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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:55:22 UTC

Update Date

2019-07-23 07:14:57 UTC

HMDB ID

HMDB0060726

Secondary Accession Numbers

HMDB60726

Metabolite Identification

Common Name

2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid

Description

2,8-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 07041311552D          

 21 22  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -1.2375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.1270    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    0.3020    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 12  1  0  0  0  0
 18 12  1  0  0  0  0
 19  8  2  0  0  0  0
 19  9  1  0  0  0  0
 20 10  2  0  0  0  0
 21 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060726

> <DATABASE_NAME>
hmdb

> <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_KEY>
QJTJIQBSZLFWFS-UHFFFAOYSA-N

> <FORMULA>
C12H5F6NO2

> <MOLECULAR_WEIGHT>
309.164

> <EXACT_MASS>
309.022447639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.005092563065865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,8-bis(trifluoromethyl)quinoline-4-carboxylic acid

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.9300306683333335

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.54541496801748

> <JCHEM_PKA_STRONGEST_BASIC>
-3.018040073859527

> <JCHEM_POLAR_SURFACE_AREA>
50.19

> <JCHEM_REFRACTIVITY>
58.8109

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,8-bis(trifluoromethyl)quinoline-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  F   UNK     0       4.001  -3.850   0.000  0.00  0.00           F+0
HETATM   14  F   UNK     0       5.541  -2.310   0.000  0.00  0.00           F+0
HETATM   15  F   UNK     0       2.461  -2.310   0.000  0.00  0.00           F+0
HETATM   16  F   UNK     0      10.669  -1.540   0.000  0.00  0.00           F+0
HETATM   17  F   UNK     0       8.566  -2.104   0.000  0.00  0.00           F+0
HETATM   18  F   UNK     0      10.106   0.564   0.000  0.00  0.00           F+0
HETATM   19  N   UNK     0       6.668  -0.770   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    7                                                       
CONECT    4    6    8                                                       
CONECT    5    2    6    9                                                  
CONECT    6    4    5   10                                                  
CONECT    7    3    9   11                                                  
CONECT    8    4   12   19                                                  
CONECT    9    5    7   19                                                  
CONECT   10    6   20   21                                                  
CONECT   11    7   13   14   15                                             
CONECT   12    8   16   17   18                                             
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   11                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19    8    9                                                       
CONECT   20   10                                                            
CONECT   21   10                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0060726
HETATM    1  O1  UNL     1       1.399  -3.052  -1.513  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.837  -1.905  -1.473  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.990  -1.577  -2.124  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.159  -0.826  -0.725  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.931   0.184  -0.183  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.422   1.190   0.585  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.274   2.327   1.117  1.00  0.00           C  
HETATM    8  F1  UNL     1       2.999   1.902   2.192  1.00  0.00           F  
HETATM    9  F2  UNL     1       3.088   2.758   0.078  1.00  0.00           F  
HETATM   10  F3  UNL     1       1.445   3.343   1.475  1.00  0.00           F  
HETATM   11  N1  UNL     1       0.102   1.178   0.813  1.00  0.00           N  
HETATM   12  C6  UNL     1      -0.682   0.208   0.301  1.00  0.00           C  
HETATM   13  C7  UNL     1      -2.047   0.275   0.501  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.573   1.344   1.388  1.00  0.00           C  
HETATM   15  F4  UNL     1      -3.944   1.300   1.411  1.00  0.00           F  
HETATM   16  F5  UNL     1      -2.195   1.032   2.700  1.00  0.00           F  
HETATM   17  F6  UNL     1      -2.050   2.563   1.028  1.00  0.00           F  
HETATM   18  C9  UNL     1      -2.886  -0.667  -0.085  1.00  0.00           C  
HETATM   19  C10 UNL     1      -2.380  -1.669  -0.864  1.00  0.00           C  
HETATM   20  C11 UNL     1      -1.004  -1.771  -1.080  1.00  0.00           C  
HETATM   21  C12 UNL     1      -0.184  -0.835  -0.493  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.876  -1.875  -1.715  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.010   0.113  -0.364  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.969  -0.591   0.110  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.034  -2.399  -1.361  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.585  -2.549  -1.719  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   22
CONECT    4    5    5   21
CONECT    5    6   23
CONECT    6    7   11   11
CONECT    7    8    9   10
CONECT   11   12
CONECT   12   13   13   21
CONECT   13   14   18
CONECT   14   15   16   17
CONECT   18   19   19   24
CONECT   19   20   25
CONECT   20   21   21   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,8-Bis-trifluoromethyl-4-quinoline carboxylate	Generator
2,8-MMQ	HMDB
2,8-Bis(trifluoromethyl)-4-quinolinecarboxylic acid	HMDB
Mefloquine carboxylic acid	HMDB
Carboxymefloquine	MeSH
2,8-Bis(trifluoromethyl)quinoline-4-carboxylate	Generator

Chemical Formula

C₁₂H₅F₆NO₂

Average Molecular Weight

309.164

Monoisotopic Molecular Weight

309.022447639

IUPAC Name

2,8-bis(trifluoromethyl)quinoline-4-carboxylic acid

Traditional Name

2,8-bis(trifluoromethyl)quinoline-4-carboxylic acid

CAS Registry Number

Not 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 Key

QJTJIQBSZLFWFS-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinoline carboxylic acids

Direct Parent

Quinoline 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060726)
Liver (HMDB: HMDB0060726)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060726)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060726)

Cellular substructure

Cytoplasm (HMDB: HMDB0060726)
Membrane (HMDB: HMDB0060726)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.93	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.81 m³·mol⁻¹	ChemAxon
Polarizability	22.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.061	30932474
DeepCCS	[M-H]-	156.703	30932474
DeepCCS	[M-2H]-	190.577	30932474
DeepCCS	[M+Na]+	165.697	30932474
AllCCS	[M+H]+	161.5	32859911
AllCCS	[M+H-H2O]+	158.0	32859911
AllCCS	[M+NH4]+	164.8	32859911
AllCCS	[M+Na]+	165.8	32859911
AllCCS	[M-H]-	150.8	32859911
AllCCS	[M+Na-2H]-	149.7	32859911
AllCCS	[M+HCOO]-	148.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid	OC(=O)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F	1892.7	Standard polar	33892256
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid	OC(=O)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F	1606.6	Standard non polar	33892256
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid	OC(=O)C1=CC(=NC2=C1C=CC=C2C(F)(F)F)C(F)(F)F	1691.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12	1572.0	Semi standard non polar	33892256
2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C12	1792.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-0091000000-e6389108c564b5ecabb4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00xu-9077000000-ceffe5da4f710f9e2e71	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 10V, Positive-QTOF	splash10-03di-0039000000-d5822cb07c09ad602d21	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 20V, Positive-QTOF	splash10-01ox-0096000000-a7dd49c53733483ed8f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 40V, Positive-QTOF	splash10-0007-0190000000-1a664fb24c1c86d66f06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 10V, Negative-QTOF	splash10-0a4i-0049000000-e719152c0ba9c8bcb5a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 20V, Negative-QTOF	splash10-08fr-0094000000-7c831241a35581999077	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid 40V, Negative-QTOF	splash10-01ox-0090000000-1ddbe8243000d74a0023	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

169721

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid (HMDB0060726)

MOL for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

3D MOL for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

3D SDF for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

3D-SDF for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

PDB for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

3D PDB for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

SMILES for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

INCHI for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

Structure for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

3D Structure for HMDB0060726 (2,8-bis-Trifluoromethyl-4-quinoline carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra