114833PathwayUbiquinone BiosynthesisUbiquinone’s distinctive structure is defined by a polyisoprenoid side chain connected to a benzoquinone ring. It serves multiple roles in plants, functioning as an electron transporter in inner mitochondrial membranes, as well as acting as an antioxidant to protect against free radicals. The biosynthesis of ubiquinone is connected to the biosynthesis of tyrosine, tryptophan, and phenylalanine through the shared compounds L-tyrosine and chorismate. Its biosynthesis also takes place in many organelles, with key steps occurring in the mitochondria, chloroplasts, and peroxisomes of plant cells. The compound L-tyrosine begins in the cytoplasm and is converted to homogentisic acid before it can enter the chloroplast through the transporter homogentisate prenyltransferase. Once in the chloroplast, homogentisic acid can follow one of three different sets of reactions, ultimately forming five different compounds, plastoquinol-9, α-tocopherol, β-tocopherol, α-tocotrienol and β-tocotrienol. Pyrophosphate compounds from reactions early in all three sets are provided as products from terpenoid backbone biosynthesis. Meanwhile, chorismate, which also begins in the cytoplasm, can follow two distinct pathways. The first involves its transfer into the mitochondrion, where it undergoes a series of reactions until it forms ubiquinone. This ubiquinone can be used for oxidative phosphorylation within the mitochondrion. The second pathway chorismate follows brings it into the chloroplast, where multiple PHYLLO enzymes catalyze a series of reactions to form 2-succinyl benzoate. With the addition of coenzyme A, 2-succinyl benzoyl-CoA can be moved out of the chloroplast and into the peroxisome. Through a pair of reactions, this compound is ultimately hydrolyzed to form 1,4-dihydroxy-2-naphthoate, which is transported back into the chloroplast to form phylloquinol. Phylloquinone can also react with a hydrogen ion to form phylloquinol in the cell membrane. MetabolicPW123993CenterPathwayVisualizationContext12426946004550#000099PathwayVisualization114696114833Ubiquinone BiosynthesisUbiquinone’s distinctive structure is defined by a polyisoprenoid side chain connected to a benzoquinone ring. It serves multiple roles in plants, functioning as an electron transporter in inner mitochondrial membranes, as well as acting as an antioxidant to protect against free radicals. The biosynthesis of ubiquinone is connected to the biosynthesis of tyrosine, tryptophan, and phenylalanine through the shared compounds L-tyrosine and chorismate. Its biosynthesis also takes place in many organelles, with key steps occurring in the mitochondria, chloroplasts, and peroxisomes of plant cells. The compound L-tyrosine begins in the cytoplasm and is converted to homogentisic acid before it can enter the chloroplast through the transporter homogentisate prenyltransferase. Once in the chloroplast, homogentisic acid can follow one of three different sets of reactions, ultimately forming five different compounds, plastoquinol-9, α-tocopherol, β-tocopherol, α-tocotrienol and β-tocotrienol. Pyrophosphate compounds from reactions early in all three sets are provided as products from terpenoid backbone biosynthesis. Meanwhile, chorismate, which also begins in the cytoplasm, can follow two distinct pathways. The first involves its transfer into the mitochondrion, where it undergoes a series of reactions until it forms ubiquinone. This ubiquinone can be used for oxidative phosphorylation within the mitochondrion. The second pathway chorismate follows brings it into the chloroplast, where multiple PHYLLO enzymes catalyze a series of reactions to form 2-succinyl benzoate. With the addition of coenzyme A, 2-succinyl benzoyl-CoA can be moved out of the chloroplast and into the peroxisome. Through a pair of reactions, this compound is ultimately hydrolyzed to form 1,4-dihydroxy-2-naphthoate, which is transported back into the chloroplast to form phylloquinol. Phylloquinone can also react with a hydrogen ion to form phylloquinol in the cell membrane. Metabolic41128572326Phenylalanine, tryptophan and tyrosine biosynthesisSubPathway112858Phenylalanine, tryptophan and tyrosine biosynthesisSubPathway335477Linka, Nicole & Theodoulou, Frederica. (2013). Metabolite Transporters of the Plant Peroxisomal Membrane: Known and Unknown. Sub-cellular biochemistry. 69. 169-194. 10.1007/978-94-007-6889-5_10. 114833Pathway335479 28018418Liu M, Lu S: Plastoquinone and Ubiquinone in Plants: Biosynthesis, Physiological Function and Metabolic Engineering. Front Plant Sci. 2016 Dec 16;7:1898. doi: 10.3389/fpls.2016.01898. eCollection 2016.114833Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404CardiomyocyteCL:00007466MyocyteCL:000018712AstrocyteCL:00001277Epithelial CellCL:00000668Beta cellCL:00006391Homo sapiens9606EukaryoteHuman4Arabidopsis thaliana3702EukaryoteThale cress12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat6Caenorhabditis elegans6239EukaryoteRoundworm3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast49Bathymodiolus platifrons220390EukaryoteDeep sea mussel10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote2Bacteria2ProkaryoteBacteria21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia419Schizosaccharomyces pombe4896Eukaryote25Escherichia coli (strain K12)83333Prokaryote202Spathaspora passalidarum340170EukaryoteSpathaspora passalidarum61Probe sp00002Eukaryote128Test1Eukaryote65actinobacillus succinogenes 130Z339671Prokaryote157Acinetobacter baumannii 107673Prokaryote151Hordeum vulgare4513EukaryoteBarley191homi sapiens101Eukaryotehuman46Oryza sativa subsp. japonica39947EukaryoteRice273Tanacetum vulgare128002EukaryoteTansy277Camellia nitidissima2774406EukaryoteCamellia nitidissima Chi62Acinetobacter baylyi (strain ATCC 33305 / BD413 / ADP1)62977Prokaryote5CytoplasmGO:00057371CytosolGO:000582935ChloroplastGO:00095072MitochondrionGO:00057396LysosomeGO:00057644PeroxisomeGO:000577713Endoplasmic ReticulumGO:000578310Cell MembraneGO:000588616Lysosomal LumenGO:00432027Endoplasmic Reticulum MembraneGO:000578911Extracellular SpaceGO:00056153Mitochondrial MatrixGO:000575918Melanosome MembraneGO:003316214Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575836MembraneGO:001602012Mitochondrial Inner MembraneGO:000574325Golgi ApparatusGO:000579431Periplasmic SpaceGO:000562027Peroxisome MembraneGO:000577815NucleusGO:000563426Golgi Apparatus MembraneGO:000013917NucleoplasmGO:000565439Mitochondrial membraneGO:003196654Endocytic VesicleGO:003013955Exocytic VesicleGO:007038220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520253Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259732Inner MembraneGO:00702588Smooth Endoplasmic Reticulum GO:000579019Sarcoplasmic ReticulumGO:001652933Outer MembraneGO:00431652Endothelium BTO:00003931LiverBTO:00007597294Adrenal MedullaBTO:000004971828StomachBTO:0001307155267Nervous SystemBTO:00014845cardiocyteBTO:00015398Blood VesselBTO:000110274119MuscleBTO:0000887141183Sympathetic Nervous 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acidHMDB00007074-Hydroxyphenylpyruvic acid (4-HPPA) is a keto acid that is involved in the tyrosine catabolism pathway. It is a product of the enzyme (R)-4-hydroxyphenyllactate dehydrogenase [EC 1.1.1.222] and is formed during tyrosine metabolism. The conversion from tyrosine to 4-HPPA is catalyzed by tyrosine aminotransferase. Additionally, 4-HPPA can be converted to homogentisic acid which is one of the precursors to ochronotic pigment. The enzyme 4-hydroxyphenylpyruvic acid dioxygenase (HPD) catalyzes the reaction that converts 4-hydroxyphenylpyruvic acid to homogentisic acid. A deficiency in the catalytic activity of HPD is known to lead to tyrosinemia type III, an autosomal recessive disorder characterized by elevated levels of blood tyrosine and massive excretion of tyrosine derivatives into urine. It has been shown that hawkinsinuria, an autosomal dominant disorder characterized by the excretion of 'hawkinsin,' may also be a result of HPD deficiency (PMID: 11073718). There are two isomers of HPPA, specifically 4HPPA and 3HPPA, of which 4HPPA is the most common.156-39-8C0117997915999P-HYDROXY-PHENYLPYRUVATE954DB07718OC(=O)C(=O)CC1=CC=C(O)C=C1C9H8O4InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)KKADPXVIOXHVKN-UHFFFAOYSA-N180.1574180.042258744FDB022193(p-hydroxyphenyl)pyruvate;(p-hydroxyphenyl)pyruvic acid;(p-hydroxyphenyl)-pyruvate;(p-hydroxyphenyl)-pyruvic acid;3-(4-hydroxyphenyl)-2-oxo-propanoate;3-(4-hydroxyphenyl)-2-oxo-propanoic acid;3-(4-hydroxyphenyl)-2-oxopropionate;3-(4-hydroxyphenyl)-2-oxopropionic acid;3-(4-hydroxyphenyl)pyruvate;3-(4-hydroxyphenyl)pyruvic acid;3-(p-hydroxyphenyl)-2-oxopropionate;3-(p-hydroxyphenyl)-2-oxopropionic acid;3-(p-hydroxyphenyl)pyruvate;3-(p-hydroxyphenyl)pyruvic acid;4-hydroxy-a-oxobenzenepropanoate;4-hydroxy-a-oxobenzenepropanoic acid;4-hydroxy-alpha-oxobenzenepropanoate;4-hydroxy-alpha-oxobenzenepropanoic acid;4-hydroxyphenylpyruvate;4hppa;Hppa;Hydroxyphenylpyruvate;Hydroxyphenylpyruvic acid;Testacid;P-hydroxyphenylpyruvic;3-(4-hydroxy-phenyl)pyruvic acid;3-(p-hydroxyphenyl)-2-oxopropanoic acid;4-hydroxy alpha-oxobenzenepropanoic acid;4-hydroxyphenylpyruvic acid;P-hydroxyphenylpyruvic acid;(4-hydroxyphenyl)pyruvate;3-(4-hydroxy-phenyl)pyruvate;3-(p-hydroxyphenyl)-2-oxopropanoate;4-hydroxy a-oxobenzenepropanoate;4-hydroxy a-oxobenzenepropanoic acid;4-hydroxy alpha-oxobenzenepropanoate;4-hydroxy α-oxobenzenepropanoate;4-hydroxy α-oxobenzenepropanoic acid;P-hydroxyphenylpyruvatePW_C0005584HPPA1287819922834322512349151770392247705525378471111791031321210041221215901241235691351241481181275533881065OxygenHMDB0001377Oxygen 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_C001065O2959110524516500185058549146252863836491067431688207541576347693383621375492016242531222803294260424747135467123548012554931265508127580910859731476129159700618870321637050160731921375332107560212839515111816216118641981188321511894211120572251206316412247286122792261232524912706291127162921300429813016300130263011303830213260223422761742657315769102937704429477214134773501117736313077377331773953327749711377512115775373347762633677723337777361127774712977756341778051147781213378070329781511327838134578805343791113601200474081203831221204264051205424071205534141205944091206014061208834151210451241211043831216054341216564291221173821225734181226893841227983741228224431230271351230603761231284471231391361231634481231761191231874501232191371232261201234594511236091181236693981241634691242144641246693991251454541252751211254254821257064781257314831257372971257404791258844811261002991262724841265224951267214891268254801269645021269862071271982091272142081272192051272225011273055041273452061275573881275745151278353891280813951280953901283125061284323911316Carbon 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_C001316CO2508121120444801350318640367731695208065113343163849174522551173144705283103532011157501085771101596810060261556078161647117866371076922190701716070351637061188716320573081987333213746122275302108215225822315191582491184927711908170124642261268829042626315435233187699429377122133771701327747033377739112777501297776334178077134784053567842733478941331792271308000836880675119807171359483638411329139111554912111995440612008912212015540712036441212055641412083341912092212412099140812128412512150538312274412012301144612319045012341845512348911812355637412385513612406339812534447912546029712551648112582449012587029912593148212628048012688750112705220612727750712733138812739050214079818584Homogentisic acidHMDB0000130Homogentisic acid, also known as melanic acid, is an intermediate in the breakdown or catabolism of tyrosine and