(2S,3S,4S,5R,6S)-6-{[1-(carbamoyloxy)-3-(2-methoxyphenoxy)(2H5)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172719
• Molecular Formular: C17H23NO11
• Molecular Mass: 417.36462
• Monoisotopic Mass: 417.12711056
• SMILES: c1(ccccc1OCC(COC(=O)N)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)OC
• Canonical SMILES: COc1ccccc1OCC(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)COC(=O)N
• InChI: InChI=1S/C17H23NO11/c1-25-9-4-2-3-5-10(9)26-6-8(7-27-17(18)24)28-16-13(21)11(19)12(20)14(29-16)15(22)23/h2-5,8,11-14,16,19-21H,6-7H2,1H3,(H2,18,24)(H,22,23)/t8?,11-,12-,13+,14-,16+/m0/s1
• InChIKey: AWABFKBRFKCYRC-YKUFYHOPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[1-(carbamoyloxy)-3-(2-methoxyphenoxy)(^2H₅)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[1-(carbamoyloxy)-3-(2-methoxyphenoxy)(^2H₅)propan-2-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[(Aminocarbonyl)oxy]-1-[(2-methoxyphenoxy)methyl]ethyl-d5 β-D-Glucopyranosiduronic Acid; Methocarbamol-d5 Glucuronide; Methocarbamol-d5 β-D-Glucuronide

Database IDs

• PubChem SID: 164228629
• PubChem CID: 71749985

CALCULATED PROPERTIES

• Acid pKa: 2.981611
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.4848213
• LogD (pH = 7.4): -4.4822555
• Log P: -1.0055149
• Molar Refractivity: 91.3481 cm^3
• Polarizability: 37.272156 Å^3
• Polar Surface Area: 187.23 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225962

A labelled metabolite of Methocarbamol (M225950).

REFERENCES

• Thompson, R.M., et al.: Xenobiotica, 5,145 (1975)