(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 159914
• Molecular Formular: C7H8N2O3S
• Molecular Mass: 200.21502
• Monoisotopic Mass: 200.02556313
• SMILES: C1(=O)[C@H]([C@@H]2N1C(=CCS2)C(=O)O)N
• Canonical SMILES: O=C1[C@@H](N)[C@@H]2N1C(=CCS2)C(=O)O
• InChI: InChI=1S/C7H8N2O3S/c8-4-5(10)9-3(7(11)12)1-2-13-6(4)9/h1,4,6H,2,8H2,(H,11,12)/t4-,6-/m1/s1
• InChIKey: RJFPBECTFIUTHB-INEUFUBQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: (6R-trans)-7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; (6R,7R)-7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid; 7-Amino-3-cephem-4-carboxylic Acid

Database IDs

• CAS Number: 36923-17-8
• PubChem SID: 162254049
• PubChem CID: 11735790

CALCULATED PROPERTIES

• Acid pKa: 3.513962
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.2145362
• LogD (pH = 7.4): -3.4905667
• Log P: -3.2188072
• Molar Refractivity: 47.5302 cm^3
• Polarizability: 18.36193 Å^3
• Polar Surface Area: 83.63 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 215-218°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A603300

Reagent used in the preparation of Cephalosporin antibiotics.

REFERENCES

• Choi, K., et al.: J. Antibiotics, 50, 279 (1997)
• Bharathi, C., et al.: J. Pharm. Biomed. Anal., 43, 733 (1997)