(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carbonyloxy]oxane-2-carboxylic acid

• ChemBase ID: 179650
• Molecular Formular: C21H27NO9S2
• Molecular Mass: 501.57038
• Monoisotopic Mass: 501.11272345
• SMILES: C1[C@H](C[C@H](N1C(=O)[C@@H](CS)C)C(=O)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)Sc1ccccc1
• Canonical SMILES: SC[C@H](C(=O)N1C[C@H](C[C@H]1C(=O)O[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O)Sc1ccccc1)C
• InChI: InChI=1S/C21H27NO9S2/c1-10(9-32)18(26)22-8-12(33-11-5-3-2-4-6-11)7-13(22)20(29)31-21-16(25)14(23)15(24)17(30-21)19(27)28/h2-6,10,12-17,21,23-25,32H,7-9H2,1H3,(H,27,28)/t10-,12+,13+,14+,15+,16-,17+,21+/m1/s1
• InChIKey: TWZNWURZDPFVQT-GUWOMVTDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carbonyloxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2S,4S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carbonyloxy]oxane-2-carboxylic acid
• Synonyms: Zofenoprilat Acyl-β-D-glucuronide

Database IDs

• PubChem SID: 164235560
• PubChem CID: 71753029

CALCULATED PROPERTIES

• Acid pKa: 3.1930861
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.8178495
• LogD (pH = 7.4): -2.9815106
• Log P: 0.4659604
• Molar Refractivity: 118.9824 cm^3
• Polarizability: 47.849907 Å^3
• Polar Surface Area: 153.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - Z587055

A metabolite of Zofenoprilat.