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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:07:19 UTC

Update Date

2021-09-26 23:04:44 UTC

HMDB ID

HMDB0252265

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Fipronil

Description

Fipronil belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Based on a literature review very few articles have been published on Fipronil. This compound has been identified in human blood as reported by (PMID: 31557052 ). Fipronil is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Fipronil 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


  Mrv1652307282022142D          

 26 27  0  0  0  0            999 V2000
   -1.4884    0.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323    0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665    3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528    0.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034    1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526    0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -0.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    2.3690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9731    0.6892    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1226   -1.1407    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9703   -0.9581    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    0.0117    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.1161    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    5.4180    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.9891    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512    3.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376    3.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.2911    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15 11  1  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 12  1  0  0  0  0
 20 12  1  0  0  0  0
 21  3  3  0  0  0  0
 22 10  1  0  0  0  0
 23  7  2  0  0  0  0
 24  8  1  0  0  0  0
 24 10  1  0  0  0  0
 24 23  1  0  0  0  0
 26  9  1  0  0  0  0
 26 12  1  0  0  0  0
 26 25  2  0  0  0  0
M  END

HMDB0252265
     RDKit          3D
Fipronil
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.9758    1.9196   -2.6074 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1763    1.4246   -1.9264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889    0.8071   -1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.4745   -1.3517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -0.1036   -0.3272 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -0.3654   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081    0.5040   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    1.7332   -2.1242 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2800    0.4479   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258   -0.4383   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946   -0.4295   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8809    0.7775   -0.7965 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8970   -1.3934   -1.1272 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8506   -0.5251    1.0212 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1608   -1.2692    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -1.2583    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481   -2.4883    1.4218 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656   -0.1572    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -0.6816    1.9750 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849    0.4080    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8557    0.6642    1.1767 S   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1729    2.1136    1.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2344   -0.2398    0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5466    0.1071   -0.7376 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3804   -0.1562    1.3133 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8881   -1.6082    0.4790 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8348    1.1420   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6587   -1.9433    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.5321    2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -0.3664    2.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 20  3  1  0
 16  6  1  0
  9 27  1  0
 15 28  1  0
 19 29  1  0
 19 30  1  0
M  END


  Mrv1652307282022142D          

 26 27  0  0  0  0            999 V2000
   -1.4884    0.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323    0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1665    3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528    0.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0034    1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526    0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830    1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -0.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    2.3690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9731    0.6892    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1226   -1.1407    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9703   -0.9581    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3052    0.0117    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.1161    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    5.4180    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.9891    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9512    3.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376    3.2361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.1965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.2911    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 15 11  1  0  0  0  0
 16 11  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 12  1  0  0  0  0
 20 12  1  0  0  0  0
 21  3  3  0  0  0  0
 22 10  1  0  0  0  0
 23  7  2  0  0  0  0
 24  8  1  0  0  0  0
 24 10  1  0  0  0  0
 24 23  1  0  0  0  0
 26  9  1  0  0  0  0
 26 12  1  0  0  0  0
 26 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252265

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=C(C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F

> <INCHI_IDENTIFIER>
InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2

> <INCHI_KEY>
ZOCSXAVNDGMNBV-UHFFFAOYSA-N

> <FORMULA>
C12H4Cl2F6N4OS

> <MOLECULAR_WEIGHT>
437.148

> <EXACT_MASS>
435.938706104

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
31.599711084540594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile

> <ALOGPS_LOGP>
4.40

> <JCHEM_LOGP>
4.489138988666667

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.7417605768951298

> <JCHEM_POLAR_SURFACE_AREA>
84.69999999999999

> <JCHEM_REFRACTIVITY>
83.66349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fipronil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252265
     RDKit          3D
Fipronil
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.9758    1.9196   -2.6074 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1763    1.4246   -1.9264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889    0.8071   -1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.4745   -1.3517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -0.1036   -0.3272 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -0.3654   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081    0.5040   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    1.7332   -2.1242 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2800    0.4479   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258   -0.4383   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946   -0.4295   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8809    0.7775   -0.7965 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8970   -1.3934   -1.1272 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8506   -0.5251    1.0212 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1608   -1.2692    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -1.2583    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481   -2.4883    1.4218 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656   -0.1572    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -0.6816    1.9750 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849    0.4080    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8557    0.6642    1.1767 S   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1729    2.1136    1.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2344   -0.2398    0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5466    0.1071   -0.7376 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3804   -0.1562    1.3133 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8881   -1.6082    0.4790 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8348    1.1420   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6587   -1.9433    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.5321    2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -0.3664    2.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 20  3  1  0
 16  6  1  0
  9 27  1  0
 15 28  1  0
 19 29  1  0
 19 30  1  0
M  END

