(2R)-1-[(2S)-3-{[(2S)-3-[(2R)-2-carboxypyrrolidin-1-yl]-2-methyl-3-oxopropyl]disulfanyl}-2-methylpropanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 163609
• Molecular Formular: C18H28N2O6S2
• Molecular Mass: 432.55472
• Monoisotopic Mass: 432.13887863
• SMILES: N1(C(=O)[C@@H](CSSC[C@H](C(=O)N2[C@H](CCC2)C(=O)O)C)C)[C@H](CCC1)C(=O)O
• Canonical SMILES: OC(=O)[C@H]1CCCN1C(=O)[C@@H](CSSC[C@H](C(=O)N1CCC[C@@H]1C(=O)O)C)C
• InChI: InChI=1S/C18H28N2O6S2/c1-11(15(21)19-7-3-5-13(19)17(23)24)9-27-28-10-12(2)16(22)20-8-4-6-14(20)18(25)26/h11-14H,3-10H2,1-2H3,(H,23,24)(H,25,26)/t11-,12-,13-,14-/m1/s1
• InChIKey: ZWKRXBCJAUKDCI-AAVRWANBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-[(2S)-3-{[(2S)-3-[(2R)-2-carboxypyrrolidin-1-yl]-2-methyl-3-oxopropyl]disulfanyl}-2-methylpropanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2R)-1-[(2S)-3-{[(2S)-3-[(2R)-2-carboxypyrrolidin-1-yl]-2-methyl-3-oxopropyl]disulfanyl}-2-methylpropanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: 1,1'-[Dithiobis[(2S)-2-methyl-1-oxo-3,1-propanediyl]]bis-L-proline CAPTOPRDS; SQ 14551; Captopril Imp. A (BP); Captopril Disulfide

Database IDs

• CAS Number: 64806-05-9
• PubChem SID: 162257744
• PubChem CID: 9802869

CALCULATED PROPERTIES

• Acid pKa: 3.4659956
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.1812599
• LogD (pH = 7.4): -5.267579
• Log P: 1.286865
• Molar Refractivity: 107.7816 cm^3
• Polarizability: 42.187477 Å^3
• Polar Surface Area: 115.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 213-217°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C175760

A metabolite of Captopril. A new antihypertensive agent.

REFERENCES

• Sprague, P., et al.: Perspect. Drug Discovery Des., 3, 21 (1995)
• Cushman, D., et al.: Nat. Med., 5, 1110 (1995)
• Jacoby, E., et al.: Drug News Perspect., 16, 93 (1995)
• Lengauer, T., et al.: Drug Discovery Today, 9, 27 (1995)