31120PathwayAndrostenedione MetabolismAndrostenedione is an endogenous weak androgen steroid hormone that is a precursor of testosterone and other androgens, as well as of estrogens like estrone . Its metabolism occurs primarily in the endoplasmic reticulum (membrane-associated enzymes are coloured dark green in the image). Conversion of androstenedione to testosterone requires the enzyme testosterone 17-beta-dehydrogenase 3. Conversion of androstenedione to estrone involves three successive reactions catalyzed by the enzyme aromatase (cytochrome P450 19A1). Androstenedione can also be converted into etiocholanolone glucuronide, androsterone glucuronide, and adrenosterone. The three-reaction subpathway to synthesize etiocholanolone glucuronide begins with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase catalyzing the conversion of androstenedione to etiocholanedione. This is followed by the conversion of etiocholanedione to etiocholanolone which is catalyzed by aldo-keto reductase family 1 member C4. Lastly, the large membrane-associated multimer UDP-glucuronosyltransferase 1-1 catalyzes the conversion of etiocholanolone to etiocholanolone glucuronide. The three-reaction subpathway to synthesize androsterone glucuronide begins with the conversion of androstenedione to androstanedione via 3-oxo-5-alpha-steroid 4-dehydrogenase 1. Anstrostanedione is then converted into androsterone via aldo-keto reductase family 1 member C4. The last reaction to form androsterone glucuronide is catalyzed by the large multimer UDP-glucuronosyltransferase 1-1. The two-reaction subpathway to synthesize adrenosterone begins in the mitochondrial inner membrane where androstenedione is first converted into 11beta-hydroxyandrost-4-ene-3,17-dione by the enzyme cytochrome P450 11B1. Following transport to the endoplasmic reticulum, 11beta-hydroxyandrost-4-ene-3,17-dione is converted into adrenosterone via corticosteroid 11-beta-dehydrogenase isozyme 1.MetabolicPW031290CenterPathwayVisualizationContext3157427002950#000099PathwayVisualization3104631120Androstenedione MetabolismAndrostenedione is an endogenous weak androgen steroid hormone that is a precursor of testosterone and other androgens, as well as of estrogens like estrone . Its metabolism occurs primarily in the endoplasmic reticulum (membrane-associated enzymes are coloured dark green in the image). Conversion of androstenedione to testosterone requires the enzyme testosterone 17-beta-dehydrogenase 3. Conversion of androstenedione to estrone involves three successive reactions catalyzed by the enzyme aromatase (cytochrome P450 19A1). Androstenedione can also be converted into etiocholanolone glucuronide, androsterone glucuronide, and adrenosterone. The three-reaction subpathway to synthesize etiocholanolone glucuronide begins with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase catalyzing the conversion of androstenedione to etiocholanedione. This is followed by the conversion of etiocholanedione to etiocholanolone which is catalyzed by aldo-keto reductase family 1 member C4. Lastly, the large membrane-associated multimer UDP-glucuronosyltransferase 1-1 catalyzes the conversion of etiocholanolone to etiocholanolone glucuronide. The three-reaction subpathway to synthesize androsterone glucuronide begins with the conversion of androstenedione to androstanedione via 3-oxo-5-alpha-steroid 4-dehydrogenase 1. Anstrostanedione is then converted into androsterone via aldo-keto reductase family 1 member C4. The last reaction to form androsterone glucuronide is catalyzed by the large multimer UDP-glucuronosyltransferase 1-1. The two-reaction subpathway to synthesize adrenosterone begins in the mitochondrial inner membrane where androstenedione is first converted into 11beta-hydroxyandrost-4-ene-3,17-dione by the enzyme cytochrome P450 11B1. Following transport to the endoplasmic reticulum, 11beta-hydroxyandrost-4-ene-3,17-dione is converted into adrenosterone via corticosteroid 11-beta-dehydrogenase isozyme 1.Metabolic18243927702664Baravalle R, Di Nardo G, Bandino A, Barone I, Catalano S, Ando S, Gilardi G: Impact of R264C and R264H polymorphisms in human aromatase function. J Steroid Biochem Mol Biol. 2017 Mar;167:23-32. doi: 10.1016/j.jsbmb.2016.09.022. Epub 2016 Oct 1.31120Pathway8244026545797Engeli RT, Rhouma BB, Sager CP, Tsachaki M, Birk J, Fakhfakh F, Keskes L, Belguith N, Odermatt A: Biochemical analyses and molecular modeling explain the functional loss of 17beta-hydroxysteroid dehydrogenase 3 mutant G133R in three Tunisian patients with 46, XY Disorders of Sex Development. J Steroid Biochem Mol Biol. 2016 Jan;155(Pt A):147-54. doi: 10.1016/j.jsbmb.2015.10.023. Epub 2015 Nov 3.31120Pathway1CellCL:00000004CardiomyocyteCL:00007465HepatocyteCL:00001823NeuronCL:000054012AstrocyteCL:00001272Platelet CL:00002337Epithelial CellCL:000006622Granulosa CellCL:000050121Theca CellCL:000050320Leydig CellCL:00001781Homo sapiens9606EukaryoteHuman12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote2Bacteria2ProkaryoteBacteria21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote60Nitzschia sp.0001EukaryoteNitzschia4202Spathaspora passalidarum340170EukaryoteSpathaspora passalidarum19Schizosaccharomyces pombe4896Eukaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel282Sus Scrofa9823EukaryotePig15Plasmodium falciparum5833Eukaryote138human0046323Eukaryote5CytoplasmGO:000573713Endoplasmic ReticulumGO:000578312Mitochondrial Inner MembraneGO:00057437Endoplasmic Reticulum MembraneGO:00057892MitochondrionGO:00057394PeroxisomeGO:00057771CytosolGO:000582910Cell MembraneGO:000588619Sarcoplasmic ReticulumGO:001652935ChloroplastGO:00095073Mitochondrial MatrixGO:000575936MembraneGO:001602032Inner MembraneGO:007025811Extracellular SpaceGO:000561514Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:000562053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:00003256LysosomeGO:000576416Lysosomal