89PathwayTryptophan MetabolismThis pathway depicts the metabolic reactions and pathways associated with tryptophan metabolism in animals. Tryptophan is an essential amino acid. This means that it cannot be synthesized by humans and other mammals and therefore must be part of the diet. Unlike animals, plants and microbes can synthesize tryptophan from shikimic acid or anthranilate. As one of the 20 proteogenic amino acids, tryptophan plays an important role in protein biosynthesis through the action of tryptophanyl-tRNA synthetase. As shown in this pathway, tryptophan can be linked to the tryptophanyl-tRNA via either the mitochondrial or cytoplasmic tryptophan tRNA ligases. Also shown in this pathway map is the conversion of tryptophan to serotonin (a neurotransmitter). In this process, tryptophan is acted upon by the enzyme tryptophan hydroxylase, which produces 5-hydroxytryptophan (5HTP). 5HTP is then converted into serotonin (5-HT) via aromatic amino acid decarboxylase. Serotonin, in turn, can be converted into N-acetyl serotonin (via serotonin-N-acetyltransferase) and then melatonin (a neurohormone), via 5-hydroxyindole-O-methyltransferase. The melatonin can be converted into 6-hydroxymelatonin via the action of cytochrome P450s in the endoplasmic reticulum. Serotonin has other fates as well. As depicted in this pathway it can be converted into N-methylserotonin via Indolethylamine-N-methyltransferase (INMT) or it can be converted into formyl-5-hydroxykynurenamine via indoleamine 2,3-dioxygenase. Serotonin may also be converted into 5-methoxyindoleacetate via a series of intermediates including 5-hydroxyindoleacetaldehyde and 5-hydroxyindoleacetic acid. Tryptophan can be converted or broken down into many other compounds as well. It can be converted into tryptamine via the action of aromatic amino acid decarboxylase. The resulting tryptamine can then be converted into indoleacetaldehyde via kynurenine 3-monooxygenase and then into indoleacetic acid via the action of aldehyde dehydrogenase. Tryptophan also leads to the production of a very important compound known as kynurenine. Kynurenine is synthesized via the action of tryptophan 2,3-dioxygnase, which produces N-formylkynurenine. This compound is converted into kynurenine via the enzyme known as kynurenine formamidase (AFMID). Kynurenine has at least 3 fates. First, kynurenine can undergo deamination in a standard transamination reaction yielding kynurenic acid. Secondly, kynurenine can undergo a series of catabolic reactions (involving kynureninase and kynurenine 3-monooxygenase) producing 3-hydroxyanthranilate plus alanine. In this reaction, kynureninase catabolizes the conversion of kynurenine into anthranilic acid while kynurenine—oxoglutarate transaminase (also known as kynurenine aminotransferase or glutamine transaminase K, GTK) catabolizes its conversion into kynurenic acid. The action of kynurenine 3-hydroxylase on kynurenic acid leads to 3-hydroxykynurenine. The oxidation of 3-hydroxyanthranilate converts it into 2-amino-3-carboxymuconic 6-semialdehyde, which has two fates. It can either degrade to form acetoacetate or it can cyclize to form quinolate. Most of the body’s 3-hydroxyanthranilate leads to the production of acetoacetate (a ketone body), which is why tryptophan is also known as a ketogenic amino acid. An important side reaction in the liver involves a non-enzymatic cyclization into quinolate followed by transamination and several rearrangements to yield limited amounts of nicotinic acid, which leads to the production of a small amount of NAD+ and NADP+.MetabolicPW000163CenterPathwayVisualizationContext17842007000#000099PathwayVisualization10889Tryptophan MetabolismThis pathway depicts the metabolic reactions and pathways associated with tryptophan metabolism in animals. Tryptophan is an essential amino acid. This means that it cannot be synthesized by humans and other mammals and therefore must be part of the diet. Unlike animals, plants and microbes can synthesize tryptophan from shikimic acid or anthranilate. As one of the 20 proteogenic amino acids, tryptophan plays an important role in protein biosynthesis through the action of tryptophanyl-tRNA synthetase. As shown in this pathway, tryptophan can be linked to the tryptophanyl-tRNA via either the mitochondrial or cytoplasmic tryptophan tRNA ligases. Also shown in this pathway map is the conversion of tryptophan to serotonin (a neurotransmitter). In this process, tryptophan is acted upon by the enzyme tryptophan hydroxylase, which produces 5-hydroxytryptophan (5HTP). 5HTP is then converted into serotonin (5-HT) via aromatic amino acid decarboxylase. Serotonin, in turn, can be converted into N-acetyl serotonin (via serotonin-N-acetyltransferase) and then melatonin (a neurohormone), via 5-hydroxyindole-O-methyltransferase. The melatonin can be converted into 6-hydroxymelatonin via the action of cytochrome P450s in the endoplasmic reticulum. Serotonin has other fates as well. As depicted in this pathway it can be converted into N-methylserotonin via Indolethylamine-N-methyltransferase (INMT) or it can be converted into formyl-5-hydroxykynurenamine via indoleamine 2,3-dioxygenase. Serotonin may also be converted into 5-methoxyindoleacetate via a series of intermediates including 5-hydroxyindoleacetaldehyde and 5-hydroxyindoleacetic acid. Tryptophan can be converted or broken down into many other compounds as well. It can be converted into tryptamine via the action of aromatic amino acid decarboxylase. The resulting tryptamine can then be converted into indoleacetaldehyde via kynurenine 3-monooxygenase and then into indoleacetic acid via the action of aldehyde dehydrogenase. Tryptophan also leads to the production of a very important compound known as kynurenine. Kynurenine is synthesized via the action of tryptophan 2,3-dioxygnase, which produces N-formylkynurenine. This compound is converted into kynurenine via the enzyme known as kynurenine formamidase (AFMID). Kynurenine has at least 3 fates. First, kynurenine can undergo deamination in a standard transamination reaction yielding kynurenic acid. Secondly, kynurenine can undergo a series of catabolic reactions (involving kynureninase and kynurenine 3-monooxygenase) producing 3-hydroxyanthranilate plus alanine. In this reaction, kynureninase catabolizes the conversion of kynurenine into anthranilic acid while kynurenine—oxoglutarate transaminase (also known as kynurenine aminotransferase or glutamine transaminase K, GTK) catabolizes its conversion into kynurenic acid. The action of kynurenine 3-hydroxylase on kynurenic acid leads to 3-hydroxykynurenine. The oxidation of 3-hydroxyanthranilate converts it into 2-amino-3-carboxymuconic 6-semialdehyde, which has two fates. It can either degrade to form acetoacetate or it can cyclize to form quinolate. Most of the body’s 3-hydroxyanthranilate leads to the production of acetoacetate (a ketone body), which is why tryptophan is also known as a ketogenic amino acid. An important side reaction in the liver involves a non-enzymatic cyclization into quinolate followed by transamination and several rearrangements to yield limited amounts of nicotinic acid, which leads to the production of a small amount of NAD+ and NADP+.Metabolic146193SubPathway738156Compound2139Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.89Pathway140Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.89Pathway28051926381576Badawy AA: Tryptophan metabolism, disposition and utilization in pregnancy. Biosci Rep. 2015 Sep 17;35(5). pii: BSR20150197. doi: 10.1042/BSR20150197.89Pathway2805206371429Bender DA: Biochemistry of tryptophan in health and disease. Mol Aspects Med. 1983;6(2):101-97.89Pathway28052116992682Hopkins FG, Cole SW: A contribution to the chemistry of proteids: Part II. The constitution of tryptophane, and the action of bacteria upon it. J Physiol. 1903 Jun 15;29(4-5):451-66. doi: 10.1113/jphysiol.1903.sp000968.89Pathway28052524129579Stavrum AK, Heiland I, Schuster S, Puntervoll P, Ziegler M: Model of tryptophan metabolism, readily scalable using tissue-specific gene expression data. J Biol Chem. 2013 Nov 29;288(48):34555-66. doi: 10.1074/jbc.M113.474908. Epub 2013 Oct 15.89Pathway28052628625179Hoglund E, Overli O, Andersson MA, Silva P, Laursen DC, Moltesen MM, Krogdahl A, Schjolden J, Winberg S, Vindas MA, Mayer I, Hillestad M: Dietary l-tryptophan leaves a lasting impression on the brain and the stress response. Br J Nutr. 2017 May;117(10):1351-1357. doi: 10.1017/S0007114517001428. Epub 2017 Jun 19.89Pathway28052728118532Li Y, Hu N, Yang D, Oxenkrug G, Yang Q: Regulating the balance between the kynurenine and serotonin pathways of tryptophan metabolism. FEBS J. 2017 Mar;284(6):948-966. doi: 10.1111/febs.14026. Epub 2017 Feb 20.89Pathway28052828737706Xu K, Liu H, Bai M, Gao J, Wu X, Yin Y: Redox Properties of Tryptophan Metabolism and the Concept of Tryptophan Use in Pregnancy. Int J Mol Sci. 2017 Jul 24;18(7). pii: ijms18071595. doi: 10.3390/ijms18071595.89Pathway280529147076Smith SA, Pogson CL: Tryptophan and the control of plasma glucose concentrations in the rat. Biochem J. 1977 Dec 15;168(3):495-506. doi: 10.1042/bj1680495.89Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404CardiomyocyteCL:00007468Beta cellCL:00006397Epithelial CellCL:00000666MyocyteCL:000018712AstrocyteCL:000012728MacrophageCL:000023523T CellCL:000008422Granulosa CellCL:00005011Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia410Drosophila melanogaster7227EukaryoteFruit fly51Picea sitchensis3332EukaryoteSitka spruce56Andro6666Eukaryote230Ambystoma mexicanum8296Eukaryoteaxolotl301Gallus Gallus1758Prokaryote11Extracellular SpaceGO:00056151CytosolGO:000582931Periplasmic SpaceGO:00056203Mitochondrial MatrixGO:00057595CytoplasmGO:000573714Mitochondrial Outer MembraneGO:00057412MitochondrionGO:000573915NucleusGO:00056344PeroxisomeGO:000577713Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588627Peroxisome MembraneGO:000577835ChloroplastGO:000950712Mitochondrial Inner MembraneGO:000574332Inner MembraneGO:00702586LysosomeGO:000576416Lysosomal LumenGO:004320218Melanosome MembraneGO:003316224Mitochondrial Intermembrane SpaceGO:000575836MembraneGO:001602020Endoplasmic Reticulum LumenGO:00057888Smooth Endoplasmic Reticulum GO:000579025Golgi ApparatusGO:000579421SynapseGO:004520253Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259719Sarcoplasmic ReticulumGO:001652939Mitochondrial membraneGO:003196617NucleoplasmGO:00056542Endothelium BTO:00003931LiverBTO:00007597297Nervous SystemBTO:000148418PancreasBTO:000098825IntestineBTO:00006488Blood VesselBTO:000110274114Adrenal MedullaBTO:000004971828StomachBTO:00013071552611HeartBTO:000056273106KidneyBTO:00006717189MuscleBTO:00008871411824BrainBTO:000014289163Sympathetic Nervous 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is an essential amino acid that is the precursor of both serotonin and melatonin. Melatonin is a hormone that is produced by the pineal gland in animals, which regulates sleep and wakefulness. Serotonin is a brain neurotransmitter, platelet clotting factor, and neurohormone found in organs throughout the body. Metabolism of tryptophan into serotonin requires nutrients such as vitamin B6, niacin, and glutathione. Niacin (also known as vitamin B3) is an important metabolite of tryptophan. It is synthesized via kynurenine and quinolinic acids, which are products of tryptophan degradation. There are a number of conditions or diseases that are characterized tryptophan deficiencies. For instance, fructose malabsorption causes improper absorption of tryptophan in the intestine, which reduces levels of tryptophan in the blood and leads to depression. High corn or other tryptophan-deficient diets can cause pellagra, which is a niacin-tryptophan deficiency disease with symptoms of dermatitis, diarrhea, and dementia. Hartnup's disease is a disorder in which tryptophan and other amino acids are not absorbed properly. Symptoms of Hartnup's disease include skin rashes, difficulty coordinating movements (cerebellar ataxia), and psychiatric symptoms such as depression or psychosis. Tryptophan supplements may be useful for treating Hartnup's. Assessment of tryptophan deficiency is done through studying excretion of tryptophan metabolites in the urine or blood. Blood may be the most sensitive test because the amino acid tryptophan is transported in a unique way. Increased