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cefoperazone   Click here for help

GtoPdb Ligand ID: 12025

Synonyms: Cefobid® | T-1551
Approved drug
cefoperazone is an approved drug (FDA (1982))
Compound class: Synthetic organic
Comment: Cefoperazone is a semisynthetic, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds [1].

cefoperazone 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 15
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 270.86
Molecular weight 645.14
XLogP -0.38
No. Lipinski's rules broken 1

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 CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c1ccc(cc1)O)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C
Isomeric SMILES CCN1CCN(C(=O)C1=O)C(=O)N[C@H](c1ccc(cc1)O)C(=O)N[C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSc1nnnn1C)C(=O)O
InChI InChI=1S/C25H27N9O8S2/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41)/t15-,16-,22-/m1/s1
InChI Key GCFBRXLSHGKWDP-XCGNWRKASA-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
Approved drug? Yes. US FDA (1982)
IUPAC Name Click here for help
(6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-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
4742 cefoperazone
Synonyms Click here for help
Cefobid® | T-1551
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefoperazone
Other databases
CAS Registry No. 62893-19-0 (source: Scifinder)
ChEBI CHEBI:3493
ChEMBL Ligand CHEMBL507674
DrugBank Ligand DB01329
DrugCentral Ligand 543
GtoPdb PubChem SID 464244166
PubChem CID 44187
Search Google for chemical match using the InChIKey GCFBRXLSHGKWDP-XCGNWRKASA-N
Search Google for chemicals with the same backbone GCFBRXLSHGKWDP
Search PubMed clinical trials cefoperazone
Search PubMed titles cefoperazone
Search PubMed titles/abstracts cefoperazone
UniChem Compound Search for chemical match using the InChIKey GCFBRXLSHGKWDP-XCGNWRKASA-N
UniChem Connectivity Search for chemical match using the InChIKey GCFBRXLSHGKWDP-XCGNWRKASA-N
Wikipedia Cefoperazone

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MedChemExpress
Cefoperazone (links to external site)
Cat. No. HY-B0210