phenylalanine. It is generated from the compound p-hydroxyphenylpyruvate through the enzyme p-hydroxyphenylpyruvate dehydrogenase. The resulting homogentisic acid is then broken down into 4-maleylacetoacetate via the enzyme homogentisate 1,2-dioxygenase. Homogentisic acid is also found in other organisms. For instance, it can found in Arbutus unedo (strawberry-tree) honey, in the bacterial plant pathogen Xanthomonas campestris as well as in the yeast Yarrowia lipolytica where it is associated with the production of brown pigments. Homogentisic acid can be oxidatively dimerized to form hipposudoric acid, one of the main constituents of the 'blood sweat' of hippopotamuses. When present in sufficiently high levels, homogentisic acid can function as an osteotoxin and a renal toxin. An osteotoxin is a substance that causes damage to bones and/or joints. A renal toxin causes damage to the kidneys. Chronically high levels of homogentisic acid are associated with alkaptonuria (OMIM: 203500), an inborn error of metabolism. Alkaptonuria is a rare inherited genetic disorder in which the body cannot process the amino acids phenylalanine and tyrosine. It is caused by a mutation in the enzyme homogentisate 1,2-dioxygenase (EC 1.13.11.5), which leads to an accumulation of homogentisic acid in the blood and tissues. Homogentisic acid and its oxidized form benzoquinone acetic acid are excreted in the urine, giving it an unusually dark color. The accumulating homogentisic acid (and benzoquinone acetic acid) causes damage to cartilage (ochronosis, leading to osteoarthritis) and heart valves as well as precipitating as kidney stones and stones in other organs. More specifically, homogentisic acid can be converted to benzoquinone acetic acid (BQA), and the resulting BQA can be readily converted to polymers that resemble the dark skin pigment melanin. These polymers are deposited in the collagen, a connective tissue protein, of particular tissues such as cartilage. This process is called ochronosis (as the tissue looks ochre); ochronotic tissue is stiffened and unusually brittle, impairing its normal function and causing damage. Homogentisic acid is the primary precursor of melanin synthesis in Vibrio cholerae.451-13-8C0054478044747759DB08327OC(=O)CC1=C(O)C=CC(O)=C1C8H8O4InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)IGMNYECMUMZDDF-UHFFFAOYSA-N168.1467168.042258744FDB021899(2,5-dihydroxyphenyl)-acetate;(2,5-dihydroxyphenyl)-acetic acid;2,5-dihydroxy-a-toluate;2,5-dihydroxy-a-toluic acid;2,5-dihydroxy-alpha-toluate;2,5-dihydroxy-alpha-toluic acid;2,5-dihydroxy-benzeneacetate;2,5-dihydroxy-benzeneacetic acid;2,5-dihydroxyphenylacetate;2,5-dihydroxyphenylacetic acid;Alcapton;Homogentisate;Homogentisate acid;Homogentisinate;Homogentisinic acid;Melanic acid;2-(3,6-dihydroxyphenyl)acetic acid;2-(3,6-dihydroxyphenyl)acetatePW_C000084HMGNCA129581996290591517847811179104132121012122121592124123577135124150118127558388104756Solanesyl pyrophosphateSolanesyl pyrophosphate has the chemical formula C45H76O7P2, and an average molecular weight of 791.044. Solanesyl pyrophosphate is involved in the Terpenoid Backbone Biosynthesis Pathway.C04145683018144CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=OC45H76O7P2InChI=1S/C45H76O7P2/c1-37(2)19-11-20-38(3)21-12-22-39(4)23-13-24-40(5)25-14-26-41(6)27-15-28-42(7)29-16-30-43(8)31-17-32-44(9)33-18-34-45(10)35-36-51-54(49,50)52-53(46,47)48/h19,21,23,25,27,29,31,33,35H,11-18,20,22,24,26,28,30,32,34,36H2,1-10H3,(H,49,50)(H2,46,47,48)/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-33+,45-35+IVLBHBFTRNVIAP-MEGGAXOGSA-N791.044790.506628783PW_C104756Sopr108886Diphosphoric acid2466-09-3C00013102329888OP(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-N177.9751177.943225506Diphosphate;Pyrophosphate;Pyrophosphoric acid;PPiPW_C108886579092-methyl-6-solanesyl-1,4-benzoquinol2-Methyl-6-solanesyl-1,4-benzoquinol, also known as MSBQ or 2-methyl-6-nonaprenyl-benzene-1,4-diol, belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position. 2-Methyl-6-solanesyl-1,4-benzoquinol is considered to be a practically insoluble (in water) and relatively neutral molecule. Outside of the human body, 2-methyl-6-solanesyl-1,4-benzoquinol can be found in a number of food items such as arctic blackberry, radish, black radish, and breadfruit. This makes 2-methyl-6-solanesyl-1,4-benzoquinol a potential biomarker for the consumption of these food products. A polyprenylhydroquinone that is 2-methylbenzene-1,4-diol substituted by a all-trans-nonaprenyl group at position 6 (ChEBI ID: 75402).C1757044237185754022-METHYL-6-SOLANYL-14-BENZOQUINONECC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O)=CC(C)=C1OC52H80O2InChI=1S/C52H80O2/c1-40(2)20-12-21-41(3)22-13-23-42(4)24-14-25-43(5)26-15-27-44(6)28-16-29-45(7)30-17-31-46(8)32-18-33-47(9)34-19-35-48(10)36-37-50-39-51(53)38-49(11)52(50)54/h20,22,24,26,28,30,32,34,36,38-39,53-54H,12-19,21,23,25,27,29,31,33,35,37H2,1-11H3/b41-22+,42-24+,43-26+,44-28+,45-30+,46-32+,47-34+,48-36+SWKACZQJGXABCN-JSGWLJPKSA-N737.21736.6158318162-methyl-6-all-trans-nonaprenyl-1,4-benzoquinol;2-methyl-6-all-trans-nonaprenyl-benzene-1,4-diol;2-methyl-6-solanyl-1,4-benzoquinol;MsbqPW_C0579092M6S14B12357225423MagnesiumHMDB0000547Magnesium 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+868227426816476272726811581918883229363998339922111674614834915294317641421241024115929422331262933737454031477491486954497456525310453291115356112537610359061475934151603815560941616250166648417865941646881160697919971702057194206722721372332117250214731021673131987473222117631321184321012312225123242491251328812581226127292901527528515337308771371337723632977937336783933347841733578489115785223317853635678574130800203688004518480048372806231188065413580865158096525381841519383238394900271085962231105593901156873981199744061200701221202473821207024071209814081211811241212654291213194191219241251220864051224084221227591201229213991233071191235463741238354641238894551244771361246373761249783751254472971255984841256694791257774811259214821259472991259734951260004901262434781265534911267533001271253891271645011273805021274073881274515071278042091281255081283473951407738911090896-Geranylgeranyl-2-methylbenzene-1,4-diolC20737254741205CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O)=CC(C)=C1OC27H40O2InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-25-19-26(28)18-24(6)27(25)29/h10,12,14,16,18-19,28-29H,7-9,11,13,15,17H2,1-6H3/b21-12+,22-14+,23-16+DOWCCBNJUZOLRJ-MLAGYPMBSA-N396.615396.302830528PW_C109089197992-Methyl-6-phytylhydroquinoneHMDB00389592-Methyl-6-phytylhydroquinone is found in green vegetables. 2-Methyl-6-phytylhydroquinone is a precursor of tocopherol synthesis in spinach chloroplasts.54432-31-4C15882237246017540624785305CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C(C)=CC(O)=C1C27H46O2InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-25-19-26(28)18-24(6)27(25)29/h16,18-22,28-29H,7-15,17H2,1-6H3/b23-16+/t21-,22-/m1/s1GTWCNYRFOZKWTL-UOFXASEASA-N402.663402.349780721C158822-methyl-6-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-benzenediol, 9ci;6-phytyltoluquinol;2-methyl-6-phytyl-1,4-hydroquinone;2-methyl-6-phytylquinol;MpbqPW_C019799MPBQ921S-AdenosylmethionineHMDB0001185S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.485-80-3C000192476216515414S-ADENOSYLMETHIONINE31983DB00118C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2NC15H23N6O5SInChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1MEFKEPWMEQBLKI-AIRLBKTGSA-O399.445399.145063566FDB022473(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;SamePW_C000921SAMe51986333070420122031880272066246811050235056041357136163754021075442137632160826615192351951187419812031222123582251529324915345181536330976897293768991647698422477488111777313387777234178099132783033517833534679155112799613618086122948303829483338611328638911328839711554339911554640112039312212053741312093940712105212412228243512317144912350511912361611812483647012585929712587948112630429912644749912732120512734020612759538812801751757910plastoquinol-9Plastoquinol-9, also known as PQH2 CPD, belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position. Plastoquinol-9 is considered to be a practically insoluble (in water) and relatively neutral molecule. A plastoquinol in which an all-E nonaprenyl group is attached to position 5 of 2,3-dimethylhydroquinone (ChEBI ID: 28026).C16695644094128026CPD-128294945177CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O)=C(C)C(C)=C1OC53H82O2InChI=1S/C53H82O2/c1-40(2)21-13-22-41(3)23-14-24-42(4)25-15-26-43(5)27-16-28-44(6)29-17-30-45(7)31-18-32-46(8)33-19-34-47(9)35-20-36-48(10)37-38-51-39-52(54)49(11)50(12)53(51)55/h21,23,25,27,29,31,33,35,37,39,54-55H,13-20,22,24,26,28,30,32,34,36,38H2,1-12H3/b41-23+,42-25+,43-27+,44-29+,45-31+,46-33+,47-35+,48-37+IJBLJLREWPLEPB-IQSNHBBHSA-N751.237750.63148188Plastoquinol aPW_C057910Plasto912360225104757Phytyl pyrophosphatePhytyl pyrophosphate has the chemical formula C20H42O7P2, and an average molecular weight of 456.497. Phytyl pyrophosphate is involved in the Terpenoid Backbone Biosynthesis Pathway.C05427779175837CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\COP(O)(=O)OP(O)(O)=OC20H42O7P2InChI=1S/C20H42O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h15,17-19H,6-14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b20-15+/t18-,19-/m1/s1ITPLBNCCPZSWEU-PYDDKJGSSA-N456.497456.240577688PW_C104757PhyPyrP1731δ-TocopherolHMDB0002902Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. -- Wikipedia; Natural vitamin E exists in eight different forms or isomers, four tocopherols and four tocotrienols. All isomers have a chromanol ring, with a hydroxyl group which can donate a hydrogen atom to reduce free radicals and a hydrophobic side chain which allows for penetration into biological membranes. There is an alpha, beta, gamma and delta form of both the tocopherols and tocotrienols, determined by the number of methyl groups on the chromanol ring. Each form has its own biological activity, the measure of potency or functional use in the body. -- Wikipedia; Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha tocopherol. It increases naturally to about 150% of normal in the maternal circulation during human pregnancies. 