disodium (2S,5R,6R)-6-[2-(2-bromophenyl)-2-carboxylatoacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 162787
• Molecular Formular: C17H15BrN2Na2O6S
• Molecular Mass: 501.25934
• Monoisotopic Mass: 499.96295777
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C)NC(=O)C(c1c(cccc1)Br)C(=O)[O-].[Na+].[Na+]
• Canonical SMILES: O=C(C(c1ccccc1Br)C(=O)[O-])N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)[O-])(C)C.[Na+].[Na+]
• InChI: InChI=1S/C17H17BrN2O6S.2Na/c1-17(2)11(16(25)26)20-13(22)10(14(20)27-17)19-12(21)9(15(23)24)7-5-3-4-6-8(7)18;;/h3-6,9-11,14H,1-2H3,(H,19,21)(H,23,24)(H,25,26);;/q;2*+1/p-2/t9?,10-,11+,14-;;/m1../s1
• InChIKey: BGHMDZLUPBPVJI-YCAHSCEMSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2S,5R,6R)-6-[2-(2-bromophenyl)-2-carboxylatoacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: disodium (2S,5R,6R)-6-[2-(2-bromophenyl)-2-carboxylatoacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• Synonyms: [2S-(2α,5α,6β)]-6-[[(2-Bromophenyl)carboxyacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Disodium Salt; 2-Bromo Carbenicillin Disodium Salt

Database IDs

• CAS Number: 59530-63-1
• PubChem SID: 162256922
• PubChem CID: 71314226

CALCULATED PROPERTIES

• Acid pKa: 2.751662
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -3.0749788
• LogD (pH = 7.4): -5.3028946
• Log P: 1.5841094
• Molar Refractivity: 120.1165 cm^3
• Polarizability: 38.531918 Å^3
• Polar Surface Area: 129.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B682200

Carbenicillin analogue, an antibacterial.

REFERENCES

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)