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.778   1.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.620   0.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.044   6.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.152   0.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.873   3.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.285   1.447   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.580   5.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.342   2.854   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   6.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.088   5.565   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.057  -0.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   8.780   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -2.499   4.422   0.000  0.00  0.00          Cl+0
HETATM   14 Cl   UNK     0       1.816   1.287   0.000  0.00  0.00          Cl+0
HETATM   15  F   UNK     0      -3.962  -2.129   0.000  0.00  0.00           F+0
HETATM   16  F   UNK     0      -1.811  -1.788   0.000  0.00  0.00           F+0
HETATM   17  F   UNK     0      -4.303   0.022   0.000  0.00  0.00           F+0
HETATM   18  F   UNK     0      -1.334   9.550   0.000  0.00  0.00           F+0
HETATM   19  F   UNK     0       0.770  10.114   0.000  0.00  0.00           F+0
HETATM   20  F   UNK     0      -0.770   7.446   0.000  0.00  0.00           F+0
HETATM   21  N   UNK     0       5.509   6.517   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -1.377   6.041   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       2.104   4.100   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       0.564   4.100   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       2.667   8.780   0.000  0.00  0.00           O+0
HETATM   26  S   UNK     0       1.334   8.010   0.000  0.00  0.00           S+0
CONECT    1    4    5                                                       
CONECT    2    4    6                                                       
CONECT    3    7   21                                                       
CONECT    4    1    2   11                                                  
CONECT    5    1    8   13                                                  
CONECT    6    2    8   14                                                  
CONECT    7    3    9   23                                                  
CONECT    8    5    6   24                                                  
CONECT    9    7   10   26                                                  
CONECT   10    9   22   24                                                  
CONECT   11    4   15   16   17                                             
CONECT   12   18   19   20   26                                             
CONECT   13    5                                                            
CONECT   14    6                                                            
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   12                                                            
CONECT   21    3                                                            
CONECT   22   10                                                            
CONECT   23    7   24                                                       
CONECT   24    8   10   23                                                  
CONECT   25   26                                                            
CONECT   26    9   12   25                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0252265
HETATM    1  N1  UNL     1      -3.976   1.920  -2.607  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.176   1.425  -1.926  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.189   0.807  -1.096  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.933   0.475  -1.352  1.00  0.00           N  
HETATM    5  N3  UNL     1      -0.294  -0.104  -0.327  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.099  -0.365  -0.351  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.908   0.504  -1.151  1.00  0.00           C  
HETATM    8 CL1  UNL     1       1.049   1.733  -2.124  1.00  0.00          CL  
HETATM    9  C5  UNL     1       3.280   0.448  -1.133  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.926  -0.438  -0.341  1.00  0.00           C  
HETATM   11  C7  UNL     1       5.395  -0.430  -0.279  1.00  0.00           C  
HETATM   12  F1  UNL     1       5.881   0.778  -0.796  1.00  0.00           F  
HETATM   13  F2  UNL     1       5.897  -1.393  -1.127  1.00  0.00           F  
HETATM   14  F3  UNL     1       5.851  -0.525   1.021  1.00  0.00           F  
HETATM   15  C8  UNL     1       3.161  -1.269   0.416  1.00  0.00           C  
HETATM   16  C9  UNL     1       1.753  -1.258   0.432  1.00  0.00           C  
HETATM   17 CL2  UNL     1       0.948  -2.488   1.422  1.00  0.00          CL  
HETATM   18  C10 UNL     1      -1.166  -0.157   0.660  1.00  0.00           C  
HETATM   19  N4  UNL     1      -1.112  -0.682   1.975  1.00  0.00           N  
HETATM   20  C11 UNL     1      -2.385   0.408   0.233  1.00  0.00           C  
HETATM   21  S1  UNL     1      -3.856   0.664   1.177  1.00  0.00           S  
HETATM   22  O1  UNL     1      -4.173   2.114   1.445  1.00  0.00           O  
HETATM   23  C12 UNL     1      -5.234  -0.240   0.593  1.00  0.00           C  
HETATM   24  F4  UNL     1      -5.547   0.107  -0.738  1.00  0.00           F  
HETATM   25  F5  UNL     1      -6.380  -0.156   1.313  1.00  0.00           F  
HETATM   26  F6  UNL     1      -4.888  -1.608   0.479  1.00  0.00           F  
HETATM   27  H1  UNL     1       3.835   1.142  -1.786  1.00  0.00           H  
HETATM   28  H2  UNL     1       3.659  -1.943   1.091  1.00  0.00           H  
HETATM   29  H3  UNL     1      -1.756  -1.532   2.100  1.00  0.00           H  
HETATM   30  H4  UNL     1      -0.575  -0.366   2.777  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5
CONECT    5    6   18
CONECT    6    7    7   16
CONECT    7    8    9
CONECT    9   10   10   27
CONECT   10   11   15
CONECT   11   12   13   14
CONECT   15   16   16   28
CONECT   16   17
CONECT   18   19   20   20
CONECT   19   29   30
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   25   26
END

