(2S,3aS,6aS)-1-[(2S)-2-{[(1R)-1-carboxy-3-(2H5)phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid

• ChemBase ID: 177353
• Molecular Formular: C21H28N2O5
• Molecular Mass: 388.45742
• Monoisotopic Mass: 388.19982201
• SMILES: c1ccccc1CC[C@@H](N[C@H](C(=O)N1[C@@H]2[C@H](C[C@H]1C(=O)O)CCC2)C)C(=O)O
• Canonical SMILES: OC(=O)[C@H](N[C@H](C(=O)N1[C@H]2CCC[C@H]2C[C@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C21H28N2O5/c1-13(22-16(20(25)26)11-10-14-6-3-2-4-7-14)19(24)23-17-9-5-8-15(17)12-18(23)21(27)28/h2-4,6-7,13,15-18,22H,5,8-12H2,1H3,(H,25,26)(H,27,28)/t13-,15-,16+,17-,18-/m0/s1
• InChIKey: KEDYTOTWMPBSLG-JFMONLCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3aS,6aS)-1-[(2S)-2-{[(1R)-1-carboxy-3-(^2H₅)phenylpropyl]amino}propanoyl]-octahydrocyclopenta[b]pyrrole-2-carboxylic acid
• IUPAC Traditional name: (2S,3aS,6aS)-1-[(2S)-2-{[(1R)-1-carboxy-3-(^2H₅)phenylpropyl]amino}propanoyl]-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid
• Synonyms: 2-[N-(R-1-Carboxy-3-phenyl-d5-propyl)-L-alanyl]-(1R,3S,5S)-2-azabicyclo[3.3.0]octane-3-carboxylic Acid; (1R)-Ramiprilat; 1-epi-Ramiprilat-d5

Database IDs

• PubChem SID: 164233263
• PubChem CID: 71751968

CALCULATED PROPERTIES

• Acid pKa: 3.1311913
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.5305548
• LogD (pH = 7.4): -3.1913881
• Log P: -0.18361667
• Molar Refractivity: 101.6691 cm^3
• Polarizability: 40.313736 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - R111013

An epimer of (S)-Ramiprilat-d5.