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 08:03:14 UTC

Update Date

2021-09-26 23:02:37 UTC

HMDB ID

HMDB0250897

Secondary Accession Numbers

None

Metabolite Identification

Common Name

1,1-Bis(p-chlorophenyl)-2-chloroethene

Description

1-chloro-2,2-bis(4'-chlorophenyl)ethylene, also known as DDMU or 1,1-bis(4-chlorophenyl)-2-chloroethylene, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 1-chloro-2,2-bis(4'-chlorophenyl)ethylene exists in all living organisms, ranging from bacteria to humans. Based on a literature review very few articles have been published on 1-chloro-2,2-bis(4'-chlorophenyl)ethylene. This compound has been identified in human blood as reported by (PMID: 31557052 ). 1,1-bis(p-chlorophenyl)-2-chloroethene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 1,1-Bis(p-chlorophenyl)-2-chloroethene 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

 
  Mrv1533006041521352D          
 
 17 18  0  0  0  0            999 V2000
   14.6999   -9.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4144  -10.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9853  -10.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6999   -8.8832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4144  -10.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1324   -9.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9853  -10.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2707   -9.7082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9853   -8.4690    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.1324  -11.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8435  -10.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2707  -11.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5562  -10.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8435  -10.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5562  -10.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5615  -11.3618    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8382  -11.3583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  2  0  0  0  0
  8 13  1  0  0  0  0
 10 14  2  0  0  0  0
 12 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250897

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H9Cl3/c15-9-14(10-1-5-12(16)6-2-10)11-3-7-13(17)8-4-11/h1-9H

> <INCHI_KEY>
LNKQQZFLNUVWQQ-UHFFFAOYSA-N

> <FORMULA>
C14H9Cl3

> <MOLECULAR_WEIGHT>
283.58

> <EXACT_MASS>
281.9769834

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
28.4838190036414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-chloro-4-[2-chloro-1-(4-chlorophenyl)ethenyl]benzene

> <ALOGPS_LOGP>
6.04

> <JCHEM_LOGP>
5.6684333413333325

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
83.70819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
TDEE

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-15         0                                  
HETATM    1  C   UNK     0      27.440 -18.122   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.774 -18.895   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.106 -18.889   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.440 -16.582   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.774 -20.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.114 -18.122   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.106 -20.435   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.772 -18.122   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      26.106 -15.809   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0      30.114 -21.209   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.441 -18.895   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.772 -21.202   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.438 -18.889   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.441 -20.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.438 -20.435   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      32.781 -21.209   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0      22.098 -21.202   0.000  0.00  0.00          Cl+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13                                                       
CONECT    9    4                                                            
CONECT   10    5   14                                                       
CONECT   11    6   14                                                       
CONECT   12    7   15                                                       
CONECT   13    8   15                                                       
CONECT   14   10   16   11                                                  
CONECT   15   12   17   13                                                  
CONECT   16   14                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0250897
HETATM    1 CL1  UNL     1       1.012  -2.657  -2.584  1.00  0.00          CL  
HETATM    2  C1  UNL     1      -0.225  -1.842  -1.669  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.071  -0.890  -0.797  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.210  -0.313  -0.408  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.357   0.949   0.102  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.545   1.494   0.564  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.687   0.729   0.517  1.00  0.00           C  
HETATM    8 CL2  UNL     1       5.177   1.420   1.100  1.00  0.00          CL  
HETATM    9  C7  UNL     1       3.596  -0.539   0.015  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.388  -1.069  -0.444  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.287  -0.340  -0.161  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.267   0.302   1.063  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.417   0.897   1.602  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.593   0.832   0.885  1.00  0.00           C  
HETATM   15 CL3  UNL     1      -5.035   1.579   1.564  1.00  0.00          CL  
HETATM   16  C13 UNL     1      -3.609   0.190  -0.332  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.473  -0.401  -0.873  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.240  -2.220  -1.869  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.511   1.627   0.122  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.578   2.516   0.961  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.515  -1.141  -0.018  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.442  -2.074  -0.795  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.364   0.303   1.630  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.353   1.381   2.546  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.528   0.139  -0.890  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.555  -0.872  -1.832  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    3   18
CONECT    3    4   11
CONECT    4    5    5   10
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8    9
CONECT    9   10   10   21
CONECT   10   22
CONECT   11   12   12   17
CONECT   12   13   23
CONECT   13   14   14   24
CONECT   14   15   16
CONECT   16   17   17   25
CONECT   17   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,1-Bis(4-chlorophenyl)-2-chloroethylene	ChEBI
1,1-Bis(p-chlorophenyl)-2-chloroethene	ChEBI
1,1-Bis(p-chlorophenyl)-2-chloroethylene	ChEBI
1-Chloro-2,2-bis(p-chlorophenyl)ethylene	ChEBI
2,2-Bis(4-chlorophenyl)-1-chloroethylene	ChEBI
2,2-Bis(p-chlorophenyl)-1-chloroethylene	ChEBI
4,4'-DDMU	ChEBI
DDMU	ChEBI
1,1-Dichloro-2,2-bis(p-chlorophenyl)ethylene	MeSH
DDE	MeSH
DDX	MeSH
Dichlorodiphenyl dichloroethylene	MeSH
Dichloroethylene, dichlorodiphenyl	MeSH
p,P'-dde	MeSH
p,p-Dichlorodiphenyldichloroethylene	MeSH

