Nalidixic acid (CED0001960)

Record Information
Version1.0
Creation Date2016-05-22 03:28:43 UTC
Update Date2026-08-18 16:38:42 UTC
Accession NumberCHEM016357
Identification
Common NameNalidixic acid
ClassSmall Molecule
Description
Nalidixic acid is an organic compound with the formula C12H12N2O3 and an average molecular weight of 232.24 g/mol. Nalidixic acid belongs to the naphthyridines, a subclass of diazanaphthalenes within the organic compounds. It is categorized as an organoheterocyclic compound. The compound is found in or released from 23 recorded sources across several sectors. In healthcare, pharmaceuticals, and veterinary products, it is used as an antibiotic and among quinolone antibacterials. It is associated with food, food processing, and cookware, specifically in food preservation, the processing of meats, and the preparation of vinegar. It is also linked to household cleaning and consumer products, including bleaching agents, pipe accessories, perfumes within detergents and soaps, cigar cigarettes, and non-electric simulated smoking devices. Within electrical and electronic equipment, sources include electrodes, antennas, electrically stimulated smoking devices, electric hearing aids, and discharge tubes with liquid pool cathodes, among four other sources. Additionally, it is found in building and construction materials such as ladders. Recorded exposure routes for the compound include oral and inhalation. At the molecular level, nalidixic acid acts on four recorded protein targets. It functions as an inhibitor of DNA gyrase subunit A (gyrA) and DNA gyrase subunit B (gyrB). Furthermore, it targets DNA topoisomerase 2-alpha (TOP2A) and DNA topoisomerase 2-beta (TOP2B).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acidChEBI
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeureChEBI
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acidChEBI
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acidChEBI
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acidChEBI
3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-oneChEBI
Acide nalidixiqueChEBI
Acido nalidixicoChEBI
Acidum nalidixicumChEBI
NAKegg
NegGramKegg
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylateGenerator
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylateGenerator
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylateGenerator
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylateGenerator
NalidixateGenerator
Acid, nalidixicHMDB
NevigramonHMDB
Sodium, nalidixateHMDB
Nalidixate sodiumHMDB
NalidixinHMDB
Sodium nalidixic acid, anhydrousHMDB
Anhydrous, nalidixate sodiumHMDB
Nalidixate sodium anhydrousHMDB
Sodium anhydrous, nalidixateHMDB
Sodium nalidixic acid, monohydrateHMDB
Chemical FormulaC12H12N2O3
Average Molecular Mass232.235 g/mol
Monoisotopic Mass232.085 g/mol
CAS Registry Number389-08-2
IUPAC Name1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Namenalidixic acid
SMILESCCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2
InChI IdentifierInChI=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)
InChI KeyMHWLWQUZZRMNGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassNaphthyridines
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
Substituents
  • Naphthyridine carboxylic acid
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Methylpyridine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.3 g/LALOGPS
logP0.95ALOGPS
logP1.01ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)5.95ChemAxon
pKa (Strongest Basic)4.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.5 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.82 m³·mol⁻¹ChemAxon
Polarizability23.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fri-1790000000-92a3a10bfaccb41342fbNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0079-8290000000-87bbcaf099e222302f02Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0590000000-0071689427e5460e9504Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053i-2920000000-a81650e261062799ba89Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-b3f65ce918413bce9fa8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0090000000-0ff01a82dbce74faefc6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0790000000-46caea0fd85329797145Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-3572ae3957b712815a4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zgr-0900000000-a89fdf787950fb2d88c2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0290000000-db7256d80ff333bc00bfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-015i-0590000000-938c78d9d632c54cdffeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014r-0590000000-0071689427e5460e9504Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-053i-2920000000-a81650e261062799ba89Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0190000000-9f01c18c495b23232800Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0490000000-2fbf36cc9f6f88d4cd65Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-1d2b6985d9b92bbb9824Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0090000000-3364d0d3d6ede5d5b1a4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0950000000-f2b2776dbe2dc1e2e9beNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pc0-0910000000-560515fc3b04b07a51e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-3390000000-17e93f93f9a5f2cf26a1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-1190000000-a192d15d35dfb6d306d7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0190000000-fef5a9adccc5a0a5ec05Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00li-0890000000-c72282680d1ade35245cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ds-1900000000-4659dda7bb11b31ca0efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0019-0960000000-660f38f48e34b738382dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0900000000-76a76cfafed1c3238f42Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1900000000-1b71f0a68ff3448016e3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-9cc5f84e471abc457e3cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0490000000-45581f40b2a4b6298cb1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-4910000000-9b179ea125d16f1ebd07Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a5i-0950000000-aad3ea9cf639abc5aa87Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-8b789633287b58237f06Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1900000000-919f2c70f956ef0060d8Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1351.0Log mg/kg[760:2400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
345Quinolone antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
498LaddersBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
515Discharge Tubes With Liquid Pool CathodesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Isocitrate lyase structureClick to view 3D structureIsocitrate lyaseP9WKK7Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)1.16774
V-type proton ATPase subunit B, brain isoform structureClick to view 3D structureV-type proton ATPase subunit B, brain isoformP21281HumansPredicted (SEA)0.233548
RISC-loading complex subunit TARBP2 structureClick to view 3D structureRISC-loading complex subunit TARBP2Q15633HumansPredicted (SEA)1.01204
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)1514.63
Click to view 3D structureDNA topoisomerase 4 subunit AP0C1U9Staphylococcus aureusPredicted (SEA)3.03612
Click to view 3D structureAdenosine receptor A1P28190Bos taurusPredicted (SEA)90.7722
Click to view 3D structureSerine/threonine-protein kinase pim-3Q86V86HumansPredicted (SEA)1192.11
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)2469.3
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)663.742
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)587.684
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)1852.97
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)1868.23
Serine/threonine-protein kinase PLK1 structureClick to view 3D structureSerine/threonine-protein kinase PLK1P53350HumansPredicted (SEA)1690.42
RAC-gamma serine/threonine-protein kinase structureClick to view 3D structureRAC-gamma serine/threonine-protein kinaseQ9Y243HumansPredicted (SEA)1548.19
5'-3' exonuclease PLD3 structureClick to view 3D structure5'-3' exonuclease PLD3Q8IV08HumansPredicted (SEA)17.2825
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)782.54
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)2536.17
Click to view 3D structureVacuolar aminopeptidase 1P14904Saccharomyces cerevisiae S288cPredicted (SEA)2.41333
Click to view 3D structureGlycoprotein GQ9IH62Henipavirus nipahensePredicted (SEA)27.9479
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)577.018
Glycogen synthase kinase-3 alpha structureClick to view 3D structureGlycogen synthase kinase-3 alphaP49840HumansPredicted (SEA)2123.8
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)2367.16
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)2198.77
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)1766.63
Serine/threonine-protein kinase D2 structureClick to view 3D structureSerine/threonine-protein kinase D2Q9BZL6HumansPredicted (SEA)1754.72
Concentrations
Not Available
External Links
DrugBank IDDB00779
HMDB IDHMDB0014917
FooDB IDFDB020181
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNalidixic_Acid
Chemspider ID4268
ChEBI ID100147
PubChem Compound ID4421
Kegg Compound IDC05079
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11321869
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12002106
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12399485
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12702698
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14107587
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16107187
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16423473
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16667857
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16803589
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17132068
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17631104
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18788798
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19071706
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217