LumenGO:004320225Golgi ApparatusGO:000579420Endoplasmic Reticulum LumenGO:000578818Melanosome MembraneGO:003316221SynapseGO:004520215NucleusGO:000563440PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:00057901LiverBTO:00007597295cardiocyteBTO:000153928StomachBTO:0001307155268Blood VesselBTO:0001102741124BrainBTO:0000142891625IntestineBTO:00006482Endothelium BTO:00003934Adrenal MedullaBTO:00000497187Nervous SystemBTO:000148411HeartBTO:000056273106KidneyBTO:000067171835OvaryBTO:000097534TestisBTO:00013638511PW_BS000008181311PW_BS000018171211PW_BS00001749711PW_BS00004913013121PW_BS0001303317121PW_BS0000281251351PW_BS000125383751PW_BS00010013613171PW_BS0001363987171PW_BS00011330013101PW_BS0000244957101PW_BS0001153951361PW_BS000113390761PW_BS0001123211PW_BS000003101711PW_BS0000105411PW_BS0000052111PW_BS00000229111PW_BS000029311511PW_BS00003114101PW_BS0000141115121PW_BS00011110813PW_BS0001081471241PW_BS00014715924PW_BS0001593551914PW_BS000035117131PW_BS000117188118PW_BS0000241632181PW_BS000163205561PW_BS0000241601181PW_BS0001602137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS0001702253541PW_BS000024151141PW_BS000151224241PW_BS0000241985181PW_BS0000242111018PW_BS000024222341PW_BS0000241644PW_BS0001642863641PW_BS000024226441PW_BS0000242491341PW_BS000024315123PW_BS0000243221231PW_BS00002429341PW_BS0000241321121PW_BS00013233217121PW_BS0000281122121PW_BS0001121151012PW_BS0001153361121PW_BS0000281192171PW_BS000119943PW_BS000094407251PW_BS000115405105PW_BS000115122551PW_BS0001221231751PW_BS000123429151PW_BS000115124151PW_BS0001243761017PW_BS0000531355171PW_BS00013544717171PW_BS0001154641171PW_BS0001151181171PW_BS0001184812101PW_BS0001152975101PW_BS0000242991101PW_BS000024206261PW_BS000024388161PW_BS000112168321PW_BS0001684311PW_BS00000415111PW_BS000015261115PW_BS000026541315PW_BS000054221411PW_BS000022422411PW_BS0000427028511PW_BS000070103331PW_BS000103107313PW_BS000107100521PW_BS000100105113PW_BS0001051553241PW_BS0001551572241PW_BS0001571613181PW_BS00016116611PW_BS0001661783211PW_BS00017815284PW_BS000152101531PW_BS0001011873118PW_BS000024219314PW_BS00002422014PW_BS00002416212181PW_BS0001621951318PW_BS0000242811251PW_BS0000242851041PW_BS0000242875341PW_BS0000242273441PW_BS0000242231241PW_BS0000242941141PW_BS0000243081011PW_BS0000243183123PW_BS0000243125231PW_BS0000243201123PW_BS0000241333121PW_BS00013313412121PW_BS0001341141112PW_BS00011432711125PW_BS00002834713125PW_BS00002834524121PW_BS0000283683601PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS000109406351PW_BS000115409115PW_BS0001154241155PW_BS0001154251355PW_BS0001154182451PW_BS0001153841251PW_BS0001001203171PW_BS0001201371117PW_BS00013745911175PW_BS00011546013175PW_BS00011545424171PW_BS00011512112171PW_BS0001214793101PW_BS0001154831110PW_BS00011548924101PW_BS00011548012101PW_BS000115501361PW_BS000115208116PW_BS0000245062461PW_BS0001153911261PW_BS00011288231202PW_BS00055288312021PW_BS000552167311PW_BS000167788241113PW_BS00052459724112PW_BS000336185321PW_BS0000243344121PW_BS000028408451PW_BS0001153744171PW_BS0000534824101PW_BS000115502461PW_BS0001159611PW_BS0000092811611PW_BS0000286131PW_BS000006951721PW_BS00009514117191PW_BS00014111PW_BS0000012164181PW_BS00002429817101PW_BS0000241136121PW_BS000113126651PW_BS0001264436171PW_BS000115432511PW_BS00004335625121PW_BS0000284192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS0001153612011PW_BS0000369225711PW_BS00009221425181PW_BS00002416212PW_BS000016204111PW_BS000020331811PW_BS0000332441011PW_BS00002413121PW_BS00001312711651PW_BS0001272156181PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS000024337116121PW_BS00002812915121PW_BS00012934141121PW_BS00002832914121PW_BS00002834318121PW_BS000028360410121PW_BS0000284141551PW_BS0001154151851PW_BS00011543441051PW_BS0001153821451PW_BS000100448116171PW_BS00011545015171PW_BS00011545118171PW_BS000115469410171PW_BS00011539914171PW_BS0001134781010PW_BS00011548414101PW_BS000115207661PW_BS000024209106PW_BS0000245041861PW_BS00011551541061PW_BS0001153891461PW_BS00011260251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097110231PW_BS000110140103PW_BS00014014315191PW_BS0001431465191PW_BS0001461802211PW_BS0001801901118PW_BS0000242771218PW_BS00002465111PW_BS0000652905491PW_BS000024253541PW_BS0000243331212PW_BS0000283522512PW_BS00002835325127PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115436255PW_BS0001154461217PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS0001155131761PW_BS0001157906111PW_BS0005248346111PW_BS000549111811PW_BS00001178811PW_BS00007899611315PW_BS000569119112821PW_BS000588118912821PW_BS00058861517151PW_BS00050384711PW_BS0005499731715PW_BS00056994935122PW_BS00056394835121PW_BS00056394734120PW_BS0005631388171385PW_BS00061937AndrostenedioneHMDB0000053Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma, and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while production of gonadal androstenedione is under control by gonadotropins.63-05-8C00280612816422ANDROST4ENE5898DB01536[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC19H26O2InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1AEMFNILZOJDQLW-QAGGRKNESA-N286.4085286.193280076FDB021807(4)-androsten-3,17-dione;17-ketotestosterone;3,17-dioxoandrost-4-ene;4-androsten-3,17-dione;4-androstene-3,17-dione;4-androstenedione;Androst-4-ene-3,17-dione;Androstendione;Androstenedione;D4-androstene-3,17-dione;Delta4-androstenedione;Fecundin;[4-14c]-androstenedione;[4-14c]androst-4-ene-3,17-dione;4-androstene-3-17-dione;Delta(4)-androsten-3,17-dione;Delta(4)-androstene-3,17-dione;δ(4)-androsten-3,17-dione;δ(4)-androstene-3,17-dionePW_C000037Adione14118222418422751742281497736213079910331122340125122679383124892136125255398126509300126813495128080395128412390146NADPHHMDB0000221Nicotinamide 