{"title":"List of biological molecules","description":"A curated list of small biological molecules, metabolites, cofactors, amino acids, nucleobases, lipids, and related structures.","slug":"biological-molecules","url":"https://proteiniq.io/datasets/biological-molecules","version":"2026.10.05","updatedAt":"2026-10-05","license":{"id":"CC-BY-4.0","name":"Creative Commons Attribution 4.0 International","url":"https://creativecommons.org/licenses/by/4.0/"},"attribution":"List of biological molecules by ProteinIQ (https://proteiniq.io/datasets/biological-molecules), compiled from ChEBI, PubChem, RDKit. Licensed under CC BY 4.0 (https://creativecommons.org/licenses/by/4.0/).","citation":"ProteinIQ (2026). List of biological molecules, version 2026.10.05. https://proteiniq.io/datasets/biological-molecules","sources":[{"name":"ChEBI","url":"https://www.ebi.ac.uk/chebi/downloadsForward.do","role":"Chemical ontology classes, biological roles, synonyms, formulas, SMILES, InChI, and ChEBI identifiers.","licenseNote":"ChEBI provides ontology, flat-file, SDF, and SQL downloads from EMBL-EBI."},{"name":"PubChem","url":"https://pubchem.ncbi.nlm.nih.gov/","role":"Canonical compound identifiers, names, formulas, structures, SMILES, and downloadable compound records.","licenseNote":"NCBI places no restrictions on PubChem data, though original submitters may retain rights in submitted records."},{"name":"RDKit","url":"https://www.rdkit.org/","role":"Derived descriptors such as molecular weight, LogP, TPSA, hydrogen-bond counts, and canonicalized structures."}],"columns":[{"key":"name","label":"Name"},{"key":"formula","label":"Formula"},{"key":"molecularWeight","label":"MW 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muscle."},{"id":"adenine","name":"Adenine","formula":"C5H5N5","molecularWeight":135.13,"category":"Nucleobase","smiles":"C1=NC2=NC=NC(=C2N1)N","pubchemCid":"190","chebiId":"CHEBI:16708","sourceIds":["PubChem CID 190","ChEBI CHEBI:16708"]},{"id":"guanine","name":"Guanine","formula":"C5H5N5O","molecularWeight":151.13,"category":"Nucleobase","smiles":"C1=NC2=C(N1)C(=O)NC(=N2)N","pubchemCid":"135398634","chebiId":"CHEBI:16235","sourceIds":["PubChem CID 135398634","ChEBI CHEBI:16235"]},{"id":"cytosine","name":"Cytosine","formula":"C4H5N3O","molecularWeight":111.1,"category":"Nucleobase","smiles":"C1=C(NC(=O)N=C1)N","pubchemCid":"597","chebiId":"CHEBI:16040","sourceIds":["PubChem CID 597","ChEBI CHEBI:16040"]},{"id":"thymine","name":"Thymine","formula":"C5H6N2O2","molecularWeight":126.12,"category":"Nucleobase","smiles":"CC1=CNC(=O)NC1=O","pubchemCid":"1135","chebiId":"CHEBI:17821","sourceIds":["PubChem CID 1135","ChEBI 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CHEBI:16750"]},{"id":"cytidine","name":"Cytidine","formula":"C9H13N3O5","molecularWeight":243.22,"category":"Nucleoside","smiles":"C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O","pubchemCid":"6175","chebiId":"CHEBI:17562","sourceIds":["PubChem CID 6175","ChEBI CHEBI:17562"]},{"id":"uridine","name":"Uridine","formula":"C9H12N2O6","molecularWeight":244.2,"category":"Nucleoside","smiles":"C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O","pubchemCid":"6029","chebiId":"CHEBI:16704","sourceIds":["PubChem CID 6029","ChEBI CHEBI:16704"]},{"id":"inosine","name":"Inosine","formula":"C10H12N4O5","molecularWeight":268.23,"category":"Nucleoside","smiles":"C1=NC2=C(C(=O)N1)N=CN2[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O","pubchemCid":"135398641","chebiId":"CHEBI:17596","sourceIds":["PubChem CID 135398641","ChEBI 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CHEBI:44215"]},{"id":"nadh","name":"NADH","formula":"C21H29N7O14P2","molecularWeight":665.45,"category":"Cofactor","smiles":"C1C=CN(C=C1C(=O)N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O","pubchemCid":"439153","chebiId":"CHEBI:16908","sourceIds":["PubChem CID 439153","ChEBI CHEBI:16908"]},{"id":"nadp","name":"NADP+","formula":"C21H28N7O17P3","molecularWeight":743.41,"category":"Cofactor","smiles":"C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N","pubchemCid":"5885","chebiId":"CHEBI:44409","sourceIds":["PubChem CID 5885","ChEBI CHEBI:44409"]},{"id":"nadph","name":"NADPH","formula":"C21H30N7O17P3","molecularWeight":745.43,"category":"Cofactor","smiles":"C1C=CN(C=C1C(=O)N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O","pubchemCid":"5884","chebiId":"CHEBI:16474","sourceIds":["PubChem CID 5884","ChEBI CHEBI:16474"]},{"id":"flavin-adenine-dinucleotide","name":"Flavin adenine dinucleotide","formula":"C27H33N9O15P2","molecularWeight":785.56,"category":"Cofactor","smiles":"CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)O","pubchemCid":"643975","chebiId":"CHEBI:16238","sourceIds":["PubChem CID 643975","ChEBI CHEBI:16238"],"notes":"FAD."},{"id":"flavin-mononucleotide","name":"Flavin mononucleotide","formula":"C17H21N4O9P","molecularWeight":456.35,"category":"Cofactor","smiles":"CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)O","pubchemCid":"643976","chebiId":"CHEBI:17621","sourceIds":["PubChem CID 643976","ChEBI CHEBI:17621"],"notes":"FMN."