ceftiolene   Click here for help

GtoPdb Ligand ID: 10784

Synonyms: 42980RP | cefatiolene | RP 42,980 | RP 42980 | RP-42980 | RP42980
Compound class: Synthetic organic
Comment: Ceftiolene is a semisynthetic, broad-spectrum, third-generation cephalosporin antibacterial [1].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 11
Topological polar surface area 310.87
Molecular weight 594.04
XLogP -2.12
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES O=CCn1c(S/C=C/C2=C(C(=O)O)N3[C@H](SC2)[C@@H](C3=O)NC(=O)/C(=N\OC)/c2csc(n2)N)n[nH]c(=O)c1=O
Isomeric SMILES O=CCn1c(S/C=C/C2=C(C(=O)O)N3[C@H](SC2)[C@@H](C3=O)NC(=O)/C(=N\OC)/c2csc(n2)N)n[nH]c(=O)c1=O
InChI InChI=1S/C20H18N8O8S3/c1-36-26-10(9-7-39-19(21)22-9)13(30)23-11-15(32)28-12(18(34)35)8(6-38-17(11)28)2-5-37-20-25-24-14(31)16(33)27(20)3-4-29/h2,4-5,7,11,17H,3,6H2,1H3,(H2,21,22)(H,23,30)(H,24,31)(H,34,35)/b5-2+,26-10-/t11-,17-/m1/s1
InChI Key WJXAHFZIHLTPFR-JLRJEBFFSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(E)-2-[[5,6-dioxo-4-(2-oxoethyl)-1H-1,2,4-triazin-3-yl]sulfanyl]ethenyl]-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
5291 ceftiolene
Synonyms Click here for help
42980RP | cefatiolene | RP 42,980 | RP 42980 | RP-42980 | RP42980
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefatiolene
Other databases
CAS Registry No. 77360-52-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL2106102
GtoPdb PubChem SID 405560225
PubChem CID 6537430
Search Google for chemical match using the InChIKey WJXAHFZIHLTPFR-JLRJEBFFSA-N
Search Google for chemicals with the same backbone WJXAHFZIHLTPFR
Search PubMed clinical trials ceftiolene
Search PubMed titles ceftiolene
Search PubMed titles/abstracts ceftiolene
UniChem Compound Search for chemical match using the InChIKey WJXAHFZIHLTPFR-JLRJEBFFSA-N
UniChem Connectivity Search for chemical match using the InChIKey WJXAHFZIHLTPFR-JLRJEBFFSA-N