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CHEBI:100147 - nalidixic acid

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ChEBI Name nalidixic acid
ChEBI ID CHEBI:100147
Definition A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7456
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Formula C12H12N2O3
Net Charge 0
Average Mass 232.23530
Monoisotopic Mass 232.085
InChI InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)
InChIKey MHWLWQUZZRMNGJ-UHFFFAOYSA-N
SMILES CCn1cc(C(O)=O)c(=O)c2ccc(C)nc12
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): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via quinolone antibiotic )
(via heterocyclic antibiotic )
DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
antibacterial drug
A drug used to treat or prevent bacterial infections.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nalidixic acid (CHEBI:100147) has role antibacterial drug (CHEBI:36047)
nalidixic acid (CHEBI:100147) has role antimicrobial agent (CHEBI:33281)
nalidixic acid (CHEBI:100147) has role DNA synthesis inhibitor (CHEBI:59517)
nalidixic acid (CHEBI:100147) is a 1,8-naphthyridine derivative (CHEBI:73537)
nalidixic acid (CHEBI:100147) is a monocarboxylic acid (CHEBI:25384)
nalidixic acid (CHEBI:100147) is a quinolone antibiotic (CHEBI:86324)
nalidixic acid (CHEBI:100147) is conjugate acid of nalidixic acid anion (CHEBI:62070)
Incoming nalidixic acid anion (CHEBI:62070) is conjugate base of nalidixic acid (CHEBI:100147)
IUPAC Name
1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
INNs Sources
acide nalidixique ChemIDplus
acido nalidixico ChemIDplus
acidum nalidixicum ChemIDplus
nalidixic acid ChemIDplus
Synonyms Sources
1,4-dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid ChemIDplus
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeure ChemIDplus
1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid ChemIDplus
1-ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acid ChemIDplus
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ChEMBL
3-carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one ChemIDplus
Nalidixic acid KEGG COMPOUND
NALIDIXIC ACID ChEMBL
Database Links Databases
BE612258 Patent
C05079 KEGG COMPOUND
D00183 KEGG DRUG
DB00779 DrugBank
LSM-5590 LINCS
Nalidixic_Acid Wikipedia
NIX PDBeChem
US3590036 Patent
View more database links
Registry Numbers Types Sources
389-08-2 CAS Registry Number KEGG COMPOUND
389-08-2 CAS Registry Number ChemIDplus
750515 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11321869 PubMed citation Europe PMC
12002106 PubMed citation Europe PMC
12399485 PubMed citation Europe PMC
12702698 PubMed citation Europe PMC
14107587 PubMed citation Europe PMC
16107187 PubMed citation Europe PMC
16423473 PubMed citation Europe PMC
16667857 PubMed citation Europe PMC
16803589 PubMed citation Europe PMC
17132068 PubMed citation Europe PMC
17631104 PubMed citation Europe PMC
18788798 PubMed citation Europe PMC
19071706 PubMed citation Europe PMC
Last Modified
25 February 2016
General Comment
2011-05-23 An orally administered antibacterial, it is used in the treatment of lower urinary-tract infections due to Gram-negative bacteria, including the majority of E. coli, Enterobacter, Klebsiella, and Proteus species.