Chemical Formula

C₁₄H₉Cl₃

Average Molecular Weight

283.58

Monoisotopic Molecular Weight

281.9769834

IUPAC Name

1-chloro-4-[2-chloro-1-(4-chlorophenyl)ethenyl]benzene

Traditional Name

TDEE

CAS Registry Number

Not Available

SMILES

ClC=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C14H9Cl3/c15-9-14(10-1-5-12(16)6-2-10)11-3-7-13(17)8-4-11/h1-9H

InChI Key

LNKQQZFLNUVWQQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Styrene
Halobenzene
Chlorobenzene
Aryl halide
Aryl chloride
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Hydrocarbon derivative
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:27454 )
chlorophenylethylene (CHEBI:27454 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.04	ALOGPS
logP	5.67	ChemAxon
logS	-6.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.71 m³·mol⁻¹	ChemAxon
Polarizability	28.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.175	30932474
DeepCCS	[M-H]-	159.779	30932474
DeepCCS	[M-2H]-	192.663	30932474
DeepCCS	[M+Na]+	168.215	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	160.3	32859911
AllCCS	[M+Na]+	161.3	32859911
AllCCS	[M-H]-	146.8	32859911
AllCCS	[M+Na-2H]-	146.3	32859911
AllCCS	[M+HCOO]-	145.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,1-Bis(p-chlorophenyl)-2-chloroethene	ClC=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1	2949.9	Standard polar	33892256
1,1-Bis(p-chlorophenyl)-2-chloroethene	ClC=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1	2064.1	Standard non polar	33892256
1,1-Bis(p-chlorophenyl)-2-chloroethene	ClC=C(C1=CC=C(Cl)C=C1)C1=CC=C(Cl)C=C1	2121.8	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 - 1,1-Bis(p-chlorophenyl)-2-chloroethene GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-0190000000-2c3394f3ee1701330e94	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 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 - 1,1-Bis(p-chlorophenyl)-2-chloroethene 10V, Positive-QTOF	splash10-001i-0090000000-3d7f09dd5e6f1da345ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 20V, Positive-QTOF	splash10-001i-0090000000-8eac035433437ddc6d8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 40V, Positive-QTOF	splash10-03e9-1950000000-e230aeaf26d2c236e4a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 10V, Negative-QTOF	splash10-001i-0090000000-9cc9e0b22de9971e326a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 20V, Negative-QTOF	splash10-001i-0090000000-9aa046cd089b5258e078	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 40V, Negative-QTOF	splash10-03di-0940000000-38c18c0785d1f847193d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 10V, Positive-QTOF	splash10-001i-0090000000-347bcd33c858233787ed	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 20V, Positive-QTOF	splash10-001j-0090000000-04809db950e115d78e0c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 40V, Positive-QTOF	splash10-0002-0190000000-825b839f461d341cb1f4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 10V, Negative-QTOF	splash10-001i-0090000000-8e4db2f8999b4f14896f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 20V, Negative-QTOF	splash10-001i-0090000000-8e4db2f8999b4f14896f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Bis(p-chlorophenyl)-2-chloroethene 40V, Negative-QTOF	splash10-01q9-1590000000-92d4e68c2646a0e54454	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

88946

KEGG Compound ID

C06637

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

98491

PDB ID

Not Available

ChEBI ID

27454

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 1,1-Bis(p-chlorophenyl)-2-chloroethene (HMDB0250897)

MOL for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

3D MOL for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

3D SDF for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

3D-SDF for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

PDB for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

3D PDB for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

SMILES for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

INCHI for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

Structure for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

3D Structure for HMDB0250897 (1,1-Bis(p-chlorophenyl)-2-chloroethene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra