115434Pathway Ubiquinone and other terpenoid-quinone biosynthesisMetabolicPW124592CenterPathwayVisualizationContext1248681000010000#000099PathwayVisualization115297115434 Ubiquinone and other terpenoid-quinone biosynthesisMetabolic1361CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404CardiomyocyteCL:00007466MyocyteCL:000018712AstrocyteCL:00001271Homo sapiens9606EukaryoteHuman4Arabidopsis thaliana3702EukaryoteThale cress12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat6Caenorhabditis elegans6239EukaryoteRoundworm3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast49Bathymodiolus platifrons220390EukaryoteDeep sea mussel10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote2Bacteria2ProkaryoteBacteria21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia4136Cannabis sativa3483Eukaryotehemp329Andrographis paniculata175694Eukaryote5CytoplasmGO: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:007038263ApoplastGO:00480462Endothelium BTO:00003931LiverBTO:00007597294Adrenal MedullaBTO:000004971828StomachBTO:0001307155267Nervous SystemBTO:00014845cardiocyteBTO:00015398Blood VesselBTO:000110274119MuscleBTO:0000887141183Sympathetic Nervous SystemBTO:000183224BrainBTO:000014289168511PW_BS0000082111PW_BS0000022253541PW_BS000024151141PW_BS000151224241PW_BS000024253541PW_BS0000241115121PW_BS0001111321121PW_BS000132122551PW_BS000122124151PW_BS0001241355171PW_BS0001351181171PW_BS000118388161PW_BS0001129611PW_BS0000095411PW_BS00000516212PW_BS000016181311PW_BS00001814101PW_BS0000142811611PW_BS0000283211PW_BS000003101711PW_BS000010311511PW_BS000031204111PW_BS00002015111PW_BS0000154311PW_BS000004331811PW_BS00003349711PW_BS0000492441011PW_BS000024221411PW_BS00002229111PW_BS000029422411PW_BS00004213121PW_BS0000131231751PW_BS0001231251351PW_BS000125126651PW_BS00012612711651PW_BS00012710813PW_BS0001081471241PW_BS00014715924PW_BS000159188118PW_BS0000241632181PW_BS0001631601181PW_BS0001602137181PW_BS00002421013181PW_BS00002421217181PW_BS0000242164181PW_BS0000241985181PW_BS0000242156181PW_BS0000242111018PW_BS0000241644PW_BS0001642863641PW_BS000024226441PW_BS0000242491341PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS00002430013101PW_BS0000243016101PW_BS000024302116101PW_BS0000242231241PW_BS000024171211PW_BS000017315123PW_BS00002429341PW_BS0000242941141PW_BS00002413412121PW_BS00013413013121PW_BS0001303317121PW_BS00002833217121PW_BS0000281136121PW_BS0001131151012PW_BS0001153344121PW_BS0000283361121PW_BS000028337116121PW_BS0000281122121PW_BS00011212915121PW_BS00012934141121PW_BS0000281141112PW_BS0001141333121PW_BS00013332914121PW_BS00002834524121PW_BS00002834318121PW_BS000028360410121PW_BS000028408451PW_BS000115405105PW_BS000115407251PW_BS0001154141551PW_BS000115409115PW_BS000115406351PW_BS0001154151851PW_BS000115383751PW_BS00010043441051PW_BS000115429151PW_BS0001153821451PW_BS0001004182451PW_BS0001153841251PW_BS0001003744171PW_BS0000534436171PW_BS0001153761017PW_BS00005344717171PW_BS00011513613171PW_BS000136448116171PW_BS0001151192171PW_BS00011945015171PW_BS0001151371117PW_BS0001371203171PW_BS00012045118171PW_BS0001153987171PW_BS000113469410171PW_BS0001154641171PW_BS00011539914171PW_BS00011345424171PW_BS00011512112171PW_BS0001214824101PW_BS0001154781010PW_BS0001154831110PW_BS0001152975101PW_BS0000244793101PW_BS0001154812101PW_BS0001152991101PW_BS00002448414101PW_BS0001154957101PW_BS00011548924101PW_BS00011548012101PW_BS000115502461PW_BS000115207661PW_BS000024209106PW_BS000024208116PW_BS000024205561PW_BS000024501361PW_BS0001155041861PW_BS000115206261PW_BS00002451541061PW_BS0001153891461PW_BS0001123951361PW_BS000113390761PW_BS0001125062461PW_BS0001153911261PW_BS00011211PW_BS000001432511PW_BS0000437028511PW_BS000070103331PW_BS000103101531PW_BS000101100521PW_BS0001001553241PW_BS0001551613181PW_BS0001611783211PW_BS000178107313PW_BS0001071901118PW_BS000024222341PW_BS0000242771218PW_BS00002417018PW_BS0001702905491PW_BS0000243183123PW_BS0000243331212PW_BS00002835625121PW_BS0000283683601PW_BS000028412125PW_BS0001154192551PW_BS0001154461217PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS000115185321PW_BS000024261115PW_BS000026397113PW_BS000039215114PW_BS00002146114PW_BS000046592711PW_BS000059231511PW_BS000023711PW_BS000007918511PW_BS000091541315PW_BS000054562611PW_BS0000561041431PW_BS00010416611PW_BS00016619914181PW_BS00002421425181PW_BS0000242881441PW_BS0000242851041PW_BS0000243081011PW_BS00002433527121PW_BS000028184121PW_BS000024372102PW_BS0000285181PW_BS00005127151PW_BS0000274222751PW_BS00011537527171PW_BS00005349127101PW_BS0001155082761PW_BS0001158911421PW_BS000552301711PW_BS000030509516PW_BS0000501951318PW_BS0000243093911PW_BS00002433817121PW_BS0