Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:20:43 UTC

Update Date

2021-09-26 23:01:45 UTC

HMDB ID

HMDB0250340

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Clofentezine

Description

Clofentezine, also known as bisclofentazin or apollo, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. It acts primarily as an ovicide, with some activity on early motile stages. Clofentezine does not pose a high toxicity risk to humans. Clofentezine is an extremely weak basic (essentially neutral) compound (based on its pKa). Clofentezine is a potentially toxic compound. Used on a wide range of crops – apples, pears, stone fruit, nuts, ornamentals, almonds etc. Clofentezine is an acaricide used for the residual control of mites. However, there is an increase of incidences of thyroid adenomas, adenocarcinomas, thyroid hyperplasia, agglomeration of colloid and thyroid hormones in rats receiving prolonged treatment of high dose of clofentezine. The main toxicological effects seen in studies in rats and dogs were hepatotoxicity and changes to the thyroid, including follicular hyperplasia. The examination also included tests for hearing, lung function, urine analysis and blood tests when these were considered appropriate. The medical examination included an extensive physical examination (including height, body weight, skin, ear, nose and throat, and respiratory, nervous, alimentary, reticulo-endothelial and cardiovascular systems, and locomotion) and specific tests for blood pressure and vision. This compound has been identified in human blood as reported by (PMID: 31557052 ). Clofentezine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Clofentezine 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


  Mrv1652307282022232D          

 20 22  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 Cl  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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
   -1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 N   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
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250340

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=CC=CC=C1C1=NN=C(N=N1)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C14H8Cl2N4/c15-11-7-3-1-5-9(11)13-17-19-14(20-18-13)10-6-2-4-8-12(10)16/h1-8H

> <INCHI_KEY>
UXADOQPNKNTIHB-UHFFFAOYSA-N

> <FORMULA>
C14H8Cl2N4

> <MOLECULAR_WEIGHT>
303.146

> <EXACT_MASS>
302.01260169

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
29.020642375683046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
bis(2-chlorophenyl)-1,2,4,5-tetrazine

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
4.152542678666666

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.6209100129222485

> <JCHEM_POLAR_SURFACE_AREA>
51.56

> <JCHEM_REFRACTIVITY>
103.8588

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clofentezine

> <JCHEM_VEBER_RULE>
0

$$$$

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 Cl   UNK     0       1.334  -5.390   0.000  0.00  0.00          Cl+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.667  -7.700   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -4.001  -6.930   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      -1.334  -5.390   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -4.001  -2.310   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0250340
HETATM    1 CL1  UNL     1       2.614   2.617   0.643  1.00  0.00          CL  
HETATM    2  C1  UNL     1       3.507   1.118   0.441  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.882   1.144   0.528  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.594  -0.020   0.372  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.922  -1.191   0.133  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.549  -1.197   0.050  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.804  -0.053   0.200  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.342  -0.055   0.113  1.00  0.00           C  
HETATM    9  N1  UNL     1       0.669  -1.194  -0.120  1.00  0.00           N  
HETATM   10  N2  UNL     1      -0.668  -1.157  -0.194  1.00  0.00           N  
HETATM   11  C8  UNL     1      -1.362  -0.016  -0.041  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.811  -0.003  -0.125  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.473  -1.179  -0.364  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.858  -1.248  -0.458  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.576  -0.080  -0.302  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.902   1.110  -0.060  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.525   1.159   0.030  1.00  0.00           C  
HETATM   18 CL2  UNL     1      -2.732   2.696   0.339  1.00  0.00          CL  
HETATM   19  N3  UNL     1      -0.679   1.119   0.193  1.00  0.00           N  
HETATM   20  N4  UNL     1       0.647   1.077   0.264  1.00  0.00           N  
HETATM   21  H1  UNL     1       5.416   2.065   0.716  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.660  -0.021   0.435  1.00  0.00           H  
HETATM   23  H3  UNL     1       5.485  -2.126   0.008  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.012  -2.138  -0.141  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.960  -2.139  -0.497  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.368  -2.178  -0.646  1.00  0.00           H  
HETATM   27  H7  UNL     1      -6.658  -0.096  -0.369  1.00  0.00           H  
HETATM   28  H8  UNL     1      -5.531   1.986   0.052  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3    7
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   23
CONECT    6    7    7   24
CONECT    7    8
CONECT    8    9    9   20
CONECT    9   10
CONECT   10   11   11
CONECT   11   12   19
CONECT   12   13   13   17
CONECT   13   14   25
CONECT   14   15   15   26
CONECT   15   16   27
CONECT   16   17   17   28
CONECT   17   18
CONECT   19   20   20
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,6-Bis(O-chlorophenyl)-1,2,4,5-tetrazine	ChEBI
Apollo	ChEBI
Bisclofentazin	ChEBI
Bisclofentazine	ChEBI
3,6-Bis(2-chlorophenyl)-1,2,4,5-tetrazine	MeSH
Bisclofentezin	MeSH

