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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:54:28 UTC

Update Date

2022-03-07 03:17:43 UTC

HMDB ID

HMDB0060334

Secondary Accession Numbers

HMDB60334

Metabolite Identification

Common Name

1,2-Dibromoethane

Description

1,2-Dibromoethane, also known as ethylene dibromide or DBE, belongs to the class of organic compounds known as organobromides. Organobromides are compounds containing a chemical bond between a carbon atom and a bromine atom. 1,2-Dibromoethane is possibly neutral. Trace amounts of 1,2-dibromoethane occur naturally in the ocean, where it is formed probably by algae and kelp. 1,2-Dibromoethane is formally rated as a probable carcinogen (by IARC 2A) and is also a potentially toxic compound. Breathing high levels may cause depression and collapse. 1,2-Dibromoethane is rapidly absorbed by ingestion, inhalation, and dermal routes, then distributed mainly to the kidneys, liver, and spleen. It can be metabolized by either the cytochrome P-450 system or the glutathione S-transferase system. These metabolites may be further broken down and excreted in the urine. The metabolite 2-bromoacetaldehyde produces liver damage by binding to cellular proteins. Long term exposure can result in liver, kidney, and reproductive system damage. 1,2-Dibromoethane is also known to have adverse effects on the brain. S-(2-bromoethyl)glutathione, another metabolite, exerts genotoxic and carcinogenic effects by binding to DNA.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha,beta-Dibromoethane	ChEBI
alpha,Omega-dibromoethane	ChEBI
DBE	ChEBI
EDB	ChEBI
Ethylene bromide	ChEBI
Ethylene dibromide	ChEBI
Sym-dibromoethane	ChEBI
a,b-Dibromoethane	Generator
Α,β-dibromoethane	Generator
a,Omega-dibromoethane	Generator
Α,omega-dibromoethane	Generator
Bromide, ethylene	HMDB
Dibromide, ethylene	HMDB
Dibromides, ethylene	HMDB
Dowfume W 85	HMDB
Dowfume w85	HMDB
Ethylene dibromides	HMDB
1,2 Dibromoethane	HMDB
Sym dibromoethane	HMDB
Carboxylic acid	Generator
Carboxylic acid	Generator

Chemical Formula

C₂H₄Br₂

Average Molecular Weight

187.861

Monoisotopic Molecular Weight

185.867975422

IUPAC Name

1,2-dibromoethane

Traditional Name

dibromoethane

CAS Registry Number

Not Available

SMILES

BrCCBr

InChI Identifier

InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2

InChI Key

PAAZPARNPHGIKF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organobromides. Organobromides are compounds containing a chemical bond between a carbon atom and a bromine atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Organobromides

Sub Class

Not Available

Direct Parent

Organobromides

Alternative Parents

Substituents

Hydrocarbon derivative
Organobromide
Alkyl halide
Alkyl bromide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

bromoalkane (CHEBI:28534 )
a bromide (12-DIBROMOETHANE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0060334)
Extracellular (HMDB: HMDB0060334)

Source

Exogenous

Exogenous (HMDB: HMDB0060334)

Process

Not Available

Role

Biological role

Industrial application

Agriculture

Pesticide

Fumigant (HMDB: HMDB0060334)

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	3.06 g/L	ALOGPS
logP	2.08	ALOGPS
logP	1.87	ChemAxon
logS	-1.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.62 m³·mol⁻¹	ChemAxon
Polarizability	10.74 Å³	ChemAxon
Number of Rings	0	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]+	120.184	30932474
DeepCCS	[M-H]-	118.308	30932474
DeepCCS	[M-2H]-	153.657	30932474
DeepCCS	[M+Na]+	127.622	30932474
AllCCS	[M+H]+	137.8	32859911
AllCCS	[M+H-H2O]+	133.8	32859911
AllCCS	[M+NH4]+	141.4	32859911
AllCCS	[M+Na]+	142.5	32859911
AllCCS	[M-H]-	186.2	32859911
AllCCS	[M+Na-2H]-	192.9	32859911
AllCCS	[M+HCOO]-	200.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	4.66 minutes	32390414
Predicted by Siyang on May 30, 2022	15.7119 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1642.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	656.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	261.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	507.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	594.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	700.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	716.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1264.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	448.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1252.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	503.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	510.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	813.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	503.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	257.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dibromoethane	BrCCBr	1219.0	Standard polar	33892256
1,2-Dibromoethane	BrCCBr	778.5	Standard non polar	33892256
1,2-Dibromoethane	BrCCBr	819.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 1,2-Dibromoethane EI-B (Non-derivatized)	splash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dibromoethane EI-B (Non-derivatized)	splash10-0a6r-5900000000-0f8e5929b65c18ffe174	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dibromoethane EI-B (Non-derivatized)	splash10-0a4i-0900000000-2ee3f4bc49d4cb3289c7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 1,2-Dibromoethane EI-B (Non-derivatized)	splash10-0a6r-5900000000-0f8e5929b65c18ffe174	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dibromoethane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-3900000000-703ca88896dc7f353fc6	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dibromoethane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dibromoethane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a6r-7900000000-505389611033d5f531b3	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dibromoethane 10V, Positive-QTOF	splash10-000i-0900000000-9059cc10a7a8eb687fac	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dibromoethane 20V, Positive-QTOF	splash10-000i-0900000000-ee5e7d28ff43cd849c39	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dibromoethane 40V, Positive-QTOF	splash10-0a4i-0900000000-2578b34097bd653c4d1b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dibromoethane 10V, Negative-QTOF	splash10-001i-0900000000-51a6eb4c9e7aa0216f9b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dibromoethane 20V, Negative-QTOF	splash10-001i-0900000000-541ce06a61a5a4e27f0a	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dibromoethane 40V, Negative-QTOF	splash10-0udi-0900000000-c16dec5f28cf43cf1857	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

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

C11088

BioCyc ID

12-DIBROMOETHANE

BiGG ID

Not Available

Wikipedia Link

1,2-Dibromoethane

METLIN ID

Not Available

PubChem Compound

7839

PDB ID

Not Available

ChEBI ID

28534

Food Biomarker Ontology

Not Available

VMH ID

M00242

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 ]

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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	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

1,2-Dibromoethane + Glutathione + Hydrogen Ion → Glutathione episulfonium ion + Bromide	details

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

Show all enzymes and transporters

Showing metabocard for 1,2-Dibromoethane (HMDB0060334)

MOL for HMDB0060334 (1,2-Dibromoethane)

3D MOL for HMDB0060334 (1,2-Dibromoethane)

3D SDF for HMDB0060334 (1,2-Dibromoethane)

3D-SDF for HMDB0060334 (1,2-Dibromoethane)

PDB for HMDB0060334 (1,2-Dibromoethane)

3D PDB for HMDB0060334 (1,2-Dibromoethane)

SMILES for HMDB0060334 (1,2-Dibromoethane)

INCHI for HMDB0060334 (1,2-Dibromoethane)

Structure for HMDB0060334 (1,2-Dibromoethane)

3D Structure for HMDB0060334 (1,2-Dibromoethane)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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