1 IU of vitamin E is defined as the biological equivalent of 0.667 milligrams of d-alpha-tocopherol, or of 1 milligram of dl-alpha-tocopherol acetate. The other isomers are slowly being recognized as research begins to elucidate their additional roles in the human body. Many naturopathic and orthomolecular medicine advocates suggest that vitamin E supplements contain at least 20% by weight of the other natural vitamin E isomers. Commercially available blends of natural vitamin E include "mixed tocopherols" and "high gamma tocopherol" formulas. Also selenium, Coenzyme Q10, and ample vitamin C have been shown to be essential cofactors of natural tocopherols. -- Wikipedia; Synthetic vitamin E, usually marked as d,l-tocopherol or d,l tocopheryl acetate, with 50% d-alpha tocopherol moiety and 50% l-alpha-tocopherol moiety, as synthesized by an earlier process is now actually manufactured as all-racemic alpha tocopherol, with only about one alpha tocopherol molecule in 8 molecules as actual d-alpha tocpherol. The synthetic form is not as active as the natural alpha tocopherol form. The 1950's thalidomide disaster with numerous severe birth defects is a common example of d- vs l- epimer forms type problem with synthesized racemic mixtures. Information on any side effects of the synthetic vitamin E epimers is not readily available. Naturopathic and orthomolecular medicine advocates have long considered the synthetic vitamin E forms to be with little or no merit for cancer, circulatory and heart diseases. -- Wikipedia; Abetalipoproteinemia is a rare inherited disorder of fat metabolism that results in poor absorption of dietary fat and vitamin E. The vitamin E deficiency associated with this disease causes problems such as poor transmission of nerve impulses, muscle weakness, and degeneration of the retina that can cause blindness. Individuals with abetalipoproteinemia may be prescribed special vitamin E supplements by a physician to treat this disorder. -- Wikipedia; Recent studies also show that vitamin E acts as an effective free radical scavenger and can lower the incidence of lung cancer in smokers. The effects are opposite to that of the clinical trials based on administering carotenoid to male smokers, that resulted in increased risk of lung cancer. Hence vitamin E is an effective antagonist to the oxidative stress that is imposed by high carotenoids in certain patients. -- Wikipedia; A cataract is a condition of clouding of the tissue of the lens of the eye. They increase the risk of disability and blindness in aging adults. Antioxidants are being studied to determine whether they can help prevent or delay cataract growth. Observational studies have found that lens clarity, which is used to diagnose cataracts, was better in regular users of vitamin E supplements and in persons with higher blood levels of vitamin E. A study of middle aged male smokers, however, did not demonstrate any effect from vitamin E supplements on the incidence of cataract formation. The effects of smoking, a major risk factor for developing cataracts, may have overridden any potential benefit from the vitamin E, but the conflicting results also indicate a need for further studies before researchers can confidently recommend extra vitamin E for the prevention of cataracts. It is important to note that the term "cataract" may be used in common parlance for an opacity involving any tissue of the eye, for example a corneal scar. Thus a character in theater or on television who is blind from cataracts might have white instead of clear corneas, covering over the iris and pupil. Since the lens is behind the pupil, real cataracts are difficult to see without special instrumentation, so people with cataracts have rather normally appearing eyes. -- Wikipedia; Alzheimer's disease is a wasting disease of the brain. An observational trial conducted by The Johns Hopkins University Bloomberg School of Public Health found that when vitamin E is taken daily in large doses (400-1000IU) in combination with vitamin C (500-1000mg) the onset of Alzheimer's was reduced between 64 and 78%. External Link - Johns Hopkins press release -- Wikipedia.119-13-1C141519209447772DELTA-TOCOPHEROL83144CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=CC(C)=C2O1C27H46O2InChI=1S/C27H46O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h18-22,28H,7-17H2,1-6H3/t21-,22-,27-/m1/s1GZIFEOYASATJEH-VHFRWLAGSA-N402.6529402.349780716FDB0024328-methyltocol;Vitamine e;Delta-tocopherol;(2r)-3,4-dihydro-2,8-dimethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-2h-1-benzopyran-6-olPW_C001731VE749S-AdenosylhomocysteineHMDB0000939S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinson's disease (PMID: 18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID: 221926).979-92-0C000212524622216680ADENOSYL-HOMO-CYS388301N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=OC14H20N6O5SInChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1ZJUKTBDSGOFHSH-WFMPWKQPSA-N384.411384.12158847DBMET00514FDB022327(s)-5'-(s)-(3-amino-3-carboxypropyl)-5'-thioadenosine;2-s-adenosyl-l-homocysteine;5'-deoxy-s-adenosyl-l-homocysteine;5'-s-(3-amino-3-carboxypropyl)-5'-thio-l-adenosine;Adenosyl-l-homocysteine;Adenosyl-homo-cys;Adenosylhomo-cys;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-s-(3-amino-3-carboxypropyl)-5'-thior-adenosine;L-s-adenosyl-homocysteine;L-s-adenosylhomocysteine;S-(5'-adenosyl)-l-homocysteine;S-(5'-deoxyadenosin-5'-yl)-l-homocysteine;S-(5'-deoxyadenosine-5')-l-homocysteine;S-adenosyl-l-homocysteine;S-adenosyl-homocysteine;Sah;(2s)-2-amino-4-({[(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid;S-[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl]-l-homocysteine;S-adenosylhomocysteinePW_C000749SAH52085751863530705201221318822720672468310502550560713671371637542210754621376341608268151923719511875198123592251529424915364309774891117761113077733338777733417809813278305351783373467915611279962361808632294831382948343861132873891132893971155443991155474011203941221204861251205394131209404071210531241222844351230371351231734491235061191236171181248384701258804811263032991264494991273412061275963881280195172725β-tocopherolHMDB0006335Beta-tocopherol is an antioxidant which is synthesized by photosynthetic organisms and play important roles in human and animal nutrition. betatocopherols can be oxidized in dry CH2Cl2 or CH3CN by one electron to form cation radicals that deprotonate to form the neutral phenoxyl radicals, which are then immediately further oxidized by one electron to the phenoxonium cations (an ECE electrochemical mechanism, where E signifies an electron transfer and C represents a chemical step, with the electrochemical mechanism having been determined by in situ spectroscopic analysis).The phenoxonium cation of beta-tocopherol is stable for several minutes. (PMID: 16771430).16698-35-4C14152685744747771BETA-TOCOPHEROL5256784CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O1C28H48O2InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1WGVKWNUPNGFDFJ-DQCZWYHMSA-N416.6795416.36543078FDB012381Beta-tocopherol;(2r)-3,4-dihydro-2,5,8-trimethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-2h-1-benzopyran-6-ol;5,8-dimethyltocol;B-tocopherol;β-tocopherolPW_C002725βT1090932,3-Dimethyl-5-phytyl-1,4-hydroquinone C15883 4720520375407CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C(C)=C(C)C(O)=C1C28H48O2InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-16-23(5)17-18-26-19-27(29)24(6)25(7)28(26)30/h17,19-22,29-30H,8-16,18H2,1-7H3/b23-17+/t21-,22-/m1/s1SUFZKUBNOVDJRR-WGEODTKDSA-N416.69416.365430786PW_C1090931149γ-TocopherolHMDB0001492Gamma-Tocopherol is a collective name for a group of closely related lipids that contain substitutions on the 2H-1-benzopyran-6-ol nucleus and a long hydrocarbon chain of isoprenoid units. They are antioxidants by virtue of the phenolic hydrogen. Tocopherols react with the most reactive form of oxygen and protect unsaturated fatty acids from oxidation.10191-41-01498629840214266CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1C28H48O2InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1QUEDXNHFTDJVIY-DQCZWYHMSA-N416.6795416.36543078FDB0024312,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol;3,4-dihydro-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2h-1-benzopyran-6-ol;7,8-dimethyltocol;7,8-dimethyltocolo-xylotocopherol;Dl-alpha-tocopherol;Methyltocols;O-xylotocopherol;Tocopherol;Tocopherols;Vitamin e gamma;Gamma-tocopherol;Dl-a-tocopherol;Dl-α-tocopherolPW_C001149Tocophe1261α-TocopherolHMDB0001893alpha-Tocopherol is traditionally recognized as the most active form of vitamin E in humans and is a powerful biological antioxidant. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to alpha-Tocopherol. Natural vitamin E exists in eight different forms or isomers: four tocopherols and four tocotrienols. In foods, the most abundant sources of vitamin E are vegetable oils such as palm oil, sunflower, corn, soybean, and olive oil. Nuts, sunflower seeds, and wheat germ are also good sources (Wikipedia).59-02-9C024771498518145CPD-112514265DB00163CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1C29H50O2InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1GVJHHUAWPYXKBD-IEOSBIPESA-N430.7061430.381080844FDB000565(+)-a-tocopherol;(+)-alpha-tocopherol;(2r)-3,4-dihydro-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-2h-1-benzopyran-6-ol;(2r,4'r,8'r)-a-tocopherol;(2r,4'r,8'r)-alpha-tocopherol;(r,r,r)-a-tocopherol;(r,r,r)-alpha-tocopherol;5,7,8-trimethyltocol;D-alpha-tocopherol;Denamone;Eprolin;Phytogermin;Phytogermine;Rrr-alpha-tocopherol;Rrr-alpha-tocopheryl;Vitamin e;Vitamin ea;A-d-tocopherol;A-tocopherol;Alpha-tocopherol;Alpha-delta-tocopherol;Delta-alpha-tocopherol;(2r,4'r,8'r)-α-tocopherol;α-tocopherol;(r,r,r)-α-tocopherol;D-a-tocopherol;D-α-tocopherolPW_C001261Eprolin2145Geranylgeranyl-PPHMDB0004486Geranylgeranyl-PP, also known as GGDP or GGPP diphosphate, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, geranylgeranyl-PP is considered to be an isoprenoid lipid molecule. Geranylgeranyl-PP is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, geranylgeranyl-PP is primarily located in the cytoplasm and membrane (predicted from logP). Outside of the human body, geranylgeranyl-PP can be found in a number of food items such as beech nut, wakame, grape, and mixed nuts. This makes geranylgeranyl-PP a potential biomarker for the consumption of these food products. Geranylgeranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids.6699-20-3C0035344727748861GERANYLGERANYL-PP394418CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=OC20H36O7P2InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+OINNEUNVOZHBOX-QIRCYJPOSA-N450.4432450.19362653FDB0233773,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl diphosphate;All-trans-geranyl-geranyl-pp;Geranylgeranyl-pp;Geranylgeranyl-diphosphate;All-trans-geranylgeranyl diphosphate;All-trans-geranylgeranyl pyrophosphate;Geranylgeranyl diphosphate;Geranylgeranyl pyrophosphate;Ggdp;All-trans-geranylgeranyl diphosphoric acid;2-trans,6-trans,10-trans-geranylgeranyl diphosphatePW_C002145GGDP832212351249123742251090916-geranylgeranyl-2,3-dimethylbenzene-1,4-diol C20738254741206CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=CC(O)=C(C)C(C)=C1OC28H42O2InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-16-23(5)17-18-26-19-27(29)24(6)25(7)28(26)30/h11,13,15,17,19,29-30H,8-10,12,14,16,18H2,1-7H3/b21-13+,22-15+,23-17+QFMVWSPTQOCGTB-TUZVQDLTSA-N410.642410.318480592PW_C1090918136γ-TocotrienolHMDB0012958gamma-tocotrienol targets cancer cells by inhibiting Id1, a key cancer-promoting protein. Gamma-tocotrienol was shown to trigger cell apoptosis and well as anti-proliferation of cancer cells. This mechanism was also observed in separate prostate cancer and melanoma cell line studies.14101-61-2C141555282349332774445514CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=CC(O)=C(C)C(C)=C2O1C28H42O2InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1OTXNTMVVOOBZCV-WAZJVIJMSA-N410.6319410.318480588C14155(2r)-2,7,8-trimethyl-2-(4',8',12'-trimethyl-trideca-3',7',11'-trienyl)-6-hydroxychromanPW_C008136γT2720α-TocotrienolHMDB0006327Alpha-Tocotrienol is found in the blood plasma and all lipoprotein subfractions. Compared to tocopherols, alpha-tocotrienols are poorly studied. Its presence in the blood plasma at nanomolar concentrations is thought to help to prevent stroke-related neurodegeneration. (PMID: 16771695 ). alpha-tocotrienol has been found to have vitamin E activity.1721-51-3C141535282347332704445512CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1C29H44O2InChI=1S/C29H44O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1RZFHLOLGZPDCHJ-XZXLULOTSA-N424.6585424.334130652FDB002434(2r,3'e,7'e)-alpha-tocotrienol;(r)-alpha-tocotrienol;D-alpha-tocotrienol;Zeta1-tocopherol;Alpha-tocotrienol;Delta-alpha-tocotrienol;Z1-tocopherol;ζ1-tocopherolPW_C002720αT11226d-TocotrienolHMDB0030008d-Tocotrienol is found in american cranberry. d-Tocotrienol is a constituent of palm oil. Nutriceutical with anticancer properties and a positive influence on the blood lipid profile.
