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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015604

Secondary Accession Numbers

HMDB15604

Metabolite Identification

Common Name

Permethrin

Description

Permethrin is only found in individuals that have used or taken this drug. It is a pyrethroid insecticide commonly used in the treatment of lice infestations and scabies. It is a yellow to light orange-brown, low melt-ing solid or viscous liquid.Permethrin acts on the nerve cell membrane to disrupt the sodium channel current by which the polarization of the membrane is regulated. Delayed repolarization and paralysis of the pests are the consequences of this disturbance.

Structure

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


  Mrv1652307282022152D          

 26 28  0  0  0  0            999 V2000
    2.2259   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.6020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 12  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 21 19  1  0  0  0  0
 22 18  1  0  0  0  0
 23 18  1  0  0  0  0
 24 20  2  0  0  0  0
 25 13  1  0  0  0  0
 25 20  1  0  0  0  0
 26 15  1  0  0  0  0
 26 16  1  0  0  0  0
M  END

HMDB0242207
     RDKit          3D
(-)-cis-Permethrin
 46 48  0  0  0  0  0  0  0  0999 V2000
   -5.9039    0.3119    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.0490    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6852    1.3722    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770   -1.0801   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -2.2701   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -2.3824   -1.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6926   -0.9857   -2.2650 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.5041   -3.9736   -1.9896 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7592   -1.0319    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3619   -0.8904    1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796   -1.4558    2.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978   -0.1688    0.6886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0880   -0.0970    1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    0.6995    0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    1.2970   -0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    2.0228   -1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    2.1727   -1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    1.5676    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851    1.7131    0.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3148    0.7569    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4668   -0.3628    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3842   -1.3342    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1515   -1.2092   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9801   -0.0651   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0654    0.9179   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    0.8557    0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3761    1.0418   -0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4199   -0.6375    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8688    0.7529    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    1.2092   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.6586    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3577    2.1539   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -0.9085   -1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618   -3.2321   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085   -1.6361    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.2775    2.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454   -1.1384    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    1.1770   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    2.4927   -2.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294    2.7361   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495   -0.4452    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4786   -2.2029    1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8838   -1.9396   -0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880    0.0329   -2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9838    1.7805   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4211    0.3979    1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  2  0
  9  2  1  0
 26 14  1  0
 25 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
M  END


  Mrv1652307282022152D          

 26 28  0  0  0  0            999 V2000
    2.2259   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4151   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7006   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5572   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.6020    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.3645    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2717   -3.6020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
 15  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 12  2  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21  2  1  0  0  0  0
 21 17  1  0  0  0  0
 21 19  1  0  0  0  0
 22 18  1  0  0  0  0
 23 18  1  0  0  0  0
 24 20  2  0  0  0  0
 25 13  1  0  0  0  0
 25 20  1  0  0  0  0
 26 15  1  0  0  0  0
 26 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015604

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3

> <INCHI_KEY>
RLLPVAHGXHCWKJ-UHFFFAOYSA-N

> <FORMULA>
C21H20Cl2O3

> <MOLECULAR_WEIGHT>
391.288

> <EXACT_MASS>
390.07894992

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
39.43070122486337

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

> <ALOGPS_LOGP>
6.24

> <JCHEM_LOGP>
5.696099242333333

> <ALOGPS_LOGS>
-6.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6914374735348043

