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

• ChemBase ID: 3573
• Molecular Formular: C14H19N3O6S
• Molecular Mass: 357.38216
• Monoisotopic Mass: 357.09945634
• SMILES: CC1=C(N2[C@@H](SC1)[C@H](NC(=O)CCC[C@H](N)C(=O)O)C2=O)C(=O)O
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@H]1SCC(=C2C(=O)O)C)CCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C14H19N3O6S/c1-6-5-24-12-9(11(19)17(12)10(6)14(22)23)16-8(18)4-2-3-7(15)13(20)21/h7,9,12H,2-5,15H2,1H3,(H,16,18)(H,20,21)(H,22,23)/t7-,9+,12-/m0/s1
• InChIKey: NNQIJOYQWYKBOW-VMAXQDLPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6S,7R)-7-[(5S)-5-amino-5-carboxypentanamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: @deacetoxycephalosporin-C
• Synonyms: Deacetoxycephalosporin-C

Database IDs

• PubChem SID: 46509194; 160967011
• PubChem CID: 46936837

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8398587
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -5.1012597
• LogD (pH = 7.4): -6.677094
• Log P: -3.4991133
• Molar Refractivity: 84.501 cm^3
• Polarizability: 33.082226 Å^3
• Polar Surface Area: 150.03 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.34
• LOG S: -2.15
• Solubility (Water): 2.51e+00 g/l

DETAILS

DrugBank - DB03938

Drug information: experimental