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

• ChemBase ID: 178076
• Molecular Formular: C20H31NO7
• Molecular Mass: 397.46264
• Monoisotopic Mass: 397.21005234
• SMILES: c1(cccc(c1)[C@@H]([C@H](CN(C)C)C)CC)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC[C@@H](c1cccc(c1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)[C@H](CN(C)C)C
• InChI: InChI=1S/C20H31NO7/c1-5-14(11(2)10-21(3)4)12-7-6-8-13(9-12)27-20-17(24)15(22)16(23)18(28-20)19(25)26/h6-9,11,14-18,20,22-24H,5,10H2,1-4H3,(H,25,26)/t11-,14+,15-,16-,17+,18-,20+/m0/s1
• InChIKey: CTYJDHSTNLOUMT-PJOQTPGLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 3-[(1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenyl β-D-Glucopyranosiduronic Acid; Tapentadol O-β-D-Glucuronide

Database IDs

• CAS Number: 1300037-86-8
• PubChem SID: 164233986
• PubChem CID: 71752323

CALCULATED PROPERTIES

• Acid pKa: 2.9902072
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.2388824
• LogD (pH = 7.4): -1.2391925
• Log P: -1.2381607
• Molar Refractivity: 101.5706 cm^3
• Polarizability: 40.640255 Å^3
• Polar Surface Area: 119.69 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T007210

A metabolite of Tapentadol (T007200).

REFERENCES

• Terlinden, R., et al.: Eur. J. Drug Metab. Pharmacokinet., 32, 163 (2007)
• Tzschentke, T., et al.: J. Pharmacol. Exp. Ther., 323, 256 (2007)
• Wade, W., et al.: Clin. Ther., 31, 2804 (2007)