(2S)-1-[(2R)-3-hydroxy-2-methylpropanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 170876
• Molecular Formular: C9H15NO4
• Molecular Mass: 201.2197
• Monoisotopic Mass: 201.10010797
• SMILES: C1C[C@H](N(C1)C(=O)[C@@H](CO)C)C(=O)O
• Canonical SMILES: OC[C@H](C(=O)N1CCC[C@H]1C(=O)O)C
• InChI: InChI=1S/C9H15NO4/c1-6(5-11)8(12)10-4-2-3-7(10)9(13)14/h6-7,11H,2-5H2,1H3,(H,13,14)/t6-,7+/m1/s1
• InChIKey: OTGZFIBHHGZWEJ-RQJHMYQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2R)-3-hydroxy-2-methylpropanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[(2R)-3-hydroxy-2-methylpropanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: 1-[(2R)-3-Hydroxy-2-methyl-1-oxopropyl]-L-proline

Database IDs

• CAS Number: 613256-52-3
• PubChem SID: 164226786
• PubChem CID: 10987292

CALCULATED PROPERTIES

• Acid pKa: 3.8971546
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.1328871
• LogD (pH = 7.4): -3.7395077
• Log P: -0.52444816
• Molar Refractivity: 48.6063 cm^3
• Polarizability: 19.044481 Å^3
• Polar Surface Area: 77.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948120

1-[(2R)-3-Hydroxy-2-methyl-1-oxopropyl]-L-proline is used in the synthesis of the antihypertensive amide Captopril (C175750).

REFERENCES

• Cushman, D., et al.: Biochemistry, 16, 5485 (1977)
• Ondetti, M., et al.: Science, 196, 441 (1977)
• Greenlee, W., et al.: Annu. Rep. Med. Chem., 26, 63 (1977)