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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (19) Show 19 proteins XML

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:54:25 UTC

Update Date

2023-02-21 17:29:53 UTC

HMDB ID

HMDB0060333

Secondary Accession Numbers

HMDB60333

Metabolite Identification

Common Name

1,1-Dichloroethylene epoxide

Description

1,1-Dichloroethylene epoxide, also known as DCE epoxide is a compound belonging to the family of compounds known as orthocarboxylic acid derivatives. These are organic compounds containing the orhtocarboxylic acid functional group, with the RC(X)(X)X (R=H, alkyl,aryl; X=OH,alkoxy,aryloxy, (substituted amino), etc. (PMID: 16098521 ). Epoxides are compounds containing a cyclic ether with three ring atoms (one oxygen and two carbon atoms). DCE epoxide is a urinary metabolite of 1,1-Dichloroethene (DCE), or vinylidine chloride (PMID: 15319346 , 11270662 ). DCE is mainly used as a comonomer in the production and polymerization of plastics such as polyvinyl chloride, acrylonitrile, and acrylates. As a result, DCE is widely distributed in the environment and in plastics. DCE was the precursor to the original form of saran-wrap or cling-wrap (clear plastic wrap used to preserve foods), but this has been phased out due to concerns over the carcinogenicity of DCE.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,2-Dichlorooxirane	Kegg

Chemical Formula

C₂H₂Cl₂O

Average Molecular Weight

112.943

Monoisotopic Molecular Weight

111.9482701

IUPAC Name

2,2-dichlorooxirane

Traditional Name

C2H2cl2O

CAS Registry Number

Not Available

SMILES

ClC1(Cl)CO1

InChI Identifier

InChI=1S/C2H2Cl2O/c3-2(4)1-5-2/h1H2

InChI Key

DPVAHOUXGQHEOI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Not Available

Direct Parent

Epoxides

Alternative Parents

Substituents

Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

epoxide (CHEBI:34032 )

Ontology

Not Available

Exogenous (HMDB: HMDB0060333)

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
Water Solubility	22.4 g/L	ALOGPS
logP	0.8	ALOGPS
logP	1.21	ChemAxon
logS	-0.7	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	21.28 m³·mol⁻¹	ChemAxon
Polarizability	8.42 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	123.075	30932474
DeepCCS	[M-H]-	121.216	30932474
DeepCCS	[M-2H]-	156.691	30932474
DeepCCS	[M+Na]+	130.785	30932474
AllCCS	[M+H]+	122.2	32859911
AllCCS	[M+H-H2O]+	117.4	32859911
AllCCS	[M+NH4]+	126.7	32859911
AllCCS	[M+Na]+	128.0	32859911
AllCCS	[M-H]-	125.5	32859911
AllCCS	[M+Na-2H]-	130.1	32859911
AllCCS	[M+HCOO]-	135.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,1-Dichloroethylene epoxide	ClC1(Cl)CO1	1031.3	Standard polar	33892256
1,1-Dichloroethylene epoxide	ClC1(Cl)CO1	626.6	Standard non polar	33892256
1,1-Dichloroethylene epoxide	ClC1(Cl)CO1	653.3	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 - 1,1-Dichloroethylene epoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01u0-9400000000-adfd34ef3b767eec93b2	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,1-Dichloroethylene epoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,1-Dichloroethylene epoxide 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-Dichloroethylene epoxide 10V, Positive-QTOF	splash10-03dl-6900000000-9180c6fa57359c415c83	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Dichloroethylene epoxide 20V, Positive-QTOF	splash10-03di-2900000000-135854f258acd9cf20b5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Dichloroethylene epoxide 40V, Positive-QTOF	splash10-0006-9000000000-86f416fd559cf62f82d4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Dichloroethylene epoxide 10V, Negative-QTOF	splash10-03di-2900000000-f8b0ce5c779f6abb8815	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Dichloroethylene epoxide 20V, Negative-QTOF	splash10-03di-2900000000-00114bde794cfc34523d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,1-Dichloroethylene epoxide 40V, Negative-QTOF	splash10-00di-9000000000-0df652363058e3bd6bdd	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