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
114.28240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.91e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
permethrin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0242207
     RDKit          3D
(-)-cis-Permethrin
 46 48  0  0  0  0  0  0  0  0999 V2000
   -5.9039    0.3119    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.0490    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6852    1.3722    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770   -1.0801   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -2.2701   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -2.3824   -1.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6926   -0.9857   -2.2650 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.5041   -3.9736   -1.9896 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7592   -1.0319    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3619   -0.8904    1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796   -1.4558    2.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978   -0.1688    0.6886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0880   -0.0970    1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    0.6995    0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    1.2970   -0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    2.0228   -1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    2.1727   -1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    1.5676    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851    1.7131    0.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3148    0.7569    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4668   -0.3628    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3842   -1.3342    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1515   -1.2092   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9801   -0.0651   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0654    0.9179   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    0.8557    0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3761    1.0418   -0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4199   -0.6375    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8688    0.7529    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    1.2092   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.6586    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3577    2.1539   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -0.9085   -1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618   -3.2321   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085   -1.6361    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.2775    2.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454   -1.1384    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    1.1770   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    2.4927   -2.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294    2.7361   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495   -0.4452    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4786   -2.2029    1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8838   -1.9396   -0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880    0.0329   -2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9838    1.7805   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4211    0.3979    1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  2  0
  9  2  1  0
 26 14  1  0
 25 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  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       4.155  -3.630   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.514  -3.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.442  -4.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.108  -3.644   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.442  -5.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.773  -3.644   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.439  -4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.774  -4.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.108  -6.724   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.107  -4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.773  -6.724   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.231  -6.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.106  -6.724   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.439  -5.954   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.774  -5.954   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.107  -5.954   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.565  -5.954   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.897  -5.954   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.438  -6.724   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       0.564  -6.724   0.000  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0       1.897  -4.414   0.000  0.00  0.00          Cl+0
HETATM   24  O   UNK     0       7.438  -8.264   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.772  -5.954   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      15.441  -6.724   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3    9                                                       
CONECT    6    7   10                                                       
CONECT    7    6   14                                                       
CONECT    8    4   15                                                       
CONECT    9    5   15                                                       
CONECT   10    6   16                                                       
CONECT   11   14   16                                                       
CONECT   12   17   18                                                       
CONECT   13   14   25                                                       
CONECT   14    7   11   13                                                  
CONECT   15    8    9   26                                                  
CONECT   16   10   11   26                                                  
CONECT   17   12   19   21                                                  
CONECT   18   12   22   23                                                  
CONECT   19   17   20   21                                                  
CONECT   20   19   24   25                                                  
CONECT   21    1    2   17   19                                             
CONECT   22   18                                                            
CONECT   23   18                                                            
CONECT   24   20                                                            
CONECT   25   13   20                                                       
CONECT   26   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0242207
HETATM    1  C1  UNL     1      -5.904   0.312   0.510  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.455   0.049   0.168  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.685   1.372   0.019  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.977  -1.080  -0.607  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.732  -2.270  -1.006  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.836  -2.382  -1.670  1.00  0.00           C  
HETATM    7 CL1  UNL     1      -6.693  -0.986  -2.265  1.00  0.00          CL  
HETATM    8 CL2  UNL     1      -6.504  -3.974  -1.990  1.00  0.00          CL  
HETATM    9  C7  UNL     1      -3.759  -1.032   0.935  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.362  -0.890   1.375  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.980  -1.456   2.453  1.00  0.00           O  
HETATM   12  O2  UNL     1      -1.398  -0.169   0.689  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.088  -0.097   1.197  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.825   0.700   0.363  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.512   1.297  -0.827  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.477   2.023  -1.510  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.764   2.173  -1.036  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.084   1.568   0.172  1.00  0.00           C  
HETATM   19  O3  UNL     1       4.385   1.713   0.663  1.00  0.00           O  
HETATM   20  C15 UNL     1       5.315   0.757   0.282  1.00  0.00           C  
HETATM   21  C16 UNL     1       5.467  -0.363   1.065  1.00  0.00           C  
HETATM   22  C17 UNL     1       6.384  -1.334   0.714  1.00  0.00           C  
HETATM   23  C18 UNL     1       7.152  -1.209  -0.403  1.00  0.00           C  
HETATM   24  C19 UNL     1       6.980  -0.065  -1.183  1.00  0.00           C  
HETATM   25  C20 UNL     1       6.065   0.918  -0.845  1.00  0.00           C  
HETATM   26  C21 UNL     1       2.122   0.856   0.834  1.00  0.00           C  
HETATM   27  H1  UNL     1      -6.376   1.042  -0.165  1.00  0.00           H  
HETATM   28  H2  UNL     1      -6.420  -0.637   0.640  1.00  0.00           H  
HETATM   29  H3  UNL     1      -5.869   0.753   1.566  1.00  0.00           H  
HETATM   30  H4  UNL     1      -2.824   1.209  -0.659  1.00  0.00           H  
HETATM   31  H5  UNL     1      -3.269   1.659   1.025  1.00  0.00           H  
HETATM   32  H6  UNL     1      -4.358   2.154  -0.359  1.00  0.00           H  
HETATM   33  H7  UNL     1      -3.045  -0.909  -1.208  1.00  0.00           H  
HETATM   34  H8  UNL     1      -4.262  -3.232  -0.672  1.00  0.00           H  
HETATM   35  H9  UNL     1      -4.408  -1.636   1.569  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.129   0.277   2.248  1.00  0.00           H  
HETATM   37  H11 UNL     1       0.345  -1.138   1.246  1.00  0.00           H  
HETATM   38  H12 UNL     1      -0.493   1.177  -1.195  1.00  0.00           H  
HETATM   39  H13 UNL     1       1.210   2.493  -2.459  1.00  0.00           H  
HETATM   40  H14 UNL     1       3.529   2.736  -1.556  1.00  0.00           H  
HETATM   41  H15 UNL     1       4.850  -0.445   1.948  1.00  0.00           H  
HETATM   42  H16 UNL     1       6.479  -2.203   1.353  1.00  0.00           H  
HETATM   43  H17 UNL     1       7.884  -1.940  -0.723  1.00  0.00           H  
HETATM   44  H18 UNL     1       7.588   0.033  -2.067  1.00  0.00           H  
HETATM   45  H19 UNL     1       5.984   1.780  -1.495  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.421   0.398   1.779  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    4    9
CONECT    3   30   31   32
CONECT    4    5    9   33
CONECT    5    6    6   34
CONECT    6    7    8
CONECT    9   10   35
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   36   37
CONECT   14   15   15   26
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   26   26
CONECT   19   20
CONECT   20   21   21   25
CONECT   21   22   41
CONECT   22   23   23   42
CONECT   23   24   43
CONECT   24   25   25   44
CONECT   25   45
CONECT   26   46
END

