(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 175592
• Molecular Formular: C23H27NO9
• Molecular Mass: 461.46178
• Monoisotopic Mass: 461.16858145
• SMILES: [C@H]12[C@H](C=C[C@@H]3[C@]41c1c(C[C@H]3NCC4)ccc(c1O2)OC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN[C@H](C2)[C@@H]4C=C[C@@H]1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C23H27NO9/c1-30-12-4-2-9-8-11-10-3-5-13(20-23(10,6-7-24-11)14(9)18(12)32-20)31-22-17(27)15(25)16(26)19(33-22)21(28)29/h2-5,10-11,13,15-17,19-20,22,24-27H,6-8H2,1H3,(H,28,29)/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-/m0/s1
• InChIKey: YWEYZPZIMCQHFM-GAROZEBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-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-14-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-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-14-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-3-methoxymorphinan-6-yl β-D-Glucopyranosiduronic Acid; Norcodeine 6-glucuronide; Norcodeine Glucuronide; Norcodeine O-β-D-Glucuronide

Database IDs

• CAS Number: 50444-03-6
• PubChem SID: 164231502
• PubChem CID: 71751177

CALCULATED PROPERTIES

• Acid pKa: 2.8711684
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -2.962996
• LogD (pH = 7.4): -2.963006
• Log P: -2.9624407
• Molar Refractivity: 111.5907 cm^3
• Polarizability: 44.414036 Å^3
• Polar Surface Area: 146.94 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N661605

Norcodeine O-β-D-Glucuronide is the glucuronide conjugate of Norcodeine (N661605) and metabolite of Codeine (C634080).

REFERENCES

• He, H. et al.: J. Chrom B Biomed. Sci. Appl., 708, 185 (1998)
• Svensson, J.O. et al.: J. Chrom B Biomed. Sci. Appl., 674, 49 (1998)