nalidixic acid (CHEBI:100147)

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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. 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:7456

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Formula

C12H12N2O3

Net Charge

Average Mass

232.23530

Monoisotopic Mass

232.08479

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.

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

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

Last Modified

19 June 2017