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cefetecol   Click here for help

GtoPdb Ligand ID: 10775

Synonyms: GR-69153 | GR-69153X | GR69153
Compound class: Synthetic organic
Comment: Cefetecol (GR69153) is a broad-spectrum, fourth-generation (catechol-substituted) parenteral cephalosporin antibacterial [1-2]. It was designed to be active against Gram +ve and -ve bacilli that cause enteric infections, but development was terminated.
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 10
Hydrogen bond donors 6
Rotatable bonds 9
Topological polar surface area 278.51
Molecular weight 535.05
XLogP -1.96
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 OC(=O)[C@H](c1ccc(c(c1)O)O)O/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O
Isomeric SMILES OC(=O)[C@H](c1ccc(c(c1)O)O)O/N=C(\c1csc(n1)N)/C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC=C2C(=O)O
InChI InChI=1S/C20H17N5O9S2/c21-20-22-8(6-36-20)12(24-34-14(19(32)33)7-1-2-10(26)11(27)5-7)15(28)23-13-16(29)25-9(18(30)31)3-4-35-17(13)25/h1-3,5-6,13-14,17,26-27H,4H2,(H2,21,22)(H,23,28)(H,30,31)(H,32,33)/b24-12+/t13-,14+,17-/m1/s1
InChI Key ILZCDOYRDFDUPN-UITOYEBDSA-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)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-[(S)-carboxy-(3,4-dihydroxyphenyl)methoxy]iminoacetyl]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
6624 cefetecol
Synonyms Click here for help
GR-69153 | GR-69153X | GR69153
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefetecol (GR69153)
Other databases
CAS Registry No. 117211-03-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL2304034
GtoPdb PubChem SID 405560216
PubChem CID 71719688
Search Google for chemical match using the InChIKey ILZCDOYRDFDUPN-UITOYEBDSA-N
Search Google for chemicals with the same backbone ILZCDOYRDFDUPN
Search PubMed clinical trials cefetecol
Search PubMed titles cefetecol
Search PubMed titles/abstracts cefetecol
UniChem Compound Search for chemical match using the InChIKey ILZCDOYRDFDUPN-UITOYEBDSA-N
UniChem Connectivity Search for chemical match using the InChIKey ILZCDOYRDFDUPN-UITOYEBDSA-N