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_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139014070616840034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-N1.00791.007825032H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039514069288214069388314069916714070716814071514140742788140743597140760185718AndrostanedioneHMDB0000899Androstanedione belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Androstanedione has been found in human hepatic and testicle tissues, and has also been detected in multiple biofluids, such as blood and urine. Within the cell, androstanedione is primarily located in the membrane (predicted from logP), endoplasmic reticulum and cytoplasm. In humans, androstanedione is involved in the androstenedione metabolism pathway. Androstanedione is a steroid metabolite and a procursor of both testosterone and estrone. It is a product of enzyme 3alpha-hydroxysteroid dehydrogenase [EC 1.1.1.50] in pathway Androgen and estrogen metabolism (KEGG).846-46-8C0067422286515994CPD-342193520DB01561[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12CC19H28O2InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1RAJWOBJTTGJROA-WZNAKSSCSA-N288.4244288.20893014FDB022307(5a)-androstane-3,17-dione;5-alpha-androstane-3,17-dione;5a-androsta-3,17-dione;5a-androstan-3,17-dione;5a-androstane-3, 17-dione;5a-androstane-3,17-dione;5a-androstanedione;5alpha-androstane-3,17-dione;Androstane-3,17-dione;Androstane-3,7-dione;AndrostanedionePW_C000718Androst422824979911331122680383125256398126814495128413390143NADPHMDB0000217Nicotinamide 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_C000143NADP18381913768578010824188392161129161749468531479614480114530811157901086017147613215962733567781177069188710516371522057206160731721373462107562212758917081972258220151841922411811198118972111200822212152164122492861259722612650249423443154374532276913293771641327738433177396332774611307751511577624336778143347787011280713119113165941201064071204294051204501221206044081206181231211421251212774291214011241214853831230633761230841351232293741232434471237131361238484641239601181240433981254734811256942971257434821262152991265284951270102061272255021275703881281003901407091681144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N665.441665.124771695FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH1434153349086481011152127551469542230492781172836293109948061848121848212849046495931516995524010353321115358112546612354791255593135569810057371085829141591514759451516027155607916163871647217867711176893160701118870991637172205719520674622228244226836022590862241180919811821216123202491300329813015300132552234240332242618315771071327712313377208134773713317765133677668334777003327770713077917113779863478000936880691119938221241105493881128549411583811811995540612017240712037812212098640812116242512124412612169342912181838312261638412274512012312744712313813612355137412373446012381444312424246412437139812518912112534547912553148112576229712580829912592648212651649512676748012688850112738550212809039012836239112842939514075918521AndrosteroneHMDB0000031Androsterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone can also be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone, or androstenedione, and is considered an inactive end product. However, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role of uridine-diphospho-glucuronosyltransferase enzymes (EC 2.4.1.17, UGT) for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and it is widely recognized that the liver is a major site of glucuronidation. However, it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid, and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanolone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution (PMID: 9188497, 17017935, 14643063, 12943709, 9699884, 17260133).53-41-8C00523587916032ANDROSTERONE5668[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12CC19H30O2InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1QGXBDMJGAMFCBF-HLUDHZFRSA-N290.4403290.224580204FDB021881(3r,5s,8r,9s,10s,13s,14s)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one;(3alpha,5alpha)-3-hydroxy-androstan-17-one;3-epihydroxyetioallocholan-17-one;3-hydroxy-(3-alpha,5-alpha)-androstan-17-one;3-hydroxyandrostan-17-one;3-alpha-hydroxy-17-androstanone;3-alpha-hydroxy-5-alpha-androstan-17-one;3-alpha-hydroxy-5-alpha-androstane-17-one;3-alpha-hydroxy-5alpha-androstan-17-one;3-alpha-hydroxyetioallocholan-17-one;3a-hydroxyetioallocholan-17-one;3alpha-hydroxy-17-androstanone;3alpha-hydroxy-5alpha-androstan-17-one;3alpha-hydroxyetioallocholan-17-one;5-alpha-androstan-3-alpha-ol-17-one;5-alpha-androstane-3alpha-ol-17-one;5-alpha-androsterone;5a-androstan-3a-ol-17-one;5a-androstane-3a-ol-17-one;5a-androsterone;5alpha-androstane-3alpha-ol-17-one;5alpha-androsterone;Androkinine;Androstanon-3-alpha-ol-17-one;Androsterone;Androtine;Atromide ici;Cis-androsteronePW_C000021Androtn42283279912132122681124125257118126815299128414388721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=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](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H27N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-N663.4251663.109121631FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD14041503353865110111421134431273514665422294927791728352931079480718481318481928490264960315167955238103533411153601125469123548212555901355610118569610057381085827141591214759421516024155607215760761616385164691786772117689016070121887097163717420571972067405198745922282412268359225908522411819216123222491300629813018300132562234240432242619315771041327712013377209134773703317765033677667334777023327770913077915113779833477840635680006368806901199382512411055238811275016611285394119929122119952406120171407120834419120984408121159425121242126121259429121817383122614384122742120123130447123141136123419455123549374123731460123812443123829464124370398125187121125319297125342479125530481125806299125825490125924482126515495126765480126885501127278507127383502128089390128360391128428395140757185746Uridine