cefaloglycin   Click here for help

GtoPdb Ligand ID: 12193

Synonyms: cephaloglycin | Kafocin®
Approved drug
cefaloglycin is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: Cefaloglycin is a semisynthetic, first generation cephalosporin belonging to the β-lactam class of antibacterial compounds. It is orally absorbed and has activity against both Gram-positive and Gram-negative bacteria [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 164.33
Molecular weight 405.1
XLogP -2.49
No. Lipinski's rules broken 0
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Canonical SMILES CC(=O)OCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)[C@@H](c1ccccc1)N
Isomeric SMILES CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](c2ccccc2)N)SC1)C(=O)O
InChI InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1970))
IUPAC Name Click here for help
(6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
1999 cefaloglycin
Synonyms Click here for help
cephaloglycin | Kafocin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cephaloglycin
Other databases
CAS Registry No. 3577-01-3 (source: Scifinder)
ChEMBL Ligand CHEMBL1200971
DrugBank Ligand DB00689
DrugCentral Ligand 572
GtoPdb PubChem SID 472319315
PubChem CID 19150
Search Google for chemical match using the InChIKey FUBBGQLTSCSAON-PBFPGSCMSA-N
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UniChem Compound Search for chemical match using the InChIKey FUBBGQLTSCSAON-PBFPGSCMSA-N
UniChem Connectivity Search for chemical match using the InChIKey FUBBGQLTSCSAON-PBFPGSCMSA-N