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cefacetrile   Click here for help

GtoPdb Ligand ID: 12192

Synonyms: Celospor® | cephacetrile
Compound class: Synthetic organic
Comment: Cefacetrile is a first generation cephalosporin belonging to the β-lactam class of antibacterial compounds [2].

cefacetrile is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 7
Topological polar surface area 162.1
Molecular weight 339.05
XLogP -1.48
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(=O)OCC1=C(N2[C@H](SC1)[C@@H](C2=O)NC(=O)CC#N)C(=O)O
Isomeric SMILES CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC#N)SC1)C(=O)O
InChI InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
InChI Key RRYMAQUWDLIUPV-BXKDBHETSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)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
3007 cefacetrile
Synonyms Click here for help
Celospor® | cephacetrile
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cephacetrile
Other databases
CAS Registry No. 10206-21-0 (source: Scifinder)
ChEBI CHEBI:135437
ChEMBL Ligand CHEMBL2110602
DrugBank Ligand DB01414
DrugCentral Ligand 524
GtoPdb PubChem SID 472319314
PubChem CID 91562
Search Google for chemical match using the InChIKey RRYMAQUWDLIUPV-BXKDBHETSA-N
Search Google for chemicals with the same backbone RRYMAQUWDLIUPV
Search PubMed clinical trials cefacetrile
Search PubMed titles cefacetrile
Search PubMed titles/abstracts cefacetrile
UniChem Compound Search for chemical match using the InChIKey RRYMAQUWDLIUPV-BXKDBHETSA-N
UniChem Connectivity Search for chemical match using the InChIKey RRYMAQUWDLIUPV-BXKDBHETSA-N

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Cefacetrile (links to external site)
Cat. No. HY-A0253