urination of tryptophan breakdown products (such as kynurenine) correlates with increased tryptophan degradation, which occurs with oral contraception, depression, mental retardation, hypertension, and anxiety states. The requirement for tryptophan and protein decreases with age. The minimum daily requirement for adults is 3 mg/kg/day or about 200 mg a day. There is 400 mg of tryptophan in a cup of wheat germ. A cup of low fat cottage cheese contains 300 mg of tryptophan and chicken and turkey contain up to 600 mg of tryptophan per pound (http://www.dcnutrition.com). Tryptophan plays a role in "feast-induced" drowsiness. Ingestion of a meal rich in carbohydrates triggers the release of insulin. Insulin, in turn, stimulates the uptake of large neutral branched-chain amino acids (BCAAs) into muscle, increasing the ratio of tryptophan to BCAA in the bloodstream. The increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAAs and tryptophan), resulting in greater uptake of tryptophan across the blood-brain barrier into the cerebrospinal fluid (CSF). Once in the CSF, tryptophan is converted into serotonin and the resulting serotonin is further metabolized into melatonin by the pineal gland, which promotes sleep. Under certain situations, tryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of tryptophan can be found in glutaric aciduria type I (glutaric acidemia type I or GA1). GA1 is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine, and tryptophan. Babies with glutaric acidemia type I are often born with unusually large heads (macrocephaly). Affected individuals may also have difficulty moving and may experience spasms, jerking, rigidity or decreased muscle tone, and muscle weakness. High levels of tryptophan have also been implicated in eosinophilia-myalgia syndrome (EMS), an incurable and sometimes fatal flu-like neurological condition linked to the ingestion of large amounts of L-tryptophan. The risk of developing EMS increases with larger doses of tryptophan and increasing age. Some research suggests that certain genetic polymorphisms may be related to the development of EMS. The presence of eosinophilia is a core feature of EMS, along with unusually severe myalgia (muscle pain). It is thought that both tryptophan and certain unidentified tryptophan contaminants may contribute to EMS (PMID: 1763543). It has also been suggested that excessive tryptophan or elevation of its metabolites could play a role in amplifying some of the pathological features of EMS (PMID: 10721094). This pathological damage is further augmented by metabolites of the kynurenine pathway (a tryptophan degradation pathway).73-22-3C00078630516828TRP6066DB00150N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=OC11H12N2O2InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1QIVBCDIJIAJPQS-VIFPVBQESA-N204.2252204.089877638FDB002250(-)-tryptophan;(2s)-2-amino-3-(1h-indol-3-yl)propanoate;(2s)-2-amino-3-(1h-indol-3-yl)propanoic acid;(l)-tryptophan;(s)-1h-indole-3-alanine;(s)-2-amino-3-(3-indolyl)propionic acid;(s)-a-amino-1h-indole-3-propanoate;(s)-a-amino-1h-indole-3-propanoic acid;(s)-a-aminoindole-3-propionate;(s)-a-aminoindole-3-propionic acid;(s)-a-amino-b-indolepropionate;(s)-a-amino-b-indolepropionic acid;(s)-alpha-amino-1h-indole-3-propanoate;(s)-alpha-amino-1h-indole-3-propanoic acid;(s)-alpha-amino-beta-(3-indolyl)-propionic acid;(s)-alpha-aminoindole-3-propionate;(s)-alpha-aminoindole-3-propionic acid;(s)-alpha-amino-beta-indolepropionate;(s)-alpha-amino-beta-indolepropionic acid;(s)-tryptophan;1-beta-3-indolylalanine;1h-indole-3-alanine;1beta-3-indolylalanine;2-amino-3-indolylpropanoate;2-amino-3-indolylpropanoic acid;3-(1h-indol-3-yl)-l-alanine;3-indol-3-ylalanine;Ardeytropin;H-trp-oh;Indole-3-alanine;Kalma;L-(-)-tryptophan;L-tryptofan;L-tryptophan;L-tryptophane;L-alpha-amino-3-indolepropionic acid;L-alpha-aminoindole-3-propionic acid;L-b-3-indolylalanine;L-beta-3-indolylalanine;Lopac-t-0254;Lyphan;Optimax;Pacitron;Sedanoct;Triptofano;Trofan;Tryptacin;Tryptan;Tryptophan;Tryptophane;Tryptophanum;Alpha'-amino-3-indolepropionic acid;Alpha-aminoindole-3-propionic acid;Trp;W;(s)-α-amino-1h-indole-3-propanoate;(s)-α-amino-1h-indole-3-propanoic acid;(s)-a-amino-b-(3-indolyl)-propionate;(s)-a-amino-b-(3-indolyl)-propionic acid;(s)-alpha-amino-beta-(3-indolyl)-propionate;(s)-α-amino-β-(3-indolyl)-propionate;(s)-α-amino-β-(3-indolyl)-propionic acid;L-β-3-indolylalaninePW_C000741Trp2977152978256671075668108588710542460318424613157906513279101114121739124121797409124290118124348137127625388127682208414Adenosine 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_C000414ATP92214608266164142247813733327995934399763210518211210214649215614216058240559243427272646281229302966316372361661361751439923447431476891486454503289503526515575205975215100525010452911015313111534611253901035406117543011854431205542129555613255691335603135562110858461435854146587610758971475924151604815561091616230166649317868391886870160697619971572057184206720921072252137229211729819873022167390217740821874321637481222749919081862251184727711903170120102811203916412178285125782261269129013264223153273084232631542621322426943187702825377218134772333297746833377632336780373327804135078168128782143517824035378411335784941157885013078865331789193348002836880046184806741198562919482612411323494113282388116280109119914122119992406120154407120245382120362412121246429121392123121397433121471408121974410122065125122079383122083405122402422122444435122919399123009446123816464123951447123956468124029374124527444124616136124630398124634376124943472124972375125011470125304297125371479125392299125515481125595484126123485126220300126234495126240478126547491126596499126913501127123389127731516127781395127796390127801209128119508128167517140770891170PyrophosphateHMDB0000250The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.14000-31-8C0001364410218361PPI559142DB04160OP(O)(=O)OP(O)(O)=OH4O7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)XPPKVPWEQAFLFU-UHFFFAOYSA-N177.9751177.943225506FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170Ppi1223546384292373532882221217316204924105928152941751448685450348952521045294101540911754241035433118545812055481115559132558413356061355655108587910762391666978199707318871341637272160731219873182138275151828321011869161120022221204116412315225123232491251228812579226126952901521930615375183476017425613154269731877235329773171287763533678416335789283317915311279950134799581308004737280417170856301947863849481412594819382986782231106343911132703951132753891155271361155323991199341221200171241200324061203304101209364071212614291213411211214863831224074221229854441235021191238314641240443981249773751253242971253952991254104791255974841256564851258764811265524911268692051269353881269505011273372061281245081407728911065OxygenHMDB0001377Oxygen 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_C001065O295911052451650018505854914625286383649106743168820754157634769338362137549201624253122280329426042474713546712354801255493126550812758091085973147612915970061887032163705016073192137533210756021283951511181621611864198118832151189421112057225120631641224728612279226123252491270629112716292130042981301630013026301130383021326022342276174265731576910293770442947721413477350111773631307737733177395332774971137751211577537334776263367772333777736112777471297775634177805114778121337807032978151132783813457880534379111360120047408120383122120426405120542407120553414120594409120601406120883415121045124121104383121605434121656429122117382122573418122689384122798374122822443123027135123060376123128447123139136123163448123176119123187450123219137123226120123459451123609118123669398124163469124214464124669399125145454125275121125425482125706478125731483125737297125740479125884481126100299126272484126522495126721489126825480126964502126986207127198209127214208127219205127222501127305504127345206127557388127574515127835389128081395128095390128312506128432391935N'-FormylkynurenineHMDB0001200N-Formylkynurenine 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. N-Formylkynurenine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Within the cell, N-formylkynurenine is primarily located in the cytoplasm. In humans, N-formylkynurenine is involved in the tryptophan metabolism pathway. N-Formylkynurenine lays an improtant role in photobiological responses. The excited state of N-formylkynurenine react to produce hydroxyl radicals.1022-31-7C0240691018377N-FORMYLKYNURENINE886NC(CC(=O)C1=CC=CC=C1NC=O)C(O)=OC11H12N2O4InChI=1S/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)BYHJHXPTQMMKCA-UHFFFAOYSA-N236.224236.079706882FDB0224863-(n-formylanthraniloyl)-alanine;Formylkynurenine;N'-formyl-kynurenine;N'-formylkynurenine;N-formyl-d-kynurenine;N-formyl-l-kynurenine;N-formyl-delta-kynurenine;Alpha-amino-2-(formylamino)-gamma-oxo-benzenebutanoate;Alpha-amino-2-(formylamino)-gamma-oxo-benzenebutanoic acid;3-(2-formamidobenzoyl)alanine;2-amino-4-(2-formamidophenyl)-4-oxobutanoatePW_C000935Formylk29832790681321217451241242961181276313881799HemeHMDB0003178Heme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.14875-96-8C0003217627HEME_A24604415DB02577CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=OC34H32FeN4O4InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;KABFMIBPWCXCRK-RGGAHWMASA-L616.487616.177297665FDB016272(protoporphyrinato)iron;Ferroheme;Ferroheme b;Ferroprotoheme;Ferroprotoporphyrin;Ferroprotoporphyrin ix;Ferrous protoheme;Ferrous protoheme ix;Haem;Hem;Heme;Iron protoporphyrin;Iron protoporphyrin ix;Iron(ii) protoporphyrin ix;Protoferroheme;Protohaem;Protoheme;Protoheme ix;Reduced hematinPW_C001799Heme2471630810324860827665124431354491413361963182806292938932381133672634211437344404331482328517095547212354851255517129583014162467862831659715170441607060161732621311835198118982111206516413009298130213004227817769152937693124977351111773641307736733177398332775171157762933677813334783801337860213278963112799321341204314051206034081209554071210853831216584291217461241219101221225704061226913841230653761231334471231441361232283741235211191236503981242164641242971181244631351251421201252771211257424821258964811261962991264992971265124951267184791268274801272245021273572061276323881280702051280833951280863901283095011284343911420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551852057Formylanthranilic acidHMDB0004089Formylanthranilic acid, also known as N-formylanthranilate or 2-(formylamino)-benzoate, belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group. Formylanthranilic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, formylanthranilic acid is primarily located in the cytoplasm. In humans, formylanthranilic acid is involved in the tryptophan metabolism pathway. Formylanthranilic acid is a polar acid metabolite of anthranilic acid, occasionally found in human urine. (PMID 7320161).3342-77-6C056531013993657591624OC(=O)C1=CC=CC=C1NC=OC8H7NO3InChI=1S/C8H7NO3/c10-5-9-7-4-2-1-3-6(7)8(11)12/h1-5H,(H,9,10)(H,11,12)LLLPDUXGHXIXIW-UHFFFAOYSA-N165.1461165.042593095FDB0233092-(formylamino)-benzoate;2-(formylamino)-benzoic acid;2-(formylamino)benzoate;2-(formylamino)benzoic acid;2-formamidobenzoate;2-formamidobenzoic acid;Formylanthranilate;N-formylanthranilatePW_C002057Formyla2985279069132121748124124299118127634388105L-AlanineHMDB0000161Alanine is a non-essential amino acid made in the body from either the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine, and glycine, is an inhibitory neurotransmitter in the brain (http://www.dcnutrition.com/AminoAcids/). L-Alanine has been found to be associated with glucagon deficiency, which is an inborn error of metabolism.56-41-7C00041595016977L-ALPHA-ALANINE5735DB00160C[C@H](N)C(O)=OC3H7NO2InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1QNAYBMKLOCPYGJ-REOHCLBHSA-N89.093289.047678473FDB000556(2s)-2-aminopropanoate;(2s)-2-aminopropanoic acid;(s)-(+)-alanine;(s)-2-aminopropanoate;(s)-2-aminopropanoic acid;(s)-2-amino-propanoate;(s)-2-amino-propanoic acid;(s)-alanine;2-aminopropanoate;2-aminopropanoic acid;2-aminopropionate;2-aminopropionic acid;2-ammoniopropanoate;2-ammoniopropanoic acid;Ala;Alanine;L-(+)-alanine;L-2-aminopropanoate;L-2-aminopropanoic acid;L-2-aminopropionate;L-2-aminopropionic acid;L-a-alanine;L-a-aminopropionate;L-a-aminopropionic acid;L-alpha-alanine;L-alpha-aminopropionate;L-alpha-aminopropionic acid;A-alanine;A-aminopropionate;A-aminopropionic acid;Alpha-alanine;Alpha-aminopropanoate;Alpha-aminopropanoic acid;Alpha-aminopropionate;Alpha-aminopropionic acid;A;L-alanin;L-α-alaninePW_C000105Ala102294316814465014535114542630221534393540711754181035431118545212055571325578133563710756381085883105652985835022512271151126203112627181523022242452320424533184253431577969346779753277798832678008111780921127916511480693135119910122120015124120026406121145423121151424121164416121220409122139407123717458123723459123736452123790137124691119125300297125393299125404479126296481126850205126933388126944501127860206538L-KynurenineHMDB0000684Kynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-Kynurenine is a central compound of the tryptophan metabolism pathway since it can change into the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders such as stroke, epilepsy, multiple sclerosis, and amyotrophic lateral sclerosis. It can also occur in neurodegenerative disorders such as Parkinson's disease, Huntington's, and Alzheimer's disease; and in mental disorders such as schizophrenia and depression. 