(6R,7R)-3-[(acetyloxy)methyl]-7-[(5R)-5-amino-5-carboxypentanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 3003
• Molecular Formular: C16H21N3O8S
• Molecular Mass: 415.41824
• Monoisotopic Mass: 415.10493565
• SMILES: O=C1N2C(=C(CS[C@@H]2[C@@H]1NC(=O)CCC[C@H](C(=O)O)N)COC(=O)C)C(=O)O
• 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
• InChI: InChI=1S/C16H21N3O8S/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)/t9-,11-,14-/m1/s1
• InChIKey: HOKIDJSKDBPKTQ-GLXFQSAKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-3-[(acetyloxy)methyl]-7-[(5R)-5-amino-5-carboxypentanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cephalosporin C
• Synonyms: Cephalosporin C; 7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid

Database IDs

• CAS Number: 61-24-5
• PubChem SID: 160966450; 46505733
• PubChem CID: 65536; 46936637
• CHEBI ID: 15776
• CHEMBL: 482858
• Chemspider ID: 58980
• Wikipedia Title: Cephalosporin_C

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8381321
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -6.068119
• LogD (pH = 7.4): -7.573742
• Log P: -4.357381
• Molar Refractivity: 95.4272 cm^3
• Polarizability: 37.63273 Å^3
• Polar Surface Area: 176.33 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.46
• LOG S: -3.34
• Solubility (Water): 2.09e-01 g/l

DETAILS

DrugBank - DB03313

Drug information: experimental