HMDB0242207
     RDKit          3D
(-)-cis-Permethrin
 46 48  0  0  0  0  0  0  0  0999 V2000
   -5.9039    0.3119    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4545    0.0490    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6852    1.3722    0.0186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9770   -1.0801   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7320   -2.2701   -1.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8360   -2.3824   -1.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6926   -0.9857   -2.2650 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.5041   -3.9736   -1.9896 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7592   -1.0319    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3619   -0.8904    1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796   -1.4558    2.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3978   -0.1688    0.6886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0880   -0.0970    1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8249    0.6995    0.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    1.2970   -0.8273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    2.0228   -1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    2.1727   -1.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    1.5676    0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3851    1.7131    0.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3148    0.7569    0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4668   -0.3628    1.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3842   -1.3342    0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1515   -1.2092   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9801   -0.0651   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0654    0.9179   -0.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    0.8557    0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3761    1.0418   -0.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4199   -0.6375    0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8688    0.7529    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8238    1.2092   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2685    1.6586    1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3577    2.1539   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -0.9085   -1.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2618   -3.2321   -0.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4085   -1.6361    1.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287    0.2775    2.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3454   -1.1384    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4927    1.1770   -1.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2103    2.4927   -2.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5294    2.7361   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495   -0.4452    1.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4786   -2.2029    1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8838   -1.9396   -0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5880    0.0329   -2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9838    1.7805   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4211    0.3979    1.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 26  2  0
  9  2  1  0
 26 14  1  0
 25 20  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  5 34  1  0
  9 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 21 41  1  0
 22 42  1  0
 23 43  1  0
 24 44  1  0
 25 45  1  0
 26 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate	ChEBI
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester	ChEBI
Elimite	Kegg
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylate, (3-phenoxyphenyl) methyl ester	Generator
(m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	MeSH
3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, ester	MeSH
3-Phenoxybenzyl-cis,trans-(1Rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	MeSH
Ambush	MeSH
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester	MeSH
NRDC 143	MeSH
NRDC 147	MeSH
NRDC-143	MeSH
NRDC-147	MeSH
NRDC143	MeSH
NRDC147	MeSH
Nittifor	MeSH
Permethrin, (1R-cis)-isomer	MeSH
Permethrin, (1R-trans)-isomer	MeSH
Permethrin, (1S-cis)-isomer	MeSH
Permethrin, (1S-trans)-isomer	MeSH
Permethrin, (cis)-isomer	MeSH
Permethrin, (cis-(+-))-isomer	MeSH
Permethrin, (trans)-isomer	MeSH
Permethrin, (trans-(+-))-isomer	MeSH
Permethrin, trans-(1Rs)-isomer	MeSH
cis Permethrin	MeSH
cis-(1Rs)-Permethrin	MeSH
cis-Permethrin	MeSH
Permethrin, cis-(1Rs)-isomer	MeSH
trans Permethrin	MeSH
trans-(1Rs)-Permethrin	MeSH
trans-Permethrin	MeSH

