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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:55:22 UTC
Update Date2019-07-23 07:14:57 UTC
HMDB IDHMDB0060726
Secondary Accession Numbers
  • HMDB60726
Metabolite Identification
Common Name2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid
Description2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid is a metabolite of mefloquine. Mefloquine hydrochloride (also known as Lariam or Mefaquin) is an orally administered medication used in the prevention and treatment of malaria. Mefloquine was developed in the 1970s at the United States Department of Defense's Walter Reed Army Institute of Research as a synthetic analogue of quinine. The brand name drug, Lariam, is manufactured by the Swiss company Hoffmann–La Roche. In August 2009, Roche stopped marketing Lariam in the United States. (Wikipedia)
Structure
Data?1563866097
Synonyms
ValueSource
2,8-Bis-trifluoromethyl-4-quinoline carboxylateGenerator
2,8-MMQHMDB
2,8-Bis(trifluoromethyl)-4-quinolinecarboxylic acidHMDB
Mefloquine carboxylic acidHMDB
CarboxymefloquineMeSH
2,8-Bis(trifluoromethyl)quinoline-4-carboxylateGenerator
Chemical FormulaC12H5F6NO2
Average Molecular Weight309.164
Monoisotopic Molecular Weight309.022447639
IUPAC Name2,8-bis(trifluoromethyl)quinoline-4-carboxylic acid
Traditional Name2,8-bis(trifluoromethyl)quinoline-4-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F
InChI Identifier
InChI=1S/C12H5F6NO2/c13-11(14,15)7-3-1-2-5-6(10(20)21)4-8(12(16,17)18)19-9(5)7/h1-4H,(H,20,21)
InChI KeyQJTJIQBSZLFWFS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinoline carboxylic acids
Direct ParentQuinoline carboxylic acids
Alternative Parents
Substituents
  • Quinoline-4-carboxylic acid
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.7ALOGPS
logP3.93ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.19 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.81 m³·mol⁻¹ChemAxon
Polarizability22.01 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+159.06130932474
DeepCCS[M-H]-156.70330932474
DeepCCS[M-2H]-190.57730932474
DeepCCS[M+Na]+165.69730932474
AllCCS[M+H]+161.532859911
AllCCS[M+H-H2O]+158.032859911
AllCCS[M+NH4]+164.832859911
AllCCS[M+Na]+165.832859911
AllCCS[M-H]-150.832859911
AllCCS[M+Na-2H]-149.732859911
AllCCS[M+HCOO]-148.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acidOC(=O)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F1892.7Standard polar33892256
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acidOC(=O)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F1606.6Standard non polar33892256
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acidOC(=O)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F1691.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C121572.0Semi standard non polar33892256
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C121792.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-0091000000-e6389108c564b5ecabb42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00xu-9077000000-ceffe5da4f710f9e2e712017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 10V, Positive-QTOFsplash10-03di-0039000000-d5822cb07c09ad602d212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 20V, Positive-QTOFsplash10-01ox-0096000000-a7dd49c53733483ed8f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 40V, Positive-QTOFsplash10-0007-0190000000-1a664fb24c1c86d66f062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 10V, Negative-QTOFsplash10-0a4i-0049000000-e719152c0ba9c8bcb5a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 20V, Negative-QTOFsplash10-08fr-0094000000-7c831241a355819990772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 40V, Negative-QTOFsplash10-01ox-0090000000-1ddbe8243000d74a00232016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound169721
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available