Chemical Formula

C₁₄H₈Cl₂N₄

Average Molecular Weight

303.146

Monoisotopic Molecular Weight

302.01260169

IUPAC Name

bis(2-chlorophenyl)-1,2,4,5-tetrazine

Traditional Name

clofentezine

CAS Registry Number

Not Available

SMILES

ClC1=CC=CC=C1C1=NN=C(N=N1)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C14H8Cl2N4/c15-11-7-3-1-5-9(11)13-17-19-14(20-18-13)10-6-2-4-8-12(10)16/h1-8H

InChI Key

UXADOQPNKNTIHB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Tetrazine
Aryl halide
Aryl chloride
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:39315 )
ring assembly (CHEBI:39315 )
organochlorine acaricide (CHEBI:39315 )
Pesticides (C18576 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Cellular substructure

Membrane (HMDB: HMDB0250340)

Process

Not Available

Role

Industrial application

Agriculture

Growth agent

mite growth regulator (HMDB: HMDB0250340)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

tetrazine acaricide (HMDB: HMDB0250340)

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	3.4	ALOGPS
logP	4.15	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.86 m³·mol⁻¹	ChemAxon
Polarizability	29.02 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	159.363	30932474
DeepCCS	[M-H]-	156.988	30932474
DeepCCS	[M-2H]-	189.873	30932474
DeepCCS	[M+Na]+	165.439	30932474
AllCCS	[M+H]+	164.6	32859911
AllCCS	[M+H-H2O]+	161.1	32859911
AllCCS	[M+NH4]+	167.8	32859911
AllCCS	[M+Na]+	168.8	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	159.1	32859911
AllCCS	[M+HCOO]-	158.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clofentezine	ClC1=CC=CC=C1C1=NN=C(N=N1)C1=CC=CC=C1Cl	3497.4	Standard polar	33892256
Clofentezine	ClC1=CC=CC=C1C1=NN=C(N=N1)C1=CC=CC=C1Cl	2370.2	Standard non polar	33892256
Clofentezine	ClC1=CC=CC=C1C1=NN=C(N=N1)C1=CC=CC=C1Cl	2581.8	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 - Clofentezine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clofentezine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 10V, Positive-QTOF	splash10-0udi-0009000000-d220243ff8b5138ff824	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 20V, Positive-QTOF	splash10-0udi-0009000000-fcadec4c8a6f9a65a53c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 40V, Positive-QTOF	splash10-0udi-2029000000-2685aaac0dd41b2dc351	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 10V, Negative-QTOF	splash10-0udi-0009000000-c5e3262bb5e4d5d156ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 20V, Negative-QTOF	splash10-0udi-0009000000-b515553871be1b93cf5e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 40V, Negative-QTOF	splash10-0udi-0159000000-29ce81bd30d833922e4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 10V, Positive-QTOF	splash10-0udi-0019000000-1d055bbed57f3855c654	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 20V, Positive-QTOF	splash10-0udi-0009000000-81653b4efc705ac4d11f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 40V, Positive-QTOF	splash10-0udi-0195000000-4107a63322ff2f2f8391	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 10V, Negative-QTOF	splash10-0udi-0009000000-bf3df37cdb42b506ae32	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 20V, Negative-QTOF	splash10-0udi-0009000000-bf3df37cdb42b506ae32	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clofentezine 40V, Negative-QTOF	splash10-0udi-0029000000-11cad6c233fe93118e97	2021-10-12	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

Not Available

KEGG Compound ID

C18576

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73670

PDB ID

Not Available

ChEBI ID

39315

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Clofentezine (HMDB0250340)

MOL for HMDB0250340 (Clofentezine)

3D MOL for HMDB0250340 (Clofentezine)

3D SDF for HMDB0250340 (Clofentezine)

3D-SDF for HMDB0250340 (Clofentezine)

PDB for HMDB0250340 (Clofentezine)

3D PDB for HMDB0250340 (Clofentezine)

SMILES for HMDB0250340 (Clofentezine)

INCHI for HMDB0250340 (Clofentezine)

Structure for HMDB0250340 (Clofentezine)

3D Structure for HMDB0250340 (Clofentezine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra