3-[(2S,4S)-4-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]disulfanyl}pyrrolidine-2-amido]benzoic acid

• ChemBase ID: 172786
• Molecular Formular: C24H26N4O6S2
• Molecular Mass: 530.61644
• Monoisotopic Mass: 530.12937657
• SMILES: c1c(cc(cc1)NC(=O)[C@@H]1C[C@@H](CN1)SS[C@@H]1CN[C@@H](C1)C(=O)Nc1cc(ccc1)C(=O)O)C(=O)O
• Canonical SMILES: O=C([C@H]1NC[C@H](C1)SS[C@@H]1CN[C@@H](C1)C(=O)Nc1cccc(c1)C(=O)O)Nc1cccc(c1)C(=O)O
• InChI: InChI=1S/C24H26N4O6S2/c29-21(27-15-5-1-3-13(7-15)23(31)32)19-9-17(11-25-19)35-36-18-10-20(26-12-18)22(30)28-16-6-2-4-14(8-16)24(33)34/h1-8,17-20,25-26H,9-12H2,(H,27,29)(H,28,30)(H,31,32)(H,33,34)/t17-,18-,19-,20-/m0/s1
• InChIKey: OUYXUDFSSQPGIH-MUGJNUQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S,4S)-4-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]disulfanyl}pyrrolidine-2-amido]benzoic acid
• IUPAC Traditional name: 3-[(2S,4S)-4-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]disulfanyl}pyrrolidine-2-amido]benzoic acid
• Synonyms: 3,3'-[Dithiobis[(2S,4S)-4,2-pyrrolidinediylcarbonylimino]]bisbenzoic Acid Dihydrochloride; (2S)-cis-3-[[(4-Mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic Acid Disulfide Dihydrochloride

Database IDs

• CAS Number: 444057-64-1
• PubChem SID: 164228696
• PubChem CID: 71750016

CALCULATED PROPERTIES

• Acid pKa: 3.5958188
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.20447
• LogD (pH = 7.4): -3.2205024
• Log P: -3.1933193
• Molar Refractivity: 140.4552 cm^3
• Polarizability: 53.22321 Å^3
• Polar Surface Area: 156.86 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M257090

(2S)-cis-3-[[(4-Mercapto-2-pyrrolidinyl)carbonyl]amino]benzoic Acid Disulfide is an impurity of Ertapenem (E635000).

REFERENCES

• Chu, D; J Med Chem 1996, 39, 3853,,,Sundelof, J; Antimicrob Agents Chemother 1997, 1743,,Sader, H; Drugs 2001, 61, 553,,