diphosphate glucuronic acidHMDB0000935Uridine diphosphate glucuronic acid is a nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP Iduronic acid, which donates Iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones. The transfer of glucuronic acid from UDP-alpha-D-glucuronic acid onto a terminal galactose residue is done by beta1,3-glucuronosyltransferases, responsible for the completion of the protein-glycosaminoglycan linkage region of proteoglycans and of the HNK1 epitope of glycoproteins and glycolipids. In humans the enzyme galactose-beta-1,3-glucuronosyltransferase I completes the synthesis of the common linker region of glycosaminoglycans (GAGs) by transferring glucuronic acid (GlcA) onto the terminal galactose of the glycopeptide primer of proteoglycans. The GAG chains of proteoglycans regulate major biological processes such as cell proliferation and recognition, extracellular matrix deposition, and morphogenesis. (PMID: 16815917).2616-64-0C001671747317200UDP-GLUCURONATE16522O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=OC15H22N2O18P2InChI=1S/C15H22N2O18P2/c18-5-1-2-17(15(26)16-5)12-9(22)6(19)4(32-12)3-31-36(27,28)35-37(29,30)34-14-10(23)7(20)8(21)11(33-14)13(24)25/h1-2,4,6-12,14,19-23H,3H2,(H,24,25)(H,27,28)(H,29,30)(H,16,18,26)/t4-,6-,7+,8+,9-,10-,11+,12-,14-/m1/s1HDYANYHVCAPMJV-LXQIFKJMSA-N580.2853580.034284934FDB022325Glucopyranuronic acid 1-ester with uridine 5'-pyrophosphate;Udp glucuronate;Udp glucuronic acid;Udp-d-glucuronate;Udp-d-glucuronic acid;Udp-glcua;Udp-glucuronate;Udp-glucuronic acid;Udp-alpha-d-glucuronate;Udp-alpha-delta-glucuronate;Udp-delta-glucuronate;Udp-delta-glucuronic acid;Udpga;Udpglucuronate;Uga;Uridine 5'-[3-(d-glucopyranosyloxyuronic acid) dihydrogen diphosphate];Uridine 5'-diphospho-a-d-glucuronate;Uridine 5'-diphospho-a-d-glucuronic acid;Uridine 5'-diphospho-alpha-delta-glucuronate;Uridine 5'-diphospho-alpha-delta-glucuronic acid;Uridine 5'-diphospho-glucuronic acid;Uridine 5'-diphosphoglucuronate;Uridine 5'-diphosphoglucuronic acid;Uridine diphosphate glucuronate;Uridine diphosphate glucuronic acid;Uridine diphosphate-glucuronate;Uridine diphospho-d-glucuronate;Uridine diphospho-d-glucuronic acid;Uridine diphospho-delta-glucuronate;Uridine diphospho-delta-glucuronic acid;Uridine diphosphoglucuronate;Uridine diphosphoglucuronic acid;Uridine pyrophosphoglucuronate;Uridine pyrophosphoglucuronic acid;Uridinediphosphoglucuronic acid;A-d-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);A-d-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Alpha-d-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid 1->5'-ester with uridine 5'-(trihydrogen pyrophosphate);Alpha-delta-glucopyranuronic acid 1-p'-ester with uridine 5'-(trihydrogen diphosphate);Alpha-delta-glucopyranuronic acid ester with uridine 5'-pyrophosphate;Uridine-5'-diphosphate-glucuronic acid;Udp-a-d-glucuronate;Udp-a-d-glucuronic acid;Udp-α-d-glucuronate;Udp-α-d-glucuronic acid;Udpglucuronic acid;Uridine diphosphoric acid glucuronic acid;Uridine-5'-diphosphate-glucuronate;Uridine-5'-diphosphoric acid-glucuronic acidPW_C000746UDPGlcA1129822194923032235194479184516104844364944925176955525130583214170551607735833178403111786151321208301221220491241223383831234151351246031181248893981258212971262012991265064951272742051280783901715Androsterone glucuronideHMDB0002829Androsterone glucuronide (ADT-G) is one of the major circulating C19-steroid metabolites in humans. Human and monkey are unique in having high levels of circulating ADT-G. Furthermore, the plasma levels of these glucuronide derivatives reflect the peripheral tissue conversion of adrenal and gonadal precursor C19-steroids to active androgens in various pathophysiological conditions. Identification and characterization of human UDP-glucuronosyltransferase 2B (UGT2Bs) demonstrated the major role that these enzymes play in androgen conjugation, with UGT2B15 and UGT2B17 (EC 2.4.1.17) being the major androsterone-conjugating isoforms. Exaggerated androsterone metabolism, is observed in hyper-androgenic as well as in some normo-androgenic women with acne and androsterone glucuronide could be a marker in differentiating acne and hirsutism in hyperandrogenic women. Present data shows that the most practical and probably only valid means of assessing androgenic activity in women is to measure ADT-G, the metabolite that accounts for 93% of the total androgen glucuronide derivatives. (PMID: 12943709, 12445184, 16621522).1852-43-3C1113511483328832Beta-D-Glucuronides102793[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=OC25H38O8InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1VFUIRAVTUVCQTF-BSOWLZGZSA-N466.5644466.256668192FDB0230703a-hydroxy-5a-androstan-17-one glucuronide;5a-androstan-3a-ol-17-one glucuronide;Androsterone 3-glucuronide;Androsterone glucosiduronate;Androsterone glucuronoside;Androsterone monoglucosiduronate;B-d-17-oxo-5a-androstan-3a-yl glucopyranosiduronic acid;3alpha-hydroxy-5alpha-androstan-17-one glucuronide;Androsterone glucuronide;Etiocholanolone glucuronide;3α-hydroxy-5α-androstan-17-one glucuronidePW_C001715AGlcA422844979913331122682383125258398126817495128415390201Uridine 5'-diphosphateHMDB0000295Uridine 5'-diphosphate is a uracil nucleotide containing a pyrophosphate group esterified to C5 of the sugar moiety. UDP is an important extracellular pyrimidine signaling molecule that mediates diverse biological effects via P1 and P2 purinergic receptors, such as the uptake of thymidine and proliferation of gliomas. (PMID: 14558596). UDP induces intracellular Ca(2+) responses and oscillations in HeLa cells, due to the activation of P2Ys (G-protein coupled ATP receptors). (PMID: 