2922-83-0C0032816116616946L-KYNURENINE141580DB02070N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=OC10H12N2O3InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1YGPSJZOEDVAXAB-QMMMGPOBSA-N208.2139208.08479226FDB022181(s)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoate;(s)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid;(alphas)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoate;(alphas)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid;3-(3-hydroxyanthraniloyl)-l-alanine;3-anthraniloyl-alanine;3-anthraniloyl-l-alanine;3-anthraniloylalanine;3-hydroxy-l-kynurenine;Dl-kynureninefree base;Dl-kynurenine;Kynurenin;Kynurenine;Quinurenine;Alpha,2-diamino-gamma-oxo-benzenebutanoate;Alpha,2-diamino-gamma-oxo-benzenebutanoic acidPW_C000538L-Kynr298727907013212175012412430111812763638892Formic acidHMDB0000142Formic acid is the simplest carboxylic acid. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a byproduct in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer.64-18-6C000581897100230751FORMATE278DB01942OC=OCH2O2InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)BDAGIHXWWSANSR-UHFFFAOYSA-N46.025446.005479308DBMET00489FDB012804Add-f;Ameisensaure;Aminate;Aminic acid;Bilorin;Collo-bueglatt;Collo-didax;Formate;Formira;Formisoton;Formylate;Formylic acid;Hydrogen carboxylate;Hydrogen carboxylic acid;Methanoate;Methanoic acid;Methanoic acid monomer;Myrmicyl;Sodium formate;Sybest;Wonderbond hardener m 600lPW_C000092Formate94689773162949194325314111534811266361077158205718620673252137616160828721011982151435223187696322578652132789343311206701221206974071214963831217511241232841351233021191240543981243021181257532971257724811264782991268214951276373881284263908772-Aminobenzoic acidHMDB00011232-Aminobenzoic acid, also known as anthranilate or vitamin L1, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 2-Aminobenzoic acid exists as a solid, slightly soluble (in water), and a weakly acidic compound (based on its pKa). 2-Aminobenzoic acid has been found in human epidermis tissue, and has also been primarily detected in feces, urine, blood, and cerebrospinal fluid. Within the cell, 2-aminobenzoic acid is primarily located in the cytoplasm and mitochondria. 2-Aminobenzoic acid exists in all living organisms, ranging from bacteria to humans. 2-Aminobenzoic acid participates in a number of enzymatic reactions. In particular, L-Glutamic acid, pyruvic acid, and 2-aminobenzoic acid can be biosynthesized from chorismate and L-glutamine; which is mediated by the enzyme anthranilate synthase. Furthermore, 2-Aminobenzoic acid and phosphoribosyl pyrophosphate can be converted into N-(5-phosphoribosyl)-anthranilate through its interaction with the enzyme anthranilate synthase component ii. Furthermore, L-Glutamic acid, pyruvic acid, and 2-aminobenzoic acid can be biosynthesized from chorismate and L-glutamine; which is mediated by the enzyme anthranilate synthase. Finally, 2-Aminobenzoic acid and phosphoribosyl pyrophosphate can be converted into N-(5-phosphoribosyl)-anthranilate; which is mediated by the enzyme anthranilate synthase component ii. In humans, 2-aminobenzoic acid is involved in the tryptophan metabolism pathway. Outside of the human body, 2-aminobenzoic acid can be found in a number of food items such as climbing bean, ginseng, black mulberry, and rambutan. This makes 2-aminobenzoic acid a potential biomarker for the consumption of these food products. 2-Aminobenzoic acid is a potentially toxic compound. 2-Aminobenzoic acid is an organic compound. It is a substrate of enzyme anthranilate hydroxylase [EC 1.14.13.35] in benzoate degradation via hydroxylation pathway (KEGG).118-92-3C0010822730754ANTHRANILATE222DB04056NC1=CC=CC=C1C(O)=OC7H7NO2InChI=1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)RWZYAGGXGHYGMB-UHFFFAOYSA-N137.136137.047678473FDB0008961-amino-2-carboxybenzene;2-amino-benzoate;2-amino-benzoic acid;2-aminobenzoate;2-aminobenzoic acid;2-aminophenylacetate;2-aminophenylacetic acid;2-carboxyaniline;Anthranate;Anthranic acid;Anthranilate;Anthranilic acid;Anthranilic acid gr;Carboxyaniline;H-2-abz-oh;Kyselina o-aminobenzoova;Kyselina anthranilova;O-amino-benzoate;O-amino-benzoic acid;O-aminobenzoate;O-aminobenzoic acid;O-anthranilate;O-anthranilic acid;O-carboxyaniline;Ortho-amidobenzoate;Ortho-amidobenzoic acid;Ortho-aminobenzoate;Ortho-aminobenzoic acid;Vitamin l;Vitamin l1;2-aminobenzoesaeure;O-aminobenzoesaeurePW_C0008772AA29892790711321217531241243041181276393887784-(2-Aminophenyl)-2,4-dioxobutanoic acidHMDB00009784-(2-Aminophenyl)-2,4-dioxobutanoic 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. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid has been primarily detected in feces. Within the cell, 4-(2-aminophenyl)-2,4-dioxobutanoic acid is primarily located in the cytoplasm and mitochondria. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid exists in all living organisms, ranging from bacteria to humans. In humans, 4-(2-aminophenyl)-2,4-dioxobutanoic acid is involved in the tryptophan metabolism pathway. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is a substrate for Kynurenine/alpha-aminoadipate aminotransferase mitochondrial.C0125247217442CPD-476459NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=OC10H9NO4InChI=1S/C10H9NO4/c11-7-4-2-1-3-6(7)8(12)5-9(13)10(14)15/h1-4H,5,11H2,(H,14,15)CAOVWYZQMPNAFJ-UHFFFAOYSA-N207.1828207.053157781FDB0223484-(2-aminophenyl)-2,4-dioxo-butanoate;4-(2-aminophenyl)-2,4-dioxo-butanoic acid;4-(2-aminophenyl)-2,4-dioxobutanoate;4-(2-aminophenyl)-2,4-dioxobutanoic acidPW_C00077842A24D2990279072132121754124124305118127640388566Kynurenic acidHMDB0000715Kynurenic acid (KYNA) is a well-known endogenous antagonist of the glutamate ionotropic excitatory amino acid receptors N-methyl-D-aspartate (NMDA), alphaamino-3-hydroxy-5-methylisoxazole-4-propionic acid and kainate receptors and of the nicotine cholinergic subtype alpha 7 receptors. KYNA neuroprotective and anticonvulsive activities have been demonstrated in animal models of neurodegenerative diseases. Because of KYNA's neuromodulatory character, its involvement has been speculatively linked to the pathogenesis of a number of neurological conditions including those in the ageing process. Different patterns of abnormalities in various stages of KYNA metabolism in the CNS have been reported in Alzheimer's disease, Parkinson's disease and Huntington's disease. In HIV-1-infected patients and in patients with Lyme neuroborreliosis a marked rise of KYNA metabolism was seen. In the ageing process KYNA metabolism in the CNS of rats shows a characteristic pattern of changes throughout the life span. A marked increase of the KYNA content in the CNS occurs before the birth, followed by a dramatic decline on the day of birth. A low activity was seen during ontogenesis, and a slow and progressive enhancement occurs during maturation and ageing. This remarkable profile of KYNA metabolism alterations in the mammalian brain has been suggested to result from the development of the organisation of neuronal connections and synaptic plasticity, development of receptor recognition sites, maturation and ageing. There is significant evidence that KYNA can improve cognition and memory, but it has also been demonstrated that it interferes with working memory. Impairment of cognitive function in various neurodegenerative disorders is accompanied by profound reduction and/or elevation of KYNA metabolism. The view that enhancement of CNS KYNA levels could underlie cognitive decline is supported by the increased KYNA metabolism in Alzheimer's disease, by the increased KYNA metabolism in down's syndrome and the enhancement of KYNA function during the early stage of Huntington's disease. Kynurenic acid is the only endogenous N-methyl-D-aspartate (NMDA) receptor antagonist identified up to now, that mediates glutamatergic hypofunction. Schizophrenia is a disorder of dopaminergic neurotransmission, but modulation of the dopaminergic system by glutamatergic neurotransmission seems to play a key role. Despite the NMDA receptor antagonism, kynurenic acid also blocks, in lower doses, the nicotinergic acetycholine receptor, i.e., increased kynurenic acid levels can explain psychotic symptoms and cognitive deterioration. Kynurenic acid levels are described to be higher in the cerebrospinal fluid (CSF) and in critical central nervous system (CNS) regions of schizophrenics as compared to controls. (PMID: 17062375, 16088227).492-27-3C017173845183443712OC(=O)C1=CC(=O)C2=CC=CC=C2N1C10H7NO3InChI=1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)HCZHHEIFKROPDY-UHFFFAOYSA-N189.1675189.042593095FDB0222002-carboxy-4-hydroxyquinoline;4-hydroxy-2-quinolinecarboxylic acid;4-hydroxy-quinaldate;4-hydroxy-quinaldic acid;4-hydroxyquinaldate;4-hydroxyquinaldic acid;4-hydroxyquinaldinate;4-hydroxyquinaldinic acid;4-hydroxyquinoline-2-carboxylate;4-hydroxyquinoline-2-carboxylic acid;Kynurenate;Kynurenic acid;Quinurenic acid;4-hydroxy-2-chinolincarbonsaeure;Kynurensaeure;4-oxo-1h-quinoline-2-carboxylate;4-hydroxy-2-quinolinecarboxylatePW_C000566Kynuren2993279073132121755124124306118127641388134Oxoglutaric 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'P18232445351812214011969620111042145050145826212010215049532511154161175421103544111854551205567132558113365338570181607167205721621272222131185816112175151126233112628181268428912689290770172537703722577041293770522247752611277764341779733467797932778292345788553327886233180696135986307119912122120024124120029406120087407120817418121149423121155424122069123122076383122834119123402454123721458123727459124620447124627398125302297125402299125407479125458481125803489126224298126231495126942388126947501126996206127258506127786513127793390146NADPHHMDB0000221Nicotinamide 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_C000146NADPH185819037781079658211883721609291615494687314793144797145310111578910859721476128159627135677911770681887103163715420572051607315213734521075592127591170819422582191518421224118121981189321112006222121501641224528612596226126482494234331543746322769112937716613277385331773943327746013077504112775111157762333680712119113164941201054071204254051204521221206161231211411251212754291214021241214833831230593761230861351232414471237121361238464641239611181240413981254724811256962971262142991265294951270092061275723881281013901407061687219L-3-HydroxykynurenineHMDB0011631L-3-Hydroxykynurenine (L-3-HK) is a metabolite in the kynurenine pathway, the major route of tryptophan degradation in mammals. Kynurenine 3-monooxygenase, an NADPH-dependent flavin monooxygenase, catalyses the hydroxylation of L-kynurenine to L-3-hydroxykynurenine. 