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

• ChemBase ID: 166428
• Molecular Formular: C22H29NO7
• Molecular Mass: 419.46816
• Monoisotopic Mass: 419.19440227
• SMILES: c1(cc2c(cc1)CC1C3C2(CCCC3)CCN1)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)NCC2)O[C@H]([C@H]1O)C(=O)O
• InChI: InChI=1S/C22H29NO7/c24-16-17(25)19(20(27)28)30-21(18(16)26)29-12-5-4-11-9-15-13-3-1-2-6-22(13,7-8-23-15)14(11)10-12/h4-5,10,13,15-19,21,23-26H,1-3,6-9H2,(H,27,28)/t13?,15?,16-,17-,18+,19-,21+,22?/m0/s1
• InChIKey: QYVMECDBFFRIEZ-JJYOAAGWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 19153-89-0
• PubChem SID: 162260561
• PubChem CID: 71315730

CALCULATED PROPERTIES

• Acid pKa: 2.8505569
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.4552598
• LogD (pH = 7.4): -1.455072
• Log P: -1.4547161
• Molar Refractivity: 104.798 cm^3
• Polarizability: 42.081486 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 223-225°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - D291600

A labelled metabolite of Dextromethorphan.

REFERENCES

• Gonzalez, F., et al.: Nature, 331, 442 (1988)
• Chen, S., et al.: Clin. Pharmacol. Ther., 60, 522 (1988)
• Hartter, S., et al.: Ther. Drug Monit., 18, 297 (1988)
• Garcia-Martin, E., et al.: Clin. Pharmacol. Ther., 71, 196 (1988)