1257952).58-98-0C00015603117659UDP5809DB03435O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(O)=O)N1C=CC(=O)NC1=OC9H14N2O12P2InChI=1S/C9H14N2O12P2/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1XCCTYIAWTASOJW-XVFCMESISA-N404.1612404.002196946FDB0075095'-udp;Udp;Uridine 5'-diphosphate;Uridine 5'-pyrophosphate;Uridine 5'-pyrophosphorate;Uridine 5'-pyrophosphoric acid;Uridine diphosphate;Uridine pyrophosphate;Uridine 5'-diphosphoric acid;Uridine diphosphoric acidPW_C000201UDP410815172154543219749235293115294463184518104846364946925178955527130583414170571607246213724821472872108433151119131641261522577304111773603317792433678255132782643561203151221212524291213651241213754191221013831223781251229701351238224641239241181239344551246523981249321361256432971260382991260484901262574951274903881275005071278203901065OxygenHMDB0001377Oxygen 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_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391201619-Hydroxyandrost-4-ene-3,17-dioneHMDB000395519-Hydroxyandrost-4-ene-3,17-dione, also known as 19-haed, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, 19-hydroxyandrost-4-ene-3,17-dione is considered to be a steroid lipid molecule. 19-Hydroxyandrost-4-ene-3,17-dione is considered to be a practically insoluble (in water) and relatively neutral molecule. 19-Hydroxyandrost-4-ene-3,17-dione has been found in human testicle, placenta and hepatic tissues, and has also been detected in multiple biofluids, such as blood and urine. Within the cell, 19-hydroxyandrost-4-ene-3,17-dione is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, 19-hydroxyandrost-4-ene-3,17-dione is involved in the androgen and estrogen metabolism pathway and the androstenedione metabolism pathway. 19-Hydroxyandrost-4-ene-3,17-dione is also involved in a couple of metabolic disorders, which include aromatase deficiency and 17-Beta hydroxysteroid dehydrogenase III deficiency. Outside of the human body, 19-hydroxyandrost-4-ene-3,17-dione can be found in a number of food items such as caraway, mentha (mint), jicama, and hard wheat. This makes 19-hydroxyandrost-4-ene-3,17-dione a potential biomarker for the consumption of these food products. 19-Hydroxyandrost-4-ene-3,17-dione is a substrate for Corticotropin-lipotropin and Cytochrome P450 19A1.510-64-5C0529025237927576221136[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12COC19H26O3InChI=1S/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1XGUHPTGEXRHMQQ-BGJMDTOESA-N302.4079302.188194698FDB02327219-hydroxy-4-androstene-3,17-dione;19-hydroxyandrostenedionePW_C00201619-Haon3338142810422961877356111799251301223361221226831251248871351252691361265042971268183001280762051284233951420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851799HemeHMDB0003178Heme 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_C001799Heme247163081032486082766512443135449141336196318280629293893238113367263421143734440433148232851709554721235485125551712958301416246786283165971517044160706016173262131183519811898211120651641300929813021300422781776915293769312497735111177364130773673317739833277517115776293367781333478380133786021327896311279932134120431405120603408120955407121085383121658429121746124121910122122570406122691384123065376123133447123144136123228374123521119123650398124216464124297118124463135125142120125277121125742482125896481126196299126499297126512495126718479126827480127224502127357206127632388128070205128083395128086390128309501128434391291919-Oxoandrost-4-ene-3,17-dioneHMDB000676819-Oxoandrost-4-ene-3,17-dione is an intermediate in Androgen and estrogen metabolism. 19-Oxoandrost-4-ene-3,17-dione is the 4th to last step in the synthesis of 2-Methoxyestrone 3-glucuronide. It is generated from 19-Hydroxyandrost-4-ene-3,17-dione and then converted to Estrone.C05297 16399653106953517465008[H]C12CCC(=O)[C@@]1(C)CCC1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C=OC19H24O3InChI=1S/C19H24O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10-11,14-16H,2-9H2,1H3/t14-,15?,16?,18-,19+/m0/s1XRCFMDPVHKVRDJ-NHMXRCTMSA-N300.3921300.172544634FDB02407019-oxoandrostenedionePW_C00291919O4e3398143024229749773491117992633112233112212268438312488213512527039812649829712681949512806920512842439094EstroneHMDB0000145Estrone is a major mammalian estrogen. The conversion of the natural C19 steroids, testosterone and androstenedione into estrone is dependent on a complex key reaction catalyzed by the cytochrome P450 aromatase (EC 1.14.14.1, unspecific monooxygenase), which is expressed in many tissues of the adult human (e.g. ovary, fat tissue), but not in the liver. The ovaries after menopause continue to produce androstenedione and testosterone in significant amounts and these androgens are converted in fat, muscle, and skin into estrone. When women between the ages of 45 and 64 years have prophylactic oophorectomy (when hysterectomy is performed for benign disease to prevent the development of ovarian cancer), evidence suggests that oophorectomy increases the subsequent risk of coronary heart disease (CHD) and osteoporosis. Whereas 14,000 women die of ovarian cancer every year nearly 490,000 women die of heart disease and 48,000 women die within 1 year after hip fracture. Therefore, the decision to perform prophylactic oophorectomy should be approached with great caution for the majority of women who are at low risk of developing ovarian cancer. Steroid sulfatase (EC 3.1.6.2, STS) hydrolyzes steroid sulfates, such as estrone sulfate to estrone which can be converted to steroids with potent estrogenic properties, that is, estradiol; STS activity is much higher in breast tumors and high levels of STS mRNA expression in tumors are associated with a poor prognosis. The biological roles of estrogens in tumorigenesis are certainly different between the endometrium and breast, although both are considered "estrogen-dependent tissues". 