},{"id":"coenzyme-a","name":"Coenzyme A","formula":"C21H36N7O16P3S","molecularWeight":767.53,"category":"Cofactor","smiles":"CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCS)O","pubchemCid":"87642","chebiId":"CHEBI:15346","sourceIds":["PubChem CID 87642","ChEBI CHEBI:15346"]},{"id":"acetyl-coa","name":"Acetyl-CoA","formula":"C23H38N7O17P3S","molecularWeight":809.57,"category":"Cofactor","smiles":"CC(=O)SCCNC(=O)CCNC(=O)[C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)O","pubchemCid":"444493","chebiId":"CHEBI:15351","sourceIds":["PubChem CID 444493","ChEBI CHEBI:15351"],"notes":"Feeds acetyl groups into the TCA cycle and fatty acid synthesis."},{"id":"s-adenosylmethionine","name":"S-Adenosylmethionine","formula":"C15H22N6O5S","molecularWeight":398.44,"category":"Cofactor","smiles":"C[S+](CC[C@@H](C(=O)[O-])N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O","pubchemCid":"34755","chebiId":"CHEBI:67040","sourceIds":["PubChem CID 34755","ChEBI CHEBI:67040"],"notes":"Main methyl group donor."},{"id":"s-adenosylhomocysteine","name":"S-Adenosylhomocysteine","formula":"C14H20N6O5S","molecularWeight":384.41,"category":"Metabolite","smiles":"C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CSCC[C@@H](C(=O)O)N)O)O)N","pubchemCid":"439155","chebiId":"CHEBI:16680","sourceIds":["PubChem CID 439155","ChEBI CHEBI:16680"],"notes":"Product of SAM-dependent methylation."},{"id":"lipoic-acid","name":"Lipoic acid","formula":"C8H14O2S2","molecularWeight":206.32,"category":"Cofactor","smiles":"C1CSS[C@@H]1CCCCC(=O)O","pubchemCid":"6112","chebiId":"CHEBI:30314","sourceIds":["PubChem CID 6112","ChEBI CHEBI:30314"]},{"id":"heme","name":"Heme","formula":"C34H32FeN4O4","molecularWeight":616.5,"category":"Cofactor","smiles":"CC1=C(C2=CC3=C(C(=C([N-]3)C=C4C(=C(C(=N4)C=C5C(=C(C(=N5)C=C1[N-]2)C)C=C)C)C=C)C)CCC(=O)O)CCC(=O)O.[Fe+2]","pubchemCid":"26945","sourceIds":["PubChem CID 26945"],"notes":"Iron porphyrin of hemoglobin and cytochromes. PubChem titles this record hemin."},{"id":"d-glucose","name":"D-Glucose","formula":"C6H12O6","molecularWeight":180.16,"category":"Monosaccharide","smiles":"C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O","pubchemCid":"5793","chebiId":"CHEBI:4167","sourceIds":["PubChem CID 5793","ChEBI CHEBI:4167"]},{"id":"d-fructose","name":"D-Fructose","formula":"C6H12O6","molecularWeight":180.16,"category":"Monosaccharide","smiles":"C1[C@H]([C@H]([C@@H](C(O1)(CO)O)O)O)O","pubchemCid":"2723872","chebiId":"CHEBI:37714","sourceIds":["PubChem CID 2723872","ChEBI CHEBI:37714"]},{"id":"d-galactose","name":"D-Galactose","formula":"C6H12O6","molecularWeight":180.16,"category":"Monosaccharide","smiles":"C([C@@H]1[C@@H]([C@@H]([C@H](C(O1)O)O)O)O)O","pubchemCid":"6036","chebiId":"CHEBI:4139","sourceIds":["PubChem CID 6036","ChEBI CHEBI:4139"]},{"id":"d-ribose","name":"D-Ribose","formula":"C5H10O5","molecularWeight":150.13,"category":"Monosaccharide","smiles":"C1[C@H]([C@H]([C@H](C(O1)O)O)O)O","pubchemCid":"10975657","chebiId":"CHEBI:47006","sourceIds":["PubChem CID 10975657","ChEBI CHEBI:47006"]},{"id":"2-deoxy-d-ribose","name":"2-Deoxy-D-ribose","formula":"C5H10O4","molecularWeight":134.13,"category":"Monosaccharide","smiles":"C1[C@@H]([C@H](OC1O)CO)O","pubchemCid":"9828112","chebiId":"CHEBI:90761","sourceIds":["PubChem CID 9828112","ChEBI CHEBI:90761"],"notes":"The sugar in DNA."},{"id":"d-glucosamine","name":"D-Glucosamine","formula":"C6H13NO5","molecularWeight":179.17,"category":"Amino sugar","smiles":"C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)N)O)O)O","pubchemCid":"439213","chebiId":"CHEBI:47977","sourceIds":["PubChem CID 439213","ChEBI CHEBI:47977"]},{"id":"n-acetylglucosamine","name":"N-Acetylglucosamine","formula":"C8H15NO6","molecularWeight":221.21,"category":"Amino sugar","smiles":"CC(=O)N[C@@H](C=O)[C@H]([C@@H]([C@@H](CO)O)O)O","pubchemCid":"1738118","chebiId":"CHEBI:17411","sourceIds":["PubChem CID 1738118","ChEBI CHEBI:17411"]},{"id":"glucuronic-acid","name":"Glucuronic acid","formula":"C6H10O7","molecularWeight":194.14,"category":"Sugar acid","smiles":"C(=O)[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O)O)O)O","pubchemCid":"65041","chebiId":"CHEBI:47953","sourceIds":["PubChem CID 65041","ChEBI CHEBI:47953"]},{"id":"inositol","name":"Inositol","formula":"C6H12O6","molecularWeight":180.16,"category":"Sugar alcohol","smiles":"C1(C(C(C(C(C1O)O)O)O)O)O","pubchemCid":"892","chebiId":"CHEBI:24848","sourceIds":["PubChem CID 892","ChEBI CHEBI:24848"],"notes":"Stereochemistry unspecified in this record; myo-inositol is the biological form."