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

• ChemBase ID: 161662
• Molecular Formular: C29H37N3O7
• Molecular Mass: 539.61998
• Monoisotopic Mass: 539.26315054
• SMILES: c1ccccc1CC[C@@H](N[C@H](C(=O)N1[C@H](CCC1)C(=O)O)CCCCNC(=O)OCc1ccccc1)C(=O)O
• Canonical SMILES: O=C(OCc1ccccc1)NCCCC[C@@H](C(=O)N1CCC[C@@H]1C(=O)O)N[C@@H](C(=O)O)CCc1ccccc1
• InChI: InChI=1S/C29H37N3O7/c33-26(32-19-9-15-25(32)28(36)37)23(31-24(27(34)35)17-16-21-10-3-1-4-11-21)14-7-8-18-30-29(38)39-20-22-12-5-2-6-13-22/h1-6,10-13,23-25,31H,7-9,14-20H2,(H,30,38)(H,34,35)(H,36,37)/t23-,24+,25+/m0/s1
• InChIKey: WIRGFGHUACTNCM-ISJGIBHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-[(2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2R)-1-[(2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(1R)-1-carboxy-3-phenylpropyl]amino}hexanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: (S)-1-[N2-(1-Carboxy-3-phenylpropyl)-N-benzyloxycarbonyl-L-lysyl]-L-proline; N-Benzyloxycarbonyl (S)-Lisinopril

Database IDs

• PubChem SID: 162255797
• PubChem CID: 71313865

CALCULATED PROPERTIES

• Acid pKa: 3.2328968
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.15899774
• LogD (pH = 7.4): -1.908104
• Log P: 1.0065776
• Molar Refractivity: 143.0491 cm^3
• Polarizability: 56.20075 Å^3
• Polar Surface Area: 145.27 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B285755

Protected Lisinopril.