000283511512PW_BS00002834695126PW_BS00002836139121PW_BS0000283863951PW_BS0001003973961PW_BS00011340139171PW_BS0001134131751PW_BS000115435155PW_BS00011544917171PW_BS0001154701517PW_BS0001154991510PW_BS000115517156PW_BS000115193513PW_BS000019105113PW_BS00010512815121PW_BS0001283775411PW_BS0000693785511PW_BS00006940254121PW_BS00011540355121PW_BS0001154415451PW_BS0001154425551PW_BS0001154101551PW_BS00011547654171PW_BS00011547755171PW_BS00011544415171PW_BS000115117131PW_BS0001171572241PW_BS00015785241011PW_BS00008522014PW_BS0000242892491PW_BS00002432711125PW_BS00002834713125PW_BS000028943PW_BS0000944239556PW_BS0001154241155PW_BS0001154251355PW_BS00011545895176PW_BS00011545911175PW_BS00011546013175PW_BS0001151873118PW_BS00002472513PW_BS000072711113PW_BS0000713201123PW_BS0000248424111PW_BS00008459724112PW_BS0003365131761PW_BS000115892351361PW_BS00055288863136PW_BS00055290911361PW_BS0005589101361PW_BS0005589173511PW_BS000558890136PW_BS000552138113291PW_BS0006031382353291PW_BS00060313833291PW_BS0006035584-Hydroxyphenylpyruvic 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-N3-(4-hydroxyphenyl)-2-oxopropanoic acid180.1574180.042258744-2.0824-hydroxyphenylpyruvic acid0-1FDB022193(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-Ndioxygen31.998831.9898292440singlet oxygen00FDB022589Dioxygen;Molecular oxygen;O2;Oxygen;Oxygen molecule;[oo];Dioxygene;Disauerstoff;E 948;E-948;E948PW_C001065O29591105245165001850585491462528638364910674316882075415763476933836213754920162425312228032942604247471354671235480125549312655081275809108597314761291597006188703216370501607319213753321075602128395151118162161186419811883215118942111205722512063164122472861227922612325249127062911271629213004298130163001302630113038302132602234227617426573157691029377044294772141347735011177363130773773317739533277497113775121157753733477626336777233377773611277747129777563417780511477812133780703297815113278381345788053437911136012004740812038312212042640512054240712055341412059440912060140612088341512104512412110438312160543412165642912211738212257341812268938412279837412282244312302713512306037612312844712313913612316344812317611912318745012321913712322612012345945112360911812366939812416346912421446412466939912514545412527512112542548212570647812573148312573729712574047912588448112610029912627248412652249512672148912682548012696450212698620712719820912721420812721920512722250112730550412734520612755738812757451512783538912808139512809539012831250612843239184Homogentisic 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-N2-(2,5-dihydroxyphenyl)acetic acid168.1467168.042258744-1.323homogentisic acid0-1FDB021899(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_C000084HMGNCA1295819962905915178478111791041321210121221215921241235771351241501181275583881316Carbon 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-Nmethanedione44.009543.9898292440.630carbon dioxide00DBMET00423FDB014084Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744PW_C001316CO25081211204448013503186403677316952080651133431638491745225511731447052831035320111575010857711015968100602615560781616471178663710769221907017160703516370611887163205730819873332137461222753021082152258223151915824911849277119081701246422612688290426263154352331876994293771221337717013277470333777391127775012977763341780771347840535678427334789413317922713080008368806751198071713594836384113291391115549121119954406120089122120155407120364412120556414120833419120922124120991408121284125121505383122744120123011446123190450123418455123489118123556374123855136124063398125344479125460297125516481125824490125870299125931482126280480126887501127052206127277507127331388127390502140798185104756Solanesyl 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-N{[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]oxy})phosphoryl]oxy}phosphonic acid791.044790.506628783-6.393solanesyl diphosphate0-2PW_C104756Sopr579092-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-N2-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]benzene-1,4-diol737.21736.615831816-6.4922-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]benzene-1,4-diol002-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_C0579092M6S14B12357225108886Diphosphoric 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-N(phosphonooxy)phosphonic acid177.9751177.9432255064pyrophosphoric acid0-3Diphosphate;Pyrophosphate;Pyrophosphoric acid;PPiPW_C108886423MagnesiumHMDB0000547Magnesium 