cefbuperazone   Click here for help

GtoPdb Ligand ID: 12253

Compound class: Synthetic organic
Comment: Cefbuperazone is a second 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 17
Hydrogen bond donors 4
Rotatable bonds 13
Topological polar surface area 280.09
Molecular weight 627.15
XLogP -1.63
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](C(=O)N[C@]1(OC)C(=O)N2[C@@H]1SCC(=C2C(=O)O)CSc1nnnn1C)[C@@H](O)C
Isomeric SMILES CCN1CCN(C(=O)C1=O)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@]1([C@@H]2N(C1=O)C(=C(CS2)CSc1nnnn1C)C(=O)O)OC
InChI InChI=1S/C22H29N9O9S2/c1-5-29-6-7-30(16(35)15(29)34)20(39)23-12(10(2)32)14(33)24-22(40-4)18(38)31-13(17(36)37)11(8-41-19(22)31)9-42-21-25-26-27-28(21)3/h10,12,19,32H,5-9H2,1-4H3,(H,23,39)(H,24,33)(H,36,37)/t10-,12+,19+,22-/m0/s1
InChI Key SMSRCGPDNDCXFR-CYWZMYCQSA-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,7S)-7-[[(2R,3S)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-3-hydroxybutanoyl]amino]-7-methoxy-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
5216 cefbuperazone
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cefbuperazone
Other databases
CAS Registry No. 76610-84-9 (source: Scifinder)
ChEBI CHEBI:135856
ChEMBL Ligand CHEMBL1908372
DrugBank Ligand DB13638
DrugCentral Ligand 3072
GtoPdb PubChem SID 473153841
PubChem CID 127527
Search Google for chemical match using the InChIKey SMSRCGPDNDCXFR-CYWZMYCQSA-N
Search Google for chemicals with the same backbone SMSRCGPDNDCXFR
Search PubMed clinical trials cefbuperazone
Search PubMed titles cefbuperazone
Search PubMed titles/abstracts cefbuperazone
UniChem Compound Search for chemical match using the InChIKey SMSRCGPDNDCXFR-CYWZMYCQSA-N
UniChem Connectivity Search for chemical match using the InChIKey SMSRCGPDNDCXFR-CYWZMYCQSA-N