D-tocotrienol belongs to the family of Tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.25612-59-39854614332768030319CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC1(C)CCC2=CC(O)=CC(C)=C2O1C27H40O2InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+ODADKLYLWWCHNB-QRCIITMISA-N396.6053396.302830524(r)-delta-tocotrienol;2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-6-chromanol;3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol, 9ci;8-methyltocotrienol;Tocotrienol, delta;Delta-tocotrienolPW_C011226DT109092β-TocotrienolC14154784696633275CC(C)=CCC\C(C)=C\CC\C(C)=C\CC[C@]1(C)CCC2=C(C)C(O)=CC(C)=C2O1C28H42O2InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1FGYKUFVNYVMTAM-WAZJVIJMSA-N410.642410.318480592PW_C109092103L-TyrosineHMDB0000158Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the body's sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the body's natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinson's, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinson's. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. (http://www.dcnutrition.com).60-18-4C00082605717895TYR5833DB00135N[C@@H](CC1=CC=C(O)C=C1)C(O)=OC9H11NO3InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1OUYCCCASQSFEME-QMMMGPOBSA-N181.1885181.073893223FDB000446(-)-a-amino-p-hydroxyhydrocinnamate;(-)-a-amino-p-hydroxyhydrocinnamic acid;(-)-alpha-amino-p-hydroxyhydrocinnamate;(-)-alpha-amino-p-hydroxyhydrocinnamic acid;(s)-(-)-tyrosine;(s)-2-amino-3-(p-hydroxyphenyl)propionate;(s)-2-amino-3-(p-hydroxyphenyl)propionic acid;(s)-3-(p-hydroxyphenyl)alanine;(s)-tyrosine;(s)-a-amino-4-hydroxybenzenepropanoate;(s)-a-amino-4-hydroxybenzenepropanoic acid;(s)-a-amino-4-hydroxy-benzenepropanoate;(s)-a-amino-4-hydroxy-benzenepropanoic acid;(s)-alpha-amino-4-hydroxybenzenepropanoate;(s)-alpha-amino-4-hydroxybenzenepropanoic acid;(s)-alpha-amino-4-hydroxy-benzenepropanoate;(s)-alpha-amino-4-hydroxy-benzenepropanoic acid;2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoate;2-amino-3-(4-hydroxyphen yl)-2-amino-3-(4-hydroxyphenyl)-propanoic acid;3-(4-hydroxyphenyl)-l-alanine;4-hydroxy-l-phenylalanine;Benzenepropanoate;Benzenepropanoic acid;L-tyrosine;L-p-tyrosine;Tyr;Tyrosine;P-tyrosine;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;L-tyrosin;Y;(-)-α-amino-p-hydroxyhydrocinnamate;(-)-α-amino-p-hydroxyhydrocinnamic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoate;(s)-α-amino-4-hydroxybenzenepropanoate;(s)-α-amino-4-hydroxybenzenepropanoic acidPW_C000103Tyr3961968620128481979247072356651075666108588610583422251234815142412318424133157705122477754341784691117904612879102132792362538218937782473378117773402117774403121001122121589124122652441122653442122655410123566135124147118125226476125227477125229444127552388134Oxoglutaric acidHMDB0000208Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207).328-50-7C0002651309152-KETOGLUTARATE50DB02926OC(=O)CCC(=O)C(O)=OC5H6O5InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)KPGXRSRHYNQIFN-UHFFFAOYSA-N146.0981146.021523302FDB0033612-ketoglutarate;2-ketoglutaric acid;2-oxo-1,5-pentanedioate;2-oxo-1,5-pentanedioic acid;2-oxoglutarate;2-oxoglutaric acid;2-oxopentanedioate;2-oxopentanedioic acid;Oxoglutarate;Alpha-ketoglutaric acid;Oxoglutaric acid;A-ketoglutarate;A-ketoglutaric acid;Alpha-ketoglutarate;α-ketoglutarate;α-ketoglutaric acidPW_C000134AKG152423141414684991867331110842126351447501455261467545375103541411754381185564132600814760361556069157609216164821786530857471222751522475191518209225837422011863198126812897705425377135133774811117752311277746129779673457797034677976327779843477842533480018368806941351131629411997240612002212412008440712017412212055241412081441812098940812114642312115242412116042512275712012283111912318645012339945412355437412371845812372445912373246012535747912540029912545548112553329712580048912592948212690050112694038812699320612706620512725550612738850295L-Glutamic acidHMDB0000148Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization. (http://en.wikipedia.org/wiki/Glutamic_acid).56-86-0C000253303216015GLT30572DB00142N[C@@H](CCC(O)=O)C(O)=OC5H9NO4InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1WHUUTDBJXJRKMK-VKHMYHEASA-N147.1293147.053157781FDB012535(2s)-2-aminopentanedioate;(2s)-2-aminopentanedioic acid;(s)-(+)-glutamate;(s)-(+)-glutamic acid;(s)-2-aminopentanedioate;(s)-2-aminopentanedioic acid;(s)-glutamate;(s)-glutamic acid;1-amino-propane-1,3-dicarboxylate;1-amino-propane-1,3-dicarboxylic acid;1-aminopropane-1,3-dicarboxylate;1-aminopropane-1,3-dicarboxylic acid;2-aminoglutarate;2-aminoglutaric acid;2-aminopentanedioate;2-aminopentanedioic acid;Aciglut;Aminoglutarate;Aminoglutaric acid;E;Glt;Glu;Glusate;Glut;Glutacid;Glutamicol;Glutamidex;Glutaminate;Glutaminic acid;Glutaminol;Glutaton;L-(+)-glutamate;L-(+)-glutamic acid;L-glu;L-glutamate;L-glutaminate;L-glutaminic acid;L-a-aminoglutarate;L-a-aminoglutaric acid;L-alpha-aminoglutarate;L-alpha-aminoglutaric acid;A-aminoglutarate;A-aminoglutaric acid;A-glutamate;A-glutamic acid;Alpha-aminoglutarate;Alpha-aminoglutaric acid;Alpha-glutamate;Alpha-glutamic acid;Acide glutamique;Acido glutamico;Acidum glutamicum;Glutamate;Glutamic acid;L-glutaminsaeurePW_C000095Glu16244365811911384164149699110542144850145626146254532311153441135415117543911855651325631107563210858591056006147607115761919465318568381876844188709272709371716520571822077514224751815182082258373220117921981185516112004222126213112683289126972904234831542349318428453207702025377332133775251127797134677977327779813477829134580649135120023124120040122120086407120347406120692126120816418121147423121153424121157425122833119122997120123299443123401454123719458123725459123729460125401299125418297125457481125667479125769301125802489126941388126995206127162501127257506140738841407395971148Pyridoxal 5'-phosphateHMDB0001491This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine). -- Pubchem; Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate) is a cofactor of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. -- Wikipedia.54-47-7C00018105118405PYRIDOXAL_PHOSPHATE1022DB00114CC1=NC=C(COP(O)(O)=O)C(C=O)=C1OC8H10NO6PInChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)NGVDGCNFYWLIFO-UHFFFAOYSA-N247.1419247.024573569FDB021820Apolon b6;Biosechs;Codecarboxylase;Coenzyme b6;Hairoxal;Hexermin-p;Hi-pyridoxin;Hiadelon;Himitan;Pal-p;Plp;Phosphopyridoxal;Phosphopyridoxal coenzyme;Pidopidon;Piodel;Pydoxal;Pyridoxal 5'-phosphate;Pyridoxal 5-phosphate;Pyridoxal p;Pyridoxal phosphate;Pyridoxal-p;Pyridoxyl phosphate;Pyromijin;Sechvitan;Vitahexin-p;Vitazechs;3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate;Phosphoric acid mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphoric acid ester;Pyridoxal 5'-(dihydrogen phosphate);Pyridoxal-5'-phosphate;Pyridoxal 5'-phosphoric acid;3-hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphoric acid;Phosphate mono-(4-formyl-5-hydroxy-6-methyl-pyridin-3-ylmethyl) ester;Pyridoxal 5-monophosphate ester;Pyridoxal 5'-(dihydrogen phosphoric acid);Pyridoxal 5-phosphoric acid;Pyridoxal phosphoric acid;Pyridoxal-5'-phosphoric acidPW_C001148Pyr-5'P182324453518122140119696201110421450501458262120102150495325111541611754211035441118545512055671325581133653385701816071672057216212722221311858161121751511262331126281812684289126892907701725377037225770412937705222477526112777643417797334677979327782923457885533278862331806961359863071199121221200241241200294061200874071208174181211494231211554241220691231220763831228341191234024541237214581237274591246204471246273981253022971254022991254074791254584811258034891262242981262314951269423881269475011269962061272585061277865131277933907748ChorismateHMDB0012199Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia.617-12-9C002511203917333CPD-951711542O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=OC10H10O6InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1WTFXTQVDAKGDEY-HTQZYQBOSA-N226.1828226.047738052C00251Chorismic acid;(3r,4r)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid;(3r-trans)-3-((1-carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylic acid;(3r,4r)-3-[(1-carboxyvinyl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylate;(3r-trans)-3-((1-carboxyethenyl)oxy)-4-hydroxy-1,5-cyclohexadiene-1-carboxylatePW_C007748Chorism5164948325225832915142309313104648IsochorismateC00885414117582 PW_C104648Isochor135703100109073Mg 2+18420[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-N24.30523.985041898PW_C109073407422-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate, also known as 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylic acid or sephchc, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate may be a unique E.coli metabolite. 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate participates in a number of enzymatic reactions. In particular, 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate can be biosynthesized from isochorismate and oxoglutaric acid; which is catalyzed by the enzyme 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase. In addition, 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate can be converted into (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate and pyruvic acid through its interaction with the enzyme (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase.C165195109084850271[H][C@@]1(O)[C@@]([H])(OC(=C)C(O)=O)C=C[C@]([H])(C(=O)CCC(O)=O)[C@@]1([H])C(O)=OC14H16O9InChI=1S/C14H16O9/c1-6(13(19)20)23-9-4-2-7(8(15)3-5-10(16)17)11(12(9)18)14(21)22/h2,4,7,9,11-12,18H,1,3,5H2,(H,16,17)(H,19,20)(H,21,22)/t7-,9+,11-,12-/m1/s1XYCATPIYKOARSZ-OAIFWDMCSA-N328.2714328.07943211PW_C040742sehcc109098Mn 2+29035[Mn++]MnInChI=1S/Mn/q+2WAEMQWOKJMHJLA-UHFFFAOYSA-N54.93854.938049636PW_C10909840743(1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate(1R,6R)-2-(3-Carboxylatopropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylate, also known as (1R,6R)-6-hydroxy-2-succinyl-cyclohexa-2,4-diene-1-carboxylate or SHCHC, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom (1R,6R)-2-(3-Carboxylatopropanoyl)-6-hydroxycyclohexa-2,4-diene-1-carboxylate is soluble (in water) and a weakly acidic compound (based on its pKa).C0581758689[H][C@@]1(O)C=CC=C(C(=O)CCC([O-])=O)[C@@]1([H])C([O-])=OC11H10O6InChI=1S/C11H12O6/c12-7(4-5-9(14)15)6-2-1-3-8(13)10(6)11(16)17/h1-3,8,10,13H,4-5H2,(H,14,15)(H,16,17)/p-2/t8-,10-/m1/s1QJYRAJSESKVEAE-PSASIEDQSA-L238.196238.048835202PW_C040743166H2S2164Pyruvic acidHMDB0000243Pyruvic acid is an intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed.) Biological Source: Intermediate in primary metabolism including fermentation processes. Present in muscle in redox equilibrium with Lactic acid. A common constituent, as a chiral cyclic acetal linked to saccharide residues, of bacterial polysaccharides. Isolated from cane sugar fermentation broth and peppermint. Constituent of Bauhinia purpurea, Cicer arietinum (chickpea), Delonix regia, Pisum sativum (pea) and Trigonella caerulea (sweet trefoil) Use/Importance: Reagent for regeneration of carbonyl compdounds from semicarbazones, phenylhydrazones and oximes. Flavoring ingredient (Dictionary of Organic Compounds).127-17-3C00022106032816PYRUVATE1031DB00119CC(=O)C(O)=OC3H4O3InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)LCTONWCANYUPML-UHFFFAOYSA-N88.062188.016043994FDB0082932-oxopropanoate;2-oxopropanoic acid;2-oxopropionate;2-oxopropionic acid;Acetylformate;Acetylformic acid;Bts;Pyroracemate;Pyroracemic acid;Pyruvate;A-ketopropionate;A-ketopropionic acid;Alpha-ketopropionate;Alpha-ketopropionic acid;2-ketopropionic acid;2-oxopropansaeure;2-oxopropionsaeure;Acide pyruvique;Alpha-oxopropionsaeure;Brenztraubensaeure;Ch3cocooh;2-ketopropionate;α-ketopropionate;α-ketopropionic acid;A-oxopropionsaeure;α-oxopropionsaeurePW_C000164Pyr172204422811813144950145726536510354051175440118544412055661325570133589395592014759511516022155606715660741616126160638316467178651017765328574572227495220820022512622311529224915349187731011177972346779783277809011280004368800423678069513511287994115683121119950406120011124120175122120878407121148423121154424123454119123720458123726459125340479125390299125534297125854481126883501126931388127067205127858206407442-succinylbenzoateO-Succinatobenzoate, also known as 2-succinylbenzoic