},{"id":"sucrose","name":"Sucrose","formula":"C12H22O11","molecularWeight":342.3,"category":"Disaccharide","smiles":"C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO)O)O)O)O","pubchemCid":"5988","chebiId":"CHEBI:17992","sourceIds":["PubChem CID 5988","ChEBI CHEBI:17992"]},{"id":"maltose","name":"Maltose","formula":"C12H22O11","molecularWeight":342.3,"category":"Disaccharide","smiles":"C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2[C@H](OC([C@@H]([C@H]2O)O)O)CO)O)O)O)O","pubchemCid":"439186","chebiId":"CHEBI:17306","sourceIds":["PubChem CID 439186","ChEBI CHEBI:17306"]},{"id":"lactose","name":"Lactose","formula":"C12H22O11","molecularWeight":342.3,"category":"Disaccharide","smiles":"C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC([C@@H]([C@H]2O)O)O)CO)O)O)O)O","pubchemCid":"440995","chebiId":"CHEBI:17716","sourceIds":["PubChem CID 440995","ChEBI CHEBI:17716"]},{"id":"glucose-6-phosphate","name":"Glucose 6-phosphate","formula":"C6H13O9P","molecularWeight":260.14,"category":"Glycolysis intermediate","smiles":"C([C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)OP(=O)(O)O","pubchemCid":"439958","chebiId":"CHEBI:15954","sourceIds":["PubChem CID 439958","ChEBI CHEBI:15954"]},{"id":"fructose-6-phosphate","name":"Fructose 6-phosphate","formula":"C6H13O9P","molecularWeight":260.14,"category":"Glycolysis intermediate","smiles":"C([C@H]([C@H]([C@@H](C(=O)CO)O)O)O)OP(=O)(O)O","pubchemCid":"69507","chebiId":"CHEBI:15946","sourceIds":["PubChem CID 69507","ChEBI CHEBI:15946"]},{"id":"glyceraldehyde-3-phosphate","name":"Glyceraldehyde 3-phosphate","formula":"C3H7O6P","molecularWeight":170.06,"category":"Glycolysis intermediate","smiles":"C([C@H](C=O)O)OP(=O)(O)O","pubchemCid":"439168","chebiId":"CHEBI:29052","sourceIds":["PubChem CID 439168","ChEBI CHEBI:29052"]},{"id":"phosphoenolpyruvic-acid","name":"Phosphoenolpyruvic acid","formula":"C3H5O6P","molecularWeight":168.04,"category":"Glycolysis intermediate","smiles":"C=C(C(=O)O)OP(=O)(O)O","pubchemCid":"1005","chebiId":"CHEBI:44897","sourceIds":["PubChem CID 1005","ChEBI CHEBI:44897"]},{"id":"pyruvic-acid","name":"Pyruvic acid","formula":"C3H4O3","molecularWeight":88.06,"category":"Glycolysis intermediate","smiles":"CC(=O)C(=O)O","pubchemCid":"1060","chebiId":"CHEBI:32816","sourceIds":["PubChem CID 1060","ChEBI CHEBI:32816"],"notes":"End product of glycolysis."},{"id":"2-3-bisphosphoglyceric-acid","name":"2,3-Bisphosphoglyceric acid","formula":"C3H8O10P2","molecularWeight":266.04,"category":"Glycolysis intermediate","smiles":"C(C(C(=O)O)OP(=O)(O)O)OP(=O)(O)O","pubchemCid":"61","chebiId":"CHEBI:28907","sourceIds":["PubChem CID 61","ChEBI CHEBI:28907"],"notes":"Regulates oxygen release from hemoglobin in red blood cells."},{"id":"lactic-acid","name":"Lactic acid","formula":"C3H6O3","molecularWeight":90.08,"category":"Fermentation product","smiles":"CC(C(=O)O)O","pubchemCid":"612","chebiId":"CHEBI:78320","sourceIds":["PubChem CID 612","ChEBI CHEBI:78320"]},{"id":"ribose-5-phosphate","name":"Ribose 5-phosphate","formula":"C5H11O8P","molecularWeight":230.11,"category":"Pentose phosphate pathway intermediate","smiles":"C([C@H]([C@H]([C@H](C=O)O)O)O)OP(=O)(O)O","pubchemCid":"77982","chebiId":"CHEBI:17797","sourceIds":["PubChem CID 77982","ChEBI CHEBI:17797"]},{"id":"sedoheptulose-7-phosphate","name":"Sedoheptulose 7-phosphate","formula":"C7H15O10P","molecularWeight":290.16,"category":"Pentose phosphate pathway intermediate","smiles":"C([C@H]([C@H]([C@H]([C@@H](C(=O)CO)O)O)O)O)OP(=O)(O)O","pubchemCid":"165007","chebiId":"CHEBI:15721","sourceIds":["PubChem CID 165007","ChEBI CHEBI:15721"]},{"id":"citric-acid","name":"Citric acid","formula":"C6H8O7","molecularWeight":192.12,"category":"TCA cycle intermediate","smiles":"C(C(=O)O)C(CC(=O)O)(C(=O)O)O","pubchemCid":"311","chebiId":"CHEBI:30769","sourceIds":["PubChem CID 311","ChEBI CHEBI:30769"]},{"id":"isocitric-acid","name":"Isocitric acid","formula":"C6H8O7","molecularWeight":192.12,"category":"TCA cycle intermediate","smiles":"C(C(C(C(=O)O)O)C(=O)O)C(=O)O","pubchemCid":"1198","chebiId":"CHEBI:30887","sourceIds":["PubChem CID 1198","ChEBI CHEBI:30887"]},{"id":"alpha-ketoglutaric-acid","name":"Alpha-ketoglutaric acid","formula":"C5H6O5","molecularWeight":146.1,"category":"TCA cycle intermediate","smiles":"C(CC(=O)O)C(=O)C(=O)O","pubchemCid":"51","chebiId":"CHEBI:30915","sourceIds":["PubChem CID 51","ChEBI CHEBI:30915"],"notes":"Also called 2-oxoglutaric acid."},{"id":"succinic-acid","name":"Succinic acid","formula":"C4H6O4","molecularWeight":118.09,"category":"TCA cycle intermediate","smiles":"C(CC(=O)O)C(=O)O","pubchemCid":"1110","chebiId":"CHEBI:15741","sourceIds":["PubChem CID 1110","ChEBI CHEBI:15741"]},{"id":"fumaric-acid","name":"Fumaric acid","formula":"C4H4O4","molecularWeight":116.07,"category":"TCA cycle intermediate","smiles":"C(=C/C(=O)O)\\C(=O)O","pubchemCid":"444972","chebiId":"CHEBI:18012","sourceIds":["PubChem CID 444972","ChEBI CHEBI:18012"]},{"id":"malic-acid","name":"Malic acid","formula":"C4H6O5","molecularWeight":134.09,"category":"TCA cycle intermediate","smiles":"C(C(C(=O)O)O)C(=O)O","pubchemCid":"525","chebiId":"CHEBI:6650","sourceIds":["PubChem CID 525","ChEBI CHEBI:6650"]},{"id":"oxaloacetic-acid","name":"Oxaloacetic acid","formula":"C4H4O5","molecularWeight":132.07,"category":"TCA cycle intermediate","smiles":"C(C(=O)C(=O)O)C(=O)O","pubchemCid":"970","chebiId":"CHEBI:30744","sourceIds":["PubChem CID 970","ChEBI CHEBI:30744"]},{"id":"acetoacetic-acid","name":"Acetoacetic acid","formula":"C4H6O3","molecularWeight":102.09,"category":"Ketone body","smiles":"CC(=O)CC(=O)O","pubchemCid":"96","chebiId":"CHEBI:15344","sourceIds":["PubChem CID 96","ChEBI CHEBI:15344"]},{"id":"3-hydroxybutyric-acid","name":"3-Hydroxybutyric acid","formula":"C4H8O3","molecularWeight":104.1,"category":"Ketone body","smiles":"CC(CC(=O)O)O","pubchemCid":"441","chebiId":"CHEBI:20067","sourceIds":["PubChem CID 441","ChEBI CHEBI:20067"],"notes":"Also called beta-hydroxybutyric acid."