cefazolin   Click here for help

GtoPdb Ligand ID: 10935

Synonyms: Ancef® | cephazolin | CEZ | Kefzol® | SK&F-41558
Compound class: Synthetic organic
Comment: Cefazolin is a β-lactam and first-generation cephalosporin antibiotic.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 11
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 234.93
Molecular weight 454.03
XLogP 0.28
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnc(s1)C)Cn1cnnn1
Isomeric SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnc(s1)C)Cn1cnnn1
InChI InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
InChI Key MLYYVTUWGNIJIB-BXKDBHETSA-N
References
1. Nudelman A, Karoly H, Braun F, Böhme EH, Erickson RC. (1978)
Semisynthetic cephalosporins. Synthesis and structure-activity relationships of 7-(1-pyrryl)- and 7-(1-indolyl)acetamidocephalosporin derivatives.
J Med Chem, 21 (9): 962-4. [PMID:722761]