(2S,3S,4S,5R,6S)-6-({17-[(benzyloxy)carbonyl]-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 161674
• Molecular Formular: C30H35NO9
• Molecular Mass: 553.6002
• Monoisotopic Mass: 553.23118171
• SMILES: c1(cc2c(cc1)CC1C3C2(CCCC3)CCN1C(=O)OCc1ccccc1)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](Oc2ccc3c(c2)C24CCCCC4C(C3)N(CC2)C(=O)OCc2ccccc2)O[C@H]([C@H]1O)C(=O)O
• InChI: InChI=1S/C30H35NO9/c32-23-24(33)26(27(35)36)40-28(25(23)34)39-19-10-9-18-14-22-20-8-4-5-11-30(20,21(18)15-19)12-13-31(22)29(37)38-16-17-6-2-1-3-7-17/h1-3,6-7,9-10,15,20,22-26,28,32-34H,4-5,8,11-14,16H2,(H,35,36)/t20?,22?,23-,24-,25+,26-,28+,30?/m0/s1
• InChIKey: TWXLLCNCSDELMS-HLHMHQGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({17-[(benzyloxy)carbonyl]-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({17-[(benzyloxy)carbonyl]-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: N-Benzyloxycarbonyl-(9α,13α,14α)-morphinan-3-yl β-D-Glucopyranosiduronic Acid; N-Benzyloxycarbonyl N-Desmethyl Dextrorphan β-D-O-Glucuronide

Database IDs

• PubChem SID: 162255809
• PubChem CID: 71313869

CALCULATED PROPERTIES

• Acid pKa: 3.10344
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.6033031
• LogD (pH = 7.4): -0.49020687
• Log P: 2.9707453
• Molar Refractivity: 140.6001 cm^3
• Polarizability: 55.885006 Å^3
• Polar Surface Area: 145.99 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B285790

An intermediate in the preparation of Dextromethorphan metabolites.