},{"id":"methylmalonic-acid","name":"Methylmalonic acid","formula":"C4H6O4","molecularWeight":118.09,"category":"Metabolite","smiles":"CC(C(=O)O)C(=O)O","pubchemCid":"487","chebiId":"CHEBI:30860","sourceIds":["PubChem CID 487","ChEBI CHEBI:30860"],"notes":"Accumulates in vitamin B12 deficiency."},{"id":"creatine","name":"Creatine","formula":"C4H9N3O2","molecularWeight":131.14,"category":"Metabolite","smiles":"CN(CC(=O)O)C(=N)N","pubchemCid":"586","chebiId":"CHEBI:16919","sourceIds":["PubChem CID 586","ChEBI CHEBI:16919"],"notes":"Stores energy in muscle as phosphocreatine."},{"id":"creatinine","name":"Creatinine","formula":"C4H7N3O","molecularWeight":113.12,"category":"Waste product","smiles":"CN1CC(=O)N=C1N","pubchemCid":"588","chebiId":"CHEBI:16737","sourceIds":["PubChem CID 588","ChEBI CHEBI:16737"]},{"id":"urea","name":"Urea","formula":"CH4N2O","molecularWeight":60.06,"category":"Waste product","smiles":"C(=O)(N)N","pubchemCid":"1176","chebiId":"CHEBI:16199","sourceIds":["PubChem CID 1176","ChEBI CHEBI:16199"],"notes":"Main nitrogen waste product in mammals."},{"id":"uric-acid","name":"Uric acid","formula":"C5H4N4O3","molecularWeight":168.11,"category":"Waste product","smiles":"C12=C(NC(=O)N1)NC(=O)NC2=O","pubchemCid":"1175","chebiId":"CHEBI:17775","sourceIds":["PubChem CID 1175","ChEBI CHEBI:17775"],"notes":"End product of purine breakdown in humans."},{"id":"allantoin","name":"Allantoin","formula":"C4H6N4O3","molecularWeight":158.12,"category":"Purine metabolite","smiles":"C1(C(=O)NC(=O)N1)NC(=O)N","pubchemCid":"204","chebiId":"CHEBI:15676","sourceIds":["PubChem CID 204","ChEBI CHEBI:15676"]},{"id":"xanthine","name":"Xanthine","formula":"C5H4N4O2","molecularWeight":152.11,"category":"Purine metabolite","smiles":"C1=NC2=C(N1)C(=O)NC(=O)N2","pubchemCid":"1188","chebiId":"CHEBI:17712","sourceIds":["PubChem CID 1188","ChEBI CHEBI:17712"]},{"id":"hypoxanthine","name":"Hypoxanthine","formula":"C5H4N4O","molecularWeight":136.11,"category":"Purine metabolite","smiles":"C1=NC2=C(N1)C(=O)NC=N2","pubchemCid":"135398638","chebiId":"CHEBI:17368","sourceIds":["PubChem CID 135398638","ChEBI CHEBI:17368"]},{"id":"orotic-acid","name":"Orotic acid","formula":"C5H4N2O4","molecularWeight":156.1,"category":"Pyrimidine metabolite","smiles":"C1=C(NC(=O)NC1=O)C(=O)O","pubchemCid":"967","chebiId":"CHEBI:16742","sourceIds":["PubChem CID 967","ChEBI CHEBI:16742"]},{"id":"dihydroorotic-acid","name":"Dihydroorotic acid","formula":"C5H6N2O4","molecularWeight":158.11,"category":"Pyrimidine metabolite","smiles":"C1C(NC(=O)NC1=O)C(=O)O","pubchemCid":"648","chebiId":"CHEBI:30865","sourceIds":["PubChem CID 648","ChEBI CHEBI:30865"]},{"id":"palmitic-acid","name":"Palmitic acid","formula":"C16H32O2","molecularWeight":256.43,"category":"Saturated fatty acid","smiles":"CCCCCCCCCCCCCCCC(=O)O","pubchemCid":"985","chebiId":"CHEBI:15756","sourceIds":["PubChem CID 985","ChEBI CHEBI:15756"]},{"id":"stearic-acid","name":"Stearic acid","formula":"C18H36O2","molecularWeight":284.48,"category":"Saturated fatty acid","smiles":"CCCCCCCCCCCCCCCCCC(=O)O","pubchemCid":"5281","chebiId":"CHEBI:28842","sourceIds":["PubChem CID 5281","ChEBI CHEBI:28842"]},{"id":"lauric-acid","name":"Lauric acid","formula":"C12H24O2","molecularWeight":200.32,"category":"Saturated fatty acid","smiles":"CCCCCCCCCCCC(=O)O","pubchemCid":"3893","chebiId":"CHEBI:30805","sourceIds":["PubChem CID 3893","ChEBI CHEBI:30805"]},{"id":"myristic-acid","name":"Myristic acid","formula":"C14H28O2","molecularWeight":228.38,"category":"Saturated fatty acid","smiles":"CCCCCCCCCCCCCC(=O)O","pubchemCid":"11005","chebiId":"CHEBI:28875","sourceIds":["PubChem CID 11005","ChEBI CHEBI:28875"]},{"id":"decanoic-acid","name":"Decanoic acid","formula":"C10H20O2","molecularWeight":172.27,"category":"Saturated fatty acid","smiles":"CCCCCCCCCC(=O)O","pubchemCid":"2969","chebiId":"CHEBI:30813","sourceIds":["PubChem CID 2969","ChEBI CHEBI:30813"],"notes":"Also called capric acid."},{"id":"octanoic-acid","name":"Octanoic acid","formula":"C8H16O2","molecularWeight":144.21,"category":"Saturated fatty acid","smiles":"CCCCCCCC(=O)O","pubchemCid":"379","chebiId":"CHEBI:28837","sourceIds":["PubChem CID 379","ChEBI CHEBI:28837"],"notes":"Also called caprylic acid."},{"id":"arachidic-acid","name":"Arachidic acid","formula":"C20H40O2","molecularWeight":312.54,"category":"Saturated fatty acid","smiles":"CCCCCCCCCCCCCCCCCCCC(=O)O","pubchemCid":"10467","chebiId":"CHEBI:28822","sourceIds":["PubChem CID 10467","ChEBI CHEBI:28822"]},{"id":"behenic-acid","name":"Behenic acid","formula":"C22H44O2","molecularWeight":340.59,"category":"Saturated fatty acid","smiles":"CCCCCCCCCCCCCCCCCCCCCC(=O)O","pubchemCid":"8215","chebiId":"CHEBI:28941","sourceIds":["PubChem CID 8215","ChEBI CHEBI:28941"]},{"id":"oleic-acid","name":"Oleic acid","formula":"C18H34O2","molecularWeight":282.47,"category":"Monounsaturated fatty acid","smiles":"CCCCCCCC/C=C\\CCCCCCCC(=O)O","pubchemCid":"445639","chebiId":"CHEBI:16196","sourceIds":["PubChem CID 445639","ChEBI CHEBI:16196"],"notes":"Omega-9."