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-Nmagnesium(2+) ion24.30523.9850418980magnesium(2+) ion22FDB003518Magnesium;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-N2-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol396.615396.302830528-5.6022-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol00PW_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-N2-methyl-6-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]benzene-1,4-diol402.663402.349780721-6.6322-methyl-6-phytylquinol00C158822-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-O[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium399.445399.145063566-2.565SAMe11FDB022473(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-N2,3-dimethyl-5-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl]benzene-1,4-diol751.237750.63148188-6.542plastoquinol-900Plastoquinol 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-N{[hydroxy({[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]oxy})phosphoryl]oxy}phosphonic acid456.497456.240577688-4.393phytyl diphosphate0-2PW_C104757PhyPyrP1090932,3-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-N2,3-dimethyl-5-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]benzene-1,4-diol416.69416.365430786-6.7022,3-dimethyl-5-phytylquinol00PW_C109093749S-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-N(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid384.411384.12158847-1.975S-adenosyl-L-homocysteine00DBMET00514FDB022327(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_C000749SAH52085751863530705201221318822720672468310502550560713671371637542210754621376341608268151923719511875198123592251529424915364309774891117761113077733338777733417809813278305351783373467915611279962361808632294831382948343861132873891132893971155443991155474011203941221204861251205394131209404071210531241222844351230371351231734491235061191236171181248384701258804811263032991264494991273412061275963881280195171149γ-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-N(2R)-2,7,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol416.6795416.36543078-7.751gamma-tocopherol00FDB0024312,7,8-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-N(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol430.7061430.381080844-7.791VitaE00FDB000565(+)-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-N{[hydroxy({[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]oxy})phosphoryl]oxy}phosphonic acid450.4432450.19362653-4.993geranylgeranyl diphosphate0-2FDB0233773,7,11,15-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-N2,3-dimethyl-5-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol410.642410.318480592-5.7422,3-dimethyl-5-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol00PW_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-N(2R)-2,7,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol410.6319410.318480588-6.081gamma-tocotrienol00C14155(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-N(2R)-2,5,7,8-tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol424.6585424.334130652-6.191α tocotrienol00FDB002434(2r,3'e,7'e)-alpha-tocotrienol;(r)-alpha-tocotrienol;D-alpha-tocotrienol;Zeta1-tocopherol;Alpha-tocotrienol;Delta-alpha-tocotrienol;Z1-tocopherol;ζ1-tocopherolPW_C002720αT103L-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-N(2S)-2-amino-3-(4-hydroxyphenyl)propanoic acid181.1885181.073893223-1.373L-tyrosine00FDB000446(-)-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-N2-oxopentanedioic acid146.0981146.021523302-0.442oxoglutarate0-2FDB0033612-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-N(2S)-2-aminopentanedioic acid147.1293147.053157781-0.263L-glutamic acid0-1FDB012535(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-N[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid247.1419247.024573569-1.643pyridoxal phosphate0-2FDB021820Apolon 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'P1823244535181221401196962011104214505014582621201021504953251115416117542110354411185455120556713255811336533857018160716720572162127222213118581611217515112623311262818126842891268929077017253770372257704129377052224775261127776434177973346779793277829234578855332788623318069613598630711991212212002412412002940612008740712081741812114942312115542412206912312207638312283411912340245412372145812372745912462044712462739812530229712540229912540747912545848112580348912622429812623149512694238812694750112699620612725850612778651312779339023751UnknownUnknown1361.14.-.