acid, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. O-Succinatobenzoate is slightly soluble (in water) and a weakly acidic compound (based on its pKa).C0273018325[O-]C(=O)CCC(=O)C1=CC=CC=C1C([O-])=OC11H8O5InChI=1S/C11H10O5/c12-9(5-6-10(13)14)7-3-1-2-4-8(7)11(15)16/h1-4H,5-6H2,(H,13,14)(H,15,16)/p-2YIVWQNVQRXFZJB-UHFFFAOYSA-L220.181220.038270517PW_C0407442sb1420WaterHMDB0002111Water 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_C001420H2O5589491095139415131621448113526156242865210691207703382318838210943113774914655415904320182425322226786027274627781728052931437031647236346145983647273749419350302751567519597521410052279452361035297105531911153431135355112540211054701235483125549212655071275534130553711455411295591135560811856221085691657591405778101584114358531465877107589095591014759401516032155605915760871616123163613315962151621816664771786507180660015267131176840188688816071622057181207719320672112117228213723821472432157295198735021673882107401212746722274922247500190758817082012258237226841416292652611850277119221641201128112213285122502861226428712327249125202271263265126932901270529112715292130072981301930013025301130373021326122313327294153403084232731542695318436913227691429377019253771021327713113377215134773783317739733277471333775161157753633477628336777223377775934177816343779823477807132978235352782423537827035679113360800143688003937080591228806561199383038394794384110557390110639391115844398119879232119915122119963406120008407120046408120113124120365412120430405120438409120606415120794414121158425121240429121351121121381419121607434122118382122384436122753120122797374122804443123012446123064376123072137123131447123142136123162448123231451123384450123730460123810464123940455124165469124670399124938471124945472125305297125353479125386481125424482125480299125682483125707478125745487126054490126238495126273484126764480126896501126963502127017388127177208127199209127227504127506507127576515127836389128082395128176513140674790140675834140755185414Adenosine 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_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171407708911099Coenzyme 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_C001099CoA211438688453879228921724075924142245952813292862313342113351184618104629584842144865544879652321025247104528010354771245734108577710160231556075161638416468178693016069611626973199708318871081637293198734721074582228229151908122690902249124170921519513013299153182492548849426163157690729377119133772221347723032977292111775501327755533477563112776333367767212977996115780473327805635078413335785671307925933379974331800053688062011880627374806351198066537693828382938343839867428811055538911056139011584239911584739811995140612014740512023138412030512212063440712076211712140612312142143312152112512166642912168240812171441412240442212274112012290412112296013512396544712397946812407913612422046412426545012497437512534147912550947812557948012559248412563429712608448112654949112656048212674630012688450112704620912710939112730120512754020612766738812812150812813350212834039514075118614076318514076789132Adenosine monophosphateHMDB0000045Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.61-19-8C00020608316027AMP5858DB00131NC1=C2N=CN([C@@H]3O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]3O)C2=NC=N1C10H14N5O7PInChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1UDMBCSSLTHHNCD-KQYNXXCUSA-N347.2212347.063084339DBMET00485FDB0218065'-amp;5'-adenosine monophosphate;5'-adenylate;5'-adenylic acid;Amp;Adenosine 5'-monophosphate;Adenosine 5'-phosphate;Adenosine 5'-phosphorate;Adenosine 5'-phosphoric acid;Adenosine phosphate;Adenosine-5'-monophosphorate;Adenosine-5'-monophosphoric acid;Adenosine-5-monophosphorate;Adenosine-5-monophosphoric acid;Adenosine-monophosphate;Adenosine-phosphate;Adenovite;Adenylate;Adenylic acid;Cardiomone;Lycedan;Muscle adenylate;Muscle adenylic acid;My-b-den;My-beta-den;Phosaden;Phosphaden;Phosphentaside;5'-o-phosphonoadenosine;Adenosine 5'-(dihydrogen phosphate);Adenosine monophosphate;Adenosine-5'p;Adenosini phosphas;Ado5'p;Fosfato de adenosina;Pa;Pado;Phosphate d'adenosine;5'-adenosine monophosphoric acid;Adenosine phosphoric acid;Adenosine 5'-(dihydrogen phosphoric acid);Adenosine 5'-monophosphoric acid;Adenosine monophosphoric acid;Adenosine-5'-monophosphate;Phosphoric acid d'adenosinePW_C000032AMP112344628270167343288122118914457254867545033895251104540811754231035432118545712055581325583133577910157951086977199707218811789198118681611198815112003222125802261263631126942901333122542266342646315772343297732511178392334788091157932011280399180684135809007119916122120016124120031406120246382120888405121954408122920399123464376124507374125306297125394299125409479125596484126853205126934388126949501127124389127311209127711502140771891432982-Succinylbenzoyl-CoA4-(2-Carboxyphenyl)-4-oxobutanoyl-CoA, also known as O-succinylbenzoyl-CoA or osb-CoA, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. 4-(2-Carboxyphenyl)-4-oxobutanoyl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). 4-(2-Carboxyphenyl)-4-oxobutanoyl-CoA can be biosynthesized from 2-succinylbenzoic acid..C0316012627915509CPD-697210128120CC(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)NCCSC(=O)CCC(=O)C1=C(C=CC=C1)C(O)=OC32H44N7O20P3SInChI=1S/C32H44N7O20P3S/c1-32(2,26(44)29(45)35-10-9-21(41)34-11-12-63-22(42)8-7-19(40)17-5-3-4-6-18(17)31(46)47)14-56-62(53,54)59-61(51,52)55-13-20-25(58-60(48,49)50)24(43)30(57-20)39-16-38-23-27(33)36-15-37-28(23)39/h3-6,15-16,20,24-26,30,43-44H,7-14H2,1-2H3,(H,34,41)(H,35,45)(H,46,47)(H,51,52)(H,53,54)(H2,33,36,37)(H2,48,49,50)/t20-,24-,25-,26+,30-/m1/s1KVAQAPQXOXTRAE-HSJNEKGZSA-N971.71971.1574690132-(3'-carboxypropionyl)benzoyl-CoA;2-succinylbenzoyl-CoA;4-(2'-carboxyphenyl)-4-oxobutyrate-coenzyme a;4-(2'-carboxyphenyl)-4-oxobutyryl-CoA;4-(2'-carboxyphenyl)-4-oxobutyryl-CoA ester;4-(2'-carboxyphenyl)-4-oxobutyryl-coenzyme a ester;o-succinylbenzoyl-CoA;Cpo-CoA ester;O-succinylbenzoyl-CoA;Osucb-CoA;succinylbenzoyl-CoAPW_C0432982sbCoA407461,4-dihydroxy-2-naphthoyl-CoA1,4-Dihydroxy-2-naphthoic acid, also known as dhna-coa, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. 1,4-Dihydroxy-2-naphthoic acid is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). 1,4-Dihydroxy-2-naphthoic acid may be a unique E.coli metabolite.C1554758897[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=OC32H38N7O19P3SInChI=1S/C32H42N7O19P3S/c1-32(2,26(44)29(45)35-8-7-21(41)34-9-10-62-31(46)18-11-19(40)16-5-3-4-6-17(16)23(18)42)13-55-61(52,53)58-60(50,51)54-12-20-25(57-59(47,48)49)24(43)30(56-20)39-15-38-22-27(33)36-14-37-28(22)39/h3-6,11,14-15,20,24-26,30,40,42-44H,7-10,12-13H2,1-2H3,(H,34,41)(H,35,45)(H,50,51)(H,52,53)(H2,33,36,37)(H2,47,48,49)/p-4/t20-,24-,25-,26+,30-/m1/s1PYTINLGPKDJURZ-HSJNEKGZSA-J949.67949.117798519PW_C04074614D2NC463Hydrogen carbonateHMDB0000595Bicarbonate, or hydrogen carbonate, is a simple single carbon molecule that plays surprisingly important roles in diverse biological processes. Among these are photosynthesis, the Krebs cycle, whole-body and cellular pH regulation, and volume regulation. Since bicarbonate is charged it is not permeable to lipid bilayers. Mammalian membranes thus contain bicarbonate transport proteins to facilitate the specific transmembrane movement of HCO3(-). Bicarbonate ion is an anion that consists of one central carbon atom surrounded by three oxygen atoms in a trigonal planar arrangement, with a hydrogen atom attached to one of the oxygens. The bicarbonate ion carries a negative one formal charge and is the conjugate base of carbonic acid, H2CO3. The carbonate radical is an elusive and strong one-electron oxidant. Bicarbonate in equilibrium with carbon dioxide constitutes the main physiological buffer. The bicarbonate-carbon dioxide pair stimulates the oxidation, peroxidation and nitration of several biological targets. The demonstration that the carbonate radical existed as an independent species in aqueous solutions at physiological pH and temperature renewed the interest in the pathophysiological roles of this radical and related species. The carbonate radical has been proposed to be a key mediator of the oxidative damage resulting from peroxynitrite production, xanthine oxidase turnover and superoxide dismutase1 peroxidase activity. The carbonate radical has also been proposed to be responsible for the stimulatory effects of the bicarbonate-carbon dioxide pair on oxidations mediated by hydrogen peroxide/transition metal ions. The ultimate precursor of the carbonate radical anion being bicarbonate, carbon dioxide, peroxymonocarbonate or complexes of transition metal ions with bicarbonate-derived species remains a matter of debate. The carbonate radical mediates some of the pathogenic effects of peroxynitrite. The carbonate radical as the oxidant produced from superoxide dismutase (EC 1.15.1.1, SOD1) peroxidase activity. Peroxymonocarbonate is a biological oxidant, whose existence is in equilibrium with hydrogen peroxide and bicarbonate. (PMID: 17505962, 17215880).71-52-3C0028876917544HCO3749OC(O)=OCH2O3InChI=1S/CH2O3/c2-1(3)4/h(H2,2,3,4)BVKZGUZCCUSVTD-UHFFFAOYSA-N62.024862.00039393FDB022134Bicarbonate;Bicarbonate (hco3-);Bicarbonate anion;Bicarbonate ion;Bicarbonate ion (hco31-);Bicarbonate ions;Carbonate;Carbonate (hco31-);Carbonate ion (hco31-);Carbonic acid;Hydrocarbonate(1-);Hydrogen carbonate;Hydrogen carbonate (hco3-);Hydrogen carbonate anion;Hydrogen carbonate ion;Hydrogen carbonate ion (hco3-);Hydrogencarbonate;Hydrogentrioxocarbonate;Monohydrogen carbonate;[co2(oh)](-);Acid carbonate;Hco3(-);Hydrogen carbonic acid;Acid carbonic acid;Bicarbonic acid;Bicarbonic acid ionPW_C000463HCO32241687823933239722613153145705391103544512055711336049155611016164941787482222909222477959112786301327876211180029368119993406121209407121436122121557124123779119123994135124115118125372479126059297126360299126541481126914501127511205127922388128114206407471,4-dihydroxy-2-naphthoate1,4-Dihydroxy-2-naphthoic acid, also known as dhna-coa, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. 1,4-Dihydroxy-2-naphthoic acid is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). 1,4-Dihydroxy-2-naphthoic acid may be a unique E.coli metabolite.C0365711173[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C1=C([O-])C2=CC=CC=C2C([O-])=C1)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=OC32H38N7O19P3SInChI=1S/C32H42N7O19P3S/c1-32(2,26(44)29(45)35-8-7-21(41)34-9-10-62-31(46)18-11-19(40)16-5-3-4-6-17(16)23(18)42)13-55-61(52,53)58-60(50,51)54-12-20-25(57-59(47,48)49)24(43)30(56-20)39-15-38-22-27(33)36-14-37-28(22)39/h3-6,11,14-15,20,24-26,30,40,42-44H,7-10,12-13H2,1-2H3,(H,34,41)(H,35,45)(H,50,51)(H,52,53)(H2,33,36,37)(H2,47,48,49)/p-4/t20-,24-,25-,26+,30-/m1/s1PYTINLGPKDJURZ-HSJNEKGZSA-J949.67949.117798519PW_C04074714D2N123782251090992-Carboxy-1,4-naphthoquinoneC22039384585099OC(=O)C1=CC(=O)C2=C(C=CC=C2)C1=OC11H6O4InChI=1S/C11H6O4/c12-9-5-8(11(14)15)10(13)7-4-2-1-3-6(7)9/h1-5H,(H,14,15)UZSCBEJDBQICON-UHFFFAOYSA-N202.165202.026608673PW_C1090992162DemethylphylloquinoneHMDB0004649Demethylphylloquinone is a form of vitamin K that occurs in nature as part of a series of compounds with a common 2-methyl-1,4 naphthoquinone nucleus and differing isoprenoid side chains at the 3 position. Vitamin K forms comprise a single major plant form, phylloquinone with a phytyl side chain and a family of bacterially synthesized menaquinones (MKs) with multiprenyl side chains. Bacterially produced menaquinones are biologically active forms of vitamin K that are present in high concentrations in the human lower bowel. Both phylloquinone and menaquinones are bioactive in hepatic gamma-carboxylation but long-chain MKs are less well absorbed. Liver stores of vitamin K are relatively small. The hepatic reserves of phylloquinone (approximately 10% of the total) are labile and turn over at a faster rate than menaquinones. Vitamin K is recognised as a factor required for normal blood coagulation, and in relation to its role in bone metabolism. Vitamin K is a substrate for a liver microsomal enzyme that catalyzes the conversion of specific glutamyl residues to gamma-carboxyglutamyl residues in a limited number of proteins. These include the vitamin K-dependent clotting factors: prothrombin (factor