MiMeDB: Showing metabocard for (-)-trans-permethrin (MMDBc0054016)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:45:56 UTC

Update Date

2022-09-01 02:26:40 UTC

Metabolite ID

MMDBc0054016

Metabolite Identification

Common Name

(-)-trans-permethrin

Description

(-)-trans-permethrin 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 (-)-trans-permethrin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004221607062D          

 28 30  0  0  0  0            999 V2000
    2.3021   -4.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701   -2.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    1.4289    0.8250    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
    2.1434   -0.4125    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
    0.0000    2.4750    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
    3.2704   -3.1895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    4.6993   -4.8395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.8395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537   -2.6061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0610   -2.2615    0.0000 H   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  6  0  0  0
 18 12  2  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  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
 17 27  1  1  0  0  0
 19 28  1  6  0  0  0
M  END


  Mrv1572004221607062D          

 28 30  0  0  0  0            999 V2000
    2.3021   -4.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6701   -2.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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
    1.4289    0.8250    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
    2.1434   -0.4125    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
    0.0000    2.4750    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
    3.2704   -3.1895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9849   -4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    4.6993   -4.8395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -4.8395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537   -2.6061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0610   -2.2615    0.0000 H   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  6  0  0  0
 18 12  2  0  0  0  0
 19 17  1  0  0  0  0
 19 20  1  1  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
 17 27  1  1  0  0  0
 19 28  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054016

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(C=C(Cl)Cl)[C@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C

> <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/t17-,19+/m0/s1

> <INCHI_KEY>
RLLPVAHGXHCWKJ-PKOBYXMFSA-N

> <FORMULA>
C21H20Cl2O3

> <MOLECULAR_WEIGHT>
391.29

> <EXACT_MASS>
390.0789499

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
40.0188181857204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3-phenoxyphenyl)methyl (1S,3R)-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>
114.28240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.91e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
elimite

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       4.297  -7.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.118  -5.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.438  -6.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.105  -5.954   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.438  -8.264   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.565  -5.954   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0       8.772  -9.034   0.000  0.00  0.00          Cl+0
HETATM   23 Cl   UNK     0       6.105  -9.034   0.000  0.00  0.00          Cl+0
HETATM   24  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       7.194  -4.865   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.847  -4.221   0.000  0.00  0.00           H+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   27                                             
CONECT   18   12   22   23                                                  
CONECT   19   17   20   21   28                                             
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                                                       
CONECT   27   17                                                            
CONECT   28   19                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

Synonyms

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

Molecular Formula

C₂₁H₂₀Cl₂O₃

Average Mass

391.29

Monoisotopic Mass

390.0789499

IUPAC Name

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

Traditional Name

elimite

CAS Registry Number

Not Available

SMILES

[H][C@]1(C=C(Cl)Cl)[C@]([H])(C(=O)OCC2=CC(OC3=CC=CC=C3)=CC=C2)C1(C)C

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/t17-,19+/m0/s1

InChI Key

RLLPVAHGXHCWKJ-PKOBYXMFSA-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

trans-permethrin (CHEBI:62523 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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	40.02 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0109000000-fdac422c546f05b83ceb	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1709000000-f755eb7d0bee859d0bb8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-97e9860533a91746241d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0519000000-0f6eb9a687fe3c0d66c4	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1923000000-a400c6833ac566d7a622	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052e-2900000000-7758be41aece58f5d5d1	2016-08-02	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19864

BioCyc ID

CPD-13112

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

40159

PDB ID

Not Available

ChEBI ID

62523

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (-)-trans-permethrin (MMDBc0054016)

MOL for #<Metabolite:0x00007fecc47a60f8>

3D MOL for #<Metabolite:0x00007fecc47a60f8>

3D SDF for #<Metabolite:0x00007fecc47a60f8>

3D-SDF for #<Metabolite:0x00007fecc47a60f8>

PDB for #<Metabolite:0x00007fecc47a60f8>

3D PDB for #<Metabolite:0x00007fecc47a60f8>

SMILES for #<Metabolite:0x00007fecc47a60f8>

INCHI for #<Metabolite:0x00007fecc47a60f8>

Structure for #<Metabolite:0x00007fecc47a60f8>

3D Structure for #<Metabolite:0x00007fecc47a60f8>