(2S,3S,4S,5R,6S)-6-(3-{2-[(dimethylamino)methyl]-1-hydroxycyclohexyl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 166600
• Molecular Formular: C21H31NO8
• Molecular Mass: 425.47274
• Monoisotopic Mass: 425.20496696
• SMILES: c1c(cccc1C1(CCCCC1CN(C)C)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CN(CC1CCCCC1(O)c1cccc(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C21H31NO8/c1-22(2)11-13-6-3-4-9-21(13,28)12-7-5-8-14(10-12)29-20-17(25)15(23)16(24)18(30-20)19(26)27/h5,7-8,10,13,15-18,20,23-25,28H,3-4,6,9,11H2,1-2H3,(H,26,27)/t13?,15-,16-,17+,18-,20+,21?/m0/s1
• InChIKey: DSBGQRZOJXSECT-VFUSOVNCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(3-{2-[(dimethylamino)methyl]-1-hydroxycyclohexyl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(3-{2-[(dimethylamino)methyl]-1-hydroxycyclohexyl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 3-[2-[(Dimethylamino)methyl]-1-hydroxycyclohexyl]phenyl β-D-Glucopyranosiduronic Acid; O-Desmethyl Tramadol β-D-Glucuronide(Mixture of Diastereomers)

Database IDs

• CAS Number: 383891-39-2
• PubChem SID: 162260733
• PubChem CID: 71315797

CALCULATED PROPERTIES

• Acid pKa: 2.8098698
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.3754015
• LogD (pH = 7.4): -2.379986
• Log P: -2.3750467
• Molar Refractivity: 105.7987 cm^3
• Polarizability: 42.488773 Å^3
• Polar Surface Area: 139.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D294735

A metabolite of Tramadol.

REFERENCES

• Raffa, R., et al.: J. Pharmacol. Exp. Ther., 267, 331 (1993)
• Pospisilova, M., et al.: J. Pharm. Biomed. Anal., 18, 777 (1993)
• Scott, L., et al.: Drugs, 60, 139 (1993)
• Wu, W., et al.: Xenobiotica, 32, 411 (1993)