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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:51:58 UTC

Update Date

2021-09-26 23:07:34 UTC

HMDB ID

HMDB0253954

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Laflunimus

Description

HR325 belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. Based on a literature review a significant number of articles have been published on HR325. This compound has been identified in human blood as reported by (PMID: 31557052 ). Laflunimus is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Laflunimus is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253954
     RDKit          3D
Laflunimus
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.7540   -1.0571    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5197   -0.3048    0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.8430    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -0.1157    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1275   -0.7596    0.5514 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190   -0.2442    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5714    0.9015   -0.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942   -1.0700    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3339   -2.4016    1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -3.4625    1.5245 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064   -0.6889    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -1.6355    0.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3246    0.5714   -0.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    1.1499   -1.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359    0.3317   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596    1.1583   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333    1.7289   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    0.9909    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    1.5950   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6820    1.6495    1.0910 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7414    0.7849   -0.9601 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9123    2.8688   -0.6152 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -2.0409    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3313   -0.5682    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3784   -1.2783   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -1.8568    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -1.7652    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6685   -2.6175    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835    1.2279    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090    0.8165   -2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967    2.2523   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2312    0.8022   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -0.6419   -1.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202    1.7840   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171    2.7381   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  3  0
  8 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  4 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 18  2  1  0
 15 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
M  END


  Mrv1652309112108342D          

 22 23  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.1434    1.2375    0.0000 N   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
    2.8579    0.0000    0.0000 O   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
    4.2868    0.8250    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
    4.6993   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   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
    3.5724    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    0.3020    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.1270    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 12 16  1  4  0  0  0
 11 17  1  0  0  0  0
 17 18  3  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253954

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C=CC(NC(=O)C(C#N)=C(O)C2CC2)=C1)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C15H13F3N2O2/c1-8-6-10(4-5-12(8)15(16,17)18)20-14(22)11(7-19)13(21)9-2-3-9/h4-6,9,21H,2-3H2,1H3,(H,20,22)

> <INCHI_KEY>
GDHFOVCRYCPOTK-UHFFFAOYSA-N

> <FORMULA>
C15H13F3N2O2

> <MOLECULAR_WEIGHT>
310.276

> <EXACT_MASS>
310.092912156

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.303070005651865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-cyano-3-cyclopropyl-3-hydroxy-N-[3-methyl-4-(trifluoromethyl)phenyl]prop-2-enamide