3-hydroxykynurenine can be converted to 3-hydroxyanthranilate by the enzyme 3-hydroxykinureninase. It may also be converted to 4-(2-amino-3-hydroxphenyl)-2,4-dioxobutanoate by the enzyme kynurenine-oxoglutarate transaminase. L-3-Hydroxykynurenine (L-3-HK) is a known generator of highly reactive free radicals. An elevation of L-3-HK levels has been shown to constitute a significant hazard in situations of excitotoxic injury. In particular, L-3-HK may contribute to the neuronal deficits underlying HIV-associated dementia (PMID: 7830088). Pharmacological interventions aimed at decreasing L-3-HK formation may therefore be particularly useful for the treatment of neurological diseases which are associated with an abnormally enhanced flux through the kynurenine pathway (PMID: 10583474).606-14-4C0322711811173803-HYDROXY-L-KYNURENINE11318N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=OC10H12N2O4InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)/t6-/m0/s1VCKPUUFAIGNJHC-LURJTMIESA-N224.2133224.079706882C032273-(2-amino-3-hydroxybenzoyl)-l-alanine;3-(3-hydroxyanthraniloyl)-l-alanine;3-hydroxy-l-kynurenine;L-3-hk;(2s)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid;L-3-hydroxykynurenine;(2s)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoatePW_C007219L-3-HK2994279074132121757124124308118127642388143NADPHMDB0000217Nicotinamide 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_C000964FAD999114518681923216425317628288251884021188141489421612291622492133582536223723264602364688314741134758104881652681035285102533511154961265511127561311860301556054156608216161161626390164751786499179666610770391637175205732121374652227487223907622411818216118872151189921112296225123282491244315112519227125952261271029112720292130293011304130243623318770802937712613377152134775011137750711277518115775413347761513277726337780543297837534578930331792223367927235880012368800343698071411911995840611999938412005140812010740712043240512045312212049012412127842912129841812141738212148938312274812012277612112280237412282344312306637612308713512316644812384946412386845412397639912404739812534847912537848012542948212547448112569729712597948912610729912627748412689150112692039112696850212698720712701120612731020912743250612760238812784038914079018514079918611373-Hydroxyanthranilic acidHMDB00014763-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, 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. 3-Hydroxyanthranilic acid exists as a solid, soluble (in water), and a moderately acidic compound (based on its pKa). 3-Hydroxyanthranilic acid has been found in human epidermis and bladder tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 3-hydroxyanthranilic acid is primarily located in the cytoplasm. 3-Hydroxyanthranilic acid exists in all living organisms, ranging from bacteria to humans. In humans, 3-hydroxyanthranilic acid is involved in the tryptophan metabolism pathway. 3-Hydroxyanthranilic acid is an oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.548-93-6C0063286157933-HYDROXY-ANTHRANILATE84DB03644NC1=C(O)C=CC=C1C(O)=OC7H7NO3InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11)WJXSWCUQABXPFS-UHFFFAOYSA-N153.1354153.042593095FDB0105822-amino-3-hydroxy-benzoate;2-amino-3-hydroxy-benzoic acid;2-amino-3-hydroxybenzoate;2-amino-3-hydroxybenzoic acid;3-hydroxanthranilate;3-hydroxy-2-aminobenzoate;3-hydroxy-2-aminobenzoic acid;3-hydroxy-anthranilate;3-hydroxy-anthranilic acid;3-hydroxy-anthranilsaeure;3-hydroxyanthranilate;3-hydroxyanthranilic acid;3-hydroxyantranilic acid;3-oh-anthranilic acid;3-ohaa;3-oxyanthranilate;3-oxyanthranilic acidPW_C0011373-OHAa29962790751321217591241243101181276443882050CinnavalininateHMDB0004078Cinnavalininate, also known as cinnabarinic acid or cinnabarinate, belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring. Cinnavalininate is considered to be a practically insoluble (in water) and relatively neutral molecule. Cinnavalininate exists in all living organisms, ranging from bacteria to humans. In humans, cinnavalininate is involved in the tryptophan metabolism pathway. Cinnavalininate is an intermediate in the tryptophan metabolic pathway [Kegg: C05640]. It is generated from 3-hydroxyanthranilate via the enzyme catalase (EC:1.11.1.6).606-59-7C05640114918102864NC1=C(C(O)=O)C2=NC3=C(C=CC=C3OC2=CC1=O)C(O)=OC14H8N2O6InChI=1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)FSBKJYLVDRVPTK-UHFFFAOYSA-N300.2231300.038235998FDB0233022-amino-3-oxo-3h-phenoxazin-1,9-dicarboxylic acid;2-amino-3h-phenoxazin-one-1,9-dicarboxylic acid;Cinnabarinic acid;Cinnavalininic acid;Cinnabarinate;2-amino-3-oxophenoxazine-1,9-dicarboxylatePW_C002050CinVal299727907613212176012412431111812764538820534-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acidHMDB00040834-(2 Amino-3-hydroxyphenyl)-2,4-dioxobutanoate is found in the tryptophan metabolic pathway and is an intermediate in tryptophan degradation [Kegg: C05645]. More specifically it is an intermediate in the conversion of 3-hydroxy-L-kynurenine to xanthurenate. The conversion is catalyzed by kynurenine aminotransferase (EC 2.6.1.7).C05645440741389612NC1=C(C=CC=C1O)C(=O)CC(=O)C(O)=OC10H9NO5InChI=1S/C10H9NO5/c11-9-5(2-1-3-6(9)12)7(13)4-8(14)10(15)16/h1-3,12H,4,11H2,(H,15,16)YCJNYHCCOXVYAF-UHFFFAOYSA-N223.1822223.048072403FDB0233054-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoate;4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoic acidPW_C00205342A3H242999279077132121762124124313118127647388703Xanthurenic acidHMDB0000881Xanthurenic acid, also known as xanthurenate or 8-hydroxykynurenate, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid exists as a solid, slightly soluble (in water), and a moderately acidic compound (based on its pKa). Xanthurenic acid has been found in human epidermis tissue, and has also been detected in multiple biofluids, such as feces, urine, and blood. In humans, xanthurenic acid is involved in the tryptophan metabolism pathway. Xanthurenic acid has been found to be associated with several diseases known as colorectal cancer, eosinophilic esophagitis, and hemodialysis; xanthurenic acid has also been linked to the inborn metabolic disorders including kynureninase deficiency. Xanthurenic acid is a metabolite from tryptophan catabolism. It is a substrate of the enzyme methyltransferases [EC 2.1.1.-] in pathway tryptophan metabolism (KEGG).59-00-7C024705699217069XANTHURENATE5497OC(=O)C1=NC2=C(O)C=CC=C2C(O)=C1C10H7NO4InChI=1S/C10H7NO4/c12-7-3-1-2-5-8(13)4-6(10(14)15)11-9(5)7/h1-4,12H,(H,11,13)(H,14,15)FBZONXHGGPHHIY-UHFFFAOYSA-N205.1669205.037507717FDB0222974,8-dihydroxy-2-quinolinecarboxylate;4,8-dihydroxy-2-quinolinecarboxylic acid;4,8-dihydroxy-quinaldate;4,8-dihydroxy-quinaldic acid;4,8-dihydroxyquinaldate;4,8-dihydroxyquinaldic acid;4,8-dihydroxyquinaldinate;4,8-dihydroxyquinaldinic acid;4,8-dihydroxyquinoline-2-carboxylate;4,8-dihydroxyquinoline-2-carboxylic acid;4-oxoxanthurenic acid;8-hydroxykynurenate;8-hydroxykynurenic acid;Oxoxanthurenate;Xanthurate;Xanthurenate;Xanthuric acid;Xanthurenic acid;8-hydroxy-4-oxo-1h-quinoline-2-carboxylatePW_C000703Xanthur300027907813212176312412431411812764838810262-Amino-3-carboxymuconic acid semialdehydeHMDB00013302-amino-3-carboxymuconic acid semialdehyde is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic semialdehyde is enzymatically converted to 2-aminomuconate via 2-aminomuconic semialdehyde. (PMID: 10510494, 16267312, 14275129).16597-58-3C0440952806739952-AMINO-3-CARBOXYMUCONATE_SEMIAL4444266N\C(C(O)=O)=C(\C=C/C=O)/C(O)=OC7H7NO5InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)/b2-1-,5-4-KACPVQQHDVBVFC-OIFXTYEKSA-N185.1342185.032422339FDB0225592-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate;2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid;2-amino-3-(3-oxoprop-1-enyl)-but-2-enedioate;2-amino-3-(3-oxoprop-1-enyl)-but-2-enedioic acid;2-amino-3-carboxymuconate semialdehyde;2-amino-3-carboxymuconate-6-semialdehyde;Acs;Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioate;Amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acidPW_C0010262Am3CSa3001279079132121764124124315118127649388544Fe2+HMDB0000692Iron is a chemical element with the symbol Fe and atomic number 26. Iron makes up 5% of the Earth's crust and is second in abundance to aluminium among the metals and fourth in abundance among the elements. Physiologically, it. exists as an ion in the body. Iron (as Fe2+, ferrous ion) is a necessary trace element used by all known living organisms. Iron-containing enzymes, usually containing heme prosthetic groups, participate in catalysis of oxidation reactions in biology, and in transport of a number of soluble gases. Iron is an essential constituent of hemoglobin, cytochrome, and other components of respiratory enzyme systems. Its chief functions are in the transport of oxygen to tissue (hemoglobin) and in cellular oxidation mechanisms. Inorganic iron involved in redox reactions is also found in the iron-sulfur clusters of many enzymes, such as nitrogenase (involved in the synthesis of ammonia from nitrogen and hydrogen) and hydrogenase. A class of non-heme iron proteins is responsible for a wide range of functions such as ribonucleotide reductase (reduces ribose to deoxyribose; DNA biosynthesis) and purple acid phosphatase (hydrolysis of phosphate esters). When the body is fighting a bacterial infection, the body sequesters iron inside of cells (mostly stored in the storage molecule ferritin) so that it cannot be used by bacteria. Depletion of iron stores may result in iron-deficiency anemia. Iron is used to build up the blood in anemia. Humans experience iron toxicity above 20 milligrams of iron for every kilogram of weight, and 60 milligrams per kilogram is a lethal dose. Over-consumption of iron, often the result of children eating large quantities of ferrous sulfate tablets intended for adult consumption, is the most common toxicological cause of death in children under six. The DRI lists the Tolerable Upper Intake Level (UL) for adults as 45 mg/day. For children under fourteen years old the UL is 40 mg/day. Iron is a metal extracted from iron ore, and is almost never found in the free elemental state.15438-31-0C148182728429033Ferric-Hydroxamate-Complexes25394DB01592[Fe++]FeInChI=1S/Fe/q+2CWYNVVGOOAEACU-UHFFFAOYSA-N55.84555.934942133FDB016251Armco iron;Carbonyl iron;Fe;Ferrovac e;Hematite;Infed;Loha;Limonite;Magnetite;Malleable iron;Metopirone;Metyrapone;Pzho;Pzh2m;Remko;Suy-b 2;Taconite;Venofer;Wrought iron;Fe (ii) ion;Fe(ii);Fe2+;Fe(2+);Ferrous ion;Iron ion(2+)PW_C000544Fe2+398196413678316922070981777270411637052160120602251214315177179132777401127775112977760341777821111205444071205574141205701221217651241231781191231914501232041351243161181261432991261854811276503881407104914071618156Quinolinic acidHMDB0000232Quinolinic acid is a metabolite of tryptophan with a possible role in neurodegenerative disorders. Elevated CSF levels of quinolinic acid are correlated with the severity of neuropsychological deficits in patients who have AIDS. Quinolinic acid (QUIN) is a product of tryptophan metabolism that can act as an endogenous brain excitotoxin when released by activated macrophages. (Valle et. al, Brain 127:1047 (2004)).89-00-9C03722106616675QUINOLINATE1037DB01796OC(=O)C1=CC=CN=C1C(O)=OC7H5NO4InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)GJAWHXHKYYXBSV-UHFFFAOYSA-N167.1189167.021857653FDB0219132,3-pyridinedicarboxylate;2,3-pyridinedicarboxylic acid;3,4-pyridinedicarboxylic acid;Pyridin-2,3-dicarbonsaeure;Pyridine-2,3-carboxylate;Pyridine-2,3-dicarboxylate;Pyridine-2,3-dicarboxylic acid;Pyridine-3,4-dicarboxylic acid;Quinolinate;Quinolinic acidPW_C000156Quinoli23752581410842661315783991321217661241243171181276513889912-Aminomuconic acid semialdehydeHMDB00012802-aminomuconic semialdehyde is an intermediate in the oxidative metabolism of tryptophan in mammals, and takes place via the kynurenine pathway, which is also used for NAD biosynthesis in all eukaryotic organisms. 