-;2.5.1.102 14080189214080288814098890914099691014108221410839171410847141143890141529151141530225141531293145319138114532013821453211383150454-hydroxyphenylpyruvate dioxygenase136PW_P015045250772375115046homogentisate solanesyltransferase136PW_P01504625078237511528423150472-methyl-6-phytyl-1,4-hydroquinone methyltransferase136PW_P015047250792375115048Homogentisate phytyltransferase 1, chloroplastic136PW_P015048250802375115049Tocopherol cyclase, chloroplastic136PW_P015049250812375115050Tocopherol O-methyltransferase, chloroplastic136PW_P015050250822375115051L-Tyrosine aminotransferase136PW_P015051250832375115291148213998PW_R213998Right8227525581Compoundfalse82275310652Compoundfalse822754841Compoundfalse82275513161Compoundfalse203603150451.13.11.27213999PW_R213999Right822756841Compoundfalse8227571047561Compoundfalse822758579091Compoundfalse8227591088861Compoundfalse82276013162Compoundfalse203604150462.5.1.117214000PW_R214000Right822761579091Compoundfalse8227621090891Compoundfalse822763197991Compoundfalse8227649211Compoundfalse822765579101Compoundfalse20360515047214001PW_R214001Right8227661047571Compoundfalse822767841Compoundfalse8227681088861Compoundfalse82276913161Compoundfalse822770197991Compoundfalse203606150482.5.1.115214002PW_R214002Right822771197991Compoundfalse8227729211Compoundfalse8227731090931Compoundfalse8227747491Compoundfalse20360715047214003PW_R214003Right8227751090931Compoundfalse82277611491Compoundfalse203608150495.5.1.24214004PW_R214004Right8227779211Compoundfalse82277811491Compoundfalse8227797491Compoundfalse82278012611Compoundfalse20360915050214005PW_R214005Right82278121451Compoundfalse822782841Compoundfalse8227831088861Compoundfalse82278413161Compoundfalse8227851090891Compoundfalse20361015048214006PW_R214006Right8227861090891Compoundfalse8227879211Compoundfalse8227887491Compoundfalse8227891090911Compoundfalse20361115047214007PW_R214007Right8227901090911Compoundfalse82279181361Compoundfalse20361215049214008PW_R214008Right8227929211Compoundfalse82279381361Compoundfalse82279427201Compoundfalse8227957491Compoundfalse20361315050214009PW_R214009Right8227961031Compoundfalse8227971341Compoundfalse8227985581Compoundfalse822799951Compoundfalse20361415051309852755890981false44041010regular2001903098528106590965false67659010regular787830985298490981false120041210regular2001903098530131690952false104659210regular787830985311047568923false164530210regular10011030985325790989281false226540210regular20020030985331088868923false201029710regular1001103098534131689252false201160210regular787830985354238929false183044910regular1002530985361090898923false265029010regular1001403098537197998923false265054710regular10011030985389218923false265069210regular10011030985395791089281false313040710regular20019030985401047578923false1695117710regular10011030985411088868923false211085310regular1001103098542131689252false2116118310regular787830985431979989281false229597610regular20019030985449218923false265086110regular100110309854510909389281false316097310regular20020030985467498923false304085810regular1001103098547114989281false366597810regular20019030985489218923false384585810regular10011030985497498923false428085510regular1001103098550126189281false441097510regular200190309855121458923false1725132210regular10011030985521088868923false2075132510regular1001103098553131689252false2091163510regular7878309855410908989281false2275143310regular20020030985559218923false2535132310regular10011030985567498923false2935132310regular100110309855710909189281false3060143310regular2002003098558813689281false3665143310regular20019030985599218923false3965133310regular1001103098560272089281false4465143010regular20019030985617498923false4330133510regular100110309856210391081false445122010regular20019030985631349103false370108010regular1001103098564959103false36567010regular100110309856511489109false60591010regular100351196305237519092false8204698uniprotregular150701196306237518922false18054698proteinregular150701196307237518922false28554678subunitregular150701196308237518922false187010378subunitregular150701196309237518922false282010368subunitregular150701196310237518922false344210388subunitregular150701196311237518922false404010388subunitregular150701196312237518922false187514978subunitregular150701196313237518922false270515008subunitregular150701196314237518922false339514988subunitregular150701196315237518922false412514988subunitregular150701196316237519102false4708958subunitregular15070940621150451152979091191334119630594062215046115297892119133511963064055530985354226679Cofactor94062315047115297892119133611963079406241504811529789211913371196308940625150471152978921191338119630994062615049115297892119133911963109406271505011529789211913401196311940628150481152978921191341119631294062915047115297892119134211963139406301504911529789211913431196314940631150501152978921191344119631594063215051115297910119134511963164055630985654226719Cofactor4226670M645 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