(2S)-2-[(3S)-3-(4-aminobutyl)-1,4-dioxo-octahydropyrrolo[1,2-a]piperazin-2-yl]-4-phenylbutanoic acid

• ChemBase ID: 172348
• Molecular Formular: C21H29N3O4
• Molecular Mass: 387.47266
• Monoisotopic Mass: 387.21580642
• SMILES: c1ccc(cc1)CC[C@H](N1[C@H](C(=O)N2C(C1=O)CCC2)CCCCN)C(=O)O
• Canonical SMILES: NCCCC[C@@H]1N([C@H](C(=O)O)CCc2ccccc2)C(=O)C2N(C1=O)CCC2
• InChI: InChI=1S/C21H29N3O4/c22-13-5-4-9-17-19(25)23-14-6-10-16(23)20(26)24(17)18(21(27)28)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18H,4-6,9-14,22H2,(H,27,28)/t16?,17-,18-/m0/s1
• InChIKey: FUEMHWCBWYXAOU-FQECFTEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(3S)-3-(4-aminobutyl)-1,4-dioxo-octahydropyrrolo[1,2-a]piperazin-2-yl]-4-phenylbutanoic acid
• IUPAC Traditional name: (2S)-2-[(3S)-3-(4-aminobutyl)-1,4-dioxo-tetrahydro-3H-pyrrolo[1,2-a]piperazin-2-yl]-4-phenylbutanoic acid
• Synonyms: (2S)-2-[(3S,8aRS)-3-(4-Aminobutyl)-1,4-dioxohexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl]-4-phenylbutanoic Acid; Lisinopril (8R,S)-Diketopiperazine (Mixture of Diastereomers)

Database IDs

• CAS Number: 1092813-99-4
• PubChem SID: 164228258
• PubChem CID: 71749823

CALCULATED PROPERTIES

• Acid pKa: 3.7910721
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.8304864
• LogD (pH = 7.4): -0.8242398
• Log P: -0.82398736
• Molar Refractivity: 104.2913 cm^3
• Polarizability: 40.971405 Å^3
• Polar Surface Area: 103.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 167-172°C

Safety Information

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

DETAILS

Toronto Research Chemicals - L468990

Lisinopril (L468985) impurity.

REFERENCES

• Drummer, O., et al.: Arzneim.-Forsch. Drug Res., 38, 647 (1988)
• Simpson, K., et al.: Drugs, 59, 1149 (1988)