17beta-hydroxysteroid dehydrogenases (EC 1.1.1.62, 17-HSDs) are enzymes involved in the formation of active sex steroids. estrone is interconverted by two enzymes 17-HSD types. Type 1 converts estrone to estradiol and Type 2 catalyzes the reverse reaction. (PMID: 17653961, 17513923, 17470679, 17464097).53-16-7C00468587017263ESTRONE5660DB00655[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3C18H22O2InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1DNXHEGUUPJUMQT-CBZIJGRNSA-N270.3661270.161979948DBMET00490FDB012798(+)-estrone;1,3,5(10)-estratrien-3-ol-17-one;3-hydroxy-17-keto-estra-1,3,5-triene;3-hydroxyestra-1,3,5(10)-trien-17-one;3-hydroxyestra-1,3,5(10)-triene-17-one;3-hydroxyoestra-1,3,5(10)-trien-17-one;D1,3,5(10)-estratrien-3-ol-17-one;3-hydroxy-1,3,5(10)-estratrien-17-one;Follicular hormone;Folliculin;OestronePW_C000094Estrone340814012422984977345111799273317998213212096212212268538312269812412352713512527139812528511812590229712682049512683629912736320512842539012844338892Formic 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_C000092Formate9468977316294919432531411153481126636107715820571862067325213761616082872101198215143522318769632257865213278934331120670122120697407121496383121751124123284135123302119124054398124302118125753297125772481126478299126821495127637388128426390157TestosteroneHMDB0000234Testosterone is the most important androgen in potency and quantity. Testosterone is synthesized and released by the Leydig cells that lie between the tubules and comprise less than 5% of the total testicular volume. testosterone diffuses into the seminiferous tubules where it is essential for maintaining spermatogenesis. Some binds to an androgen-binding protein (ABP) that is produced by the Sertoli cells and is homologous to the sex-hormone binding globulin that transports testosterone in the general circulation. The ABP carries testosterone in the testicular fluid where it maintains the activity of the accessory sex glands and may also help to retain testosterone within the tubule and bind excess free hormone. Some testosterone is converted to estradiol by Sertoli cell-derived aromatase enzyme. Leydig cell steroidogenesis is controlled primarily by luteinizing hormone with negative feedback of testosterone on the hypothalamic-pituitary axis. The requirement of spermatogenesis for high local concentrations of testosterone means that loss of androgen production is likely to be accompanied by loss of spermatogenesis. Indeed, if testicular androgen production is inhibited by the administration of exogenous androgens then spermatogenesis ceases. This is the basis of using exogenous testosterone as a male contraceptive. testosterone is converted to dihydrotestosterone by 5a-reductase type 2 (EC 1.3.1.22, SRD5A2), the androgen with the highest affinity for the androgen receptor. SRD5A2 deficiency illustrates the importance of dihydrotestosterone for external virilization, as individuals with this condition have normal male internal structures but their external genitalia are of female appearance. There is now clear evidence that the human fetal testis and also the fetal adrenal gland is capable of testosterone biosynthesis during the first trimester. Regardless of the source of androgen production, the target tissue responds by male sexual differentiation of the external genitalia by the end of the first trimester. It is clear that testicular damage may result in loss of testosterone production or the loss of spermatogenesis or both. Loss of androgen production results in hypogonadism, the symptoms of which reflect the functions of testosterone. Male hypogonadism is defined as failure of the testes to produce normal amounts of testosterone, combined with signs and symptoms of androgen deficiency. Systemic testosterone levels fall by about 1% each year in men. Therefore, with increasing longevity and the aging of the population, the number of older men with testosterone deficiency will increase substantially over the next several decades. Serum testosterone levels decrease progressively in aging men, but the rate and magnitude of decrease vary considerably. Approximately 1% of healthy young men have total serum testosterone levels below normal; in contrast, approximately 20% of healthy men over age 60 years have serum testosterone levels below normal. (PMID: 17904450, 17875487).58-22-0C005356013173475791DB00624[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC19H28O2InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1MUMGGOZAMZWBJJ-DYKIIFRCSA-N288.4244288.20893014FDB011544(+)-testosterone;(+-)-8-iso-testosterone;(+-)-retrotestosterone;(+-)-testosterone;(17b)-17-hydroxy-androst-4-en-3-one;13-iso-testosterone;17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one;17-hydroxy-d4-androsten-3-one;17-hydroxy-androst-4-en-3-one;17a-hydroxy-(13a)-androst-4-en-3-one;17a-hydroxy-13a-androst-4-en-3-one;17a-hydroxy-14b-androst-4-en-3-one;17a-hydroxy-androst-4-en-3-one;17b-hydroxy-(10a)-androst-4-en-3-one;17b-hydroxy-(13a)-androst-4-en-3-one;17b-hydroxy-(8a)-androst-4-en-3-one;17b-hydroxy-(8a,10a)-androst-4-en-3-one;17b-hydroxy-(9b)-androst-4-en-3-one;17b-hydroxy-(9b,10a)-androst-4-en-3-one;17b-hydroxy-13a-androst-4-en-3-one;17b-hydroxy-8a-androst-4-en-3-one;17b-hydroxy-d4-androsten-3-one;17b-hydroxy-androst-4-en-3-on;17b-hydroxy-androst-4-en-3-one;17b-hydroxyandrost-4-en-3-one;17b-hydroxyandrost-4-ene-3-one;17b-testosterone;4-androsten-3-one-17b-ol;8-iso-testosterone;9b,10a-testosterone;9b-testosterone;Androgel;Androderm;Androlin;Andronaq;Andropatch;Androst-4-en-17b-ol-3-one;Androst-4-ene-17b-ol-3-one;Andrusol;Cristerona t;D4-androsten-17b-ol-3-one;Epitestosteron;Geno-cristaux gremy;Homosteron;Homosterone;Lumitestosteron;Mertestate;Neotestis;Oreton;Orquisteron;Perandren;Percutacrine androgenique;Primotest;Primoteston;Rac-17b-hydroxy-(13a)androst-4-en-3-one;Rac-17b-hydroxy-(8a)-androst-4-en-3-one;Rac-17b-hydroxy-(9b,10a)androst-4-en-3-one;Rac-17b-hydroxy-androst-4-en-3-one;Relibra;Retrotestosterone;Sustanon;Sustanone;Sustason 250;Synandrol f;Teslen;Testandrone;Testiculosterone;Testim;Testobase;Testoderm;Testogel;Testolent;Testolin;Testopropon;Testosteroid;Testosteron;Testoviron schering;Testoviron t;Testro aq;Testrone;Testryl;Tostrelle;Tostrex;Viatrel;Virormone;Virosterone;17beta-hydroxy-4-androsten-3-one;4-androsten-17beta-ol-3-one;Testosterona;Testosteronum;17b-hydroxy-4-androsten-3-one;17β-hydroxy-4-androsten-3-one;4-androsten-17b-ol-3-one;4-androsten-17β-ol-3-onePW_C000157Oreton31981409222374942299187737633179928130122345383122686125124898398125272136126521495126822300128094390128427395292411b-Hydroxyandrost-4-ene-3,17-dioneHMDB000677311beta-Hydroxyandrost-4-ene-3,17-dione is an intermediate in adrenosterone production. 