2-Aminomuconic semialdehyde is reported to be unstable and spontaneously converted to picolinic acid (regarded as metabolically inert and is excreted in the urine as a glycine conjugate), and enzymatically converted to 2-aminomuconic acid through the action of 2-aminomuconic semialdehyde dehydrogenase. (PMID: 10510494, 16267312, 14275129).245128-91-0C038245280625157452-AMINOMUCONATE_SEMIALDEHYDE4444230N\C(=C\C=C/C=O)C(O)=OC6H7NO3InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+QCGTZPZKJPTAEP-REDYYMJGSA-N141.1247141.042593095FDB0225322-aminomuconate 6-semialdehyde;2-aminomuconate semialdehyde;2-aminomuconic semialdehyde;2-aminomuconic acid 6-semialdehyde;(2e,4z)-2-amino-6-oxohexa-2,4-dienoate;2-aminomuconic acid semialdehydePW_C0009912-AaSa30022790801321217671241243181181276523881316Carbon 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_C001316CO2508121120444801350318640367731695208065113343163849174522551173144705283103532011157501085771101596810060261556078161647117866371076922190701716070351637061188716320573081987333213746122275302108215225822315191582491184927711908170124642261268829042626315435233187699429377122133771701327747033377739112777501297776334178077134784053567842733478941331792271308000836880675119807171359483638411329139111554912111995440612008912212015540712036441212055641412083341912092212412099140812128412512150538312274412012301144612319045012341845512348911812355637412385513612406339812534447912546029712551648112582449012587029912593148212628048012688750112705220612727750712733138812739050214079818519TetrahydrobiopterinHMDB0000027Tetrahydrobiopterin or BH4 is a cofactor in the synthesis of nitric oxide. In fact it is used by all three human nitric-oxide synthases (NOS) eNOS, nNOS, and iNOS as well as the enzyme glyceryl-ether monooxygenase. It is also essential in the conversion of phenylalanine to tyrosine by the enzyme phenylalanine-4-hydroxylase; the conversion of tyrosine to L-dopa by the enzyme tyrosine hydroxylase; and conversion of tryptophan to 5-hydroxytryptophan via tryptophan hydroxylase. Specifically, tetrahydrobiopterin is a cofactor for tryptophan 5-hydroxylase 1, tyrosine 3-monooxygenase, and phenylalanine hydroxylase all of which are essential for the formation of the neurotransmitters dopamine, noradrenaline and adrenaline. Tetrahydrobiopterin has been proposed to be involved in promotion of neurotransmitter release in the brain and the regulation of human melanogenesis. A defect in BH4 production and/or a defect in the enzyme dihydropteridine reductase (DHPR) causes phenylketonuria type IV, as well as dopa-responsive dystonias. BH4 is also implicated in Parkinson's disease, Alzheimer's disease and depression. Tetrahydrobiopterin is present in probably every cell or tissue of higher animals. On the other hand, most bacteria, fungi and plants do not synthesize tetrahydrobiopterin. -- Wikipedia.17528-72-2C00272112515372TETRA-H-BIOPTERIN1093DB00360[H][C@@]1(CNC2=C(N1)C(=O)N=C(N)N2)[C@@H](O)[C@H](C)OC9H15N5O3InChI=1S/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1FNKQXYHWGSIFBK-RPDRRWSUSA-N241.2471241.117489371FDB021880(1r,2s)-(2-amino-3,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)-1,2-propandiol;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1h)-5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1h)-pteridinone;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(1h)-pteridinone;5,6,7,8-erythro-tetrahydrobiopterin;5,6,7,8-tetra-h-biopterin;5,6,7,8-tetrahydro-2-amino-6-(1,2-dihydroxypropyl)-4(1h)-pteridinone;5,6,7,8-tetrahydrobiopterin;L-erythro-2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3h)-pteridinon;Tetra-h-biopterin;Tetra-hydro-biopterin;Tetrahydrobiopterin;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1h)-pteridinone;Bh4PW_C000019BH419572408584800144803144962311190121177520115786631321204344051216161241230683761241741181264932991275853883585-Hydroxy-L-tryptophanHMDB00004725-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic L-amino acid decarboxylase (EC 4.1.1.28) (AADC1 also known as DOPA decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency (AADC deficiency) (OMIM: 608643) accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific. 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinson's patients with severe postural instability and gait disorders. The amount of endogenous 5-hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase (TDO) (EC 1.13.11.11). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to its use in the treatment of depression, the therapeutic administration of 5-hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties (PMID: 9295177, 17240182, 16023217). When present in sufficiently high levels, 5-hydroxytryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells or tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Signs and symptoms of AADC deficiency generally appear in the first year of life. Affected infants may have severe developmental delay, weak muscle tone (hypotonia), muscle stiffness, difficulty moving, and involuntary writhing movements of the limbs (athetosis). They may be lacking in energy (lethargic), feed poorly, startle easily, and have sleep disturbances. Since 5-hydroxytryptophan is a precursor to serotonin, altered levels of serotonin can accumulate in the brain, which leads to abnormal neural signalling. Infants with AADC deficiency have very low levels of neural signalling molecules while individuals who consume high levels of 5-hydroxytryptophan will have very high levels of neural signalling molecules. Both conditions can lead to vomiting, nausea, extreme drowsiness, and lethargy. 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN) is sold over-the-counter in the United Kingdom, the United States, and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. It is also marketed in many European countries for the indication of major depression under trade names such as Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high-quality studies has been noted. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression.4350-09-8C00643439280177805-HYDROXY-TRYPTOPHAN388413DB02959N[C@@H](CC1=CNC2=C1C=C(O)C=C2)C(O)=OC11H12N2O3InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1LDCYZAJDBXYCGN-VIFPVBQESA-N220.2246220.08479226FDB006231(+-)-5-hydroxytryptophan;(s)-5-hydroxytryptophan;5-hydroxy-l-tryptophan;5-hydroxy-tryptophan;5-hydroxyl-l-tryptophan;5-hydroxytryptophan;5-hydroxytryptophan l form;5-hydroxytryptophan l-form;Cincofarm;Hydroxytryptophan;L-5-hydroxytryptophan;Levothym;Levotinine;Oxitriptan;Oxyfan;Oxytryptophan;Pretonine;Quietim;Serotonyl;Telesol;Triptene;Tript-OH;5-htp;5-hydroxy-dl-tryptophan;5-hydroxytryptophan dl-form;Dl-5-htp;Dl-5-hydroxytryptophanPW_C0003585-HTP300427908113212176912412432011812765438815414a-HydroxytetrahydrobiopterinHMDB0002281Tetrahydrobiopterin (BH4) is essential to catalyze the conversion of phenylalanine to tyrosine by phenylalanine hydroxylase. During this physiological reaction, the oxidation of BH4 creates 4a-hydroxytetrahydropterin intermediates and hydrogen peroxide is formed. The hydrogen peroxide and the hydroxytetrahydropterin can both derive from alternate routes of breakdown of a common precursor, the corresponding 4a-hydroperoxytetrahydropterin. (PMID 8323303).70110-58-6C1552212980315374114908[H][C@@]1(CNC2=NC(N)=NC(=O)[C@]2(O)N1)[C@@H](O)[C@H](C)OC9H15N5O4InChI=1S/C9H15N5O4/c1-3(15)5(16)4-2-11-6-9(18,14-4)7(17)13-8(10)12-6/h3-5,14-16,18H,2H2,1H3,(H3,10,11,12,13,17)/t3-,4+,5-,9-/m0/s1KJKIEFUPAPPGBC-XXKOCQOQSA-N257.25257.112403983FDB022944(6r)-6-(l-erythro-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxypterin;2-amino-6-(1,2-dihydroxypropyl)-4a-hydroxy-5,6,7,8-tetrahydropteridin-4(4ah)-one;2-amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4a-hydroxy-4(4ah)-pteridinone;2-amino-6-[(1r,2s)-1,2-dihydroxypropyl]-4a-hydroxy-1,5,6,7-tetrahydropteridin-4-one;4a-hydroxy-5,6,7,8-tetrahydrobiopterin;4a-hydroxytetrahydrobiopterin;4alpha-hydroxytetrahydrobiopterin;4a-hydroxy-5,6,4,8-tetrahydrobiopterinPW_C0015414aHtHbp12858202627847011179082132121002122121617124123567135124175118127586388178SerotoninHMDB0000259Serotonin is a biochemical messenger and regulator, synthesized from the essential amino acid L-Tryptophan. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns , including those responsible for feeding. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep, the arousal state , sexual behavior, and others, and deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. The three modes can affect a single neuronal circuit. (PMID: 16047543).50-67-9C007805202287905013NCCC1=CNC2=C1C=C(O)C=C2C10H12N2OInChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2QZAYGJVTTNCVMB-UHFFFAOYSA-N176.2151176.094963016FDB0121583-(2-aminoethyl)-1h-indol-5-ol;3-(2-aminoethyl)indol-5-ol;3-(b-aminoethyl)-5-hydroxyindole;5-ht;5-hta;5-hydroxy-3-(b-aminoethyl)indole;5-hydroxy-tryptamine;5-hydroxyltryptamine;5-hydroxytriptamine;5-hydroxytryptamine;Antemovis;Ds substance;Enteramin;Enteramine;Serotonine;Thrombocytin;ThrombotoninPW_C0001785-HT300623181743182713186155012807908313212177112412432211812765638820475-HydroxyindoleacetaldehydeHMDB00040735-Hydroxyindoleacetaldehyde, also known as 5-hial, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 5-Hydroxyindoleacetaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-Hydroxyindoleacetaldehyde has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as feces, urine, and blood. Within the cell, 5-hydroxyindoleacetaldehyde is primarily located in the cytoplasm and mitochondria. In humans, 5-hydroxyindoleacetaldehyde is involved in the tryptophan metabolism pathway. Outside of the human body, 5-hydroxyindoleacetaldehyde can be found in a number of food items such as sweet rowanberry, rose hip, summer savory, and gram bean. This makes 5-hydroxyindoleacetaldehyde a potential biomarker for the consumption of these food products. 5-Hydroxyindoleacetaldehyde is a biogenic aldehyde of serotonin derived from the action of monoamine oxidase (MAO). (PMIDs 11306106, 2470392).1892-21-3C05634746885015767261OC1=CC2=C(NC=C2CC=O)C=C1C10H9NO2InChI=1S/C10H9NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,4-6,11,13H,3H2OBFAPCIUSYHFIE-UHFFFAOYSA-N175.184175.063328537DBMET00564FDB023299(5-hydroxy-1h-indol-3-yl)acetaldehyde;(5-hydroxyindol-3-yl)acetaldehyde;5-hial;5-hydroxy-1h-indole-3-acetaldehyde;5-hydroxyindole-3-acetaldehyde;Hydroxyindoleacetaldehyde;5-hydroxyindoleacetaldehydePW_C0020475-Hial3007279084132121772124124323118127657388721NADHMDB0000902NAD (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_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951407571856095-Hydroxyindoleacetic acidHMDB00007635-hydroxyindoleacetic acid (5HIAA) is a breakdown product of serotonin that is excreted in the urine. Serotonin is a hormone found at high levels in many body tissues. Serotonin and 5HIAA are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors. (NCI).54-16-0C056351826278235-HYDROXYINDOLE_ACETATE1760OC(=O)CC1=CNC2=C1C=C(O)C=C2C10H9NO3InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)DUUGKQCEGZLZNO-UHFFFAOYSA-N191.1834191.058243159FDB0014035-hiaa;5-hydroxy-1h-indole-3-acetate;5-hydroxy-1h-indole-3-acetic acid;5-hydroxy-3-indolylacetate;5-hydroxy-iaa;5-hydroxy-indole-3-acetate;5-hydroxy-indole-3-acetic acid;5-hydroxyheteroauxin;5-hydroxyindol-3-ylacetate;5-hydroxyindol-3-ylacetic acid;5-hydroxyindole acetate;5-hydroxyindole-3-acetate;5-hydroxyindole-3-acetic acid;5-hydroxyindoleacetate;5-hydroxyindoleacetic acid;5-oxyindoleacetate;5-oxyindoleacetic acid;5hiaa;Hydroxyindoleacetate;2-(5-hydroxy-1h-indol-3-yl)acetatePW_C0006095HIDA30082790851321217731241243241181276583881144NADHHMDB0001487NADH 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_C001144NADH14341533490864810111521275514695422304927811728362931099480618481218482128490464959315169955240103533211153581125466123547912555931355698100573710858291415915147594515160271556079161638716472178677111768931607011188709916371722057195206746222282442268360225908622411809198118212161232024913003298130153001325522342403322426183157710713277123133772081347737133177651336776683347770033277707130779171137798634780009368806911199382212411054938811285494115838118119955406120172407120378122120986408121162425121244126121693429121818383122616384122745120123127447123138136123551374123734460123814443124242464124371398125189121125345479125531481125762297125808299125926482126516495126767480126888501127385502128090390128362391128429395140759185921S-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_C000921SAMe51986333070420122031880272066246811050235056041357136163754021075442137632160826615192351951187419812031222123582251529324915345181536330976897293768991647698422477488111777313387777234178099132783033517833534679155112799613618086122948303829483338611328638911328839711554339911554640112039312212053741312093940712105212412228243512317144912350511912361611812483647012585929712587948112630429912644749912732120512734020612759538812801751720605-MethoxyindoleacetateHMDB00040965-Methoxyindoleacetic acid (5-MIAA) is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 µg/mL using GC-MS (PMID: 12908946). An increase in urinary 5-MIAA excretion was shown in patients with cancer of the stomach, rectum, and lung (PMID: 2446428).3471-31-6C05660189862828117924COC1=CC2=C(NC=C2CC(O)=O)C=C1C11H11NO3InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)COCNDHOPIHDTHK-UHFFFAOYSA-N205.2099205.073893223FDB0233125-methoxyindol-3-ylacetate;5-methoxyindol-3-ylacetic acid;5-methoxyindole-3-acetate;5-methoxyindole-3-acetic acid;5-methoxyindoleacetate;5-methoxyindoleacetic acid;Methoxyindoleacetate;Methoxyindoleacetic acid;2-(5-methoxy-1h-indol-3-yl)acetatePW_C002060Methoxy3010279086132121775124124326118127660388749S-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_C000749SAH520857518635307052012213188227206724683105025505607136713716375422107546213763416082681519237195118751981235922515294249153643097748911177611130777333387777334178098132783053517833734679156112799623618086322948313829483438611328738911328939711554439911554740112039412212048612512053941312094040712105312412228443512303713512317344912350611912361711812483847012588048112630329912644949912734120612759638812801951720555-Hydroxy-N-formylkynurenineHMDB00040865-Hydroxy-N-formylkynurenine 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. 