(2S,3S,4S,5R,6S)-6-(4-{2-[(3-carboxypropyl)(ethyl)amino]propyl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 166476
• Molecular Formular: C21H31NO9
• Molecular Mass: 441.47214
• Monoisotopic Mass: 441.19988158
• SMILES: c1c(ccc(c1)CC(N(CCCC(=O)O)CC)C)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@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C)CCCC(=O)O
• InChI: InChI=1S/C21H31NO9/c1-3-22(10-4-5-15(23)24)12(2)11-13-6-8-14(9-7-13)30-21-18(27)16(25)17(26)19(31-21)20(28)29/h6-9,12,16-19,21,25-27H,3-5,10-11H2,1-2H3,(H,23,24)(H,28,29)/t12?,16-,17-,18+,19-,21+/m0/s1
• InChIKey: HMJRMNFIOHPIHI-ATVZYYHQSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162260609
• PubChem CID: 71315750

CALCULATED PROPERTIES

• Acid pKa: 2.9645388
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.0935502
• LogD (pH = 7.4): -4.856516
• Log P: -2.1572022
• Molar Refractivity: 108.0548 cm^3
• Polarizability: 43.09234 Å^3
• Polar Surface Area: 156.99 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D291885

A metabolite of Mebeverine (M202490), an antispasmodic.