(1S,4R,5R,13R,14S,17R)-14-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-4-ium-4-olate

• ChemBase ID: 164881
• Molecular Formular: C18H21NO4
• Molecular Mass: 315.36364
• Monoisotopic Mass: 315.14705816
• SMILES: [C@H]12[C@H](C=C[C@@H]3[C@]41c1c(C[C@H]3[N@@+](CC4)([O-])C)ccc(c1O2)OC)O
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CC[N@+]([C@H](C2)[C@@H]4C=C[C@@H]1O)([O-])C
• InChI: InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)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-,19+/m0/s1
• InChIKey: BDLSDHWCOJPHIE-PEKXWBJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R,5R,13R,14S,17R)-14-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-4-ium-4-olate
• IUPAC Traditional name: (1S,4R,5R,13R,14S,17R)-14-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-4-ium-4-olate
• Synonyms: (5α,6α-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol 17-Oxide; Codeigene; Gencodeine; Genkodein; Genocodein; Genocodeine; Codeine N-Oxide

Database IDs

• CAS Number: 3688-65-1
• PubChem SID: 162259015
• PubChem CID: 71314936

CALCULATED PROPERTIES

• Acid pKa: 13.782468
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.21843928
• LogD (pH = 7.4): 0.2185742
• Log P: 0.2185761
• Molar Refractivity: 86.6496 cm^3
• Polarizability: 32.91707 Å^3
• Polar Surface Area: 65.57 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C634095

A metabolite of Codeine (C634075). Analgesic (narcotic); antitussive.

REFERENCES

• Frances, B., et al.: J. Pharm. Exp. Ther., 25, 262 (1992)
• Osborne, R., et al.: Br. J. Clin. Pharm., 34, 130, (1992)