cefazaflur   Click here for help

GtoPdb Ligand ID: 10770

Synonyms: SK&F 59962
Compound class: Synthetic organic
Comment: Cefazaflur (SK&F 59962) is a semisynthetic first generation cephalosporin antibacterial [1]. It did not progress beyond preclinical development. Cefazaflur binds to and inactivates penicillin-binding proteins (PBPs) and thereby disrupts normal bacterial cell wall assembly.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 206.21
Molecular weight 470.01
XLogP 1.17
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)CSC(F)(F)F
Isomeric SMILES O=C(N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)CSC(F)(F)F
InChI InChI=1S/C13H13F3N6O4S3/c1-21-12(18-19-20-21)28-3-5-2-27-10-7(9(24)22(10)8(5)11(25)26)17-6(23)4-29-13(14,15)16/h7,10H,2-4H2,1H3,(H,17,23)(H,25,26)/t7-,10-/m1/s1
InChI Key HGXLJRWXCXSEJO-GMSGAONNSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(6R,7R)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-7-[[2-(trifluoromethylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
4099 cefazaflur
Synonyms Click here for help
SK&F 59962
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1039
Other databases
CAS Registry No. 58665-96-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL2110623
GtoPdb PubChem SID 405560211
PubChem CID 40240
Search Google for chemical match using the InChIKey HGXLJRWXCXSEJO-GMSGAONNSA-N
Search Google for chemicals with the same backbone HGXLJRWXCXSEJO
Search PubMed clinical trials cefazaflur
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Search PubMed titles/abstracts cefazaflur
UniChem Compound Search for chemical match using the InChIKey HGXLJRWXCXSEJO-GMSGAONNSA-N
UniChem Connectivity Search for chemical match using the InChIKey HGXLJRWXCXSEJO-GMSGAONNSA-N