(1S,4S,5R,13R,14S,17R)-14-hydroxy-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-4-ium-4-olate

• ChemBase ID: 1352
• Molecular Formular: C18H21NO4
• Molecular Mass: 315.36364
• Monoisotopic Mass: 315.14705816
• SMILES: O1[C@@H]2[C@]34[C@H]([C@H]([N@@+]([O-])(CC3)C)Cc3c4c1c(OC)cc3)C=C[C@@H]2O
• 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-KFUGMXNISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,13R,14S,17R)-14-hydroxy-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-4-ium-4-olate
• IUPAC Traditional name: @codeine-N-oxide
• Synonyms: Codeine-N-oxide

Database IDs

• CAS Number: 3688-65-1
• PubChem SID: 46504794; 160964812
• PubChem CID: 5359929

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -0.48
• LOG S: -3.36
• Solubility (Water): 1.38e-01 g/l

DETAILS

DrugBank - DB01568

Drug information: illicit; experimental