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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:13 UTC
Update Date2019-07-23 06:09:25 UTC
HMDB IDHMDB0031754
Secondary Accession Numbers
  • HMDB31754
Metabolite Identification
Common NameNequinate
DescriptionNequinate, also known as nequinic acid or methyl benzoquate, belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Nequinate is an extremely weak basic (essentially neutral) compound (based on its pKa). Nequinate is an antiprotozoan used as a coccidiostat for poultry and rabbits.
Structure
Data?1563862165
Synonyms
ValueSource
Nequinic acidGenerator
Methyl benzoquateHMDB
NeoquateHMDB
AY-20385ici-55052nequinateHMDB
Methyl benzoquic acidHMDB
Neoquic acidHMDB
AY-20385ici-55052nequinic acidHMDB
AY 20385HMDB
Methyl 6-butyl-1,4-dihydro-4-oxo-7-(phenylmethoxy)-3-quinolinecarboxylate, 9ciHMDB
Methyl 7-(benzyloxy)-6-butyl-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 8ciHMDB
Methyl benzoquate, banHMDB
NequinatoHMDB
NequinatumHMDB
StatylHMDB
MethylbenzoquateMeSH
Methyl 7-(benzyloxy)-6-butyl-1,4-dihydro-4-oxo-3-quinolinecarboxylateMeSH
Chemical FormulaC22H23NO4
Average Molecular Weight365.4223
Monoisotopic Molecular Weight365.162708229
IUPAC Namemethyl 7-(benzyloxy)-6-butyl-4-oxo-1,4-dihydroquinoline-3-carboxylate
Traditional Namenequinate
CAS Registry Number13997-19-8
SMILES
CCCCC1=CC2=C(NC=C(C(=O)OC)C2=O)C=C1OCC1=CC=CC=C1
InChI Identifier
InChI=1S/C22H23NO4/c1-3-4-10-16-11-17-19(23-13-18(21(17)24)22(25)26-2)12-20(16)27-14-15-8-6-5-7-9-15/h5-9,11-13H,3-4,10,14H2,1-2H3,(H,23,24)
InChI KeyNNOPDLNHPOLRRE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentHydroquinolones
Alternative Parents
Substituents
  • Dihydroquinolone
  • Dihydroquinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point287 - 288 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00076 g/LALOGPS
logP4.34ALOGPS
logP5.33ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)6.15ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.63 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.78 m³·mol⁻¹ChemAxon
Polarizability41.02 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9026000000-e1ea082463dac513c2b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1009000000-7d1416127f7d953a1799Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-9028000000-10c2406f1c0aec7e026bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9110000000-5021f3cbdaa1afbdad9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-d62b7a636ef0b9e518f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2069000000-f8fda0433a437e68994bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9470000000-cc0fa9d968ee293dd882Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11433
Phenol Explorer Compound IDNot Available
FooDB IDFDB008423
KNApSAcK IDNot Available
Chemspider ID24579
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26383
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .