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

• ChemBase ID: 172346
• Molecular Formular: C21H31N3O5
• Molecular Mass: 405.48794
• Monoisotopic Mass: 405.22637111
• SMILES: c1ccccc1CC[C@@H](N[C@H](C(=O)N1[C@H](CCC1)C(=O)O)CCCCN)C(=O)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@@H]1C(=O)O)N[C@@H](C(=O)O)CCc1ccccc1
• InChI: InChI=1S/C21H31N3O5/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: RLAWWYSOJDYHDC-RCCFBDPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-[(2S)-6-amino-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2R)-1-[(2S)-6-amino-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: (S)-1-[N2-(1-Carboxy-3-phenylpropyl)-L-lysyl]-L-proline, Dihydrate, MK-521, Acerbon, Alapril, Carace, Coric, Novatec, Prinil, Prinivil, Tensopril, Vivatec, Zestril; (S)-Lisinopril

Database IDs

• CAS Number: 83915-83-7
• PubChem SID: 164228256
• PubChem CID: 40468044

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: 42.540714 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 Solid
• Melting Point: 175-177°C

Safety Information

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

DETAILS

Toronto Research Chemicals - L468985

An orally active angiotensin-converting enzyme (ACE) inhibitor. S,S,S-Isomer of Lisinopril.

REFERENCES

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