},{"id":"nervonic-acid","name":"Nervonic acid","formula":"C24H46O2","molecularWeight":366.63,"category":"Monounsaturated fatty acid","smiles":"CCCCCCCC/C=C\\CCCCCCCCCCCCCC(=O)O","pubchemCid":"5281120","chebiId":"CHEBI:44247","sourceIds":["PubChem CID 5281120","ChEBI CHEBI:44247"],"notes":"Omega-9."},{"id":"linoleic-acid","name":"Linoleic acid","formula":"C18H32O2","molecularWeight":280.45,"category":"Polyunsaturated fatty acid","smiles":"CCCCC/C=C\\C/C=C\\CCCCCCCC(=O)O","pubchemCid":"5280450","chebiId":"CHEBI:17351","sourceIds":["PubChem CID 5280450","ChEBI CHEBI:17351"],"notes":"Omega-6."},{"id":"arachidonic-acid","name":"Arachidonic acid","formula":"C20H32O2","molecularWeight":304.47,"category":"Polyunsaturated fatty acid","smiles":"CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(=O)O","pubchemCid":"444899","chebiId":"CHEBI:15843","sourceIds":["PubChem CID 444899","ChEBI CHEBI:15843"],"notes":"Omega-6; precursor of prostaglandins."},{"id":"alpha-linolenic-acid","name":"alpha-Linolenic acid","formula":"C18H30O2","molecularWeight":278.44,"category":"Polyunsaturated fatty acid","smiles":"CC/C=C\\C/C=C\\C/C=C\\CCCCCCCC(=O)O","pubchemCid":"5280934","chebiId":"CHEBI:27432","sourceIds":["PubChem CID 5280934","ChEBI CHEBI:27432"],"notes":"Omega-3."},{"id":"eicosapentaenoic-acid","name":"Eicosapentaenoic acid","formula":"C20H30O2","molecularWeight":302.46,"category":"Polyunsaturated fatty acid","smiles":"CC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O","pubchemCid":"5282847","sourceIds":["PubChem CID 5282847"],"notes":"Omega-3 (EPA)."},{"id":"docosahexaenoic-acid","name":"Docosahexaenoic acid","formula":"C22H32O2","molecularWeight":328.5,"category":"Polyunsaturated fatty acid","smiles":"CC/C=C\\C/C=C\\C/C=C\\C/C=C\\C/C=C\\C/C=C\\CCC(=O)O","pubchemCid":"445580","chebiId":"CHEBI:28125","sourceIds":["PubChem CID 445580","ChEBI CHEBI:28125"],"notes":"Omega-3 (DHA)."},{"id":"glycerol","name":"Glycerol","formula":"C3H8O3","molecularWeight":92.09,"category":"Lipid backbone","smiles":"C(C(CO)O)O","pubchemCid":"753","chebiId":"CHEBI:17754","sourceIds":["PubChem CID 753","ChEBI CHEBI:17754"],"notes":"Backbone of triglycerides and glycerophospholipids."},{"id":"sphingosine","name":"Sphingosine","formula":"C18H37NO2","molecularWeight":299.5,"category":"Lipid backbone","smiles":"CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O","pubchemCid":"5280335","chebiId":"CHEBI:16393","sourceIds":["PubChem CID 5280335","ChEBI CHEBI:16393"],"notes":"Backbone of sphingolipids."},{"id":"choline","name":"Choline","formula":"C5H14NO+","molecularWeight":104.17,"category":"Nutrient","smiles":"C[N+](C)(C)CCO","pubchemCid":"305","chebiId":"CHEBI:15354","sourceIds":["PubChem CID 305","ChEBI CHEBI:15354"],"notes":"Head group of phosphatidylcholine and precursor of acetylcholine."},{"id":"carnitine","name":"Carnitine","formula":"C7H15NO3","molecularWeight":161.2,"category":"Metabolite","smiles":"C[N+](C)(C)CC(CC(=O)[O-])O","pubchemCid":"288","chebiId":"CHEBI:17126","sourceIds":["PubChem CID 288","ChEBI CHEBI:17126"],"notes":"Carries fatty acids into mitochondria. Stereochemistry unspecified in this record."},{"id":"betaine","name":"Betaine","formula":"C5H11NO2","molecularWeight":117.15,"category":"Metabolite","smiles":"C[N+](C)(C)CC(=O)[O-]","pubchemCid":"247","chebiId":"CHEBI:17750","sourceIds":["PubChem CID 247","ChEBI CHEBI:17750"],"notes":"Osmolyte and methyl donor."},{"id":"cholesterol","name":"Cholesterol","formula":"C27H46O","molecularWeight":386.66,"category":"Sterol","smiles":"C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C","pubchemCid":"5997","chebiId":"CHEBI:16113","sourceIds":["PubChem CID 5997","ChEBI CHEBI:16113"]},{"id":"squalene","name":"Squalene","formula":"C30H50","molecularWeight":410.73,"category":"Isoprenoid","smiles":"CC(=CCC/C(=C/CC/C(=C/CC/C=C(/CC/C=C(/CCC=C(C)C)\\C)\\C)/C)/C)C","pubchemCid":"638072","chebiId":"CHEBI:15440","sourceIds":["PubChem CID 638072","ChEBI CHEBI:15440"],"notes":"Precursor of cholesterol."},{"id":"mevalonic-acid","name":"Mevalonic acid","formula":"C6H12O4","molecularWeight":148.16,"category":"Isoprenoid","smiles":"CC(CCO)(CC(=O)O)O","pubchemCid":"449","chebiId":"CHEBI:194519","sourceIds":["PubChem CID 449","ChEBI CHEBI:194519"],"notes":"Product of HMG-CoA reductase, the target of statins."