP51A17q21.2U5168711.14.13.7016304913578618142687531426889731427601047256Delta(14)-sterol reductaseO76062Involved in the conversion of lanosterol to cholesterol.
HMDBP00262TM7SF211q13AK29093511.3.1.7016324913577618257Methylsterol monooxygenase 1Q15800HMDBP00263MSMO14q32-q34BC01065311.14.13.7216364913578018258Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylatingQ15738HMDBP00264NSDHLXq28BC00024511.1.1.170163949135787187933-keto-steroid reductaseP56937Responsible for the reduction of the keto group on the C-3 of sterols.
HMDBP00848HSD17B71q23AF16276111.1.1.270; 1.1.1.62164149135779148923-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseQ15125Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
HMDBP00949EBPXp11.23-p11.22BC00154915.3.3.5164449130Lathosterol oxidaseO75845Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
HMDBP00135SC5DL11q23.3BC01233311.14.21.61660498533-Hydroxy-3-methylglutaryl-coenzyme A reductaseP04035Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
HMDBP00910HMGCR5q13.3-q14AF27376211.1.1.3479851524819681813577249138780101405141484Sterol O-acyltransferase 1P35610Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
HMDBP00504SOAT11q25CH47106712.3.1.26166949469851432081121221Lysosomal acid lipase/cholesteryl ester hydrolaseP38571Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
HMDBP00227LIPA10q23.2-q23.3AK31466513.1.1.13170692844291432181125144028118936Acetyl-CoA acetyltransferase, mitochondrialP24752Plays a major role in ketone body metabolism.
HMDBP00038ACAT111q22.3CH47106512.3.1.9594410503528110313563313313965178514098213141289238Hydroxymethylglutaryl-CoA synthase, mitochondrialP54868This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
HMDBP00040HMGCS21p13-p12U8185612.3.3.10596410523803338137841713229Acetyl-CoA acetyltransferase, cytosolic1PW_P000229247134230Hydroxymethylglutaryl-CoA synthase, cytoplasmic1PW_P000230248512232Mevalonate kinase1PW_P000232250990233Phosphomevalonate kinase1PW_P000233251955234Diphosphomevalonate decarboxylase1PW_P000234252954429Isopentenyl-diphosphate Delta-isomerase 11PW_P000429452142912024231236Farnesyl pyrophosphate synthase1PW_P00023625487522074233238Geranylgeranyl pyrophosphate synthase1PW_P00023825687462064233237Squalene synthase1PW_P00023725525411114231240Squalene monooxygenase1PW_P00024025814811129641239Lanosterol synthase1PW_P0002392574211441Delta(24)-sterol reductase1PW_P000441464168812129641442Lanosterol 14-alpha demethylase1PW_P000442465259121317991443Delta(14)-sterol reductase1PW_P0004434662561444Methylsterol monooxygenase 11PW_P000444467257121497941445Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating1PW_P00044546825814463-keto-steroid reductase1PW_P00044646979314473-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase1PW_P0004474708921451Lathosterol oxidase1PW_P0004514741301215979412313-Hydroxy-3-methylglutaryl-coenzyme A reductase1PW_P0002312498532455Sterol O-acyltransferase 11PW_P0004554784841456Lysosomal acid lipase/cholesteryl ester hydrolase1PW_P0004564792211179Acetyl-CoA acetyltransferase, mitochondrial1PW_P000179197364180Hydroxymethylglutaryl-CoA synthase, mitochondrial1PW_P000180198382681falsePW_R000681Both27919402Compoundtrue279211421Compoundfalse279310991Compoundtrue1781792.3.1.95172292.3.1.9682falsePW_R000682Right27949401Compoundfalse279511421Compoundfalse279614201Compoundtrue279710631Compoundfalse279810991Compoundtrue20891802.3.3.10734falsePW_R000734Right29931521Compoundfalse29944141Compoundtrue299510361Compoundfalse299610341Compoundtrue2492322.7.1.36464falsePW_R000464Right19274141Compoundtrue192810361Compoundfalse192910341Compoundtrue19308571Compoundfalse5272332.7.4.2398falsePW_R000398Right16344141Compoundtrue16358571Compoundfalse163610341Compoundtrue163711041Compoundtrue163810391Compoundfalse163913161Compoundtrue5302344.1.1.33334falsePW_R000334Both138910391Compoundfalse13908741Compoundfalse5434295.3.3.2957falsePW_R000957Right37758741Compoundfalse377610391Compoundfalse37779931Compoundfalse37931701Compoundtrue555236556238739falsePW_R000739Right30109931Compoundfalse301110391Compoundfalse30127681Compoundfalse30131701Compoundtrue254236564238740falsePW_R000740Right30147682Compoundfalse30151461Compoundtrue30161751Compoundfalse30171431Compoundtrue37941702Compoundtrue2552372.5.1.21742falsePW_R000742Right30211751Compoundfalse302210651Compoundtrue30231461Compoundtrue30249241Compoundfalse302514201Compoundtrue30261431Compoundtrue2572401.14.13.132743falsePW_R000743Right30279241Compoundfalse30289661Compoundfalse2582395.4.99.7964falsePW_R000964Both37959661Compoundfalse37961461Compoundtrue379729621Compoundfalse37981431Compoundtrue5654411.3.1.72965falsePW_R000965Right37999661Compoundfalse380010653Compoundtrue38011463Compoundtrue38028091Compoundfalse3803921Compoundtrue38041433Compoundtrue380514204Compoundtrue5664421.14.13.70966falsePW_R000966Right38068091Compoundfalse38071461Compoundtrue38089941Compoundfalse38091431Compoundtrue5674431.3.1.70967