sodium (2S,3S,4S,5R,6S)-6-({[1-(2,6-dimethylphenoxy)propan-2-yl]carbamoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 174609
• Molecular Formular: C18H24NNaO9
• Molecular Mass: 421.37423
• Monoisotopic Mass: 421.13487563
• SMILES: c1(cccc(c1OCC(NC(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])C)C)C.[Na+]
• Canonical SMILES: CC(NC(=O)O[C@@H]1O[C@@H](C(=O)[O-])[C@H]([C@@H]([C@@H]1O)O)O)COc1c(C)cccc1C.[Na+]
• InChI: InChI=1S/C18H25NO9.Na/c1-8-5-4-6-9(2)14(8)26-7-10(3)19-18(25)28-17-13(22)11(20)12(21)15(27-17)16(23)24;/h4-6,10-13,15,17,20-22H,7H2,1-3H3,(H,19,25)(H,23,24);/q;+1/p-1/t10?,11-,12-,13+,15-,17-;/m0./s1
• InChIKey: HEJJSRPFAUQEMM-BCTACURGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-6-({[1-(2,6-dimethylphenoxy)propan-2-yl]carbamoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-6-({[1-(2,6-dimethylphenoxy)propan-2-yl]carbamoyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 1-[N-[2-(2,6-Dimethylphenoxy)-1-methylethyl]carbamate] β-D-Glucopyranuronic Acid Sodium Salt; Mexiletine N-Carbonyloxy β-D-Glucuronide Sodium Salt

Database IDs

• CAS Number: 915202-34-5
• PubChem SID: 164230519
• PubChem CID: 71750727

CALCULATED PROPERTIES

• Acid pKa: 3.3135798
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.3635017
• LogD (pH = 7.4): -2.6167374
• Log P: 0.80645865
• Molar Refractivity: 104.4062 cm^3
• Polarizability: 37.318752 Å^3
• Polar Surface Area: 157.61 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M340810

A Mexiletine (M340800) metabolite on skeletal muscle sodium.

REFERENCES

• Vandamme, N., et al.: J. Cardiovasc. Pharmacol., 21, 77 (1993)
• Senda, C., et al.: Xenobiotica, 33, 871 (1993)
• Yarov-Yarovoy, V., et al.: J. Biol. Chem., 277, 35393 (1993)