(2S,3S,4S,5R,6S)-6-[(2R,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 179647
• Molecular Formular: C28H31NO10S2
• Molecular Mass: 605.67644
• Monoisotopic Mass: 605.1389382
• SMILES: c1cccc(c1)C(=O)SC[C@H](C(=O)N1C[C@H](C[C@@H]1C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Sc1ccccc1)C
• Canonical SMILES: O=C([C@H]1C[C@@H](CN1C(=O)[C@@H](CSC(=O)c1ccccc1)C)Sc1ccccc1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C28H31NO10S2/c1-15(14-40-27(37)16-8-4-2-5-9-16)24(33)29-13-18(41-17-10-6-3-7-11-17)12-19(29)26(36)39-28-22(32)20(30)21(31)23(38-28)25(34)35/h2-11,15,18-23,28,30-32H,12-14H2,1H3,(H,34,35)/t15-,18+,19-,20+,21+,22-,23+,28+/m1/s1
• InChIKey: QUARLWGKRRAIPG-RUGCSQBJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2R,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(2R,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Zofenopril Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 164235557
• PubChem CID: 71753028

CALCULATED PROPERTIES

• Acid pKa: 3.1930852
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 0.07694272
• LogD (pH = 7.4): -1.0859181
• Log P: 2.3607423
• Molar Refractivity: 149.1207 cm^3
• Polarizability: 59.327133 Å^3
• Polar Surface Area: 170.9 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - Z587010

A metabolite of Zofenopril.