11beta-Hydroxyandrost-4-ene-3,17-dione is produced from androst-4-ene-3,17-dione, a reaction catalyzed by the enzyme cytochrome P450 B [EC:1.14.15.4]. 11beta-Hydroxyandrost-4-ene-3,17-dione is then converted into adrenosterone by the enzyme 11beta-hydroxysteroid dehydrogenase [EC:1.1.1.146].382-44-5C05284941412796784958[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC19H26O3InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1WSCUHXPGYUMQEX-KCZNZURUSA-N302.4079302.188194698FDB02407511beta-hydroxyandrost-4-ene-3,17-dione;4-androsten-11beta-ol-3,17-dione;Androst-4-ene-3,17-dione-11beta-ol;4-androsten-11b-ol-3,17-dione;4-androsten-11β-ol-3,17-dione;Androst-4-ene-3,17-dione-11b-ol;Androst-4-ene-3,17-dione-11β-olPW_C0029244AO3D4227717423044979931134799373311226903841226963831252761211252833981268264801268334951284333911284403902923AdrenosteroneHMDB0006772Adrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichstein's substance G.(Wikipedia). Andrenosterone is created from androst-4-ene-3,17-dione by the work of two enzymes, CYP11B (E1.14.15.4) and 11beta-hydroxysteroid dehydrogenase [EC:1.1.1.146].382-45-6C05285223997607862194597[H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12CC19H24O3InChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1RZRPTBIGEANTGU-IRIMSJTPSA-N300.3921300.172544634FDB024074PW_C002923Adreno4228049799383311226973831252843981268344951284413901967Etiocholanedione HMDB0003769Etiocholanedione is a 5-beta metabolite product of the catabolism of androgens. Etiocholanedione has been identified as a ketosteroid and isolated from the urine of healthy and diseased persons. Etiocholanedione has been identified as a metabolite of an altered androgen metabolism that eventually leads hepatocellular carcinoma to impaired hormone responsiveness in human. Etiocholanedione has been identified as a metabolite of 17alpha-hydroxyprogesterone in some patients affected by congenital adrenal hyperplasia, although it doesn't appear to account for the masculinization observed in congenital hyperplasia. Etiocholanedione can be the product of microbial contamination of urine since a few organisms are able to synthesize it using endogenous steroids as substrates. Human axillary bacteria are able to produce small amounts of etiocholanedione from testosterone. (PMID: 12161001, 13795320, 11161304, 2026727).1229-12-5C0377244011416985389114DB07375[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12CC19H28O2InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1RAJWOBJTTGJROA-QJISAEMRSA-N288.4244288.20893014FDB023225(5b)-androstane-3,17-dione;5b-androstane-3,17-dione;5b-androstanedione;5beta-androstane-3,17-dione;Etiochola-3,17-dione;Etiocholane-3,17-dione;EtiocholanedionePW_C001967Etiocon42300279934132122693124125279118126829299128436388372EtiocholanoloneHMDB0000490Etiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness).53-42-9C04373588028195ALPHA-ANDROSTAN-3BETA17BETA-DIOL5669DB02854[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@]([H])(O)CC[C@]12CC19H30O2InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1QGXBDMJGAMFCBF-BNSUEQOYSA-N290.4403290.224580204FDB0220723a-etiocholanolone;3a-hydroxy-5b-androstane-17-one;3alpha-hydroxy-5beta-androstan-17-one;3alpha-hydroxyetiocholan-17-one;5 beta androsterone;5-isoandrosterone;5b-androstan-3a-ol-17-one;5b-androstane-3a-ol-17-one;5b-androsterone;Aetiocholanolone;A-etiocholanolone;Alpha-etiocholanolone;Etiocholan-3alpha-ol-17-one;3a-hydroxy-5b-androstan-17-one;3α-hydroxy-5β-androstan-17-one;Etiocholan-3a-ol-17-one;Etiocholan-3α-ol-17-one;3a-hydroxyetiocholan-17-one;3α-hydroxyetiocholan-17-onePW_C000372Etiocho423022799351321226941241252811181268312991284383882144Etiocholanolone glucuronideHMDB0004484Etiocholanolone glucuronide is a natural human metabolite of etiocholanolone generated in the liver by UDP glucuonyltransferase. Etiocholanolone (or 5-isoandrosterone) is a metabolite of testosterone. Classified a ketosteroid, it causes fever, immunostimulation and leukocytosis. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.3602-09-3C1113644307837451Beta-D-Glucuronides391377[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=OC25H38O8InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13-,14+,15+,16+,18+,19+,20-,21+,23-,24+,25+/m1/s1VFUIRAVTUVCQTF-SDHZCXLISA-N466.5644466.256668192FDB02337617-oxoandrostan-3-yl hexopyranosiduronic acid;3alpha-hydroxy-5beta-androstan-17-one 3-glucuronide;3alpha-hydroxyetiocholan-17-one 3-glucuronide;5alpha.-androstan-3.alpha.-ol-17-one glucoronide;5beta-androstan-3alpha-ol-17-one 3-glucuronide;Etiocholan-3alpha-ol-17-one 3-glucuronide;Etiocholan-3alpha-ol-17-one 3-glucuronoside;Etiocholanolone 3-glucuronide;3alpha-hydroxyetiocholan-17-one 3-glucosiduronic acid;3a-hydroxyetiocholan-17-one 3-glucosiduronate;3a-hydroxyetiocholan-17-one 3-glucosiduronic acid;3alpha-hydroxyetiocholan-17-one 3-glucosiduronate;3α-hydroxyetiocholan-17-one 3-glucosiduronate;3α-hydroxyetiocholan-17-one 3-glucosiduronic acidPW_C002144Etiocho42303497993633112269538312528239812683249512843939037Reduced flavoproteinProteinComplexPW_EC0000375086ChEBIRF38Oxidized flavoproteinProteinComplexPW_EC0000385086ChEBIOF33Reduced adrenal ferredoxinProteinComplexPW_EC00003316906ChEBIRAF34Oxidized adrenal ferredoxinProteinComplexPW_EC00003416341ChEBIOAF6633-oxo-5-alpha-steroid 4-dehydrogenase 1P18405Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
