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cefatrizine   Click here for help

GtoPdb Ligand ID: 12204

Synonyms: BL-S640
Compound class: Synthetic organic
Comment: Cefatrizine is a semisynthetic first generation cephalosporin belonging to the β-lactam class of antibacterial compounds.
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 5
Rotatable bonds 8
Topological polar surface area 225.13
Molecular weight 462.08
XLogP -1.55
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 O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1n[nH]nc1
Isomeric SMILES C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](c1ccc(cc1)O)N)C(=O)O)CSc1n[nH]nc1
InChI InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12-,13-,17-/m1/s1
InChI Key UOCJDOLVGGIYIQ-PBFPGSCMSA-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-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(2H-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
3839 cefatrizine
Synonyms Click here for help
BL-S640
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefatrizine
Other databases
CAS Registry No. 51627-14-6 (source: Scifinder)
ChEBI CHEBI:131730
ChEMBL Ligand CHEMBL1095284
DrugBank Ligand DB13266
DrugCentral Ligand 529
GtoPdb PubChem SID 472319324
PubChem CID 6410758
Search Google for chemical match using the InChIKey UOCJDOLVGGIYIQ-PBFPGSCMSA-N
Search Google for chemicals with the same backbone UOCJDOLVGGIYIQ
Search PubMed clinical trials cefatrizine
Search PubMed titles cefatrizine
Search PubMed titles/abstracts cefatrizine
UniChem Compound Search for chemical match using the InChIKey UOCJDOLVGGIYIQ-PBFPGSCMSA-N
UniChem Connectivity Search for chemical match using the InChIKey UOCJDOLVGGIYIQ-PBFPGSCMSA-N