(2S,3S,4S,5R,6S)-6-[(2S,4S)-4-cyclohexyl-1-{2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169450
• Molecular Formular: C29H42NO11P
• Molecular Mass: 611.617641
• Monoisotopic Mass: 611.2495478
• SMILES: c1ccccc1CCCCP(=O)(CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O
• Canonical SMILES: O=C([C@@H]1C[C@H](CN1C(=O)CP(=O)(CCCCc1ccccc1)O)C1CCCCC1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C29H42NO11P/c31-22(17-42(38,39)14-8-7-11-18-9-3-1-4-10-18)30-16-20(19-12-5-2-6-13-19)15-21(30)28(37)41-29-25(34)23(32)24(33)26(40-29)27(35)36/h1,3-4,9-10,19-21,23-26,29,32-34H,2,5-8,11-17H2,(H,35,36)(H,38,39)/t20-,21+,23+,24+,25-,26+,29+/m1/s1
• InChIKey: MEKOZVBEQBWEGK-CXOPANLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[(2S,4S)-4-cyclohexyl-1-{2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[(2S,4S)-4-cyclohexyl-1-{2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carbonyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: trans-4-Cyclohexyl-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline β-D-Glucopyranuronosyl Ester; Fosinoprilat Acyl-β-D-Glucuronide

Database IDs

• CAS Number: 113411-09-9
• PubChem SID: 162263582
• PubChem CID: 71316973

CALCULATED PROPERTIES

• Acid pKa: 1.7418263
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.8016622
• LogD (pH = 7.4): -5.093144
• Log P: 0.738
• Molar Refractivity: 148.3282 cm^3
• Polarizability: 59.42193 Å^3
• Polar Surface Area: 191.13 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: N/A

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F727820

A metabolite of Fosinoprilat (F727810).

REFERENCES

• Singhvi, S.M., et al.: Br. J. Clin. Pharmacol., 25, 9 (1988)