HMDBP00699SRD5A15p15M6888411.3.1.22325814143622414914520999671Aldo-keto reductase family 1 member C4P17516Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
HMDBP00074AKR1C410p15.1AL35530311.1.1.-; 1.1.1.357; 1.1.1.225; 1.1.1.502050828002285029144016119114402911891452109965738DnaJ homolog subfamily B member 11Q9UBS4DNAJB11AK07543013252236882938689389026443531445060448118451910518195422854913547611356876151359893321410208471429339735739HSP90B1 proteinQ96GW1HSP90B1 BC0091951325323689293869938912644363144516044821845201051829542286491354771135688615135990332141021847142934973574078 kDa glucose-regulated proteinP11021HSPA5AJ27172913254236902938709389226443731445260448318452110518395422874913547811356896151359913321410228471429359735741HYOU1 proteinQ6IN67HYOU1 BC07243613255236912938719389326443831445360448418452210518495422884913547911356906151359923321410238471429369735742Protein disulfide-isomerase A2Q13087PDIA2U1994815.3.4.13256236922938729389426443931445460448518452310518595422894913548011356916151359933321410248471429379735743Protein disulfide-isomerase A4P13667PDIA4BC00634415.3.4.13257236932938739389526444031445560448618452410518695422904913548111356926151359943321410258471429389735744Protein disulfide-isomerase A6Q15084PDIA6AK28942815.3.4.13258236942938749389626444131445660448718452510518795422914913548211356936151359953321410268471429399734776Peptidyl-prolyl cis-trans isomerase BP23284PPIases accelerate the folding of proteins. It catalyzes the cis-trans isomerization of proline imidic peptide bonds in oligopeptidesHMDBP10692PPIB15q21-q22AY96231015.2.1.83259236952938759389726444231445760448818452610518895422924913548311356946151359963321410278471429409735745Stromal cell-derived factor 2-like protein 1Q9HCN8SDF2L1CR4565701326023696293876938982644433144586044891845271051899542293491354841135695615135997332141028847142941973465UDP-glucuronosyltransferase 1-1P22309UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
HMDBP00483UGT1A12q37M8412412.4.1.173261236972938779389926444431445960449018452810519095422944913548511356966151359983321410298471429429735746Endoplasmic reticulum resident protein 29P30040ERP29BC10149313262236982938789390026444531446060449118452910519195422954913548611356976151359993321410308471429439731449Cytochrome P450 19A1P11511Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
HMDBP01561CYP19A115q21.1J0412711.14.14.1433210334814102222518223849141516949791Testosterone 17-beta-dehydrogenase 3P37058Favors the reduction of androstenedione to testosterone. Uses NADPH while the two other EDH17B enzymes use NADH.
HMDBP00846HSD17B39q22U0565911.1.1.643208422741814151494814151594914160194714276549432Cytochrome P450 11B1, mitochondrialP15538Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
HMDBP00445CYP11B18q21M3287811.14.15.4218334227917681Corticosteroid 11-beta-dehydrogenase isozyme 1P28845Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
HMDBP00718HSD11B11q32-q41M7666411.1.1.14622021822504914254497314536013881453648471454039965223-oxo-5-beta-steroid 4-dehydrogenaseP51857Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
HMDBP00550AKR1D17q32-q33AF28365811.3.1.321758280229423012142764491440171189243-oxo-5-alpha-steroid 4-dehydrogenase 11PW_P00002425663536Aldo-keto reductase family 1 member C41PW_P00053656871807UDP-glucuronosyltransferase 1-11PW_P00080791257381913573919145740191557411916574219175743191857441919477619205745192146519225746130Cytochrome P450 19A11PW_P0000303114491201799123Testosterone 17-beta-dehydrogenase 31PW_P00002324791567Cytochrome P450 11B11PW_P000567608432127417991573Corticosteroid 11-beta-dehydrogenase isozyme 11PW_P00057361468125643-oxo-5-beta-steroid 4-dehydrogenase1PW_P000564605522172867PW_R072867Right250408371Compoundfalse2504091461Compoundtrue250410400341Compoundtrue2504117181Compoundfalse2504121431Compoundtrue629962472868PW_R072868Right2504137181Compoundfalse25041411441Compoundtrue250415400341Compoundtrue250416211Compoundfalse2504177211Compoundtrue62997536 1.1.1.5072869PW_R072869Right250418211Compoundfalse2504197461Compoundtrue25042017151Compoundfalse2504212011Compoundtrue629988072.4.1.1733falsePW_R000033Right122371Compoundfalse470510651Compoundtrue4706371ElementCollectiontrue12320161Compoundfalse470714201Compoundtrue4708381ElementCollectiontrue33301.14.14.1434falsePW_R000034Right12420161Compoundfalse468710651Compoundtrue4688371ElementCollectiontrue12529191Compoundfalse468914202Compoundtrue4690381ElementCollectiontrue34301.14.14.1435falsePW_R000035Right12629191Compoundfalse466610651Compoundtrue4667371ElementCollectiontrue127941Compoundfalse4668921Compoundtrue466914201Compoundtrue4670381ElementCollectiontrue35301.14.14.14229falsePW_R000229Both9911571Compoundfalse9927211Compoundtrue993371Compoundfalse99411441Compoundtrue995400341Compoundtrue946231.1.1.6472862PW_R072862Right250382332ElementCollectiontrue250383371Compoundfalse25038410651Compoundtrue250385400342Compoundtrue25038629241Compoundfalse250387342ElementCollectiontrue25038814201Compoundtrue6299156772864PW_R072864Right250394371Compoundfalse2503951461Compoundtrue250396400341Compoundtrue2503971431Compoundtrue25039819671Compoundfalse6299356472866PW_R072866Right2504043721Compoundfalse2504057461Compoundtrue25040621441Compoundfalse2504072011Compoundtrue629958072.4.1.1772863PW_R072863Right25038929241Compoundfalse2503901431Compoundtrue2503911461Compoundtrue250392400341Compoundtrue25039329231Compoundfalse6299257372865PW_R072865Right25039919671Compoundfalse25040011441Compoundtrue250401400341Compoundtrue2504023721Compoundfalse2504037211Compoundtrue62994536 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