5-Hydroxy-N-formylkynurenine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). In humans, 5-hydroxy-N-formylkynurenine is involved in the tryptophan metabolism pathway. 5-Hydroxy-N-formylkynurenine is an intermediate in tryptophan metabolism. 5-Hydroxy-N-formylkynurenine is converted from 5-Hydroxy-L-tryptophan via the enzyme, indoleamine 2,3-dioxygenase [EC:1.13.11.52].C056484407442065389615NC(CC(=O)C1=C(NC=O)C=CC(O)=C1)C(O)=OC11H12N2O5InChI=1S/C11H12N2O5/c12-8(11(17)18)4-10(16)7-3-6(15)1-2-9(7)13-5-14/h1-3,5,8,15H,4,12H2,(H,13,14)(H,17,18)LSTOUSIIVKMJBU-UHFFFAOYSA-N252.2234252.074621504FDB023307PW_C0020555HNFKN303627908713212177712412432811812766138880925-HydroxykynurenineHMDB00128195-Hydroxykynurenine is found in the tryptophan metabolism pathway. It is created from 5-Hydroxy-N-formylkynurenine through the action of arylformamidase [EC:3.5.1.9]. 5-Hydroxykynurenine is then converted to 5-Hydroxykynurenamine by the action of dopa decarboxylase [EC:4.1.1.28].720-00-3C056514407452076389616NC(CC(=O)C1=C(N)C=CC(O)=C1)C(O)=OC10H12N2O4InChI=1S/C10H12N2O4/c11-7-2-1-5(13)3-6(7)9(14)4-8(12)10(15)16/h1-3,8,13H,4,11-12H2,(H,15,16)OTDQYOVYQQZAJL-UHFFFAOYSA-N224.2133224.079706882C056515-hydroxy-l-kynurenine;2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoic acid;2-amino-4-(2-amino-5-hydroxyphenyl)-4-oxobutanoatePW_C0080925HKnn303927908813212177812412432911812766238820485-HydroxykynurenamineHMDB00040765-Hydroxykynurenamine, also known as mausamine, 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. 5-Hydroxykynurenamine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). In humans, 5-hydroxykynurenamine is involved in the tryptophan metabolism pathway. 5-Hydroxykynurenamine is an intermediate in the tryptophan metabolic pathway [Kegg: C05638]. It is generated from 5-hydroxykynurenine via the enzyme DOPA decarboxylase.708-23-6C0563816471928715144400NCCC(=O)C1=C(N)C=CC(O)=C1C9H12N2O2InChI=1S/C9H12N2O2/c10-4-3-9(13)7-5-6(12)1-2-8(7)11/h1-2,5,12H,3-4,10-11H2JANBBPTXDKFOQR-UHFFFAOYSA-N180.2038180.089877638FDB0233005-hydroxykynuramine;Mausamine;Mousamine;3-amino-1-(2-amino-5-hydroxyphenyl)-1-propanonePW_C0020485-Hkynm304127908913212178012412433111812766338820494,6-DihydroxyquinolineHMDB00040774,6-Dihydroxyquinoline, also known as quinoline-4,6-diol, belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. 4,6-Dihydroxyquinoline is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4,6-Dihydroxyquinoline has been primarily detected in feces. Within the cell, 4,6-dihydroxyquinoline is primarily located in the cytoplasm. In humans, 4,6-dihydroxyquinoline is involved in the tryptophan metabolism pathway. 4,6-Dihydroxyquinoline is the product of the conversion of 5-hydroxykynurenamine by the enzyme monoamine oxidase, both metabolites from the 5-hydroxytryptophan metabolism. (PMIDs 7160021, 312499).3517-61-1C0563944073828799389609OC1=CC2=C(O)C=CN=C2C=C1C9H7NO2InChI=1S/C9H7NO2/c11-6-1-2-8-7(5-6)9(12)3-4-10-8/h1-5,11H,(H,10,12)XFALURCRIGINGT-UHFFFAOYSA-N161.1574161.047678473FDB0233014,6-quinolinediol;Quinoline-4,6-diol;4,6-dihydroxyquinolinePW_C00204946Q3046279090132121781124124332118127664388940Acetyl-CoAHMDB0001206The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.72-89-9C0002444449315351ACETYL-COA392413CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC23H38N7O17P3SInChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1ZSLZBFCDCINBPY-ZSJPKINUSA-N809.571809.125773051FDB022491Ac-coa;Ac-coenzyme a;Ac-s-coa;Ac-s-coenzyme a;Acetyl coenzyme-a;Acetyl-coa;Acetyl-coenzyme a;Acetyl-s-coa;Acetyl-s-coenzyme a;Acetylcoenzyme-a;S-acetate coa;S-acetate coenzyme a;S-acetyl coenzyme a;Accoa;Acetyl coenzyme a;S-acetyl-coa;S-acetyl-coenzyme a;Acetylcoenzyme aPW_C000940Ac-CoA2134385884232416224465289617334011484014527810354761245733108602515560771616386164701786923160710616372911987460222824515182772101258222613012299426153157712113377291111775621127770613277994115783551347843333480007368806341198066337690124170119953406120145405120304122120632407122417408122626384122743120122959135123137118124986374125200121125343479125507478125633297126564482126572481126778480126886501127044209127394205127665388128137502128145206128374391140762185956N-AcetylserotoninHMDB0001238N-Acetylserotonin is an intermediate in the metabolic pathway of melatonin and indoleamine in the pineal gland of mammalians. Serotonin-N-acetyltransferase (SNAT), which regulates the rate of melatonin biosynthesis in the pineal gland, catalyzes the acetylation of 5HT to N-acetylserotonin (NAS). A methyl group from S-adenosylmethionine is transferred to NAS by hydroxyindole-O-methyltransferase (HIOMT), and finally NAS is converted to 5-methoxy-N-acetyltryptamine, or melatonin. In most mammalian species the content of NAS (and melatonin) in the pineal gland shows clear circadian changes with the highest level occurring during the dark period. This elevation of the contents of NAS (and melatonin) in the dark period is due to the increase of SNAT activity and the elevation of SNAT gene expression. Experimental studies show that N-acetylserotonin possess free radical scavenging activity. Acute administration of irreversible and reversible selective MAO-A inhibitors and high doses (or chronic administration of low doses) of relatively selective MAO-B inhibitors (but not of highly selective MAO-B inhibitors) suppressed MAO-A activity and stimulated N-acetylation of pineal serotonin into N-acetylserotonin, the immediate precursor of melatonin. N-acetylserotonin increase after MAO-A inhibitors might mediate their antidepressive and antihypertensive effects. N-Acetylserotonin is the product of the O-demethylation of melatonin mediated by cytochrome P-450 isoforms: Cytochrome p450, subfamily IIc, polypeptide 19 (CYP2C19, a clinically important enzyme that metabolizes a wide variety of drugs), with a minor contribution from Cytochrome p450, subfamily I, polypeptide (2CYP1A2, involved in O-deethylation of phenacetin). (PMID 15616152, 11103901, 10721079, 10591054).1210-83-9C0097890317697N-ACETYL-SEROTONIN879DB04275CC(=O)NCCC1=CNC2=C1C=C(O)C=C2C12H14N2O2InChI=1S/C12H14N2O2/c1-8(15)13-5-4-9-7-14-12-3-2-10(16)6-11(9)12/h2-3,6-7,14,16H,4-5H2,1H3,(H,13,15)MVAWJSIDNICKHF-UHFFFAOYSA-N218.2518218.105527702DBMET00411FDB0225055-hydroxy-n-acetyltryptamine;5-hydroxymelatonin;Ase;N-acetyl-5-hydroxytryptamine;Desmethylmelatonin;O-demethylmelatonin;N-(2-(5-hydroxy-1h-indol-3-yl)ethyl)acetamidePW_C000956NAsertn30522790911321217821241243331181276663881099Coenzyme 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_C001099CoA21143868845387922892172407592414224595281329286231334211335118461810462958484214486554487965232102524710452801035477124573410857771016023155607516163841646817869301606961162697319970831887108163729319873472107458222822915190812269090224912417092151951301329915318249254884942616315769072937711913377222134772303297729211177550132775553347756311277633336776721297799611578047332780563507841333578567130792593337997433180005368806201188062737480635119806653769382838293834383986742881105553891105613901158423991158473981199514061201474051202313841203051221206344071207621171214061231214214331215211251216664291216824081217144141224044221227411201229041211229601351239654471239794681240791361242204641242654501249743751253414791255094781255794801255924841256342971260844811265494911265604821267463001268845011270462091271093911273012051275402061276673881281215081281335021283403951407511861407631851407678911074MelatoninHMDB0001389Melatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B.Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and. lowering the body temperature. Melatonin is also implicated in the regulation of mood,learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders(ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits. were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.73-31-4C0159889616796N-ACETYL-5-METHOXY-TRYPTAMINE872DB01065COC1=CC2=C(NC=C2CCNC(C)=O)C=C1C13H16N2O2InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)DRLFMBDRBRZALE-UHFFFAOYSA-N232.2783232.121177766FDB0042345-methoxy-n-acetyltryptamine;Circadin;Mt6;Melatol;Melatonin;Melatonin (synth.) standard-grade;Melatonin (synth.) ultra-pure;Melatonine;Melovine;N-(2-(5-methoxy-1h-indol-3-yl)ethyl)acetamide;N-(2-(5-methoxyindol-3-yl)ethyl)-acetamide;N-(2-(5-methoxyindol-3-yl)ethyl)acetamide;N-acetyl-5-methoxy-tryptamine;N-acetyl-5-methoxy-tryptamine melatonine;N-acetyl-5-methoxytryptamine;N-[2-(5-methoxy-1h-indol-3-yl)ethyl)acetamide;N-[2-(5-methoxy-1h-indol-3-yl)ethyl]-acetamide;N-[2-(5-methoxy-1h-indol-3-yl)ethyl]acetamide;N-[2-(5-methoxyindol-3-yl)ethyl]-acetamide;N-[2-(5-methoxyindol-3-yl)ethyl]acetamide;Regulin;{n-[2-(5-methoxy-1h-indol-3-yl)ethyl]-} acetamide;{n-[2-(5-methoxyindol-3-yl)ethyl]-} acetamidePW_C001074Meltn305427909213212178412412433511812766838820526-HydroxymelatoninHMDB00040816-Hydroxymelatonin, also known as lopac-H-0627, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 6-Hydroxymelatonin is considered to be a practically insoluble (in water) and relatively neutral molecule. 6-Hydroxymelatonin has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 6-hydroxymelatonin is primarily located in the cytoplasm. 6-Hydroxymelatonin is the main primary metabolite that can be biosynthesized from melatonin through its interaction with the enzyme cytochrome P450 (CYP) 1A2 (PMID: 11452239). In humans, 6-hydroxymelatonin is involved in the tryptophan metabolism pathway.2208-41-5C0564318643080791794COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1C13H16N2O3InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)OMYMRCXOJJZYKE-UHFFFAOYSA-N248.2777248.116092388DBMET00258FDB023304Lopac-H-0627;6-Hydroxy-N-acetyl-5-methoxytryptaminePW_C0020526HMeltn30552790931321217851241243361181276693882112Acetyl-N-formyl-5-methoxykynurenamineHMDB0004259Acetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O)-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a species formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration. AFMK was also found in some patients to exceed the concentration of melatonin normally found in serum (PMID: 16150112).52450-38-1C05642171161149637COC1=CC(C(=O)CCNC(C)=O)=C(NC=O)C=C1C13H16N2O4InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)JYWNYMJKURVPFH-UHFFFAOYSA-N264.2771264.11100701FDB023355AFMK;Formyl-n-acetyl-5-methoxykynurenamine;N-acetyl-n-formyl-5-methoxykynurenamine;N-[3-(2-formamido-5-methoxy-phenyl)-3-oxo-propyl]acetamide;N-acetyl-n-formyl-5-methoxykynuraminePW_C002112AceNf5m30582790941321217871241243381181276713882132N-MethylserotoninHMDB0004369N-Methylserotonin belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. N-Methylserotonin is considered to be a practically insoluble (in water) and relatively neutral molecule. N-Methylserotonin has been primarily detected in blood. Within the cell, N-methylserotonin is primarily located in the cytoplasm. In humans, N-methylserotonin is involved in the tryptophan metabolism pathway. Outside of the human body, N-methylserotonin can be found in citrus. This makes N-methylserotonin a potential biomarker for the consumption of this food product. N-methylserotonin is a product of the serotonin-degradative pathway, found in urine specimens of patients with psychiatric disorders (PubMed ID 8747157 ).1134-01-6C0621215088548294132989CNCCC1=CNC2=C1C=C(O)C=C2C11H14N2OInChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3ASUSBMNYRHGZIG-UHFFFAOYSA-N190.2417190.11061308FDB0172733-(2-(methylamino)ethyl)-1h-indol-5-ol;3-[2-(methylamino)ethyl]-1h-indol-5-ol;Lopac-m-1514PW_C002132NMetser30592790951321217881241243391181276723888135Formyl-5-hydroxykynurenamineHMDB0012948Formyl-5-hydroxykynurenamine 