},{"id":"farnesyl-pyrophosphate","name":"Farnesyl pyrophosphate","formula":"C15H28O7P2","molecularWeight":382.33,"category":"Isoprenoid","smiles":"CC(=CCC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)C","pubchemCid":"445713","chebiId":"CHEBI:17407","sourceIds":["PubChem CID 445713","ChEBI CHEBI:17407"]},{"id":"geranylgeranyl-pyrophosphate","name":"Geranylgeranyl pyrophosphate","formula":"C20H36O7P2","molecularWeight":450.45,"category":"Isoprenoid","smiles":"CC(=CCC/C(=C/CC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)/C)C","pubchemCid":"447277","chebiId":"CHEBI:48861","sourceIds":["PubChem CID 447277","ChEBI CHEBI:48861"]},{"id":"cholic-acid","name":"Cholic acid","formula":"C24H40O5","molecularWeight":408.58,"category":"Bile acid","smiles":"C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C","pubchemCid":"221493","chebiId":"CHEBI:16359","sourceIds":["PubChem CID 221493","ChEBI CHEBI:16359"]},{"id":"chenodeoxycholic-acid","name":"Chenodeoxycholic acid","formula":"C24H40O4","molecularWeight":392.58,"category":"Bile acid","smiles":"C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C","pubchemCid":"10133","chebiId":"CHEBI:16755","sourceIds":["PubChem CID 10133","ChEBI CHEBI:16755"]},{"id":"deoxycholic-acid","name":"Deoxycholic acid","formula":"C24H40O4","molecularWeight":392.58,"category":"Bile acid","smiles":"C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C","pubchemCid":"222528","chebiId":"CHEBI:28834","sourceIds":["PubChem CID 222528","ChEBI CHEBI:28834"]},{"id":"glycocholic-acid","name":"Glycocholic acid","formula":"C26H43NO6","molecularWeight":465.63,"category":"Bile acid","smiles":"C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C","pubchemCid":"10140","chebiId":"CHEBI:17687","sourceIds":["PubChem CID 10140","ChEBI CHEBI:17687"]},{"id":"taurocholic-acid","name":"Taurocholic acid","formula":"C26H45NO7S","molecularWeight":515.71,"category":"Bile acid","smiles":"C[C@H](CCC(=O)NCCS(=O)(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C","pubchemCid":"6675","chebiId":"CHEBI:28865","sourceIds":["PubChem CID 6675","ChEBI CHEBI:28865"]},{"id":"cortisol","name":"Cortisol","formula":"C21H30O5","molecularWeight":362.47,"category":"Steroid hormone","smiles":"C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O","pubchemCid":"5754","chebiId":"CHEBI:17650","sourceIds":["PubChem CID 5754","ChEBI CHEBI:17650"]},{"id":"cortisone","name":"Cortisone","formula":"C21H28O5","molecularWeight":360.45,"category":"Steroid hormone","smiles":"C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2C(=O)C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C","pubchemCid":"222786","chebiId":"CHEBI:16962","sourceIds":["PubChem CID 222786","ChEBI CHEBI:16962"]},{"id":"aldosterone","name":"Aldosterone","formula":"C21H28O5","molecularWeight":360.45,"category":"Steroid hormone","smiles":"C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C=O)O","pubchemCid":"5839","chebiId":"CHEBI:27584","sourceIds":["PubChem CID 5839","ChEBI CHEBI:27584"]},{"id":"testosterone","name":"Testosterone","formula":"C19H28O2","molecularWeight":288.43,"category":"Steroid hormone","smiles":"C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@]34C","pubchemCid":"6013","chebiId":"CHEBI:17347","sourceIds":["PubChem CID 6013","ChEBI CHEBI:17347"]},{"id":"dehydroepiandrosterone","name":"Dehydroepiandrosterone","formula":"C19H28O2","molecularWeight":288.43,"category":"Steroid hormone","smiles":"C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C","pubchemCid":"5881","chebiId":"CHEBI:28689","sourceIds":["PubChem CID 5881","ChEBI CHEBI:28689"],"notes":"DHEA."},{"id":"progesterone","name":"Progesterone","formula":"C21H30O2","molecularWeight":314.47,"category":"Steroid hormone","smiles":"CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C","pubchemCid":"5994","chebiId":"CHEBI:17026","sourceIds":["PubChem CID 5994","ChEBI CHEBI:17026"]},{"id":"estradiol","name":"Estradiol","formula":"C18H24O2","molecularWeight":272.39,"category":"Steroid hormone","smiles":"C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O","pubchemCid":"5757","chebiId":"CHEBI:16469","sourceIds":["PubChem CID 5757","ChEBI CHEBI:16469"]},{"id":"estrone","name":"Estrone","formula":"C18H22O2","molecularWeight":270.37,"category":"Steroid hormone","smiles":"C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O","pubchemCid":"5870","chebiId":"CHEBI:17263","sourceIds":["PubChem CID 5870","ChEBI CHEBI:17263"]},{"id":"estriol","name":"Estriol","formula":"C18H24O3","molecularWeight":288.39,"category":"Steroid hormone","smiles":"C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4)O","pubchemCid":"5756","chebiId":"CHEBI:27974","sourceIds":["PubChem CID 5756","ChEBI CHEBI:27974"]},{"id":"calcitriol","name":"Calcitriol","formula":"C27H44O3","molecularWeight":416.65,"category":"Steroid hormone","smiles":"C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\\2[C@@]1(CCC/C2=C\\C=C/3\\C[C@H](C[C@@H](C3=C)O)O)C","pubchemCid":"5280453","chebiId":"CHEBI:17823","sourceIds":["PubChem CID 5280453","ChEBI CHEBI:17823"],"notes":"Active hormonal form of vitamin D."},{"id":"thyroxine","name":"Thyroxine","formula":"C15H11I4NO4","molecularWeight":776.86,"category":"Thyroid hormone","smiles":"C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)C[C@@H](C(=O)O)N","pubchemCid":"5819","chebiId":"CHEBI:18332","sourceIds":["PubChem CID 5819","ChEBI CHEBI:18332"],"notes":"T4."},{"id":"triiodothyronine","name":"Triiodothyronine","formula":"C15H12I3NO4","molecularWeight":650.96,"category":"Thyroid hormone","smiles":"C1=CC(=C(C=C1OC2=C(C=C(C=C2I)C[C@@H](C(=O)O)N)I)I)O","pubchemCid":"5920","chebiId":"CHEBI:18258","sourceIds":["PubChem CID 5920","ChEBI CHEBI:18258"],"notes":"T3."