HMDB0252265
     RDKit          3D
Fipronil
 30 31  0  0  0  0  0  0  0  0999 V2000
   -3.9758    1.9196   -2.6074 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1763    1.4246   -1.9264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1889    0.8071   -1.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    0.4745   -1.3517 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2945   -0.1036   -0.3272 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0994   -0.3654   -0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9081    0.5040   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    1.7332   -2.1242 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2800    0.4479   -1.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258   -0.4383   -0.3409 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3946   -0.4295   -0.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8809    0.7775   -0.7965 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8970   -1.3934   -1.1272 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8506   -0.5251    1.0212 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1608   -1.2692    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -1.2583    0.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481   -2.4883    1.4218 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656   -0.1572    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118   -0.6816    1.9750 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3849    0.4080    0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8557    0.6642    1.1767 S   0  0  0  0  0  4  0  0  0  0  0  0
   -4.1729    2.1136    1.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2344   -0.2398    0.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5466    0.1071   -0.7376 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3804   -0.1562    1.3133 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8881   -1.6082    0.4790 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8348    1.1420   -1.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6587   -1.9433    1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7563   -1.5321    2.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -0.3664    2.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
 16 17  1  0
  5 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 20  3  1  0
 16  6  1  0
  9 27  1  0
 15 28  1  0
 19 29  1  0
 19 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Amino-1-(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitile	MeSH

Chemical Formula

C₁₂H₄Cl₂F₆N₄OS

Average Molecular Weight

437.148

Monoisotopic Molecular Weight

435.938706104

IUPAC Name

5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethanesulfinyl-1H-pyrazole-3-carbonitrile

Traditional Name

fipronil

CAS Registry Number

Not Available

SMILES

NC1=C(C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F

InChI Identifier

InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2

InChI Key

ZOCSXAVNDGMNBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

Alternative Parents

Substituents

Phenylpyrazole
Trifluoromethylbenzene
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Trihalomethane
Sulfoxide
Azacycle
Sulfinyl compound
Carbonitrile
Nitrile
Alkyl fluoride
Organonitrogen compound
Organofluoride
Organochloride
Organohalogen compound
Organosulfur compound
Primary amine
Hydrocarbon derivative
Halomethane
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alkyl halide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazoles (CHEBI:83394 )
sulfoxide (CHEBI:83394 )
primary amino compound (CHEBI:83394 )
nitrile (CHEBI:83394 )
dichlorobenzene (CHEBI:83394 )
(trifluoromethyl)benzenes (CHEBI:83394 )
Pyrazole insecticides (C11099 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0252265)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

agrochemical (HMDB: HMDB0252265)
acaricide (HMDB: HMDB0252265)

Biological role

GABA-gated chloride channel antagonist (HMDB: HMDB0252265)