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. Formyl-5-hydroxykynurenamine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Formyl-5-hydroxykynurenamine can be biosynthesized from serotonin; which is mediated by the enzyme indoleamine 2,3-dioxygenase 1 [EC 1.13.11.52]. In humans, formyl-5-hydroxykynurenamine is involved in the tryptophan metabolism pathway.958733-17-0C0564744074328736389614NCCC(=O)C1=C(NC=O)C=CC(O)=C1C10H12N2O3InChI=1S/C10H12N2O3/c11-4-3-10(15)8-5-7(14)1-2-9(8)12-6-13/h1-2,5-6,14H,3-4,11H2,(H,12,13)CKAXPTWYSHDIBN-UHFFFAOYSA-N208.2139208.08479226C056473-(n-acetylaminoethyl)-6-hydroxy-5-methoxyindole;N-(2(6-hydroxy-5-methoxy-1h-indol-3-yl)ethyl)acetamide;N-(2-(6-hydroxy-5-methoxy-1h-indol-3-yl)ethyl)-acetamide;N-(2-(6-hydroxy-5-methoxyindol-3-yl)ethyl)-acetamide;N-[2-(6-hydroxy-5-methoxy-1h-indol-3-yl)ethyl]-acetamide;N-[2-(6-hydroxy-5-methoxyindol-3-yl)ethyl]-acetamidePW_C008135F5H3061279096132121789124124340118127673388207TryptamineHMDB0000303Tryptamine is a monoamine compound that is common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle.61-54-1C00398115016765TRYPTAMINE1118DB08653NCCC1=CNC2=C1C=CC=C2C10H12N2InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2APJYDQYYACXCRM-UHFFFAOYSA-N160.2157160.100048394FDB000917(3-indolyl)ethylamine;1h-indole-3-ethanamine;2-(1h-indol-3-yl)ethanamine;2-(1h-indol-3-yl)ethylamine;2-(3-indolyl)ethylamine;2-indol-3-yl-aethylamin;2-indol-3-yl-ethylamine;3-(2-aminoethyl)-1h-indole;3-(2-aminoethyl)indole;3-indoleethanamine;3-indoleethylamine;Tryptamin;Tryptamine;TryptaminiumPW_C000207Tryptam3062283941517699022779097132121790124124341118127674388926IndoleacetaldehydeHMDB0001190Indoleacetaldehyde is a substrate for Retina-specific copper amine oxidase, Aldehyde dehydrogenase X (mitochondrial), Amine oxidase B, Amiloride-sensitive amine oxidase, Aldehyde dehydrogenase (mitochondrial), Fatty aldehyde dehydrogenase, 4-trimethylaminobutyraldehyde dehydrogenase, Aldehyde dehydrogenase (dimeric NADP-preferring), Aldehyde dehydrogenase family 7 member A1, Amine oxidase A, Aldehyde dehydrogenase 1A3 and Membrane copper amine oxidase.2591-98-2C0063780018086INDOLE_ACETALDEHYDE778O=CCC1=CNC2=C1C=CC=C2C10H9NOInChI=1S/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2WHOOUMGHGSPMGR-UHFFFAOYSA-N159.1846159.068413915FDB0139501h-indol-3-ylacetaldehyde;1h-indole-3-acetaldehyde;2-(3-indolyl)acetaldehyde;2-(indol-3-yl)acetaldehyde;Indol-3-ylacetaldehyde;Indole-3-acetaldehyde;Indoleacetaldehyde;TryptaldehydePW_C000926Tryptal30652839715179098132121791124124342118127675388128Indoleacetic acidHMDB0000197Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria ((PMID: 13610897). Using material extracted from human urine, it was discovered by Kogl in 1933 that Indoleacetic acid is also an important plant hormone (PMID: 13610897). Specifically IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan. (wikipedia) IAA and some derivatives can be oxidised by horseradish peroxidase (HRP) to cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy. (PMID: 11163327).87-51-4C0095480216411780DB07950OC(=O)CC1=CNC2=C1C=CC=C2C10H9NO2InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)SEOVTRFCIGRIMH-UHFFFAOYSA-N175.184175.063328537DBMET00497FDB000933(1h-indol-3-yl)-acetate;(1h-indol-3-yl)-acetic acid;1h-indol-3-ylacetate;1h-indol-3-ylacetic acid;1h-indole-3-acetate;1h-indole-3-acetic acid;2-(1h-indol-3-yl)acetate;2-(1h-indol-3-yl)acetic acid;2-(3-indolyl)acetate;2-(3-indolyl)acetic acid;3-(carboxymethyl)indole;3-iaa;3-indole-acetic acid;3-indoleacetate;3-indoleacetic acid;3-indolylacetate;3-indolylacetic acid;Heteroauxin;Indol-3-ylacetate;Indol-3-ylacetic acid;Indole-3-acetate;Indole-3-acetic acid;Indoleacetate;Indoleacetic acid;Indolyl-3-acetate;Indolyl-3-acetic acid;Indolylacetate;Indolylacetic acid;Kyselina 3-indolyloctova;Rhizopin;Rhizopon a;Skatole carboxylate;Skatole carboxylic acid;Alpha-indol-3-yl-acetic acid;B-indoleacetate;B-indoleacetic acid;B-indolylacetate;B-indolylacetic acid;Beta-indole-3-acetic acid;Beta-indoleacetate;Beta-indoleacetic acid;Beta-indolylacetate;Beta-indolylacetic acid;(indol-3-yl)acetate;(indol-3-yl)acetic acid;2-(indol-3-yl)ethanoic acid;3-indolylessigsaeure;Iaa;Ies;2-(indol-3-yl)ethanoatePW_C000128Indolaa30662790991321217921241243431181276773882133N-MethyltryptamineHMDB0004370N-Methyltryptamine (NMT), or monomethyltryptamine, is a tryptamine alkaloid that has been found in the bark, shoots and leaves of numerous plants. (wikipedia). N-Methyltryptamine was detected in urine from all autistic patients with mental retardation and epilepsy and many autistic patients (32/47) with mental retardation (PubMed ID 8747157 ).61-49-4C06213608828136BUFOTENINE5863CNCCC1=CNC2=CC=CC=C12C11H14N2InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3NCIKQJBVUNUXLW-UHFFFAOYSA-N174.2423174.115698458FDB0233681-methyl-2-(3-indolyl)ethylamine;2-(1h-indol-3-yl)-n-methylethanamine;3-(2-(methylamino)ethyl)indole;Dipterine;Dl-methyltryptamine;Methyltryptamine;N-methylindoleethylamine;N-monomethyltryptamine;N-omega-methyltryptamine;3-(2-methylaminoethyl)indole;N-methyl-1h-indole-3-ethanamine;N(omega)-methyltryptaminePW_C002133N-Metrp30672791001321217931241243441181276783881783Hydrogen peroxideHMDB0003125Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colourless in a dilute solution, slightly more viscous than water. It is a weak acid. It has strong oxidizing properties and is therefore a powerful bleaching agent that is mostly used for bleaching paper, but has also found use as a disinfectant and as an oxidizer. Hydrogen peroxide in the form of carbamide peroxide is widely used for tooth whitening (bleaching), both in professionally- and in self-administered products. Hydrogen peroxide (H2O2) is a well-documented component of living cells. It plays important roles in host defense and oxidative biosynthetic reactions. In addition there is growing evidence that at low levels, H2O2 also functions as a signaling agent, particularly in higher organisms. H2O2 has increasingly been viewed as an important cellular signaling agent in its own right, capable of modulating both contractile and growth-promoting pathways with more far-reaching effects. Due to the accumulation of hydrogen peroxide in the skin of patients with the depigmentation disorder vitiligo, the human epidermis cannot have the normal capacity for autocrine synthesis, transport and degradation of acetylcholine as well as the muscarinic (m1-m5) and nicotinic signal transduction in keratinocytes and melanocytes. Accumulating evidence suggests that hydrogen peroxide (H(2)O(2)) plays an important role in cancer development. Experimental data have shown that cancer cells produce high amounts of H(2)O(2). An increase in the cellular levels of H(2)O(2) has been linked to several key alterations in cancer, including DNA alterations, cell proliferation, apoptosis resistance, metastasis, angiogenesis and hypoxia-inducible factor 1 (HIF-1) activation. (PMID: 17150302, 17335854, 16677071, 16607324, 16514169).7722-84-1C0002778416240HYDROGEN-PEROXIDE763OOH2O2InChI=1S/H2O2/c1-2/h1-2HMHAJPDPJQMAIIY-UHFFFAOYSA-N34.014734.005479308FDB014562Adeka super el;Albone;Albone 35;Albone ds;Anti-keim 50;Asepticper;Baquashock;Cix;Clarigel gold;Crestal whitestrips;Crystacide;Dentasept;Deslime lp;Hioxyl;Hipox;Hybrite;Hydrogen dioxide;Hydrogen peroxide;Inhibine;Lase peroxide;Lensan a;Magic bleaching;Metrokur;Mirasept;Nite white excel 2;Odosat d;Opalescence xtra;Oxigenal;Oxydol;Oxyfull;Oxysept;Oxysept i;Pegasyl;Perhydrol;Perone;Peroxaan;Peroxclean;Quasar brite;Select bleach;Superoxol;T-stuff;Whiteness hp;Whitespeed;Xtra white;[oh(oh)];Dihydrogen dioxide;H2o2;HoohPW_C001783H2O298911351888551146272875515124331691217495125342238181047491347523154951265502123551012758101086005147703816383961511181721611886215124612261270929112719292130283011303529813040302134052224265831577022225770472947707929377500113775403347759811577720332777253377780611477810111778193267807332978152132785981121200504081201021221204634051205954091206094161209544071210471241221203821228013741228144431228391351230973761231574471231654481232201371232344521235201191236111181246723991254284821254692971257094781257324831257484881258954811261032991262754841269675021269782071270062051272012091272152081272305051273562061276013881278383891491MolybdopterinHMDB0002206Molybdenum cofactor is a cofactor required for the activity of enzymes such as sulfite oxidase, xanthine oxidoreductase, and aldehyde oxidase. It is a coordination complex formed between molybdopterin (which, despite the name, does not contain molybdenum) and an oxide of molybdenum. Molybdopterins, in turn, are synthesized from guanosine triphosphate. Molybdenum cofactor functions directly in ethylbenzene dehydrogenase, glyceraldehyde-3-phosphate ferredoxin oxidoreductase, and respiratory arsenate reductase. In animals and plants these enzymes use molybdenum bound at the active site in a tricyclic molybdenum cofactor. All molybdenum-using enzymes so far identified in nature use this cofactor The simplest structure of molybdopterin contains a pyranopterin coordinated to molybdenum. The pyranopterin structure is a fused ring system containing a pyran fused to pterin. In addition, the pyran ring is substituted with two thiols and an alkyl phosphate. In molybdopterin, the thiols coordinate to molybdenum. In some cases, the alkyl phosphate group is replaced by an alkyl diphosphate nucleotide. -- Wikipedia.73508-07-3C059242330423721437CPD0-18824883416O.O.[Mo++].[H]C1(COP(O)([O-])=O)OC2([H])NC3=C(NC2([H])C(S)=C1S)C([O-])=NC(=N)N3C10H16MoN5O8PS2InChI=1S/C10H14N5O6PS2.Mo.2H2O/c11-10-14-7-4(8(16)15-10)12-3-6(24)5(23)2(21-9(3)13-7)1-20-22(17,18)19;;;/h2-3,9,12,23-24H,1H2,(H2,17,18,19)(H4,11,13,14,15,16);;2*1H2/q;+2;;/p-2VUKICSJFFDCESC-UHFFFAOYSA-L525.31526.923197FDB022906Moco;Molybdenum cofactor;Molybdenum enzyme molybdenum cofactor;Molybdoenzyme molybdenum-containing cofactor;Nitrate reductase molybdenum cofactor;Pterin molybdenum cofactorPW_C001491mlyBdpn16848170423918263953294388346275475331483094838285498126551312712038151130313011304330277716113777283377838513279206112121585407121794124123153443123168448124143119124345118126108299127679388405582Fe-2SHMDB0061344Bis(λ²-iron(2+) ion) disulfane tetrasulfanide belongs to the class of inorganic compounds known as transition metal sulfides. These are inorganic compounds containing a sulfur atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a transition metal.S.S.[SH-].[SH-].[SH-].[SH-].[Fe++].[Fe++]Fe2H8S6InChI=1S/2Fe.6H2S/h;;6*1H2/q2*+2;;;;;;/p-4MZMMVZPHZTYDNI-UHFFFAOYSA-J312.11311.764899PW_C0405582Fe2S3742240128425717438934626547543148299483728505645497126551212770461601303030113042302777151137772733778377134783861327920711211781113312158640712179512412256738412266440612315244312316744812414411912434611812514012112523912012618929912671548012679647912768038812830639112839450132Adenosine 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_C000032AMP11234462827016734328812211891445725486754503389525110454081175423103543211854571205558132558313357791015795108697719970721881178919811868161119881511200322212580226126363112694290133312254226634264631577234329773251117839233478809115793201128039918068413580900711991612212001612412003140612024638212088840512195440812292039912346437612450737412530629712539429912540947912559648412685320512693438812694950112712438912731120912771150214077189137Reduced flavoproteinProteinComplexPW_EC0000375086ChEBIRF38Oxidized flavoproteinProteinComplexPW_EC0000385086ChEBIOF25L-Tryptophyl-tRNA(Trp)RNAPW_NA00002529159LTTT2979279066132121741124124292118127627388133702813381511113386012213389713543tRNA(Trp)RNA948275PW_NA000043TRNATRP1337008133814111133859122133896135133907205137107117593Tryptophan--tRNA ligase, mitochondrialQ9UGM6HMDBP00626WARS21p12BC03988916.1.1.2298222452Tryptophan 2,3-dioxygenaseP48775Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
HMDBP05537TDO24q31-q32CH47105611.13.11.112984213559626135597393140581311438631169319KynureninaseQ16719Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
HMDBP00325KYNU2q22.2AC01343713.7.1.329862135600393146135262622Kynurenine formamidaseQ63HM1Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites (By similarity).
