Nalidixic acid (CHEM016357)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:28:43 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016357
Identification
Common NameNalidixic acid
ClassSmall Molecule
DescriptionNalidixic acid is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fri-1790000000-92a3a10bfaccb41342fbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8290000000-87bbcaf099e222302f02Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014r-0590000000-0071689427e5460e9504Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-053i-2920000000-a81650e261062799ba89Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0090000000-b3f65ce918413bce9fa8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0090000000-0ff01a82dbce74faefc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014r-0790000000-46caea0fd85329797145Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-3572ae3957b712815a4fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0zgr-0900000000-a89fdf787950fb2d88c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0a4i-0290000000-db7256d80ff333bc00bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-015i-0590000000-938c78d9d632c54cdffeSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014r-0590000000-0071689427e5460e9504Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-053i-2920000000-a81650e261062799ba89Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-001i-0190000000-9f01c18c495b23232800Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4i-0490000000-2fbf36cc9f6f88d4cd65Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0090000000-1d2b6985d9b92bbb9824Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-0090000000-3364d0d3d6ede5d5b1a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a4i-0950000000-f2b2776dbe2dc1e2e9beSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0pc0-0910000000-560515fc3b04b07a51e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001r-3390000000-17e93f93f9a5f2cf26a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-001i-1190000000-a192d15d35dfb6d306d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0190000000-fef5a9adccc5a0a5ec05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00li-0890000000-c72282680d1ade35245cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-1900000000-4659dda7bb11b31ca0efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0960000000-660f38f48e34b738382dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0900000000-76a76cfafed1c3238f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-1b71f0a68ff3448016e3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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