Chemical Formula

C₂₁H₂₀Cl₂O₃

Average Molecular Weight

391.288

Monoisotopic Molecular Weight

390.07894992

IUPAC Name

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Traditional Name

permethrin

CAS Registry Number

52645-53-1

SMILES

CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3

InChI Key

RLLPVAHGXHCWKJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Pyrethroids

Alternative Parents

Substituents

Pyrethroid skeleton
Diphenylether
Diaryl ether
Benzyloxycarbonyl
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Cyclopropanecarboxylic acid or derivatives
Benzenoid
Carboxylic acid ester
Ketene acetal or derivatives
Carboxylic acid derivative
Chloroalkene
Haloalkene
Ether
Vinyl halide
Monocarboxylic acid or derivatives
Vinyl chloride
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:34911 )
cyclopropanecarboxylate ester (CHEBI:34911 )
a monoterpenoid (CPD-13115 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

extracellular (HMDB: HMDB0015604)
Membrane (HMDB: HMDB0015604)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

agrochemical (HMDB: HMDB0015604)
pyrethroid ester acaricide (HMDB: HMDB0015604)
scabicide (HMDB: HMDB0015604)

Agriculture

Pesticide

Insecticide

pyrethroid ester insecticide (HMDB: HMDB0015604)
ectoparasiticide (HMDB: HMDB0015604)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	34 °C	Not Available
Boiling Point	465.90 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6.9e-05 g/L	Not Available
LogP	6.50	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.9e-05 g/L	ALOGPS
logP	6.24	ALOGPS
logP	5.7	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.28 m³·mol⁻¹	ChemAxon
Polarizability	39.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	186.25	30932474
DeepCCS	[M-H]-	183.892	30932474
DeepCCS	[M-2H]-	218.139	30932474
DeepCCS	[M+Na]+	193.985	30932474
AllCCS	[M+H]+	189.1	32859911
AllCCS	[M+H-H2O]+	186.5	32859911
AllCCS	[M+NH4]+	191.5	32859911
AllCCS	[M+Na]+	192.2	32859911
AllCCS	[M-H]-	184.6	32859911
AllCCS	[M+Na-2H]-	184.0	32859911
AllCCS	[M+HCOO]-	183.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Permethrin	CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1	3814.6	Standard polar	33892256
Permethrin	CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1	2655.5	Standard non polar	33892256
Permethrin	CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1	2650.3	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 - Permethrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-3900000000-469dc103f8f391a6bb7f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Permethrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Permethrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Permethrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Permethrin 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 - Permethrin LC-ESI-QFT , positive-QTOF	splash10-0002-1900000000-956860faa94e3dea2ee2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin LC-ESI-QFT , positive-QTOF	splash10-0002-1900000000-ce2901f0a3049806d95f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin LC-ESI-QFT , positive-QTOF	splash10-0002-1900000000-b5846ca870454df7f44f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin LC-ESI-QFT , positive-QTOF	splash10-0002-0900000000-474995c2ccb155f0975c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin LC-ESI-QFT , positive-QTOF	splash10-0002-1900000000-261c3708f1e50c4a8418	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin LC-ESI-QFT , positive-QTOF	splash10-006t-2900000000-4915b2e2cee108c117a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin 60V, Positive-QTOF	splash10-0002-0900000000-a73154cdccdc124955c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin 75V, Positive-QTOF	splash10-0002-1900000000-2f9800db80661116530a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin 45V, Positive-QTOF	splash10-0002-1900000000-bf65bfc29edf7e8f72d6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin 30V, Positive-QTOF	splash10-0002-1900000000-91cb4c87ae286d88f203	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Permethrin 15V, Positive-QTOF	splash10-0002-1900000000-2546d86434c241ad989e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 10V, Positive-QTOF	splash10-0006-0519000000-0f6eb9a687fe3c0d66c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 20V, Positive-QTOF	splash10-0006-1923000000-a400c6833ac566d7a622	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 40V, Positive-QTOF	splash10-052e-2900000000-7758be41aece58f5d5d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 10V, Negative-QTOF	splash10-000i-0109000000-fdac422c546f05b83ceb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 20V, Negative-QTOF	splash10-000i-1709000000-f755eb7d0bee859d0bb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 40V, Negative-QTOF	splash10-0006-9500000000-97e9860533a91746241d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 10V, Positive-QTOF	splash10-0536-0429000000-98939aa3532b9312d6ac	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 20V, Positive-QTOF	splash10-001i-2923000000-0cd57653df5af5d7ac42	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 40V, Positive-QTOF	splash10-001l-8911000000-9f85adb3775c89af21a5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 10V, Negative-QTOF	splash10-000i-0119000000-eda907ff628cd2b35844	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 20V, Negative-QTOF	splash10-03ki-1902000000-84bc834f9310543ce7d7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Permethrin 40V, Negative-QTOF	splash10-0006-9211000000-bcaffb823cfb3efededa	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB04930	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04930	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04930

