(2S,3S,4S,5R,6S)-6-[(4-{ethyl[1-(4-hydroxyphenyl)propan-2-yl]amino}butanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 166475
• Molecular Formular: C21H31NO9
• Molecular Mass: 441.47214
• Monoisotopic Mass: 441.19988158
• SMILES: C(CCN(C(Cc1ccc(cc1)O)C)CC)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CCN(C(Cc1ccc(cc1)O)C)CCCC(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H31NO9/c1-3-22(12(2)11-13-6-8-14(23)9-7-13)10-4-5-15(24)30-21-18(27)16(25)17(26)19(31-21)20(28)29/h6-9,12,16-19,21,23,25-27H,3-5,10-11H2,1-2H3,(H,28,29)/t12?,16-,17-,18+,19-,21+/m0/s1
• InChIKey: XECNCQZXJCJOOB-ATVZYYHQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(4-{ethyl[1-(4-hydroxyphenyl)propan-2-yl]amino}butanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(4-{ethyl[1-(4-hydroxyphenyl)propan-2-yl]amino}butanoyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-[Ethyl[2-(4-hydroxyphenyl)-1-methylethyl]amino]butanoic Acid β-D-Glucuronide; O-Desmethyl Mebeverine Acid Acyl-β-D-Glucuronide

Database IDs

• PubChem SID: 162260608
• PubChem CID: 71315749

CALCULATED PROPERTIES

• Acid pKa: 3.0399609
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -2.003104
• LogD (pH = 7.4): -2.0047514
• Log P: -2.002331
• Molar Refractivity: 108.3416 cm^3
• Polarizability: 43.266003 Å^3
• Polar Surface Area: 156.99 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D291880

A metabolite of Mebeverine (M202490), an antispasmodic.