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

• ChemBase ID: 167252
• Molecular Formular: C20H29NO8
• Molecular Mass: 411.44616
• Monoisotopic Mass: 411.18931689
• SMILES: C1CCC[C@@]([C@H]1CNC)(c1cc(ccc1)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)O
• Canonical SMILES: CNC[C@H]1CCCC[C@]1(O)c1cccc(c1)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C20H29NO8/c1-21-10-12-5-2-3-8-20(12,27)11-6-4-7-13(9-11)28-19-16(24)14(22)15(23)17(29-19)18(25)26/h4,6-7,9,12,14-17,19,21-24,27H,2-3,5,8,10H2,1H3,(H,25,26)/t12-,14+,15+,16-,17+,19-,20+/m1/s1
• InChIKey: HBTIGWZPLHUAQY-RINYIIKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenoxy}oxane-2-carboxylic acid
• Synonyms: rel-3-[(1R,2R)-1-Hydroxy-2-[(methylamino)methyl]cyclohexyl]phenyl β-D-Glucopyranosiduronic Acid; rac N,O-Didesmethyl Tramadol O-β-D-Glucuronide

Database IDs

• PubChem SID: 162261385
• PubChem CID: 29919009

CALCULATED PROPERTIES

• Acid pKa: 2.8098707
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -2.499104
• LogD (pH = 7.4): -2.4996538
• Log P: -2.4986367
• Molar Refractivity: 100.504 cm^3
• Polarizability: 40.661488 Å^3
• Polar Surface Area: 148.71 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D441235

N,O-Didesmethyl Tramadol O-β-D-Glucuronide is the racemic glucuronide conjugate of a didesmethylated metabolite of Tramadol (T712500).

REFERENCES

• Wu, W.N. et al.: Xenobiotica, 32, 411 (2002)