sodium (2S,3S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5S,13R,14S,17R)-10-methoxy-4-(2H3)methyl-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-carboxylate

• ChemBase ID: 164880
• Molecular Formular: C24H28NNaO9
• Molecular Mass: 497.47019
• Monoisotopic Mass: 497.16617576
• SMILES: [C@H]12[C@H](C=C[C@@H]3[C@]41c1c(C[C@@H]3N(CC4)C)ccc(c1O2)OC)O[C@H]1[C@H](C([C@@H]([C@@H](O1)C(=O)[O-])O)O)O.[Na+]
• 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([C@@H]1O)O)O)C.[Na+]
• InChI: InChI=1S/C24H29NO9.Na/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25;/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30);/q;+1/p-1/t11-,12-,14-,16?,17-,18+,20-,21-,23+,24-;/m0./s1
• InChIKey: PXJIWCXZTGPMDS-SQKCCCLQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5S,13R,14S,17R)-10-methoxy-4-(^2H₃)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-14-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5S,13R,14S,17R)-10-methoxy-4-(^2H₃)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-14-yl]oxy}oxane-2-carboxylate
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-(methyl-d3)-morphinan-6-yl β-D-Glucopyranosiduronic Acid Sodium Salt; Codeine-d3 Glucuronide Sodium Salt; Codeine-6-glucuronide-d3 Sodium Salt; Codeine-d3 6-β-D-Glucuronide Sodium Salt

Database IDs

• CAS Number: 219533-59-2
• PubChem SID: 162259014
• PubChem CID: 71314934

CALCULATED PROPERTIES

• Acid pKa: 2.8711138
• H Acceptors: 10
• H Donor: 3
• LogD (pH = 5.5): -2.8392801
• LogD (pH = 7.4): -2.8442082
• Log P: -2.838862
• Molar Refractivity: 127.7225 cm^3
• Polarizability: 46.12398 Å^3
• Polar Surface Area: 140.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 205-208°C (dec.)

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - C634092

A labelled 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)