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.076073907333333

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.084512345659181

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.272427287074806

> <JCHEM_PKA_STRONGEST_BASIC>
-2.629041975664676

> <JCHEM_POLAR_SURFACE_AREA>
73.12

> <JCHEM_REFRACTIVITY>
76.62740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-cyano-3-cyclopropyl-3-hydroxy-N-[3-methyl-4-(trifluoromethyl)phenyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253954
     RDKit          3D
Laflunimus
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.7540   -1.0571    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5197   -0.3048    0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.8430    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -0.1157    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1275   -0.7596    0.5514 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190   -0.2442    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5714    0.9015   -0.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942   -1.0700    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3339   -2.4016    1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -3.4625    1.5245 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064   -0.6889    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -1.6355    0.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3246    0.5714   -0.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    1.1499   -1.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359    0.3317   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596    1.1583   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333    1.7289   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    0.9909    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    1.5950   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6820    1.6495    1.0910 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7414    0.7849   -0.9601 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9123    2.8688   -0.6152 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -2.0409    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3313   -0.5682    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3784   -1.2783   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -1.8568    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -1.7652    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6685   -2.6175    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835    1.2279    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090    0.8165   -2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967    2.2523   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2312    0.8022   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -0.6419   -1.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202    1.7840   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171    2.7381   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  3  0
  8 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  4 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 18  2  1  0
 15 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.772  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.232  -1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.668   5.390   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  F   UNK     0      -2.667  -1.540   0.000  0.00  0.00           F+0
HETATM   21  F   UNK     0      -2.104   0.564   0.000  0.00  0.00           F+0
HETATM   22  F   UNK     0      -0.564  -2.104   0.000  0.00  0.00           F+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13                                                       
CONECT   16   12                                                            
CONECT   17   11   18                                                       
CONECT   18   17                                                            
CONECT   19    3   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0253954
HETATM    1  C1  UNL     1      -4.754  -1.057   0.863  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.520  -0.305   0.533  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.263  -0.843   0.681  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.109  -0.116   0.364  1.00  0.00           C  
HETATM    5  N1  UNL     1       0.128  -0.760   0.551  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.419  -0.244   0.304  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.571   0.902  -0.129  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.594  -1.070   0.566  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.334  -2.402   1.103  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.143  -3.463   1.525  1.00  0.00           N  
HETATM   11  C8  UNL     1       3.806  -0.689   0.353  1.00  0.00           C  
HETATM   12  O2  UNL     1       4.825  -1.635   0.678  1.00  0.00           O  
HETATM   13  C9  UNL     1       4.325   0.571  -0.185  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.990   1.150  -1.479  1.00  0.00           C  
HETATM   15  C11 UNL     1       5.236   0.332  -1.432  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.260   1.158  -0.102  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.533   1.729  -0.260  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.648   0.991   0.059  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.985   1.595  -0.110  1.00  0.00           C  
HETATM   20  F1  UNL     1      -5.682   1.650   1.091  1.00  0.00           F  
HETATM   21  F2  UNL     1      -5.741   0.785  -0.960  1.00  0.00           F  
HETATM   22  F3  UNL     1      -4.912   2.869  -0.615  1.00  0.00           F  
HETATM   23  H1  UNL     1      -4.436  -2.041   1.270  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.331  -0.568   1.686  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.378  -1.278  -0.023  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.200  -1.857   1.053  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.132  -1.765   0.926  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.668  -2.617   0.554  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.783   1.228   0.592  1.00  0.00           H  
HETATM   30  H8  UNL     1       3.209   0.817  -2.161  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.197   2.252  -1.585  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.231   0.802  -1.385  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.199  -0.642  -1.916  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.420   1.784  -0.368  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.617   2.738  -0.630  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    3   18
CONECT    3    4   26
CONECT    4    5   16   16
CONECT    5    6   27
CONECT    6    7    7    8
CONECT    8    9   11   11
CONECT    9   10   10   10
CONECT   11   12   13
CONECT   12   28
CONECT   13   14   15   29
CONECT   14   15   30   31
CONECT   15   32   33
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19
CONECT   19   20   21   22
END

HMDB0253954
     RDKit          3D
Laflunimus
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.7540   -1.0571    0.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5197   -0.3048    0.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.8430    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -0.1157    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1275   -0.7596    0.5514 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4190   -0.2442    0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5714    0.9015   -0.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942   -1.0700    0.5663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3339   -2.4016    1.1029 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -3.4625    1.5245 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8064   -0.6889    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253   -1.6355    0.6779 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3246    0.5714   -0.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9901    1.1499   -1.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2359    0.3317   -1.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596    1.1583   -0.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5333    1.7289   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483    0.9909    0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9846    1.5950   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6820    1.6495    1.0910 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7414    0.7849   -0.9601 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9123    2.8688   -0.6152 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4362   -2.0409    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3313   -0.5682    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3784   -1.2783   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -1.8568    1.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -1.7652    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6685   -2.6175    0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835    1.2279    0.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090    0.8165   -2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1967    2.2523   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2312    0.8022   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1986   -0.6419   -1.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4202    1.7840   -0.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6171    2.7381   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  3  0
  8 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
  4 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 18  2  1  0
 15 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  5 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₃F₃N₂O₂

Average Molecular Weight

310.276

Monoisotopic Molecular Weight

310.092912156

IUPAC Name

2-cyano-3-cyclopropyl-3-hydroxy-N-[3-methyl-4-(trifluoromethyl)phenyl]prop-2-enamide

Traditional Name

2-cyano-3-cyclopropyl-3-hydroxy-N-[3-methyl-4-(trifluoromethyl)phenyl]prop-2-enamide

CAS Registry Number

Not Available

SMILES

CC1=C(C=CC(NC(=O)C(C#N)=C(O)C2CC2)=C1)C(F)(F)F

InChI Identifier

InChI=1S/C15H13F3N2O2/c1-8-6-10(4-5-12(8)15(16,17)18)20-14(22)11(7-19)13(21)9-2-3-9/h4-6,9,21H,2-3H2,1H3,(H,20,22)