falsePW_R000967Right38109941Compoundfalse38111461Compoundtrue381229631Compoundfalse38131431Compoundtrue5684411.3.1.72968falsePW_R000968Right38149941Compoundfalse38151463Compoundtrue381610653Compoundtrue381730091Compoundfalse38181433Compoundtrue381914204Compoundtrue5694441.14.13.72969falsePW_R000969Right382030091Compoundfalse38211431Compoundtrue382229611Compoundfalse38231461Compoundtrue382413161Compoundtrue5704451.1.1.170970falsePW_R000970Right382529611Compoundfalse38261461Compoundtrue38279461Compoundfalse38281431Compoundtrue571446971truePW_R000971Right38299461Compoundfalse383026971Compoundfalse242falsePW_R000242Right104226971Compoundfalse104329651Compoundfalse5724475.3.3.5972falsePW_R000972Right383126971Compoundfalse38321461Compoundtrue383329641Compoundfalse38341431Compoundtrue5734411.3.1.72977falsePW_R000977Both384729651Compoundfalse38481461Compoundtrue38499081Compoundfalse38501431Compoundtrue5784411.3.1.72241falsePW_R000241Right10409081Compoundfalse104129641Compoundfalse5794475.3.3.5978PW_R000978Right385129651Compoundfalse385219891Compoundfalse988falsePW_R000988Right3873221Compoundfalse38741461Compoundtrue3875471Compoundfalse38761431Compoundtrue5954475.3.3.5989PW_R000989Right387719891Compoundfalse387816901Compoundfalse501falsePW_R000501Both20969081Compoundfalse20971461Compoundtrue209910651Compoundtrue2100221Compoundfalse21011431Compoundtrue210214202Compoundtrue5844511.14.21.6990falsePW_R000990Both387919891Compoundfalse38801461Compoundtrue3881221Compoundfalse38821431Compoundtrue5964411.3.1.72991falsePW_R000991Both388316901Compoundfalse38841461Compoundtrue3885471Compoundfalse38861431Compoundtrue5974411.3.1.72995truePW_R000995Right3900221Compoundfalse39016991Compoundfalse996truePW_R000996Right3902221Compoundfalse390313601Compoundfalse733falsePW_R000733Right298910631Compoundfalse29901461Compoundtrue29911521Compoundfalse29921431Compoundtrue843610991Compoundtrue2482311.1.1.341001falsePW_R001001Right3912471Compoundfalse3913407051Compoundtrue3914407041Compoundfalse391514201Compoundtrue6104552.3.1.266114563.1.1.132468940882false60564010regular30028024691142882false118064010regular30028024701099885false112068510regular503024711420849false100091510regular787824721063882false890125510regular30028024731099885false910120510regular50302490152881false940181510regular2001902506414842false920202010regular503025071036881false940224010regular20019025081034843false920219510regular50302512414542false910244510regular503025131034543false910261510regular50302514857581false940266510regular2001902528414842false920289010regular503025291034843false910307510regular503025301104846false1098312310regular444325311039881false942318510regular20019025321316852false1158305610regular78782547874581false427318510regular200190254842359false732323010regular100252593993881false680362510regular2001902594170845false608358810regular6343259542389false630346010regular10025259642389false830346510regular100252597768882false1592358310regular3002802598170845false1435381610regular6343259942389false1217363310regular10025260042389false1217378810regular1002526051464962false1917379310regular503026061754982false2297358110regular30028026071434961false2162379610regular503026081704945false2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780 C935 780 935 780 965 780 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3616M1180 780 C1150 780 1135 780 1105 780 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3617M1145 715 C1145 741 1135 780 1105 780 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3618M899 916 C990 946 1040 1065 1040 1095 5false183619M1189 915 C1108 939 1040 1065 1040 1095 5false183620M1039 993 C1038 1024 1040 1065 1040 1095 5false183621M1040 1255 C1040 1225 1040 1195 1040 1165 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3622M960 1220 C993 1220 1040 1195 1040 1165 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3686M1040 2005 C1040 2035 1040 2060 1040 2090 5false183687M970 2035 C1002 2035 1040 2060 1040 2090 5false183688M1040 2240 C1040 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25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3831M671 3609.5 C704 3609.5 775 3552 775 3505 5false7trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3832M945 3440 L945 3490 L995 3440 z10true183833M1055 3440 L1055 3490 L1105 3440 z10true183834M880 3720 C924 3720 1513 3723 1592 3723 5true183835M1042 3375 C1046 3603 1070 3723 1262 3718 5false73836M1592 3723 C1562 3723 916 3720 880 3720 5false7trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3837M1466.5 3816 C1466.5 3785 1438 3720 1262 3718 5false7trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3838M1497 3448 L1497 3498 L1547 3448 z10true183839M1497 3608 L1497 3658 L1547 3608 z10true183845M1892 3723 C1922 3723 1962 3723 1992 3723 5false183846M1942 3793 C1942 3768 1962 3723 1992 3723 5false183847M2297 3721 C2267 3721 2172 3723 2142 3723 5false18trueM 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