1.0 2016-09-30 23:14:28 UTC 2020-05-11 20:05:22 UTC BMDB0004995 BMDB04995 Codeine C18H21NO3 299.37 299.15214354 (1S,14S)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol (1S,14S)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol [H]C12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)C([H])(C4)C1([H])C=C[C@]2([H])O InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11?,12?,13-,17?,18-/m0/s1 OROGSEYTTFOCAN-GLAODNLDSA-N belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Organic compounds Alkaloids and derivatives Morphinans Morphinans Alkyl aryl ethers Anisoles Aralkylamines Azacyclic compounds Coumarans Hydrocarbon derivatives Organopnictogen compounds Oxacyclic compounds Phenanthrenes and derivatives Piperidines Secondary alcohols Tetralins Trialkylamines Alcohol Alkyl aryl ether Amine Anisole Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Coumaran Ether Hydrocarbon derivative Morphinan Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Phenanthrene Phenol ether Piperidine Secondary alcohol Tertiary aliphatic amine Tertiary amine Tetralin Aromatic heteropolycyclic compounds Solid logp 1.20 ALOGPS logs -2.72 ALOGPS logp 1.34 ChemAxon pka_strongest_acidic 13.78 ChemAxon pka_strongest_basic 9.19 ChemAxon iupac (1S,14S)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol ChemAxon average_mass 299.37 ChemAxon mono_mass 299.15214354 ChemAxon smiles [H]C12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)C([H])(C4)C1([H])C=C[C@]2([H])O ChemAxon formula C18H21NO3 ChemAxon inchi InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11?,12?,13-,17?,18-/m0/s1 ChemAxon inchikey OROGSEYTTFOCAN-GLAODNLDSA-N ChemAxon polar_surface_area 41.93 ChemAxon refractivity 84.6 ChemAxon polarizability 32.05 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon number_of_rings 5 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 1258165 Specdb::MsMs 1258166 Specdb::MsMs 1258167 Specdb::MsMs 1373320 Specdb::MsMs 1373321 Specdb::MsMs 1373322 Epidermis 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 Hair 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 53477788 Codeine Gates, Marshall. The conversion of codeinone to codeine. Journal of the American Chemical Society (1953), 75 4340-1.