InChI Key

GDHFOVCRYCPOTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Anilide
N-arylamide
Toluene
Vinylogous acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Enol
Carbonitrile
Nitrile
Alkyl fluoride
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Cyanide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alkyl halide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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
logP	2.96	ALOGPS
logP	3.08	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.27	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	73.12 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.63 m³·mol⁻¹	ChemAxon
Polarizability	28.3 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]+	169.263	30932474
DeepCCS	[M-H]-	166.905	30932474
DeepCCS	[M-2H]-	200.841	30932474
DeepCCS	[M+Na]+	176.108	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Laflunimus	CC1=C(C=CC(NC(=O)C(C#N)=C(O)C2CC2)=C1)C(F)(F)F	2806.9	Standard polar	33892256
Laflunimus	CC1=C(C=CC(NC(=O)C(C#N)=C(O)C2CC2)=C1)C(F)(F)F	2013.9	Standard non polar	33892256
Laflunimus	CC1=C(C=CC(NC(=O)C(C#N)=C(O)C2CC2)=C1)C(F)(F)F	2155.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Laflunimus,2TMS,isomer #1	CC1=CC(N(C(=O)C(C#N)=C(O[Si](C)(C)C)C2CC2)[Si](C)(C)C)=CC=C1C(F)(F)F	2084.9	Semi standard non polar	33892256
Laflunimus,2TMS,isomer #1	CC1=CC(N(C(=O)C(C#N)=C(O[Si](C)(C)C)C2CC2)[Si](C)(C)C)=CC=C1C(F)(F)F	2052.0	Standard non polar	33892256
Laflunimus,2TMS,isomer #1	CC1=CC(N(C(=O)C(C#N)=C(O[Si](C)(C)C)C2CC2)[Si](C)(C)C)=CC=C1C(F)(F)F	2264.9	Standard polar	33892256
Laflunimus,2TBDMS,isomer #1	CC1=CC(N(C(=O)C(C#N)=C(O[Si](C)(C)C(C)(C)C)C2CC2)[Si](C)(C)C(C)(C)C)=CC=C1C(F)(F)F	2542.8	Semi standard non polar	33892256
Laflunimus,2TBDMS,isomer #1	CC1=CC(N(C(=O)C(C#N)=C(O[Si](C)(C)C(C)(C)C)C2CC2)[Si](C)(C)C(C)(C)C)=CC=C1C(F)(F)F	2429.1	Standard non polar	33892256
Laflunimus,2TBDMS,isomer #1	CC1=CC(N(C(=O)C(C#N)=C(O[Si](C)(C)C(C)(C)C)C2CC2)[Si](C)(C)C(C)(C)C)=CC=C1C(F)(F)F	2486.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Laflunimus GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-8591000000-98632418df42ccea8843	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laflunimus GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laflunimus GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laflunimus GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laflunimus GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laflunimus GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Laflunimus 10V, Positive-QTOF	splash10-03di-0009000000-06c26579e7acf81f6412	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laflunimus 20V, Positive-QTOF	splash10-00kn-9610000000-41ca477d818136d066fd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laflunimus 40V, Positive-QTOF	splash10-0f6x-9370000000-61e2c274a1cabfe0c19b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laflunimus 10V, Negative-QTOF	splash10-0a4i-0109000000-6697548fde914fa9a731	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laflunimus 20V, Negative-QTOF	splash10-0a4i-5914000000-0c0bf353d99efd8f4ca2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laflunimus 40V, Negative-QTOF	splash10-00xr-7920000000-26fc4d6a053f67b2f3e4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	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

58190890

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66583751

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Laflunimus (HMDB0253954)

MOL for HMDB0253954 (Laflunimus)

3D MOL for HMDB0253954 (Laflunimus)

3D SDF for HMDB0253954 (Laflunimus)

3D-SDF for HMDB0253954 (Laflunimus)

PDB for HMDB0253954 (Laflunimus)

3D PDB for HMDB0253954 (Laflunimus)

SMILES for HMDB0253954 (Laflunimus)

INCHI for HMDB0253954 (Laflunimus)

Structure for HMDB0253954 (Laflunimus)

3D Structure for HMDB0253954 (Laflunimus)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra