(2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid; 2-methylpropan-2-amine

• ChemBase ID: 153985
• Molecular Formular: C23H43N3O5
• Molecular Mass: 441.60462
• Monoisotopic Mass: 441.32027149
• SMILES: CCC[C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)O.CC(C)(C)N
• Canonical SMILES: CC(N)(C)C.CCC[C@@H](C(=O)OCC)N[C@H](C(=O)N1[C@H]2CCCC[C@H]2C[C@H]1C(=O)O)C
• InChI: InChI=1S/C19H32N2O5.C4H11N/c1-4-8-14(19(25)26-5-2)20-12(3)17(22)21-15-10-7-6-9-13(15)11-16(21)18(23)24;1-4(2,3)5/h12-16,20H,4-11H2,1-3H3,(H,23,24);5H2,1-3H3/t12-,13-,14-,15-,16-;/m0./s1
• InChIKey: IYNMDWMQHSMDDE-MHXJNQAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3aS,7aS)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxopentan-2-yl]amino}propanoyl]-octahydro-1H-indole-2-carboxylic acid; 2-methylpropan-2-amine
• IUPAC Traditional name: erbumine; perindopril
• Synonyms: (2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)butyl]amino]-1-oxopropyl]octahydro-1H-indole-2-carboxylic acid tert-butylamine salt; S-9490; Perindopril erbumine

Database IDs

• CAS Number: 107133-36-8
• MDL Number: MFCD02313824
• PubChem SID: 162248124
• PubChem CID: 441313

CALCULATED PROPERTIES

• Acid pKa: 3.7860548
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.4626669
• LogD (pH = 7.4): -0.8469951
• Log P: 0.63074386
• Molar Refractivity: 95.6928 cm^3
• Polarizability: 38.332016 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: solid

Safety Information

• RTECS: NL5999600
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H32N2O5 · C4H11N

DETAILS

Sigma Aldrich - P0094

Biochem/physiol Actions
Perindopril erbumine is an angiotensin converting enzyme (ACE) inhibitor; antihypertensive; becomes hydrolyzed in vivo to the active diacid metabolite; unlike the other ACE inhibitors, inhibits tumor growth in hepatocellular carcinoma cells due to suppression of VEGF levels; also suppresses angiotensin II production in vitro. Long-term therapy with this agent has a beneficial effect on the cerebral circulation by improving cerebral perfusion reserve in patients with previous minor stroke.