(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[17-(2H3)methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 166734
• Molecular Formular: C23H31NO7
• Molecular Mass: 433.49474
• Monoisotopic Mass: 433.21005234
• SMILES: c1(cc2c(cc1)CC1C3C2(CCCC3)CCN1C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](Oc2ccc3c(c2)C24CCCCC4C(C3)N(CC2)C)O[C@H]([C@H]1O)C(=O)O
• InChI: InChI=1S/C23H31NO7/c1-24-9-8-23-7-3-2-4-14(23)16(24)10-12-5-6-13(11-15(12)23)30-22-19(27)17(25)18(26)20(31-22)21(28)29/h5-6,11,14,16-20,22,25-27H,2-4,7-10H2,1H3,(H,28,29)/t14?,16?,17-,18-,19+,20-,22+,23?/m0/s1
• InChIKey: YQAUTKINOXBFCA-IGGZQXCCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[17-(^2H₃)methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[17-(^2H₃)methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (9α,13α,14α)-17-(Methyl-d3)morphinan-3-yl β-D-Glucopyranosiduronic Acid; Dextrorphan-d3 3-Glucuronide; Dextrorphan-d3 Glucuronide; Dextrorphan-d3 β-D-O-Glucuronide

Database IDs

• CAS Number: 524713-58-4
• PubChem SID: 162260867
• PubChem CID: 71315861

CALCULATED PROPERTIES

• Acid pKa: 2.850454
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.331574
• LogD (pH = 7.4): -1.3321391
• Log P: -1.3310599
• Molar Refractivity: 110.0927 cm^3
• Polarizability: 43.911407 Å^3
• Polar Surface Area: 119.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Hot Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 200-205°C

DETAILS

Toronto Research Chemicals - D299502

A Labelled metabolite of Dextrorphan.

REFERENCES

• Gonzalez, F., et al.: Nature, 331, 442 (1988)
• Meyer, U., et al.: Pharmacol. Ther., 46, 297 (1988)
• Rogers, J., et al.: Am. J. Med., 113, 746 (1988)
• Huang, W., et al.: Drug Metab. Dispos., 32, 1434 (1988)