II), factor VII, factor IX, and factor X. In the absence of vitamin K, nonfunctional clotting factors are synthesized and hemorrhage can result. Vitamin K is a coenzyme for glutamate carboxylase, which mediates the conversion of glutamate to gamma-carboxyglutamate (Gla). There are at least three Gla proteins associated with bone tissue, of which osteocalcin is the most abundant and best known. Trabecular and cortical bone appear to contain substantial concentrations of both phylloquinone and menaquinones. (PMID: 8642453, 8527227, 15018483, 1573141).C1330911954010CPD0-95410128305CC(C)CCCC(C)CCCC(C)CCC\C(C)=C\CC1=CC(=O)C2=CC=CC=C2C1=OC30H44O2InChI=1S/C30H44O2/c1-22(2)11-8-12-23(3)13-9-14-24(4)15-10-16-25(5)19-20-26-21-29(31)27-17-6-7-18-28(27)30(26)32/h6-7,17-19,21-24H,8-16,20H2,1-5H3/b25-19+UDYIPZFWVJJQJF-NCELDCMTSA-N436.6692436.334130652FDB0233912-phytyl-1,4-naphthoquinone;DemethylphylloquinonePW_C002162DMPQONE12380225146NADPHHMDB0000221Nicotinamide 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+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039514069288214069388314069916714070716814071514140742788140743597140760185109100DemethylphylloquinolC21084295369346CC(C)CCCC(C)CCCC(C)CCC\C(C)=C\CC1=CC(O)=C2C=CC=CC2=C1OC30H46O2InChI=1S/C30H46O2/c1-22(2)11-8-12-23(3)13-9-14-24(4)15-10-16-25(5)19-20-26-21-29(31)27-17-6-7-18-28(27)30(26)32/h6-7,17-19,21-24,31-32H,8-16,20H2,1-5H3/b25-19+AEFNZGGBWOQYID-NCELDCMTSA-N438.696438.349780721PW_C109100143NADPHMDB0000217Nicotinamide 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_C000143NADP1838191376857801082418839216112916174946853147961448011453081115790108601714761321596273356778117706918871051637152205720616073172137346210756221275891708197225822015184192241181119811897211120082221215216412249286125972261265024942344315437453227691329377164132773843317739633277461130775151157762433677814334778701128071311911316594120106407120429405120450122120604408120618123121142125121277429121401124121485383123063376123084135123229374123243447123713136123848464123960118124043398125473481125694297125743482126215299126528495127010206127225502127570388128100390140709168964FADHMDB0001248FAD, 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_C000964FAD999114518681923216425317628288251884021188141489421612291622492133582536223723264602364688314741134758104881652681035285102533511154961265511127561311860301556054156608216161161626390164751786499179666610770391637175205732121374652227487223907622411818216118872151189921112296225123282491244315112519227125952261271029112720292130293011304130243623318770802937712613377152134775011137750711277518115775413347761513277726337780543297837534578930331792223367927235880012368800343698071411911995840611999938412005140812010740712043240512045312212049012412127842912129841812141738212148938312274812012277612112280237412282344312306637612308713512316644812384946412386845412397639912404739812534847912537848012542948212547448112569729712597948912610729912627748412689150112692039112696850212698720712701120612731020912743250612760238812784038914079018514079918657915PhylloquinolHMDB0060502Phylloquinol, also known as phytonadiol or dihydrovitamin K1, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, phylloquinol is considered to be a quinone lipid molecule. Phylloquinol is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, phylloquinol is primarily located in the membrane (predicted from logP) and cytoplasm. Outside of the human body, phylloquinol can be found in a number of food items such as amaranth, strawberry, summer grape, and prunus (cherry, plum). This makes phylloquinol a potential biomarker for the consumption of these food products. Phylloquinol is the final product of phylloquinol biosynthesis.572-96-3C03313528058528433CPD-128314444201CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(O)C2=C(C=CC=C2)C(O)=C1CC31H48O2InChI=1S/C31H48O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24,32-33H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1BUFJIHPUGZHTHL-NKFFZRIASA-N452.7116452.36543078[R-[R*,R*-(E)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenediol;2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenediol;(E)-2-Methyl-3-phytyl-1,4-naphthalenediol;2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-1,4-naphthalenediol;2-Methyl-3-phytyl-1,4-naphthohydroquinone;Dihydrovitamin K1;Dihydro-phylloquinone;Phytonadiol;Reduced phylloquinone;Vitamin K1 hydroquinone;α-Phyllohydroquinone;alpha-PhyllohydroquinonePW_C057915Phyl123822253824-Hydroxybenzoic acidHMDB00005004-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid exists as a solid, soluble (in water), and a weakly acidic compound (based on its pKa). 4-Hydroxybenzoic acid has been detected in most biofluids, including urine, blood, feces, and saliva. Within the cell, 4-hydroxybenzoic acid is primarily located in the cytoplasm and mitochondria. 4-Hydroxybenzoic acid exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzoic acid participates in a number of enzymatic reactions. In particular, Pyruvic acid and 4-hydroxybenzoic acid can be biosynthesized from chorismate through the action of the enzyme chorismate lyase. Furthermore, 4-Hydroxybenzoic acid and octaprenyl diphosphate can be converted into 3-octaprenyl-4-hydroxybenzoate; which is catalyzed by the enzyme 4-hydroxybenzoate octaprenyltransferase. Furthermore, Pyruvic acid and 4-hydroxybenzoic acid can be biosynthesized from chorismate; which is mediated by the enzyme chorismate lyase. Finally, 4-Hydroxybenzoic acid and octaprenyl diphosphate can be converted into 3-octaprenyl-4-hydroxybenzoate through its interaction with the enzyme 4-hydroxybenzoate octaprenyltransferase. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis pathway. 4-Hydroxybenzoic acid, or p-hydroxybenzoic acid, is a phenolic derivative of benzoic acid. It a white crystalline solid that is slightly soluble in water and chloroform, but well soluble in alcohols, ether, and acetone.99-96-7C0015613530763132DB04242OC(=O)C1=CC=C(O)C=C1C7H6O3InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)FJKROLUGYXJWQN-UHFFFAOYSA-N138.122138.031694053FDB0105084-carboxyphenol;4-hydroxy-benzoate;4-hydroxy-benzoesaeure;4-hydroxy-benzoic acid;4-hydroxybenzoate;4-hydroxybenzoic acid;Paraben-acid;P-carboxyphenol;P-hydroxy-benzoate;P-hydroxy-benzoic acid;P-hydroxybenzoate;P-hydroxybenzoic acid;P-salicylate;P-salicylic acidPW_C0003824-HBA1214371311637915011280000364800013638000236680003365120933407123499119125873481127334206109102Polyprenyl diphosphateC05847814037531CC(C)=CCC\C(C)=C\COP(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-N314.2091314.068426018PW_C109102109103 4-Hydroxy-3-polyprenylbenzoateC0584881411845CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=OC17H22O3InChI=1S/C17H22O3/c1-12(2)5-4-6-13(3)7-8-14-11-15(17(19)20)9-10-16(14)18/h5,7,9-11,18H,4,6,8H2,1-3H3,(H,19,20)/b13-7+HKIMBCGCVPYUTJ-NTUHNPAUSA-N274.3548274.15689457PW_C1091031091043-Polyprenyl-4,5-dihydroxybenzoateC175549602389964694CC(C)=CCC\C(C)=C\CC1=CC(=CC(O)=C1O)C(O)=OC17H22O4InChI=1S/C17H22O4/c1-11(2)5-4-6-12(3)7-8-13-9-14(17(20)21)10-15(18)16(13)19/h5,7,9-10,18-19H,4,6,8H2,1-3H3,(H,20,21)/b12-7+GJZLZMVQYJZMIO-KPKJPENVSA-N290.3542290.1518091923,4-Dihydroxy-5-polyprenylbenzoatePW_C1091041091053-Polyprenyl-4-hydroxy-5-methoxybenzoateC175599602390481182COC1=C(O)C(C\C=C(/C)CCC=C(C)C)=CC(=C1)C(O)=OC18H24O4InChI=1S/C18H24O4/c1-12(2)6-5-7-13(3)8-9-14-10-15(18(20)21)11-16(22-4)17(14)19/h6,8,10-11,19H,5,7,9H2,1-4H3,(H,20,21)/b13-8+HKFHKFTYNQVIHQ-MDWZMJQESA-N304.3808304.167459256PW_C1091051091062-Polyprenyl-6-methoxyphenolC175529602389781179COC1=CC=CC(C\C=C(/C)CCC=C(C)C)=C1OC17H24O2InChI=1S/C17H24O2/c1-13(2)7-5-8-14(3)11-12-15-9-6-10-16(19-4)17(15)18/h6-7,9-11,18H,5,8,12H2,1-4H3/b14-11+ZNGWNKADFSBHQZ-SDNWHVSQSA-N260.3713260.177630012PW_C1091061091072-Polyprenyl-6-methoxy-1,4-benzoquinoneC175609602390581183COC1=CC(=O)C=C(C\C=C(/C)CCC=C(C)C)C1=OC17H22O3InChI=1S/C17H22O3/c1-12(2)6-5-7-13(3)8-9-14-10-15(18)11-16(20-4)17(14)19/h6,8,10-11H,5,7,9H2,1-4H3/b13-8+CNUQZHQKEQFDPU-MDWZMJQESA-N274.3548274.15689457PW_C109107109112 2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinoneC175619602390681184COC1=CC(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=OC18H24O3InChI=1S/C18H24O3/c1-12(2)7-6-8-13(3)9-10-15-14(4)16(19)11-17(21-5)18(15)20/h7,9,11H,6,8,10H2,1-5H3/b13-9+GKCNNWJPOJGTLV-UKTHLTGXSA-N288.3814288.172544634PW_C109112109110 2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinoneC175629602390781185COC1=C(O)C(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=OC18H24O4InChI=1S/C18H24O4/c1-11(2)7-6-8-12(3)9-10-14-13(4)15(19)17(21)18(22-5)16(14)20/h7,9,21H,6,8,10H2,1-5H3/b12-9+JVLAJUCFVRPDAQ-FMIVXFBMSA-N304.3808304.167459256PW_C109110109111UbiquinoneC00399368916389COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=OC19H26O4InChI=1S/C19H26O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10H,7,9,11H2,1-6H3/b13-10+SQQWBSBBCSFQGC-JLHYYAGUSA-N318.4073318.18310932Coenzyme Q;CoQPW_C1091111144NADHHMDB0001487NADH 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_C001144NADH14341533490864810111521275514695422304927811728362931099480618481218482128490464959315169955240103533211153581125466123547912555931355698100573710858291415915147594515160271556079161638716472178677111768931607011188709916371722057195206746222282442268360225908622411809198118212161232024913003298130153001325522342403322426183157710713277123133772081347737133177651336776683347770033277707130779171137798634780009368806911199382212411054938811285494115838118119955406120172407120378122120986408121162425121244126121693429121818383122616384122745120123127447123138136123551374123734460123814443124242464124371398125189121125345479125531481125762297125808299125926482126516495126767480126888501127385502128090390128362391128429395140759185109101PhylloquinoneC02059514818067CC(C)CCCC(C)CCCC(C)CCC\C(C)=C\CC1=C(C)C(=O)C2=CC=CC=C2C1=OC31H46O2InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+MBWXNTAXLNYFJB-LKUDQCMESA-N450.6957450.349780716PW_C109101721NADHMDB0000902NAD (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_C000721NAD14041503353865110111421134431273514665422294927791728352931079480718481318481928490264960315167955238103533411153601125469123548212555901355610118569610057381085827141591214759421516024155607215760761616385164691786772117689016070121887097163717420571972067405198745922282412268359225908522411819216123222491300629813018300132562234240432242619315771041327712013377209134773703317765033677667334777023327770913077915113779833477840635680006368806901199382512411055238811275016611285394119929122119952406120171407120834419120984408121159425121242126121259429121817383122614384122742120123130447123141136123419455123549374123731460123812443123829464124370398125187121125319297125342479125530481125806299125825490125924482126515495126765480126885501127278507127383502128089390128360391128428395140757185104784FMNThe trianion arising from deprotonation of the diphosphate hydroxy groups and the imide nitrogen of flavin mononucleotide (FMN).C000614422919958210CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)C1=NC(=O)[N-]C(=O)C1=N2C17H18N4O9PInChI=1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H3,20,25,26,27,28,29)/p-3/t11-,12+,14-/m0/s1ANKZYBDXHMZBDK-SCRDCRAPSA-K453.325453.082785913flavin mononucleotide;riboflavin 5'-phosphatePW_C104784FMN112914-hydroxyphenylpyruvate dioxygenaseP93836HPD41.13.11.27906015113957029313957125314059087114090890614140193514206521436051153143796117523560Homogentisate prenyltransferaseF4J8K0HST413957222511556homogentisate solanesyltransferaseQ1ACB3Homogentisate solanesyltransferase is an enzyme localized to the chloroplast membrane that catalyzes a reaction in the plastoquinol-9 biosynthesispathway whereby solanesyl diphosphate and homogentisate are converted into 2-methyl-6-solanesyl-1,4-benzoquinol. It requires magnesium ion as a cofactor.HST42.5.1.1171234422514059187214090990714140293614206691714360611541437971176115572-methyl-6-phytyl-1,4-hydroquinone methyltransferaseQ9LY742-methyl-6-phytyl-1,4-hydroquinone methyltransferase is an enzyme localized to the chloroplast membrane that catalyzes a reaction in the plastoquinol-9 biosynthesis pathway whereby 2-methyl-6-solanesyl-1,4-benzoquinol is converted into plastoquinol-9.