},{"id":"melatonin","name":"Melatonin","formula":"C13H16N2O2","molecularWeight":232.28,"category":"Hormone","smiles":"CC(=O)NCCC1=CNC2=C1C=C(C=C2)OC","pubchemCid":"896","chebiId":"CHEBI:16796","sourceIds":["PubChem CID 896","ChEBI CHEBI:16796"],"notes":"Regulates the sleep-wake cycle."},{"id":"epinephrine","name":"Epinephrine","formula":"C9H13NO3","molecularWeight":183.21,"category":"Hormone and neurotransmitter","smiles":"CNC[C@@H](C1=CC(=C(C=C1)O)O)O","pubchemCid":"5816","chebiId":"CHEBI:28918","sourceIds":["PubChem CID 5816","ChEBI CHEBI:28918"],"notes":"Also called adrenaline."},{"id":"norepinephrine","name":"Norepinephrine","formula":"C8H11NO3","molecularWeight":169.18,"category":"Hormone and neurotransmitter","smiles":"C1=CC(=C(C=C1[C@H](CN)O)O)O","pubchemCid":"439260","chebiId":"CHEBI:18357","sourceIds":["PubChem CID 439260","ChEBI CHEBI:18357"],"notes":"Also called noradrenaline."},{"id":"dopamine","name":"Dopamine","formula":"C8H11NO2","molecularWeight":153.18,"category":"Neurotransmitter","smiles":"C1=CC(=C(C=C1CCN)O)O","pubchemCid":"681","chebiId":"CHEBI:18243","sourceIds":["PubChem CID 681","ChEBI CHEBI:18243"]},{"id":"serotonin","name":"Serotonin","formula":"C10H12N2O","molecularWeight":176.22,"category":"Neurotransmitter","smiles":"C1=CC2=C(C=C1O)C(=CN2)CCN","pubchemCid":"5202","chebiId":"CHEBI:28790","sourceIds":["PubChem CID 5202","ChEBI CHEBI:28790"]},{"id":"acetylcholine","name":"Acetylcholine","formula":"C7H16NO2+","molecularWeight":146.21,"category":"Neurotransmitter","smiles":"CC(=O)OCC[N+](C)(C)C","pubchemCid":"187","chebiId":"CHEBI:15355","sourceIds":["PubChem CID 187","ChEBI CHEBI:15355"],"notes":"Quaternary ammonium cation."},{"id":"gamma-aminobutyric-acid","name":"Gamma-aminobutyric acid","formula":"C4H9NO2","molecularWeight":103.12,"category":"Neurotransmitter","smiles":"C(CC(=O)O)CN","pubchemCid":"119","chebiId":"CHEBI:16865","sourceIds":["PubChem CID 119","ChEBI CHEBI:16865"],"notes":"GABA, the main inhibitory neurotransmitter in the brain."},{"id":"histamine","name":"Histamine","formula":"C5H9N3","molecularWeight":111.15,"category":"Neurotransmitter","smiles":"C1=C(NC=N1)CCN","pubchemCid":"774","chebiId":"CHEBI:18295","sourceIds":["PubChem CID 774","ChEBI CHEBI:18295"],"notes":"Also mediates allergic and inflammatory responses."},{"id":"putrescine","name":"Putrescine","formula":"C4H12N2","molecularWeight":88.15,"category":"Polyamine","smiles":"C(CCN)CN","pubchemCid":"1045","chebiId":"CHEBI:17148","sourceIds":["PubChem CID 1045","ChEBI CHEBI:17148"]},{"id":"spermidine","name":"Spermidine","formula":"C7H19N3","molecularWeight":145.25,"category":"Polyamine","smiles":"C(CCNCCCN)CN","pubchemCid":"1102","chebiId":"CHEBI:16610","sourceIds":["PubChem CID 1102","ChEBI CHEBI:16610"]},{"id":"spermine","name":"Spermine","formula":"C10H26N4","molecularWeight":202.35,"category":"Polyamine","smiles":"C(CCNCCCN)CNCCCN","pubchemCid":"1103","chebiId":"CHEBI:15746","sourceIds":["PubChem CID 1103","ChEBI CHEBI:15746"]},{"id":"thiamine","name":"Thiamine","formula":"C12H17N4OS+","molecularWeight":265.36,"category":"Vitamin","smiles":"CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO","pubchemCid":"1130","chebiId":"CHEBI:18385","sourceIds":["PubChem CID 1130","ChEBI CHEBI:18385"],"notes":"Vitamin B1."},{"id":"riboflavin","name":"Riboflavin","formula":"C17H20N4O6","molecularWeight":376.37,"category":"Vitamin","smiles":"CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O","pubchemCid":"493570","chebiId":"CHEBI:17015","sourceIds":["PubChem CID 493570","ChEBI CHEBI:17015"],"notes":"Vitamin B2."},{"id":"niacin","name":"Niacin","formula":"C6H5NO2","molecularWeight":123.11,"category":"Vitamin","smiles":"C1=CC(=CN=C1)C(=O)O","pubchemCid":"938","chebiId":"CHEBI:15940","sourceIds":["PubChem CID 938","ChEBI CHEBI:15940"],"notes":"Vitamin B3 (nicotinic acid)."},{"id":"pantothenic-acid","name":"Pantothenic acid","formula":"C9H17NO5","molecularWeight":219.24,"category":"Vitamin","smiles":"CC(C)(CO)[C@H](C(=O)NCCC(=O)O)O","pubchemCid":"6613","chebiId":"CHEBI:46905","sourceIds":["PubChem CID 6613","ChEBI CHEBI:46905"],"notes":"Vitamin B5."},{"id":"pyridoxine","name":"Pyridoxine","formula":"C8H11NO3","molecularWeight":169.18,"category":"Vitamin","smiles":"CC1=NC=C(C(=C1O)CO)CO","pubchemCid":"1054","chebiId":"CHEBI:16709","sourceIds":["PubChem CID 1054","ChEBI CHEBI:16709"],"notes":"Vitamin B6."},{"id":"biotin","name":"Biotin","formula":"C10H16N2O3S","molecularWeight":244.31,"category":"Vitamin","smiles":"C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)O)NC(=O)N2","pubchemCid":"171548","chebiId":"CHEBI:15956","sourceIds":["PubChem CID 171548","ChEBI CHEBI:15956"],"notes":"Vitamin B7."},{"id":"folic-acid","name":"Folic acid","formula":"C19H19N7O6","molecularWeight":441.4,"category":"Vitamin","smiles":"C1=CC(=CC=C1C(=O)N[C@@H](CCC(=O)O)C(=O)O)NCC2=CN=C3C(=N2)C(=O)NC(=N3)N","pubchemCid":"135398658","chebiId":"CHEBI:27470","sourceIds":["PubChem CID 135398658","ChEBI CHEBI:27470"],"notes":"Vitamin B9."},{"id":"l-ascorbic-acid","name":"L-Ascorbic acid","formula":"C6H8O6","molecularWeight":176.12,"category":"Vitamin","smiles":"C([C@@H]([C@@H]1C(=C(C(=O)O1)O)O)O)O","pubchemCid":"54670067","chebiId":"CHEBI:29073","sourceIds":["PubChem CID 54670067","ChEBI CHEBI:29073"],"notes":"Vitamin C."