1.0 2016-09-30 23:07:46 UTC 2020-05-21 16:27:05 UTC BMDB0004081 BMDB04081 6-Hydroxymelatonin 6-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 possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Hydroxymelatonin exists in all living organisms, ranging from bacteria to humans. 6-Hydroxymelatonin can be biosynthesized from melatonin through its interaction with the enzyme cytochrome P450 1A1. In cattle, 6-hydroxymelatonin is involved in the metabolic pathway called the tryptophan metabolism pathway. Lopac-H-0627 6-Oxymelatonin 6-Hydroxy-N-acetyl-5-methoxytryptamine 6-Hydroxy-N-acetyl-5-methoxytryptamine C13H16N2O3 248.2777 248.116092388 N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide 2208-41-5 COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1 InChI=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-N belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. Organic compounds Organoheterocyclic compounds Indoles and derivatives Hydroxyindoles Hydroxyindoles 1-hydroxy-2-unsubstituted benzenoids 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 1-hydroxy-2-unsubstituted benzenoid 3-alkylindole Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Azacycle Benzenoid Carboximidic acid Carboximidic acid derivative Ether Heteroaromatic compound Hydrocarbon derivative Hydroxyindole Indole 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 a small molecule acetamides tryptamines Solid logp 0.80 ALOGPS logs -2.72 ALOGPS logp 0.84 ChemAxon pka_strongest_acidic 9.29 ChemAxon pka_strongest_basic -0.94 ChemAxon iupac N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide ChemAxon average_mass 248.2777 ChemAxon mono_mass 248.116092388 ChemAxon smiles COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1 ChemAxon formula C13H16N2O3 ChemAxon inchi InChI=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) ChemAxon inchikey OMYMRCXOJJZYKE-UHFFFAOYSA-N ChemAxon polar_surface_area 74.35 ChemAxon refractivity 68.26 ChemAxon polarizability 26.65 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 3 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::CMs 2008 Specdb::CMs 24875 Specdb::CMs 31498 Specdb::CMs 38708 Specdb::CMs 162112 Specdb::MsMs 90558 Specdb::MsMs 90559 Specdb::MsMs 90560 Specdb::MsMs 153744 Specdb::MsMs 153745 Specdb::MsMs 153746 Specdb::MsMs 374822 Specdb::MsMs 451520 Specdb::MsMs 2827083 Specdb::MsMs 2827084 Specdb::MsMs 2827085 Specdb::MsMs 2851393 Specdb::MsMs 2851394 Specdb::MsMs 2851395 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 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 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 1864 FDB023304 1794 C05643 2198 46185 6-Hydroxymelatonin 7013 Karam, Omar; Zunino, Fabien; Chagnaut, Vincent; Jouannetaud, Marie Paule; Jacquesy, Jean Claude. An efficient synthesis of 6-hydroxymelatonin, a human metabolite of melatonin. Tetrahedron Letters (2003), 44(7), 1511-1513. BMDBP00042 Cytochrome P450 2U1 Q0IIF9 CYP2U1 Enzyme