CHEBI:138856 - oxolinic acid

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ChEBI Name oxolinic acid
ChEBI ID CHEBI:138856
Definition A quinolinemonocarboxylic acid having the carboxy group at position 7 as well as oxo and ethyl groups at positions 4 and 1 respectively and a dioxolo ring fused at the 5- and 6-positions. A synthetic antibiotic, it is used in veterinary medicine for the treatment of bacterial infections in cattle, pigs and poultry.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44731, CHEBI:7848
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Formula C13H11NO5
Net Charge 0
Average Mass 261.23010
Monoisotopic Mass 261.064
InChI InChI=1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17)
InChIKey KYGZCKSPAKDVKC-UHFFFAOYSA-N
SMILES CCn1cc(C(O)=O)c(=O)c2cc3OCOc3cc12
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via quinolone antibiotic )
(via heterocyclic antibiotic )
antibacterial drug
A drug used to treat or prevent bacterial infections.
enzyme inhibitor
A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Application(s): antiinfective agent
A substance used in the prophylaxis or therapy of infectious diseases.
antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oxolinic acid (CHEBI:138856) has role antibacterial drug (CHEBI:36047)
oxolinic acid (CHEBI:138856) has role antifungal agent (CHEBI:35718)
oxolinic acid (CHEBI:138856) has role antiinfective agent (CHEBI:35441)
oxolinic acid (CHEBI:138856) has role antimicrobial agent (CHEBI:33281)
oxolinic acid (CHEBI:138856) has role enzyme inhibitor (CHEBI:23924)
oxolinic acid (CHEBI:138856) is a aromatic carboxylic acid (CHEBI:33859)
oxolinic acid (CHEBI:138856) is a organic heterotricyclic compound (CHEBI:26979)
oxolinic acid (CHEBI:138856) is a oxacycle (CHEBI:38104)
oxolinic acid (CHEBI:138856) is a quinolinemonocarboxylic acid (CHEBI:26512)
oxolinic acid (CHEBI:138856) is a quinolone antibiotic (CHEBI:86324)
oxolinic acid (CHEBI:138856) is conjugate acid of oxolinate (CHEBI:59066)
Incoming oxolinate (CHEBI:59066) is conjugate base of oxolinic acid (CHEBI:138856)
IUPAC Name
5-ethyl-8-oxo-5,8-dihydro[1,3]dioxolo[4,5-g]quinoline-7-carboxylic acid
INNs Sources
acide oxolinique ChemIDplus
ácido oxolínico WHO MedNet
acidum oxolinicum ChemIDplus
oxolinic acid KEGG DRUG
oxolinic acid WHO MedNet
Synonyms Sources
1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinolinecarboxylic acid ChemIDplus
1-Ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylic acid ChemIDplus
5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)quinoline-7-carboxylic acid ChemIDplus
OA KEGG DRUG
Manual Xrefs Databases
1879 VSDB
2024 DrugCentral
C11342 KEGG COMPOUND
D02301 KEGG DRUG
LSM-5811 LINCS
OXI PDBeChem
Oxolinic_acid Wikipedia
US3287458 Patent
View more database links
Registry Numbers Types Sources
14698-29-4 CAS Registry Number KEGG COMPOUND
14698-29-4 CAS Registry Number ChemIDplus
2609419 Gmelin Registry Number Gmelin
620635 Beilstein Registry Number Beilstein
620635 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
1245092 PubMed citation Europe PMC
1245092 PubMed citation Europe PMC
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20151406 PubMed citation Europe PMC
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Last Modified
20 June 2018