(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-[(2R,3R)-2-methyl-1-(methylamino)pentan-3-yl]phenoxy}oxane-2-carboxylic acid

• ChemBase ID: 166585
• Molecular Formular: C19H29NO7
• Molecular Mass: 383.43606
• Monoisotopic Mass: 383.19440227
• SMILES: c1(cccc(c1)[C@@H]([C@H](CNC)C)CC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CNC[C@@H]([C@H](c1cccc(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CC)C
• InChI: InChI=1S/C19H29NO7/c1-4-13(10(2)9-20-3)11-6-5-7-12(8-11)26-19-16(23)14(21)15(22)17(27-19)18(24)25/h5-8,10,13-17,19-23H,4,9H2,1-3H3,(H,24,25)/t10-,13+,14-,15-,16+,17-,19+/m0/s1
• InChIKey: NZXQRBQRSILIIJ-WDRIRZBNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-[(2R,3R)-2-methyl-1-(methylamino)pentan-3-yl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-[(2R,3R)-2-methyl-1-(methylamino)pentan-3-yl]phenoxy}oxane-2-carboxylic acid
• Synonyms: 3-[(1R,2R)-1-Ethyl-2-methyl-3-(methylamino)propyl]phenyl β-D-Glucopyranosiduronic Acid; N-Desmethyl Tapentadol O-β-D-Glucuronide

Database IDs

• PubChem SID: 162260718
• PubChem CID: 71315793

CALCULATED PROPERTIES

• Acid pKa: 2.990212
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.3625759
• LogD (pH = 7.4): -1.361898
• Log P: -1.3616626
• Molar Refractivity: 96.2759 cm^3
• Polarizability: 38.80983 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D294005

N-Desmethyl Tapentadol O-β-D-Glucuronide is the glucuronide conjugate of N-Desmethyl Tapentadol (D294000) and a metabolite of Tapentadol (T007200).

REFERENCES

• Terlinden, R. et al.: Meth. Find. Exp. Clin. Pharmacol., 32, 31 (2010)
• Bourland, J.A. et al.: J. Anal. Toxicol., 34, 450 (2010)