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flomoxef   Click here for help

GtoPdb Ligand ID: 12251

Synonyms: 6315-S | Flumarin®
Compound class: Synthetic organic
Comment: Flomoxef is a second generation cephalosporin, belonging to the β-lactam class of antibacterial compounds and developed by the Shionogi Research Laboratories (Osaka, Japan) [1].
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 12
Hydrogen bond donors 3
Rotatable bonds 12
Topological polar surface area 219.6
Molecular weight 496.06
XLogP -0.88
No. Lipinski's rules broken 2

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 OCCn1nnnc1SCC1=C(C(=O)O)N2[C@H](OC1)[C@](C2=O)(OC)NC(=O)CSC(F)F
Isomeric SMILES CO[C@@]1([C@@H]2N(C1=O)C(=C(CO2)CSc1nnnn1CCO)C(=O)O)NC(=O)CSC(F)F
InChI InChI=1S/C15H18F2N6O7S2/c1-29-15(18-8(25)6-31-13(16)17)11(28)23-9(10(26)27)7(4-30-12(15)23)5-32-14-19-20-21-22(14)2-3-24/h12-13,24H,2-6H2,1H3,(H,18,25)(H,26,27)/t12-,15+/m1/s1
InChI Key UHRBTBZOWWGKMK-DOMZBBRYSA-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-{2-[(difluoromethyl)sulfanyl]acetamido}-3-({[1-(2-hydroxyethyl)-1H-1,2,3,4-tetrazol-5-yl]sulfanyl}methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5935 flomoxef
Synonyms Click here for help
6315-S | Flumarin®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Flomoxef
Other databases
CAS Registry No. 99665-00-6 (source: Scifinder)
ChEBI CHEBI:135813
ChEMBL Ligand CHEMBL15413
DrugBank Ligand DB11935
DrugCentral Ligand 1179
GtoPdb PubChem SID 473153839
PubChem CID 65864
Search Google for chemical match using the InChIKey UHRBTBZOWWGKMK-DOMZBBRYSA-N
Search Google for chemicals with the same backbone UHRBTBZOWWGKMK
Search PubMed clinical trials flomoxef
Search PubMed titles flomoxef
Search PubMed titles/abstracts flomoxef
UniChem Compound Search for chemical match using the InChIKey UHRBTBZOWWGKMK-DOMZBBRYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UHRBTBZOWWGKMK-DOMZBBRYSA-N