methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[1-(carbamoyloxy)-3-(2-methoxyphenoxy)propan-2-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 172720
• Molecular Formular: C24H31NO14
• Molecular Mass: 557.50124
• Monoisotopic Mass: 557.17445468
• SMILES: c1(ccccc1OCC(COC(=O)N)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC(COc2ccccc2OC)COC(=O)N)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C24H31NO14/c1-12(26)35-18-19(36-13(2)27)21(37-14(3)28)23(39-20(18)22(29)32-5)38-15(11-34-24(25)30)10-33-17-9-7-6-8-16(17)31-4/h6-9,15,18-21,23H,10-11H2,1-5H3,(H2,25,30)/t15?,18-,19-,20-,21+,23+/m0/s1
• InChIKey: PFGXEGAFNCPPGI-ORPDCHPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[1-(carbamoyloxy)-3-(2-methoxyphenoxy)propan-2-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[1-(carbamoyloxy)-3-(2-methoxyphenoxy)propan-2-yl]oxy}oxane-2-carboxylate
• Synonyms: 2-[(Aminocarbonyl)oxy]-1-[(2-methoxyphenoxy)methyl]ethyl 2,3,4-tri-O-Acetyl-β-D-glucopyranosiduronic Acid Methyl Ester; Methocarbamol 2,3,4-tri-O-Acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 164228630
• PubChem CID: 71749986

CALCULATED PROPERTIES

• Acid pKa: 14.447524
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 0.4637554
• LogD (pH = 7.4): 0.46375543
• Log P: 0.4637554
• Molar Refractivity: 123.5717 cm^3
• Polarizability: 50.885387 Å^3
• Polar Surface Area: 194.44 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - M225965

A protected metabolite of Methocarbamol (M225950).

REFERENCES

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