HMDBP07392AFMID17q25.3BC13282413.5.1.92988213559839314369711641438661169143987261440371197370Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialQ8N5Z0Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro).
HMDBP00378AADAT4q33AK05595212.6.1.39; 2.6.1.710723299122014Kynurenine 3-monooxygenaseO15229Catalyzes the hydroxylation of L-kynurenine (L-Kyn) to form 3-hydroxy-L-kynurenine (L-3OHKyn). Required for synthesis of quinolinic acid, a neurotoxic NMDA receptor antagonist and potential endogenous inhibitor of NMDA receptor signaling in axonal targeting, synaptogenesis and apoptosis during brain development. Quinolinic acid may also affect NMDA receptor signaling in pancreatic beta cells, osteoblasts, myocardial cells, and the gastrointestinal tract.
HMDBP02606KMO1q42-q44Y1315311.14.13.92995213215271356013931470CatalaseP04040Occurs in almost all aerobically respiring organisms and serves to protect cells from the toxic effects of hydrogen peroxide. Promotes growth of cells including T-cells, B-cells, myeloid leukemia cells, melanoma cells, mastocytoma cells and normal and transformed fibroblast cells.
HMDBP01582CAT11p13X0409011.11.1.676752998214354516610613-hydroxyanthranilate 3,4-dioxygenaseP46952Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
HMDBP01128HAAO2p21BC02951011.13.11.62084213560339313707382552-amino-3-carboxymuconate-6-semialdehyde decarboxylaseQ8TDX5Converts alpha-amino-beta-carboxymuconate-epsilon-semialdehyde (ACMS) to alpha-aminomuconate semialdehyde (AMS). ACMS can be converted non-enzymatically to quinolate (QA), a key precursor of NAD, and a potent endogenous excitotoxin of neuronal cells which is implicated in the pathogenesis of various neurodegenerative disorders. In the presence of ACMSD, ACMS is converted to AMS, a benign catabolite. ACMSD ultimately controls the metabolic fate of tryptophan catabolism along the kynurenine pathway.
HMDBP00261ACMSD2q21.3BC01601814.1.1.4530032452Tryptophan 5-hydroxylase 1P17752HMDBP00469TPH111p15.3-p14CH47106411.14.16.43005213939587139447481413047714296878914318239145633912272Aromatic-L-amino-acid decarboxylaseP20711Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
HMDBP00278DDC7p12.2M8458814.1.1.2840219697202009213558659913939687139448481396957891405493314055086514130577143183391433632614396860145635912289Aldehyde dehydrogenase, mitochondrialP05091HMDBP00295ALDH212q24.2K0300111.2.1.354741321818713300921354921814157795614202197914347554144669129214583712098Acetylserotonin O-methyltransferaseP46597Isoform 1 catalyzes the transfer of a methyl group onto N-acetylserotonin, producing melatonin (N-acetyl-5-methoxytryptamine). Isoform 2 and isoform 3 lack enzyme activity.
HMDBP00101ASMTXp22.3 or Yp11.3U1109412.1.1.43011213939887428Indoleamine 2,3-dioxygenase 1P14902Catalyzes the cleavage of the pyrrol ring of tryptophan and incorporates both atoms of a molecule of oxygen.
HMDBP00437IDO18p12-p11M8647411.13.11.5230372143141789143696116414383723143864116914387011711439712614400232144036119730Serotonin N-acetyltransferaseQ16613Controls the night/day rhythm of melatonin production in the pineal gland. Catalyzes the N-acetylation of serotonin into N-acetylserotonin, the penultimate step in the synthesis of melatonin.
HMDBP00030AANAT17q25BC09243012.3.1.8730532139397871443Cytochrome P450 1A1P04798Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
HMDBP01555CYP1A115q24.1AK22311311.14.14.13056243380491408592914111765141123847141528949406Indolethylamine N-methyltransferaseO95050Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
HMDBP00415INMT7p14.3AB04136212.1.1.49; 2.1.1.9630602986468121Aldehyde oxidaseQ06278HMDBP00126AOX12q33CH47106311.2.3.1; 1.17.3.-168581705239192639542943903475531543Tryptophan--tRNA ligase, cytoplasmicP23381Isoform 1, isoform 2 and T1-TrpRS have aminoacylation activity while T2-TrpRS lacks it. Isoform 2, T1-TrpRS and T2-TrpRS possess angiostatic activity whereas isoform 1 lacks it. T2-TrpRS inhibits fluid shear stress-activated responses of endothelial cells. Regulates ERK, Akt, and eNOS activation pathways that are associated with angiogenesis, cytoskeletal reorganization and shear stress-responsive gene expression.
HMDBP00574WARS14q32.31X6792616.1.1.2298021337018740Tryptophan--tRNA ligase, mitochondrial1PW_P0007408355931741Tryptophan 2,3-dioxygenase1PW_P0007418362452133017992742Kynureninase1PW_P00074283731913311701743Kynurenine formamidase1PW_P00074383826221296Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial1PW_P000296315370213111481744Kynurenine 3-monooxygenase1PW_P000744839201413329641219Catalase1PW_P0002192371470410317991104143176555463,4-Dihydroxyphenylacetaldehyde1PW_P0005465861061233354417452-amino-3-carboxymuconate-6-semialdehyde decarboxylase1PW_P0007458402551746Tryptophan 5-hydroxylase 11PW_P0007468414521334544196Aromatic-L-amino-acid decarboxylase1PW_P0000961112724911481159Aldehyde dehydrogenase, mitochondrial1PW_P00015917728945454747Acetylserotonin O-methyltransferase1PW_P000747842981751Indoleamine 2,3-dioxygenase 11PW_P000751846428133517991752Serotonin N-acetyltransferase1PW_P000752847301753Cytochrome P450 1A11PW_P0007538481443133617991755Indolethylamine N-methyltransferase1PW_P0007558504061461Aldehyde oxidase1PW_P0004614841211218964121914911427405581739Tryptophan--tRNA ligase, cytoplasmic1PW_P00073983454321609falsePW_R001609Right61337411Compoundfalse613410651Compoundtrue61359351Compoundfalse13517411.13.11.111610falsePW_R001610Right61369351Compoundfalse613714201Compoundtrue613820571Compoundfalse61391051Compoundtrue13527423.7.1.31611falsePW_R001611Right61409351Compoundfalse614114201Compoundtrue61425381Compoundfalse6143921Compoundtrue13537433.5.1.91612falsePW_R001612Right614420571Compoundfalse614514201Compoundtrue61468771Compoundfalse6147921Compoundtrue13547433.5.1.91613falsePW_R001613Right61485381Compoundfalse614914201Compoundtrue61508771Compoundfalse61511051Compoundtrue13557423.7.1.31615PW_R001615Right61567781Compoundfalse61575661Compoundfalse1614falsePW_R001614Right61525381Compoundfalse61531341Compoundtrue61547781Compoundfalse6155951Compoundtrue13562961616falsePW_R001616Right61585381Compoundfalse61591461Compoundtrue616010651Compoundtrue616172191Compoundfalse61621431Compoundtrue616314201Compoundtrue13577441.14.13.91617falsePW_R001617Right616472191Compoundfalse616514201Compoundtrue616611371Compoundfalse61671051Compoundtrue13587423.7.1.31618falsePW_R001618Right616811372Compoundfalse616910651Compoundtrue617020501Compoundfalse617114202Compoundtrue13592191.11.1.61619falsePW_R001619Right617272191Compoundfalse61731341Compoundtrue617420531Compoundfalse6175951Compoundtrue13602961620PW_R001620Right617620531Compoundfalse61777031Compoundfalse1621falsePW_R001621Right617811371Compoundfalse617910651Compoundtrue618010261Compoundfalse13615461.13.11.61622PW_R001622Right618110261Compoundfalse61821561Compoundfalse1623falsePW_R001623Right618310261Compoundfalse61849911Compoundfalse618513161Compoundtrue13627454.1.1.451624falsePW_R001624Right61867411Compoundfalse6187191Compoundtrue618810651Compoundtrue61893581Compoundfalse619015411Compoundtrue13637461.14.16.41625falsePW_R001625Right61913581Compoundfalse61921781Compoundfalse619313161Compoundtrue1364964.1.1.281627falsePW_R001627Right61971781Compoundfalse61981461Compoundtrue619910651Compoundtrue620020471Compoundfalse62011431Compoundtrue620214201Compoundtrue13667441.14.13.91628falsePW_R001628Right620320471Compoundfalse62047211Compoundtrue620514201Compoundtrue62066091Compoundfalse620711441Compoundtrue13671591.2.1.31630falsePW_R001630Right62136091Compoundfalse62149211Compoundtrue621520601Compoundfalse62167491Compoundtrue13717472.1.1.41633falsePW_R001633Right622320551Compoundfalse622414201Compoundtrue622580921Compoundfalse6226921Compoundtrue13747433.5.1.91632falsePW_R001632Right62203581Compoundfalse622110651Compoundtrue622220551Compoundfalse13737511.13.11.521634falsePW_R001634Right622780921Compoundfalse622820481Compoundfalse622913161Compoundtrue1375964.1.1.281635falsePW_R001635Right623020481Compoundfalse62311461Compoundtrue623210651Compoundtrue623320491Compoundfalse62341431Compoundtrue623514201Compoundtrue13767441.14.13.91636falsePW_R001636Right62361781Compoundfalse62379401Compoundtrue62389561Compoundfalse623910991Compoundtrue13777522.3.1.871637falsePW_R001637Right62409561Compoundfalse62419211Compoundtrue624210741Compoundfalse62437491Compoundtrue13787472.1.1.41638falsePW_R001638Right624410741Compoundfalse624510651Compoundtrue6246371ElementCollectiontrue624720521Compoundfalse624814201Compoundtrue6249381ElementCollectiontrue13797531.14.14.11639falsePW_R001639Right625010741Compoundfalse625110651Compoundtrue625221121Compoundfalse13807511.13.11.521640falsePW_R001640Right62531781Compoundfalse62549211Compoundtrue625521321Compoundfalse62567491Compoundtrue13817551641falsePW_R001641Right62571781Compoundfalse625810651Compoundtrue625981351Compoundfalse13827511.13.11.521642falsePW_R001642Right62607411Compoundfalse62612071Compoundfalse626213161Compoundtrue1383964.1.1.281644falsePW_R001644Right62652071Compoundfalse62661461Compoundtrue626710651Compoundtrue62689261Compoundfalse62691431Compoundtrue627014201Compoundtrue13847441.14.13.91645falsePW_R001645Right62719261Compoundfalse62727211Compoundtrue627314201Compoundtrue62741281Compoundfalse627511441Compoundtrue13851591.2.1.31646falsePW_R001646Right62762071Compoundfalse62779211Compoundtrue627821331Compoundfalse62797491Compoundtrue1386755106falsePW_R000106Right42420471Compoundfalse42510651Compoundtrue42614201Compoundtrue4276091Compoundfalse42817831Compoundtrue13704612210falsePW_R002210Right78077411Compoundfalse780810651Compoundtrue78099351Compoundfalse20597511.13.11.52178712PW_R178712Right6744734141Compoundfalse6744747411Compoundfalse674475431NucleicAcidfalse674476321Compoundfalse6744771701Compoundfalse674478251NucleicAcidfalse168806739168807740138PW_T0001381607411Compound152Right59587411581false266010510regular2001905959741281false266070010regular2001905960414242false249569510regular50305962170245false217886110regular63435963414242false2395116510regular50305965170245false2101100810regular634359661065265false2623107110regular78785967935281false2664140510regular2001905968179929false2717120210regular1002559691420249false2594128510regular787859702057281false2074140510regular2001905971105281false2254121510regular200190597217029false244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