VTE342.1.1.295123462251405928721409109071414039361420679171436071154143798117623526Homogentisate phytyltransferase 1, chloroplasticQ8VWJ1
Involved in the synthesis of tocopherol (vitamin E). Catalyzes the condensation of homogentisate and phytyl diphosphate to form dimethylphytylhydrquinone. Low activity with geranylgeranyl diphosphate as substrate, but no activity with farnesyl diphosphate or solanesyl diphosphate. Tocopherol functions to limit lipid oxidation during seed desiccation, quiescence and germination and early seedling development. Protects thylakoid membrane lipids from photooxidation and is required for low-temperature adaptation.
HPT142.5.1.1151394642251405938721409119071414049361420689171436081154143799117623527Tocopherol cyclase, chloroplasticQ94FY7
Involved in the synthesis of both tocopherols and tocotrienols (vitamin E), which presumably protect photosynthetic complexes from oxidative stress. Catalyzes the conversion of 2-methyl-6-phytyl-1,4-hydroquinone and 2,3-dimethyl-5-phytyl-1,4-hydroquinone (DMPQ) to delta- and gamma-tocopherol respectively. Converts also 2,3-dimethyl-5-geranylgeranyl-1,4-hydroquinone (DMGQ) to gamma-tocotrienol.
VTE145.5.1.241394662251405948721409129071414059361420699171436091154143800117623528Tocopherol O-methyltransferase, chloroplasticQ9ZSK1
Involved in the synthesis of tocopherol (vitamin E). Methylates gamma- and delta-tocopherol to form beta- and alpha-tocopherol, respectively.
VTE442.1.1.951394682251405958721409139071414069361420709171436101154143801117613577Tyrosine aminotransferaseQ9LVY1
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using L-glutamate in vitro. Can convert phenylalanine to phenylpyruvate and catalyze the reverse reaction in vitro.
TAT42.6.1.5769991517705322477058253140100293140596873140907222140914908141407937142071414343771436111155143802117714407212089659UnknownUnknown45.4.99.-; 4.2.1.-; 4.99.1.7; 1.14.14.77; 2.4.1.354; 2.4.1-;593015174662227490223749422481712259272221809622538096337980964380136607293137045693137051249139126286139146227139233226140267285140378714042984614065229414346811471435941150143638116223529Isochorismate synthase 1, chloroplasticQ9S7H8
Involved in the synthesis of salicylic acid (SA) required for both local and systemic acquired resistance (LAR and SAR) while SA synthesized through the phenylalanine ammonium lyase (PAL) pathway seems to potentiate plant cell death. Also involved in phylloquinone (vitamin K1) synthesis. Has no isochorismate pyruvate lyase (IPL) activity.
ICS145.4.4.213947022523551Protein PHYLLO, chloroplasticQ15KI9
Multifunctional enzyme required for phylloquinone (vitamin K1) biosynthesis.
PHYLLO42.2.1.9; 4.2.1.113; 4.2.99.20139553225235522-succinylbenzoate--CoA ligase, chloroplastic/peroxisomalQ8VYJ1
Involved in the biosynthesis of phylloquinone (vitamin K1). Converts 2-succinylbenzoate (OSB) to 2-succinylbenzoyl-CoA (OSB-CoA).
AAE1446.2.1.2613955422523562ABC transporter D family member 1Q94FB9
Contributes to the transport of fatty acids and their derivatives (acyl CoAs) across the peroxisomal membrane. Provides acetate to the glyoxylate cycle in developing seedlings. Involved in pollen tube elongation, ovule fertilization, and seeds germination after imbibition (controls the switch between the opposing developmental programs of dormancy and germination), probably by promoting beta-oxidation of storage lipids during gluconeogenesis. Required for biosynthesis of jasmonic acid and conversion of indole butyric acid to indole acetic acid. Confers sensitivity to monofluoroacetic acid (FAc), a toxic acetate analog, and to 2,4-dichlorophenoxybutyric acid (2,4-DB) and indole-3-butyric acid (IBA), two precursors of auxin after beta-oxidation.
ABCD147.6.2.4139589226235531,4-dihydroxy-2-naphthoyl-CoA synthase, peroxisomalQ8GYN9
Involved in the biosynthesis of phylloquinone (vitamin K1). Converts o-succinylbenzoyl-CoA (OSB-CoA) to 1,4-dihydroxy-2-naphthoyl-CoA (DHNA-CoA) (By similarity).
MENB44.1.3.36139557226235541,4-dihydroxy-2-naphthoyl-CoA thioesterase 1Q9SX65
Catalyzes the hydrolysis of the thioester bond of 1,4-dihydroxy-2-naphthoyl-CoA (DHNA-CoA) in peroxisomes, a necessary step to form the naphthoquinone ring of phylloquinone (vitamin K(1)). Is not active on benzoyl-CoA, phenylacetyl-CoA, succinyl-CoA and palmitoyl-CoA thioesters.
DHNAT143.1.2.-139559226115612-carboxy-1,4-naphthoquinone phytyltransferaseQ0WUA32-carboxy-1,4-naphthoquinone phytyltransferase is an enzyme localized to the chloroplast membrane that catalyzes a reaction in the phylloquinol biosynthesis pathway whereby phytyl diphosphate and 2-carboxy-1,4-naphthoquinone are converted into demethylphylloquinone.ABC442.5.1.1301236522511562demethylphylloquinone dehydrogenaseQ8GXR9Demethylphylloquinone dehydrogenase is an enzyme in the chloroplast that catalyzes a reaction in the phylloquinol biosynthesis pathway whereby demethylphylloquinone is converted into demethylphylloquinol. It requires FAD as a cofactor.NDC141.6.5.121236722511563demethylphylloquinol methyltransferaseQ3ED65Demethylphylloquinol methyltransferase is an enzyme in the chloroplast that catalyzes a reaction in the phylloquinol biosynthesis pathway whereby demethylphylloquinol is converted into phylloquinol.MENG42.1.1.-12369225235564-hydroxybenzoate polyprenyltransferase, mitochondrialQ93YP7
Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB, generating the first membrane-bound Q intermediate. Required for embryo development.
PPT142.5.1.3913956322423557Ubiquinone biosynthesis O-methyltransferase, mitochondrialO49354
O-methyltransferase that catalyzes the 2 O-methylation steps in the ubiquinone biosynthetic pathway.
COQ342.1.1.64; 2.1.1.11413959622414034871523558Ubiquinone biosynthesis monooxygenase COQ6, mitochondrialF4J6I6
FAD-dependent monooxygenase required for the C5-ring hydroxylation during ubiquinone biosynthesis. Catalyzes the hydroxylation of 3-polyprenyl-4-hydroxybenzoic acid to 3-polyprenyl-4,5-dihydroxybenzoic acid. The electrons required for the hydroxylation reaction may be funneled indirectly from NADPH via a ferredoxin/ferredoxin reductase system to COQ6.
COQ641.14.13.-139566224235592-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial\Q9LVC8413956822423555NAD(P)H dehydrogenase (quinone) FQR1Q9LSQ5
Catalyzes the transfer of electrons from NADH and NADPH to several quinones in vitro. May act as detoxification enzyme, and protect against auxin-induced oxidative stress.
