(2S,3S,4S,5R,6S)-6-{[(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 159766
• Molecular Formular: C28H30N2O10
• Molecular Mass: 554.5452
• Monoisotopic Mass: 554.19004517
• SMILES: [C@@H]1(OC(=O)[C@@H](Oc2nc(cc(n2)C)C)C(c2ccccc2)(c2ccccc2)OC)O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: COC([C@@H](C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)Oc1nc(C)cc(n1)C)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C28H30N2O10/c1-15-14-16(2)30-27(29-15)39-23(25(36)40-26-21(33)19(31)20(32)22(38-26)24(34)35)28(37-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19-23,26,31-33H,1-3H3,(H,34,35)/t19-,20-,21+,22-,23+,26-/m0/s1
• InChIKey: QBHJFBFSJYTXDX-MVTLKLODSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(αS)-α-[(4,6-Dimethyl-2-pyrimidinyl)oxy]-β-methoxy-β-phenylbenzenepropanoate] β-D-Glucopyranuronic Acid; Ambrisentan Acyl β-D-Glucuronide

Database IDs

• CAS Number: 1106685-58-8
• PubChem SID: 162253901
• PubChem CID: 25183667

CALCULATED PROPERTIES

• Acid pKa: 3.030357
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -0.83095235
• LogD (pH = 7.4): -1.6726005
• Log P: 1.2503493
• Molar Refractivity: 136.4725 cm^3
• Polarizability: 54.292927 Å^3
• Polar Surface Area: 177.76 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A575870

A glucuronide metabolite of Ambrisentan (A575860).