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	4.4	ALOGPS
logP	4.49	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	0.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	84.7 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.66 m³·mol⁻¹	ChemAxon
Polarizability	31.6 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]+	178.328	30932474
DeepCCS	[M-H]-	175.97	30932474
DeepCCS	[M-2H]-	210.055	30932474
DeepCCS	[M+Na]+	185.332	30932474
AllCCS	[M+H]+	178.7	32859911
AllCCS	[M+H-H2O]+	176.3	32859911
AllCCS	[M+NH4]+	181.0	32859911
AllCCS	[M+Na]+	181.6	32859911
AllCCS	[M-H]-	158.0	32859911
AllCCS	[M+Na-2H]-	156.7	32859911
AllCCS	[M+HCOO]-	155.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fipronil	NC1=C(C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F	3235.6	Standard polar	33892256
Fipronil	NC1=C(C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F	2469.9	Standard non polar	33892256
Fipronil	NC1=C(C(=NN1C1=C(Cl)C=C(C=C1Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F	2132.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fipronil,1TMS,isomer #1	C[Si](C)(C)NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl	2189.2	Semi standard non polar	33892256
Fipronil,1TMS,isomer #1	C[Si](C)(C)NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl	2525.4	Standard non polar	33892256
Fipronil,1TMS,isomer #1	C[Si](C)(C)NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl	3119.8	Standard polar	33892256
Fipronil,2TMS,isomer #1	C[Si](C)(C)N(C1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl)[Si](C)(C)C	2281.3	Semi standard non polar	33892256
Fipronil,2TMS,isomer #1	C[Si](C)(C)N(C1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl)[Si](C)(C)C	2737.4	Standard non polar	33892256
Fipronil,2TMS,isomer #1	C[Si](C)(C)N(C1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl)[Si](C)(C)C	2956.3	Standard polar	33892256
Fipronil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl	2367.5	Semi standard non polar	33892256
Fipronil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl	2797.2	Standard non polar	33892256
Fipronil,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl	3168.0	Standard polar	33892256
Fipronil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl)[Si](C)(C)C(C)(C)C	2601.9	Semi standard non polar	33892256
Fipronil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl)[Si](C)(C)C(C)(C)C	3178.8	Standard non polar	33892256
Fipronil,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl)[Si](C)(C)C(C)(C)C	3095.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fipronil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fipronil 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 30V, positive-QTOF	splash10-014i-0009000000-334b13092f28e3fec2e5	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 13V, positive-QTOF	splash10-00kr-0008900000-9323fcb965734859dca3	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 26V, positive-QTOF	splash10-014i-0029000000-e0abfbca9e3c21404e2e	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 39V, positive-QTOF	splash10-0udr-0090000000-f7a89980ca0ba058ebc4	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 52V, positive-QTOF	splash10-0uk9-0090000000-774c92f3b5c696a2b92d	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 65V, positive-QTOF	splash10-0h99-0090000000-5daadc5c9b866be9d969	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 78V, positive-QTOF	splash10-000i-0390000000-98dad3fc291cebd5b250	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 35V, positive-QTOF	splash10-014i-0009000000-34b3700f2952e8157152	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 35V, positive-QTOF	splash10-014i-0009000000-bb516888cbc97c7be410	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 35V, positive-QTOF	splash10-014i-0009000000-997cb32c3d6ddd079aa1	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 65V, positive-QTOF	splash10-014i-0009000000-c8e20e8be0f7bf23ab33	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-QTOF 10V, negative-QTOF	splash10-003r-0006900000-7e2a16a8403fc19b5c86	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-QTOF 20V, negative-QTOF	splash10-004i-0009000000-6fcca9a8920f4069a07b	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-QTOF 30V, negative-QTOF	splash10-004j-0298000000-e5b4a2f041e4729bdddf	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-QTOF 40V, negative-QTOF	splash10-003s-0391000000-4428966fce32d1360f4c	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-QTOF 50V, negative-QTOF	splash10-001i-0960000000-0efa5c7f8eb7eb83a258	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 30V, negative-QTOF	splash10-004j-0009000000-707b4841356803f9754b	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 13V, negative-QTOF	splash10-004i-0009200000-bc7b0dbfd3097ff34236	2020-08-04	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fipronil LC-ESI-ITFT 26V, negative-QTOF	splash10-004i-0039000000-f2b91a8120f3ba256b46	2020-08-04	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fipronil 10V, Positive-QTOF	splash10-000i-0000900000-f562c603052e9b1cf559	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fipronil 20V, Positive-QTOF	splash10-000i-0004900000-9f31da92517ecaab9b63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fipronil 40V, Positive-QTOF	splash10-014i-2191000000-bdb48ae35693024eabbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fipronil 10V, Negative-QTOF	splash10-001i-0000900000-d727fa54e3c5656179e9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fipronil 20V, Negative-QTOF	splash10-001i-0200900000-5e6ddc958202f2b2c0d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fipronil 40V, Negative-QTOF	splash10-00mo-4490000000-e1ad4fbd38d1a8f3a235	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

3235

KEGG Compound ID

C11099

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fipronil

METLIN ID

Not Available

PubChem Compound

3352

PDB ID

Not Available

ChEBI ID

83394

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1669371

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 Fipronil (HMDB0252265)

MOL for HMDB0252265 (Fipronil)

3D MOL for HMDB0252265 (Fipronil)

3D SDF for HMDB0252265 (Fipronil)

3D-SDF for HMDB0252265 (Fipronil)

PDB for HMDB0252265 (Fipronil)

3D PDB for HMDB0252265 (Fipronil)

SMILES for HMDB0252265 (Fipronil)

INCHI for HMDB0252265 (Fipronil)

Structure for HMDB0252265 (Fipronil)

3D Structure for HMDB0252265 (Fipronil)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra