(2R)-1-[(2S)-6-amino-2-{[(1R)-1-carboxy-3-(2H5)phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid sodium

• ChemBase ID: 172347
• Molecular Formular: C21H31N3NaO5
• Molecular Mass: 428.47771
• Monoisotopic Mass: 428.21614039
• SMILES: c1ccccc1CC[C@@H](N[C@H](C(=O)N1[C@H](CCC1)C(=O)O)CCCCN)C(=O)O.[Na]
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@@H]1C(=O)O)N[C@@H](C(=O)O)CCc1ccccc1.[Na]
• InChI: InChI=1S/C21H31N3O5.Na/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15;/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29);/t16-,17+,18+;/m0./s1
• InChIKey: YIQJJOKNXHVFQD-QQBJDQAASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-[(2S)-6-amino-2-{[(1R)-1-carboxy-3-(^2H₅)phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid sodium
• IUPAC Traditional name: (2R)-1-[(2S)-6-amino-2-{[(1R)-1-carboxy-3-(^2H₅)phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid sodium
• Synonyms: (S)-1-[N2-(1-Carboxy-3-phenylpropyl)-L-lysyl]-L-proline-d5 Sodium; (S)-Lisinopril-d5 Sodium

Database IDs

• CAS Number: 1356847-28-3
• PubChem SID: 164228257
• PubChem CID: 71749821

CALCULATED PROPERTIES

• Acid pKa: 3.1725657
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.1054642
• LogD (pH = 7.4): -3.1834292
• Log P: -3.1026032
• Molar Refractivity: 107.3691 cm^3
• Polarizability: 42.561996 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Crystalline Powder
• Melting Point: 169-172°C

Safety Information

• Storage Condition: -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - L468987

Labelled Lisinopril, an orally active angiotensin-converting enzyme (ACE) inhibitor.

REFERENCES

• Goa, K.L., et al.: Drugs, 52, 564 (1996)
• Chaturvedi, N., et al.: Lancet, 351, 28 (1998)