CHEBI:100147 - nalidixic acid

ChEBI IDCHEBI:100147
ChEBI Namenalidixic acid
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:7456
Last Modified19 June 2017
DownloadsMolfile
FormulaC12H12N2O3
Net Charge0
Average Mass232.239
Monoisotopic Mass232.08479
SMILESCCn1cc(C(=O)O)c(=O)c2ccc(C)nc21
InChIInChI=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)
InChIKeyMHWLWQUZZRMNGJ-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial drug  A drug used to treat or prevent bacterial infections.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antibacterial drug  A drug used to treat or prevent bacterial infections.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
acide nalidixiqueChemIDplus
acido nalidixicoChemIDplus
acidum nalidixicumChemIDplus
nalidixic acidChemIDplus
Synonyms  Source
1,4-dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acidChemIDplus
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeureChemIDplus
1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acidChemIDplus
1-ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acidChemIDplus
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acidChEMBL
3-carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-oneChemIDplus
Manual XrefsDatabases
1875DrugCentral
1880VSDB
BE612258Patent
C05079KEGG COMPOUND
D00183KEGG DRUG
DB00779DrugBank
LSM-5590LINCS
Nalidixic_AcidWikipedia
NIXPDBeChem
US3590036Patent
Registry NumbersSources
Reaxys:750515Reaxys
CAS:389-08-2KEGG COMPOUND
CAS:389-08-2ChemIDplus
Citations