1.0 2016-09-30 22:45:15 UTC 2020-06-04 18:59:03 UTC BMDB0001389 BMDB01389 Melatonin Melatonin, also known as circadin or melatol, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Melatonin is a drug which is used orally for jet lag, insomnia, shift-work disorder, circadian rhythm disorders in the blind (evidence for efficacy), and benzodiazepine and nicotine withdrawal. evidence indicates that melatonin is likely effective for treating circadian rhythm sleep disorders in blind children and adults. it has received fda orphan drug status as an oral medication for this use. a number of studies have shown that melatonin may be effective for treating sleep-wake cycle disturbances in children and adolescents with mental retardation, autism, and other central nervous system disorders. it appears to decrease the time to fall asleep in children with developmental disabilities, such as cerebral palsy, autism, and mental retardation. it may also improve secondary insomnia associated with various sleep-wake cycle disturbances. other possible uses for which there is some evidence for include: benzodiazepine withdrawal, cluster headache, delayed sleep phase syndrome (dsps), primary insomnia, jet lag, nicotine withdrawal, preoperative anxiety and sedation, prostate cancer, solid tumors (when combined with il-2 therapy in certain cancers), sunburn prevention (topical use), tardive dyskinesia, thrombocytopenia associated with cancer, chemotherapy and other disorders. . Melatonin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Melatonin exists in all living organisms, ranging from bacteria to humans. Melatonin participates in a number of enzymatic reactions, within cattle. In particular, Melatonin and S-adenosylhomocysteine can be biosynthesized from N-acetylserotonin and S-adenosylmethionine through the action of the enzyme acetylserotonin O-methyltransferase. In addition, Melatonin can be converted into 6-hydroxymelatonin; which is mediated by the enzyme cytochrome P450 1A1. In cattle, melatonin is involved in the metabolic pathway called the tryptophan metabolism pathway. Melatonin is a potentially toxic compound. 5-Methoxy-N-acetyltryptamine Melatonine N-[2-(5-Methoxyindol-3-yl)ethyl]acetamide N-Acetyl-5-methoxytryptamine Melatonina Circadin Melatol Melatonin (synth.) standard-grade Melatonin (synth.) ultra-pure Melovine MT6 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-[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 Regulin {N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-} acetamide {N-[2-(5-methoxyindol-3-yl)ethyl]-} acetamide 3-(2-Acetamidoethyl)-5-methoxyindole Melatonin C13H16N2O2 232.2783 232.121177766 N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide melatonin 73-31-4 COC1=CC2=C(NC=C2CCNC(C)=O)C=C1 InChI=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-N belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Organic compounds Organoheterocyclic compounds Indoles and derivatives Indoles 3-alkylindoles Alkyl aryl ethers Anisoles Azacyclic compounds Carboximidic acids Heteroaromatic compounds Hydrocarbon derivatives Organonitrogen compounds Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Substituted pyrroles 3-alkylindole Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Azacycle Benzenoid Carboximidic acid Carboximidic acid derivative Ether Heteroaromatic compound Hydrocarbon derivative Organic 1,3-dipolar compound Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Pyrrole Substituted pyrrole Aromatic heteropolycyclic compounds Indole alkaloids Melatonin a small molecule acetamides tryptamines Solid logp 1.42 ALOGPS logs -3.21 ALOGPS logp 1.15 ChemAxon pka_strongest_acidic 15.8 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac N-[2-(5-methoxy-1H-indol-3-yl)ethyl]acetamide ChemAxon average_mass 232.2783 ChemAxon mono_mass 232.121177766 ChemAxon smiles COC1=CC2=C(NC=C2CCNC(C)=O)C=C1 ChemAxon formula C13H16N2O2 ChemAxon inchi InChI=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) ChemAxon inchikey DRLFMBDRBRZALE-UHFFFAOYSA-N ChemAxon polar_surface_area 54.12 ChemAxon refractivity 66.28 ChemAxon polarizability 25.65 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Tryptophan Metabolism SMP0087237 Specdb::NmrTwoD 1634 Specdb::NmrOneD 1693 Specdb::NmrOneD 2600 Specdb::NmrOneD 3303 Specdb::CMs 735 Specdb::CMs 736 Specdb::CMs 737 Specdb::CMs 1945 Specdb::CMs 7100 Specdb::CMs 31319 Specdb::CMs 32276 Specdb::CMs 32277 Specdb::CMs 32278 Specdb::CMs 137803 Specdb::CMs 145537 Specdb::EiMs 505 Specdb::MsMs 1547 Specdb::MsMs 1548 Specdb::MsMs 1549 Specdb::MsMs 5222 Specdb::MsMs 5223 Specdb::MsMs 5224 Specdb::MsMs 5225 Specdb::MsMs 5226 Specdb::MsMs 5227 Specdb::MsMs 5228 Specdb::MsMs 5229 Specdb::MsMs 5230 Specdb::MsMs 5231 Specdb::MsMs 5232 Specdb::MsMs 5233 Specdb::MsMs 251712 Specdb::MsMs 251713 Specdb::MsMs 251714 Specdb::MsMs 271653 Specdb::MsMs 271654 Specdb::MsMs 271655 Specdb::MsMs 374102 Specdb::MsMs 374103 Specdb::MsMs 374702 Specdb::MsMs 438131 Adipose Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Adrenal Cortex Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Adrenal Gland Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Adrenal Medulla Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Bladder Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Kidney Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Leukocyte Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 0.00003 - 0.00006458 uM Raw milk from early lactation, diurnal range Eriksson L, Valtonen M, Laitinen JT, Paananen M, Kaikkonen M: Diurnal rhythm of melatonin in bovine milk: pharmacokinetics of exogenous melatonin in lactating cows and goats. Acta Vet Scand. 1998;39(3):301-10. 9787493 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Ovary Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Pancreas Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Pineal Gland Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Testis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C01598 FDB004234 872 896 DB01065 16796 N-ACETYL-5-METHOXY-TRYPTAMINE Melatonin 37965 73 Reddy, Gaddam Om; Sarma, Mamillapilli Ramabhadra; Prabhakar, Chebiyyam. An improved process for the preparation of melatonin. Indian (2001), 30 pp. Eriksson L, Valtonen M, Laitinen JT, Paananen M, Kaikkonen M: Diurnal rhythm of melatonin in bovine milk: pharmacokinetics of exogenous melatonin in lactating cows and goats. Acta Vet Scand. 1998;39(3):301-10. 9787493 BMDBP00042 Cytochrome P450 2U1 Q0IIF9 CYP2U1 Enzyme BMDBP00410 Acetylserotonin O-methyltransferase P10950 ASMT Enzyme BMDBP01828 Melatonin receptor type 1A O02769 MTNR1A Enzyme BMDBP02000 Melatonin receptor 1A B5LED7 Enzyme BMDBP02001 Melatonin receptor 1A B5LED8 Enzyme BMDBP02931 Indoleamine 2,3-dioxygenase 1 F1N7C5 IDO1 Enzyme