zinc(2+) ion (6R,7R)-3-[(acetyloxy)methyl]-7-[(5R)-5-amino-5-carboxylatopentanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

• ChemBase ID: 163981
• Molecular Formular: C16H19N3O8SZn
• Molecular Mass: 478.78236
• Monoisotopic Mass: 477.01842758
• SMILES: [C@H]1(C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])COC(=O)C)NC(=O)CCC[C@H](C(=O)[O-])N.[Zn+2]
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)[O-])COC(=O)C)CCC[C@H](C(=O)[O-])N.[Zn+2]
• InChI: InChI=1S/C16H21N3O8S.Zn/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24;/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26);/q;+2/p-2/t9-,11-,14-;/m1./s1
• InChIKey: TVMXJQZBKOMFQK-OOARYINLSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: zinc(2+) ion (6R,7R)-3-[(acetyloxy)methyl]-7-[(5R)-5-amino-5-carboxylatopentanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• IUPAC Traditional name: zinc(2+) ion (6R,7R)-3-[(acetyloxy)methyl]-7-[(5R)-5-amino-5-carboxylatopentanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• Synonyms: (6R,7R)-3-[(Acetyloxy)methyl]-7-[[(5R)-5-amino-5-carboxy-1-oxopentyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Zinc Salt; , [6R-[6α,7β(R*)]]-3-[(Acetyloxy)methyl]-7-[(5-amino-5-carboxy-1-oxopentyl)amino]-8-oxo-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Zinc Salt; Cephalosporin C Zinc Salt

Database IDs

• CAS Number: 59143-60-1
• PubChem SID: 162258116
• PubChem CID: 11957494

CALCULATED PROPERTIES

• Acid pKa: 1.8381321
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -6.068119
• LogD (pH = 7.4): -7.573742
• Log P: -4.357381
• Molar Refractivity: 117.1014 cm^3
• Polarizability: 37.399696 Å^3
• Polar Surface Area: 181.99 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid
• Apperance: White Solid
• Melting Point: 240-242°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C258750

An antibiottic used to study the effect of transpeptidase expression, binding, and inhibition on bacterial cell wall mucopeptide synthesis.

REFERENCES

• Staub, I. et al.: J. Am. Clin. Soc., 130, 13400 (2008)