C14857

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119521

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

M00227

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Feldman HJ, Dumontier M, Ling S, Haider N, Hogue CW: CO: A chemical ontology for identification of functional groups and semantic comparison of small molecules. FEBS Lett. 2005 Aug 29;579(21):4685-91. doi: 10.1016/j.febslet.2005.07.039. [PubMed:16098521 ]
Simmonds AC, Reilly CA, Baldwin RM, Ghanayem BI, Lanza DL, Yost GS, Collins KS, Forkert PG: Bioactivation of 1,1-dichloroethylene to its epoxide by CYP2E1 and CYP2F enzymes. Drug Metab Dispos. 2004 Sep;32(9):1032-9. [PubMed:15319346 ]
Forkert PG: Mechanisms of 1,1-dichloroethylene-induced cytotoxicity in lung and liver. Drug Metab Rev. 2001 Feb;33(1):49-80. doi: 10.1081/dmr-100000140. [PubMed:11270662 ]

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Glutathione S-transferase Mu 2

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTM2
Uniprot ID:: P28161
Molecular weight:: 25744.395

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

2. Glutathione S-transferase Mu 1

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTM1
Uniprot ID:: P09488
Molecular weight:: 25711.555

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

3. Glutathione S-transferase kappa 1

General function:: Involved in protein disulfide oxidoreductase activity
Specific function:: Significant glutathione conjugating activity is found only with the model substrate, 1-chloro-2,4-dinitrobenzene (CDNB).
Gene Name:: GSTK1
Uniprot ID:: Q9Y2Q3
Molecular weight:: 31565.605

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

4. Microsomal glutathione S-transferase 3

General function:: Involved in glutathione transferase activity
Specific function:: Also functions as a glutathione peroxidase.
Gene Name:: MGST3
Uniprot ID:: O14880
Molecular weight:: 16516.185

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

5. Glutathione S-transferase Mu 3

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May govern uptake and detoxification of both endogenous compounds and xenobiotics at the testis and brain blood barriers.
Gene Name:: GSTM3
Uniprot ID:: P21266
Molecular weight:: 26559.32

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

6. Glutathione S-transferase A1

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTA1
Uniprot ID:: P08263
Molecular weight:: 25630.785

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

7. Microsomal glutathione S-transferase 1

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Has a wide substrate specificity.
Gene Name:: MGST1
Uniprot ID:: P10620
Molecular weight:: 17598.45

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

8. Glutathione S-transferase Mu 4

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Active on 1-chloro-2,4-dinitrobenzene.
Gene Name:: GSTM4
Uniprot ID:: Q03013
Molecular weight:: 25561.095

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

9. Glutathione S-transferase Mu 5

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTM5
Uniprot ID:: P46439
Molecular weight:: 25674.455

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Enzyme Details

10. Microsomal glutathione S-transferase 2

General function:: Involved in enzyme activator activity
Specific function:: Can catalyze the production of LTC4 from LTA4 and reduced glutathione. Can catalyze the conjugation of 1-chloro-2,4-dinitrobenzene with reduced glutathione.
Gene Name:: MGST2
Uniprot ID:: Q99735
Molecular weight:: 16620.4

Reactions

1,1-Dichloroethylene epoxide + Glutathione → 2-(S-Glutathionyl)acetyl chloride + Hydrochloric acid	details

Only showing the first 10 proteins. There are 19 proteins in total.

Show all enzymes and transporters

Showing metabocard for 1,1-Dichloroethylene epoxide (HMDB0060333)

MOL for HMDB0060333 (1,1-Dichloroethylene epoxide)

3D MOL for HMDB0060333 (1,1-Dichloroethylene epoxide)

3D SDF for HMDB0060333 (1,1-Dichloroethylene epoxide)

3D-SDF for HMDB0060333 (1,1-Dichloroethylene epoxide)

PDB for HMDB0060333 (1,1-Dichloroethylene epoxide)

3D PDB for HMDB0060333 (1,1-Dichloroethylene epoxide)

SMILES for HMDB0060333 (1,1-Dichloroethylene epoxide)

INCHI for HMDB0060333 (1,1-Dichloroethylene epoxide)

Structure for HMDB0060333 (1,1-Dichloroethylene epoxide)

3D Structure for HMDB0060333 (1,1-Dichloroethylene epoxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

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