FQR141.6.5.213956128550204-hydroxyphenylpyruvate dioxygenase4PW_P005020123101129114428Homogentisate prenyltransferase4PW_P01442824381235601395732255434homogentisate solanesyltransferase4PW_P00543412788115566914231234522554352-methyl-6-phytyl-1,4-hydroquinone methyltransferase4PW_P00543512789115571234722514393Homogentisate phytyltransferase 1, chloroplastic4PW_P014393243452352613946522514394Tocopherol cyclase, chloroplastic4PW_P014394243462352713946722514395Tocopherol O-methyltransferase, chloroplastic4PW_P01439524347235281394692256664L-Tyrosine aminotransferase4PW_P006664144071357775811487700015114430Chorismate chloroplast transporter4PW_P01443024384965913958722514396Isochorismate synthase 1, chloroplastic4PW_P0143962434823529142310907313947122514419Protein PHYLLO, chloroplastic4PW_P014419243722355114271090731428109098144202-succinylbenzoate--CoA ligase, chloroplastic/peroxisomal4PW_P0144202437323552139555225139556226144312-succinylbenozyl-CoA chloroplast transporter4PW_P01443124385965913958822514432ABC transporter D family member 14PW_P0144322438623562139590226144211,4-dihydroxy-2-naphthoyl-CoA synthase, peroxisomal4PW_P01442124374235531429463139558226144221,4-dihydroxy-2-naphthoyl-CoA thioesterase 14PW_P0144222437523554139560226144331,4-dihydroxy-2-naphthoate peroxisome transporter4PW_P014433243879659139593226144341,4-dihydroky-2-naphthoate chloroplast transpoerter4PW_P01443424388965913959422554392-carboxy-1,4-naphthoquinone phytyltransferase4PW_P0054391279311561123662255440demethylphylloquinone dehydrogenase4PW_P0054401279411562692964123682255441demethylphylloquinol methyltransferase4PW_P005441127951156312370225144364-hydroxybenzoic acid mitochondrial transporter4PW_P014436243909659139595224144244-hydroxybenzoate polyprenyltransferase, mitochondrial4PW_P0144242437723556143110907313956422414425Ubiquinone biosynthesis O-methyltransferase, mitochondrial4PW_P014425243782355713956522414426Ubiquinone biosynthesis monooxygenase COQ6, mitochondrial4PW_P01442624379235581432964139567224144272-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial4PW_P014427243802355913956922414437Phylloquinol chloropast transporter4PW_P01443724391965913959722514423NAD(P)H dehydrogenase (quinone) FQR14PW_P014423243762355514301047841395622857368falsePW_R007368Right304905581Compoundfalse3049110651Compoundtrue3049213161Compoundtrue30493841Compoundfalse733750201.13.11.27213113PW_R213113Right8194211047561Compoundfalse819422841Compoundfalse8194231088861Compoundfalse819424579091Compoundfalse81942513161Compoundfalse2027315434213114PW_R213114Right819426579091Compoundfalse8194271090891Compoundfalse819428197991Compoundfalse8194299211Compoundfalse819430579101Compoundfalse2027325435213115PW_R213115Right8194311047571Compoundfalse819432841Compoundfalse8194331088861Compoundfalse81943413161Compoundfalse819435197991Compoundfalse202733143932.5.1.115213116PW_R213116Right819436197991Compoundfalse81944017311Compoundfalse202734143945.5.1.24213117PW_R213117Right8194449211Compoundfalse81944617311Compoundfalse8194497491Compoundfalse81945127251Compoundfalse202735143952.1.1.95213118PW_R213118Right819454197991Compoundfalse8194559211Compoundfalse8194561090931Compoundfalse8194577491Compoundfalse2027365435213119PW_R213119Right8194581090931Compoundfalse81945911491Compoundfalse202737143945.5.1.24213120PW_R213120Right8194609211Compoundfalse81946111491Compoundfalse8194627491Compoundfalse81946312611Compoundfalse20273814395213121PW_R213121Right81946421451Compoundfalse819465841Compoundfalse8194661088861Compoundfalse81946713161Compoundfalse8194681090891Compoundfalse20273914393213122PW_R213122Right8194691090891Compoundfalse8194709211Compoundfalse8194717491Compoundfalse8194721090911Compoundfalse2027405435213123PW_R213123Right8194731090911Compoundfalse81947481361Compoundfalse20274114394213124PW_R213124Right8194759211Compoundfalse81947681361Compoundfalse81947727201Compoundfalse8194787491Compoundfalse20274214395213125PW_R213125Right8194791090891Compoundfalse819480112261Compoundfalse20274314394213126PW_R213126Right8194819211Compoundfalse819482112261Compoundfalse8194831090921Compoundfalse8194847491Compoundfalse20274414395213111PW_R213111Right8194131031Compoundfalse8194141341Compoundfalse8194155581Compoundfalse819416951Compoundfalse2027296664213127PW_R213127Both81948577481Compoundfalse8194861046481Compoundfalse202745143965.4.4.2213163PW_R213163Right8196281046481Compoundfalse8196291341Compoundfalse81963013161Compoundfalse819631407421Compoundfalse202780144192.2.1.9,4.2.1.113, 4.2.99.20213164PW_R213164Right819632407421Compoundfalse819633407431Compoundfalse8196341641Compoundfalse20278114419213165PW_R213165Right819635407431Compoundfalse819636407441Compoundfalse81963714201Compoundfalse20278214419213166PW_R213166Right8196384141Compoundfalse819639407441Compoundfalse81964010991Compoundfalse819641321Compoundfalse8196421088861Compoundfalse819643432981Compoundfalse202783144206.2.1.26213167PW_R213167Right819644432981Compoundfalse819645407461Compoundfalse81964614201Compoundfalse202784144214.1.3.36213168PW_R213168Right819647407461Compoundfalse81964814201Compoundfalse819649407471Compoundfalse81965010991Compoundfalse202785144223.1.2.-213169PW_R213169Right8196511047571Compoundfalse8196521090991Compoundfalse81965313161Compoundfalse8196541088861Compoundfalse81965521621Compoundfalse2027865439213170PW_R213170Right81965621621Compoundfalse8196571461Compoundfalse819658400341Compoundfalse8196591091001Compoundfalse8196601431Compoundfalse20278754401.6.5.12213171PW_R213171Right8196611091001Compoundfalse8196629211Compoundfalse8196637491Compoundfalse819664579151Compoundfalse2027885441213178PW_R213178Both81969077481Compoundfalse8196911641Compoundfalse8196923821Compoundfalse213173PW_R213173Right8196703821Compoundfalse8196711091021Compoundfalse8196721088861Compoundfalse8196731091031Compoundfalse202790144242.5.1.39213180PW_R213180Right8196951091031Compoundfalse8196961091041Compoundfalse213174PW_R213174Right8196749211Compoundfalse8196751091041Compoundfalse8196767491Compoundfalse8196771091051Compoundfalse202791144252.1.1.64,2.1.1.114213181PW_R213181Right8196971091051Compoundfalse8196981091061Compoundfalse213175PW_R213175Right8196781091061Compoundfalse81967910651Compoundfalse81968014201Compoundfalse8196811091071Compoundfalse202792144261.14.13.-213176PW_R213176Right8196829211Compoundfalse8196831091071Compoundfalse8196847491Compoundfalse8196851091121Compoundfalse20279314427213182PW_R213182Right8196991091121Compoundfalse8197001091101Compoundfalse213177PW_R213177Right8196869211Compoundfalse8196871091101Compoundfalse8196887491Compoundfalse8196891091111Compoundfalse202794144252.1.1.64,2.1.1.114213172PW_R213172Right81966511441Compoundfalse8196661091011Compoundfalse819669400341Compoundfalse819667579151Compoundfalse8196687211Compoundfalse202789144231.6.5.210892PW_T01089211277841Compound253225Right2058144282020-07-20T14:20:21-06:002020-07-20T14:20:21-06:0022510893PW_T0108931127877481Compound253225Right2059144302020-07-21T11:24:56-06:002020-07-21T11:24:56-06:0022510894PW_T01089411279432981Compound225253Right2060144312020-07-21T12:04:54-06:002020-07-21T12:04:54-06:0022510895PW_T01089511280432981Compound253226Right2061144322020-07-21T12:13:58-06:002020-07-21T12:13:58-06:0022610896PW_T01089611281407471Compound226253Right2062144332020-07-21T12:29:24-06:002020-07-21T12:29:24-06:0022610897PW_T01089711282407471Compound253225Right2063144342020-07-21T13:33:44-06:002020-07-21T13:33:44-06:0022510900PW_T010900112853821Compound253224Right2066144362020-07-21T16:50:16-06:002020-07-21T16:50:16-06:0022410901PW_T01090111286579151Compound225253Right2067144372020-07-21T18:11:51-06:002020-07-21T18:11:51-06:0022530836455582533false40079510regular1001203083646106525365false54670010regular78783083647131625352false81669810regular78783083648842533false97080110regular1001103083649842253false151580110regular10011030836501047562253false170538110regular10011030836511088862253false205537910regular1001103083652579092253false240550410regular1001303083653131622552false206662910regular787830836544232259false187551810regular1002530836551090892253false260536010regular1001403083656197992253false247035910regular10011030836579212253false257565410regular1001103083658579102253false297551410regular10010030836591047572253false190084610regular10011030836601088862253false229084210regular1001103083661131622552false2246104210regular78783083662197992253false247594010regular100110308366317312253false313084510regular10010030836649212253false326073010regular10011030836657492253false359072510regular100110308366627252253false377084510regular10010030836679212253false268599010regular10011030836681090932253false3160108710regular10012030836697492253false300599210regular100110308367011492253false3560109710regular10010030836719212253false367099210regular10011030836727492253false396099210regular100110308367312612253false4115109710regular100100308367421452253false1755133110regular10011030836751088862253false2070132910regular1001103083676131622552false2061152910regular787830836771090892253false2310142710regular10014030836789212253false2430124710regular10011030836797492253false2715124710regular10011030836801090912253false2890133210regular100140308368181362253false3330135210regular10010030836829212253false3470125210regular100110308368327202253false3985135710regular10010030836847492253false3765125210regular1001103083685112262253false2780163710regular10010030836869212253false2885152210regular10011030836871090922253false3315163710regular10010030836887492253false3170152710regular1001103083689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855 C530 855 610 854 640 854 5false184202701M585 778 C585 828 610 854 640 854 5false184202702M855 776 C857 831 820 854 790 854 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false4202703M970 856 C940 856 820 854 790 854 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false4202704M1070 856 C1100 856 1200 856 1230 856 83false184202705M1515 856 C1485 856 1410 856 1380 856 83false18trueM 1165.9468550441647 13.26155629629604 L 1151 12 L 1157.380887721186 25.575134323078345false4202706M1755 491 C1757 549 1820 563 1850 563 5false184202707M1565 801 C1563 783 1564 586 1564 566 C1584 564 1820 567 1850 563 5false184202708M2105 489 C2105 549 2030 563 2000 563 5false18trueM 1490.9468550441647 358.261556296296 L 1476 357 L 1482.380887721186 370.5751343230783false4202709M2405 564 C2375 564 2030 563 2000 563 5false18trueM 1490.9468550441647 358.261556296296 L 1476 357 L 1482.380887721186 370.5751343230783false4202710M2105 629 C2098 572 2030 563 2000 563 5false18trueM 1490.9468550441647 358.261556296296 L 1476 357 L 1482.380887721186 370.5751343230783false4202711M1710 553.5 L1710 603.5 L1760 553.5 z10true184202712M2505 564 C2535 564 2675 564 2705 564 5false184202713M2655 500 C2655 550 2675 564 2705 564 5false184202714M2520 469 C2523 539 2668 564 2705 564 5false184202715M2630 654 C2636 604 2675 564 2705 564 5false184202716M2975 564 C2945 564 2885 564 2855 564 5false18trueM 2215.9468550441647 88.26155629629604 L 2201 87 L 2207.380887721186 100.57513432307834false4202717M2000 901 C2005 960 2045 996 2075 996 5false184202718M1565 911 C1564 946 1564 983 1564 999 C1582 999 2043 998 2075 996 5false184202719M2290 897 C2292 965 2255 996 2225 996 5false18trueM 1202.9468550441647 98.26155629629604 L 1188 97 L 1194.380887721186 110.57513432307834false4202720M2285 1042 C2279 1006 2265 996 2225 996 5false18trueM 1202.9468550441647 98.26155629629604 L 1188 97 L 1194.380887721186 110.57513432307834false4202721M2475 995 C2445 995 2255 996 2225 996 5false18trueM 1202.9468550441647 98.26155629629604 L 1188 97 L 1194.380887721186 110.57513432307834false4202722M2525 940 C2523 916 2526 914 2525 896 C2543 895 2740 895 2760 895 5false184202723M3130 895 C3100 895 2940 895 2910 895 5false18trueM 2347.9468550441647 498.261556296296 L 2333 497 L 2339.380887721186 510.5751343230783false4202724M3310 840 C3312 875 3375 897 3405 897 5false184202725M3230 895 C3260 895 3375 897 3405 897 5false184202726M3640 835 C3640 879 3585 897 3555 897 5false18trueM 2347.9468550441647 498.261556296296 L 2333 497 L 2339.380887721186 510.5751343230783false4202727M3770 895 C3740 895 3585 897 3555 897 5false18trueM 2347.9468550441647 498.261556296296 L 2333 497 L 2339.380887721186 510.5751343230783false4202728M2525 1050 C2527 1070 2524 1130 2525 1150 C2544 1150 2789 1148 2815 1150 5false184202729M2735 1100 C2737 1130 2785 1150 2815 1150 5false184202730M3160 1147 C3130 1147 2995 1150 2965 1150 5false18trueM 2155.9468550441647 755.261556296296 L 2141 754 L 2147.380887721186 767.5751343230784false4202731M3055 1102 C3054 1136 2995 1150 2965 1150 5false18trueM 2155.9468550441647 755.261556296296 L 2141 754 L 2147.380887721186 767.5751343230784false4202732M3260 1147 C3290 1147 3305 1147 3335 1147 5false184202733M3560 1147 C3530 1147 3515 1147 3485 1147 5false18trueM 3039.9468550441647 755.261556296296 L 3025 754 L 3031.380887721186 767.5751343230784false4202734M3720 1102 C3722 1137 3750 1149 3780 1149 5false184202735M3660 1147 C3690 1147 3750 1149 3780 1149 5false184202736M4010 1102 C4011 1147 3947 1152 3930 1149 5false18trueM 3039.9468550441647 755.261556296296 L 3025 754 L 3031.380887721186 767.5751343230784false4202737M4115 1147 C4072 1150 3960 1149 3930 1149 5false18trueM 3039.9468550441647 755.261556296296 L 3025 754 L 3031.380887721186 767.5751343230784false4202738M1805 1441 C1805 1475 1855 1496 1885 1496 5false184202739M1565 911 C1565 944 1559 1480 1559 1496 C1576 1497 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