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

36845

KEGG Compound ID

C14388

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Permethrin

METLIN ID

Not Available

PubChem Compound

40326

PDB ID

Not Available

ChEBI ID

34911

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1338011

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Abedin S, Narang M, Gandhi V, Narang S: Efficacy of permethrin cream and oral ivermectin in treatment of scabies. Indian J Pediatr. 2007 Oct;74(10):915-6. [PubMed:17978449 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Sodium channel protein type 1 subunit alpha

General function:: Involved in ion channel activity
Specific function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
Gene Name:: SCN1A
Uniprot ID:: P35498
Molecular weight:: 228969.5

References

Cao Z, Shafer TJ, Murray TF: Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons. J Pharmacol Exp Ther. 2011 Jan;336(1):197-205. doi: 10.1124/jpet.110.171850. Epub 2010 Sep 29. [PubMed:20881019 ]
Liu N, Xu Q, Li T, He L, Zhang L: Permethrin resistance and target site insensitivity in the mosquito Culex quinquefasciatus in Alabama. J Med Entomol. 2009 Nov;46(6):1424-9. [PubMed:19960691 ]
Breckenridge CB, Holden L, Sturgess N, Weiner M, Sheets L, Sargent D, Soderlund DM, Choi JS, Symington S, Clark JM, Burr S, Ray D: Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides. Neurotoxicology. 2009 Nov;30 Suppl 1:S17-31. doi: 10.1016/j.neuro.2009.09.002. Epub 2009 Sep 18. [PubMed:19766671 ]
Chang C, Shen WK, Wang TT, Lin YH, Hsu EL, Dai SM: A novel amino acid substitution in a voltage-gated sodium channel is associated with knockdown resistance to permethrin in Aedes aegypti. Insect Biochem Mol Biol. 2009 Apr;39(4):272-8. doi: 10.1016/j.ibmb.2009.01.001. Epub 2009 Jan 10. [PubMed:19171193 ]
McMahon C, Krober T, Guerin PM: In vitro assays for repellents and deterrents for ticks: differing effects of products when tested with attractant or arrestment stimuli. Med Vet Entomol. 2003 Dec;17(4):370-8. [PubMed:14651650 ]

Showing metabocard for Permethrin (HMDB0015604)

MOL for HMDB0015604 (Permethrin)

3D MOL for HMDB0015604 (Permethrin)

3D SDF for HMDB0015604 (Permethrin)

3D-SDF for HMDB0015604 (Permethrin)

PDB for HMDB0015604 (Permethrin)

3D PDB for HMDB0015604 (Permethrin)

SMILES for HMDB0015604 (Permethrin)

INCHI for HMDB0015604 (Permethrin)

Structure for HMDB0015604 (Permethrin)

3D Structure for HMDB0015604 (Permethrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References