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CHEBI:48947 - clavulanic acid

ChEBI IDCHEBI:48947
ChEBI Nameclavulanic acid
Stars
DefinitionAntibiotic isolated from Streptomyces clavuligerus. It acts as a suicide inhibitor of bacterial β-lactamase enzymes.
Secondary ChEBI IDsCHEBI:3736, CHEBI:43442
Last Modified22 February 2017
SubmitterKirill Degtyarenko
DownloadsMolfile
FormulaC8H9NO5
Net Charge0
Average Mass199.162
Monoisotopic Mass199.04807
SMILES[H][C@@]12CC(=O)N1[C@@H](C(=O)O)/C(=C/CO)O2
InChIInChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
InChIKeyHZZVJAQRINQKSD-PBFISZAISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces clavuligerus (ncbitaxon:1901) - PubMed (18450406)
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 3.5.2.6 (beta-lactamase) inhibitor  An EC 3.5.2.* (non-peptide cyclic amide C-N hydrolase) inhibitor that interferes with the action of β-lactamase (EC 3.5.2.6).
antibacterial drug  A drug used to treat or prevent bacterial infections.
Applications:
anxiolytic drug  Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
clavulanic acid (CHEBI:48947) has role antibacterial drug (CHEBI:36047)
clavulanic acid (CHEBI:48947) has role anxiolytic drug (CHEBI:35474)
clavulanic acid (CHEBI:48947) has role bacterial metabolite (CHEBI:76969)
clavulanic acid (CHEBI:48947) has role EC 3.5.2.6 (β-lactamase) inhibitor (CHEBI:35625)
clavulanic acid (CHEBI:48947) is a oxapenam (CHEBI:64509)
clavulanic acid (CHEBI:48947) is conjugate acid of clavulanate (CHEBI:487869)
Incoming Relation(s)
clavulanate (CHEBI:487869) is conjugate base of clavulanic acid (CHEBI:48947)
IUPAC Name 
(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
INNs  Source
clavulanic acidChemIDplus
acide clavulaniqueChemIDplus
ácido clavulánicoChemIDplus
acidum clavulanicumChemIDplus
Synonyms  Source
Clavulanic acidKEGG COMPOUND
ClavulanateKEGG COMPOUND
(2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-OXO-4-OXA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACIDPDBeChem
(Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acidChemIDplus
ClavulansäureChemIDplus
antibiotic MM 14151ChemIDplus
Manual XrefsDatabases
C06662KEGG COMPOUND
J01PDBeChem
DE2517316Patent
DB00766DrugBank
Clavulanic_AcidWikipedia
C00018091KNApSAcK
D07711KEGG DRUG
HMDB0014904HMDB
669DrugCentral
1930VSDB
Registry NumbersSources
Beilstein:787059Beilstein
Reaxys:787059Reaxys
CAS:58001-44-8KEGG COMPOUND
CAS:58001-44-8ChemIDplus
CAS:58001-44-8DrugBank
Citations