},{"id":"retinol","name":"Retinol","formula":"C20H30O","molecularWeight":286.46,"category":"Vitamin","smiles":"CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C","pubchemCid":"445354","chebiId":"CHEBI:17336","sourceIds":["PubChem CID 445354","ChEBI CHEBI:17336"],"notes":"Vitamin A."},{"id":"cholecalciferol","name":"Cholecalciferol","formula":"C27H44O","molecularWeight":384.65,"category":"Vitamin","smiles":"C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\\2[C@@]1(CCC/C2=C\\C=C/3\\C[C@H](CCC3=C)O)C","pubchemCid":"5280795","chebiId":"CHEBI:28940","sourceIds":["PubChem CID 5280795","ChEBI CHEBI:28940"],"notes":"Vitamin D3."},{"id":"ergocalciferol","name":"Ergocalciferol","formula":"C28H44O","molecularWeight":396.66,"category":"Vitamin","smiles":"C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]\\2[C@@]1(CCC/C2=C\\C=C/3\\C[C@H](CCC3=C)O)C","pubchemCid":"5280793","chebiId":"CHEBI:28934","sourceIds":["PubChem CID 5280793","ChEBI CHEBI:28934"],"notes":"Vitamin D2."},{"id":"alpha-tocopherol","name":"alpha-Tocopherol","formula":"C28H48O2","molecularWeight":416.69,"category":"Vitamin","smiles":"CC1=C(C=C2CCC(OC2=C1C)(C)CCCC(C)CCCC(C)CCCC(C)C)O","pubchemCid":"14986","sourceIds":["PubChem CID 14986"],"notes":"Vitamin E. Stereochemistry unspecified in this record."},{"id":"phylloquinone","name":"Phylloquinone","formula":"C31H46O2","molecularWeight":450.71,"category":"Vitamin","smiles":"CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C","pubchemCid":"5284607","chebiId":"CHEBI:18067","sourceIds":["PubChem CID 5284607","ChEBI CHEBI:18067"],"notes":"Vitamin K1."},{"id":"menaquinone-4","name":"Menaquinone-4","formula":"C31H40O2","molecularWeight":444.66,"category":"Vitamin","smiles":"CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\\C)/CC/C=C(\\C)/CC/C=C(\\C)/CCC=C(C)C","pubchemCid":"5282367","chebiId":"CHEBI:78277","sourceIds":["PubChem CID 5282367","ChEBI CHEBI:78277"],"notes":"A form of vitamin K2."},{"id":"5-aminolevulinic-acid","name":"5-Aminolevulinic acid","formula":"C5H9NO3","molecularWeight":131.13,"category":"Heme metabolism","smiles":"C(CC(=O)O)C(=O)CN","pubchemCid":"137","chebiId":"CHEBI:17549","sourceIds":["PubChem CID 137","ChEBI CHEBI:17549"],"notes":"First committed precursor of heme."},{"id":"porphobilinogen","name":"Porphobilinogen","formula":"C10H14N2O4","molecularWeight":226.23,"category":"Heme metabolism","smiles":"C1=C(C(=C(N1)CN)CC(=O)O)CCC(=O)O","pubchemCid":"1021","chebiId":"CHEBI:17381","sourceIds":["PubChem CID 1021","ChEBI CHEBI:17381"]},{"id":"biliverdin","name":"Biliverdin","formula":"C33H34N4O6","molecularWeight":582.66,"category":"Heme metabolism","smiles":"CC\\1=C(/C(=C/C2=C(C(=C(N2)/C=C\\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/N/C1=C\\C4=NC(=O)C(=C4C)C=C)CCC(=O)O","pubchemCid":"5280353","chebiId":"CHEBI:188102","sourceIds":["PubChem CID 5280353","ChEBI CHEBI:188102"],"notes":"Green pigment from heme breakdown."},{"id":"bilirubin","name":"Bilirubin","formula":"C33H36N4O6","molecularWeight":584.67,"category":"Heme metabolism","smiles":"CC1=C(NC(=C1CCC(=O)O)CC2=C(C(=C(N2)/C=C\\3/C(=C(C(=O)N3)C)C=C)C)CCC(=O)O)/C=C\\4/C(=C(C(=O)N4)C=C)C","pubchemCid":"5280352","chebiId":"CHEBI:16990","sourceIds":["PubChem CID 5280352","ChEBI CHEBI:16990"],"notes":"Yellow pigment from heme breakdown."},{"id":"l-kynurenine","name":"L-Kynurenine","formula":"C10H12N2O3","molecularWeight":208.22,"category":"Tryptophan metabolite","smiles":"C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)O)N)N","pubchemCid":"161166","chebiId":"CHEBI:16946","sourceIds":["PubChem CID 161166","ChEBI CHEBI:16946"]},{"id":"anthranilic-acid","name":"Anthranilic acid","formula":"C7H7NO2","molecularWeight":137.14,"category":"Tryptophan metabolite","smiles":"C1=CC=C(C(=C1)C(=O)O)N","pubchemCid":"227","chebiId":"CHEBI:30754","sourceIds":["PubChem CID 227","ChEBI CHEBI:30754"]},{"id":"phenylpyruvic-acid","name":"Phenylpyruvic acid","formula":"C9H8O3","molecularWeight":164.16,"category":"Phenylalanine metabolite","smiles":"C1=CC=C(C=C1)CC(=O)C(=O)O","pubchemCid":"997","chebiId":"CHEBI:30851","sourceIds":["PubChem CID 997","ChEBI CHEBI:30851"],"notes":"Accumulates in phenylketonuria."},{"id":"homogentisic-acid","name":"Homogentisic acid","formula":"C8H8O4","molecularWeight":168.15,"category":"Tyrosine metabolite","smiles":"C1=CC(=C(C=C1O)CC(=O)O)O","pubchemCid":"780","chebiId":"CHEBI:44747","sourceIds":["PubChem CID 780","ChEBI CHEBI:44747"],"notes":"Accumulates in alkaptonuria."},{"id":"shikimic-acid","name":"Shikimic acid","formula":"C7H10O5","molecularWeight":174.15,"category":"Plant and microbial metabolite","smiles":"C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O","pubchemCid":"8742","chebiId":"CHEBI:16119","sourceIds":["PubChem CID 8742","ChEBI CHEBI:16119"],"notes":"Precursor of aromatic amino acids in plants and bacteria."},{"id":"indole-3-acetic-acid","name":"Indole-3-acetic acid","formula":"C10H9NO2","molecularWeight":175.19,"category":"Plant hormone","smiles":"C1=CC=C2C(=C1)C(=CN2)CC(=O)O","pubchemCid":"802","chebiId":"CHEBI:16411","sourceIds":["PubChem CID 802","ChEBI CHEBI:16411"],"notes":"The main natural auxin."}]}