(3R,4R,4aS,5R)-6-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-3,5-dimethyl-1-oxo-1H,3H,4H,4aH,5H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid

• ChemBase ID: 163781
• Molecular Formular: C23H25N3O9S
• Molecular Mass: 519.5243
• Monoisotopic Mass: 519.1311504
• SMILES: N12[C@H]([C@H](C(=C1C(=O)O)S[C@@H]1CN[C@@H](C1)C(=O)Nc1cc(ccc1)C(=O)O)C)[C@H]([C@H](OC2=O)C)C(=O)O
• Canonical SMILES: O=C([C@H]1NC[C@H](C1)SC1=C(C(=O)O)N2[C@H]([C@H]1C)[C@@H](C(=O)O)[C@H](OC2=O)C)Nc1cccc(c1)C(=O)O
• InChI: InChI=1S/C23H25N3O9S/c1-9-16-15(21(30)31)10(2)35-23(34)26(16)17(22(32)33)18(9)36-13-7-14(24-8-13)19(27)25-12-5-3-4-11(6-12)20(28)29/h3-6,9-10,13-16,24H,7-8H2,1-2H3,(H,25,27)(H,28,29)(H,30,31)(H,32,33)/t9-,10-,13+,14+,15+,16-/m1/s1
• InChIKey: GXFHAVHBDSPPAG-FKTXGUMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,4aS,5R)-6-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-3,5-dimethyl-1-oxo-1H,3H,4H,4aH,5H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid
• IUPAC Traditional name: (3R,4R,4aS,5R)-6-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-3,5-dimethyl-1-oxo-3H,4H,4aH,5H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid
• Synonyms: (3S,4S,4aS,5R)-6-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4,4a,5-tetrahydro-3,5-dimethyl-1-oxo-1H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic Acid Hydrochloride (~50%)

Database IDs

• CAS Number: 866186-68-7
• PubChem SID: 162257916
• PubChem CID: 71314550

CALCULATED PROPERTIES

• Acid pKa: 3.1032162
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -5.1243954
• LogD (pH = 7.4): -8.402173
• Log P: -2.2988744
• Molar Refractivity: 127.8101 cm^3
• Polarizability: 48.683556 Å^3
• Polar Surface Area: 182.57 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C179030

(3S,4S,4aS,5R)-6-[[(3S,5S)-5-[[(3-Carboxyphenyl)amino]carbonyl]-3-pyrrolidinyl]thio]-3,4,4a,5-tetrahydro-3,5-dimethyl-1-oxo-1H-pyrrolo[1,2-c][1,3]oxazine-4,7-dicarboxylic acid is an impurity of Ertapenem (E635000).

REFERENCES

• Kahan, J., et al.: J. Antibiot., 32, 1 (1979)
• Kropp, H., et al.: Antimicrob. Agents Chemother., 17, 993 (1979)
• Goldhaber, M., et al.: Science, 266, 1462 (1979)