(2S,3S,4S,5R,6S)-6-[(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174693
• Molecular Formular: C31H38N2O13
• Molecular Mass: 646.63902
• Monoisotopic Mass: 646.23738929
• SMILES: c1(c(cc2c(c1)C[C@H](N(C2)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)O)C)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)OC)OC
• Canonical SMILES: COc1cc2CN([C@@H](Cc2cc1OC)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C(=O)[C@@H](N[C@H](C(=O)O)CCc1ccccc1)C
• InChI: InChI=1S/C31H38N2O13/c1-15(32-19(28(38)39)10-9-16-7-5-4-6-8-16)27(37)33-14-18-13-22(44-3)21(43-2)12-17(18)11-20(33)30(42)46-31-25(36)23(34)24(35)26(45-31)29(40)41/h4-8,12-13,15,19-20,23-26,31-32,34-36H,9-11,14H2,1-3H3,(H,38,39)(H,40,41)/t15-,19-,20-,23-,24-,25+,26-,31-/m0/s1
• InChIKey: GRZLEQLIJFMAST-OWQQGPOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(3S)-2-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-3-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-[2-(1-Carboxy-3-phenyl-propylamino)propionyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylate Acid β-D-Glucopyranuronic Acid; Moexiprilat Acyl-β-D-glucuronide, >65%

Database IDs

• CAS Number: 1260613-88-4
• PubChem SID: 164230603
• PubChem CID: 71750768

CALCULATED PROPERTIES

• Acid pKa: 2.7463498
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -3.7502532
• LogD (pH = 7.4): -5.172329
• Log P: -1.889229
• Molar Refractivity: 155.6631 cm^3
• Polarizability: 62.149033 Å^3
• Polar Surface Area: 221.62 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M485365

A glucuronide metabolite of Moexiprilat (M485360).