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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:44:43 UTC

Update Date

2023-02-21 17:27:53 UTC

HMDB ID

HMDB0040207

Secondary Accession Numbers

HMDB40207

Metabolite Identification

Common Name

Ethyl hydrogen fumarate

Description

Ethyl hydrogen fumarate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on Ethyl hydrogen fumarate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl hydrogen fumaric acid	Generator
(2E)-4-Ethoxy-4-oxo-2-butenoic acid	HMDB
2-Butenedioic acid (e)-, monoethyl ester	HMDB
Fumaric acid monoethyl ester	HMDB
Monoethyl fumarate	HMDB
Potassium ethyl fumarate	HMDB
Ethyl hydrogen maleate	MeSH
Diethyl maleate	MeSH
Diethyl maleic acid diester	MeSH
Ethyl maleate	MeSH
Maleic acid diethyl ester	MeSH
Maleic acid, ethyl ester	MeSH
Diethylmaleate	MeSH
Monoethyl maleate	MeSH

Chemical Formula

C₆H₈O₄

Average Molecular Weight

144.1253

Monoisotopic Molecular Weight

144.042258744

IUPAC Name

(2Z)-4-ethoxy-4-oxobut-2-enoic acid

Traditional Name

(2Z)-4-ethoxy-4-oxobut-2-enoic acid

CAS Registry Number

2459-05-4

SMILES

CCOC(=O)\C=C/C(O)=O

InChI Identifier

InChI=1S/C6H8O4/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3,(H,7,8)/b4-3-

InChI Key

XLYMOEINVGRTEX-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0040207)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040207)

Source

Endogenous

Endogenous (HMDB: HMDB0040207)

Animal

Animal (HMDB: HMDB0040207)

Exogenous

Food

Food (HMDB: HMDB0040207)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0040207)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0040207)

Cellular process

Cell signaling (HMDB: HMDB0040207)

Biochemical process

Lipid transport (HMDB: HMDB0040207)

Role

Biological role

Energy storage (HMDB: HMDB0040207)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040207)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	66 - 68 °C	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	25.2 g/L	ALOGPS
logP	0.86	ALOGPS
logP	0.7	ChemAxon
logS	-0.76	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	34.12 m³·mol⁻¹	ChemAxon
Polarizability	13.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	131.609	31661259
DarkChem	[M-H]-	126.763	31661259
DeepCCS	[M+H]+	126.563	30932474
DeepCCS	[M-H]-	122.935	30932474
DeepCCS	[M-2H]-	159.761	30932474
DeepCCS	[M+Na]+	135.122	30932474
AllCCS	[M+H]+	132.9	32859911
AllCCS	[M+H-H2O]+	128.8	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.8	32859911
AllCCS	[M-H]-	129.6	32859911
AllCCS	[M+Na-2H]-	131.9	32859911
AllCCS	[M+HCOO]-	134.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ethyl hydrogen fumarate	CCOC(=O)\C=C/C(O)=O	2319.8	Standard polar	33892256
Ethyl hydrogen fumarate	CCOC(=O)\C=C/C(O)=O	1205.9	Standard non polar	33892256
Ethyl hydrogen fumarate	CCOC(=O)\C=C/C(O)=O	1257.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethyl hydrogen fumarate,1TMS,isomer #1	CCOC(=O)/C=C\C(=O)O[Si](C)(C)C	1265.8	Semi standard non polar	33892256
Ethyl hydrogen fumarate,1TBDMS,isomer #1	CCOC(=O)/C=C\C(=O)O[Si](C)(C)C(C)(C)C	1505.4	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 - Ethyl hydrogen fumarate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0092-9000000000-eb17e7385d8add87de15	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl hydrogen fumarate GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-7900000000-75b83d7232ea5a5cd8f9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethyl hydrogen fumarate 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 - Ethyl hydrogen fumarate 10V, Positive-QTOF	splash10-004j-2900000000-bf6448b653c3c620a5e7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 20V, Positive-QTOF	splash10-0002-9200000000-b285533b01fedf776b7e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 40V, Positive-QTOF	splash10-0fb9-9000000000-9b697ef41b8b526f4b64	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 10V, Negative-QTOF	splash10-0005-6900000000-79344665a0da0e9680f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 20V, Negative-QTOF	splash10-0002-9400000000-7ba5363e1bf1d3aa4d53	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 40V, Negative-QTOF	splash10-0f6t-9000000000-a58e9ee3334c12ca9f41	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 10V, Negative-QTOF	splash10-0002-9100000000-8597f839d7c649e71a0a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 20V, Negative-QTOF	splash10-0gi1-9000000000-d576ba5f59716220347c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 40V, Negative-QTOF	splash10-00xs-9000000000-06a99448184870f7a5b0	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 10V, Positive-QTOF	splash10-000t-9100000000-093702f284ef987fe3e8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 20V, Positive-QTOF	splash10-0aba-9000000000-987adc5d33d18745c5a8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethyl hydrogen fumarate 40V, Positive-QTOF	splash10-052f-9000000000-bd3aafd589c3414a6733	2021-09-25	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

IR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB019919

KNApSAcK ID

Not Available

Chemspider ID

4510650

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5354457

PDB ID

Not Available

ChEBI ID

Not Available

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Ethyl hydrogen fumarate (HMDB0040207)

MOL for HMDB0040207 (Ethyl hydrogen fumarate)

3D MOL for HMDB0040207 (Ethyl hydrogen fumarate)

3D SDF for HMDB0040207 (Ethyl hydrogen fumarate)

3D-SDF for HMDB0040207 (Ethyl hydrogen fumarate)

PDB for HMDB0040207 (Ethyl hydrogen fumarate)

3D PDB for HMDB0040207 (Ethyl hydrogen fumarate)

SMILES for HMDB0040207 (Ethyl hydrogen fumarate)

INCHI for HMDB0040207 (Ethyl hydrogen fumarate)

Structure for HMDB0040207 (Ethyl hydrogen fumarate)

3D Structure for HMDB0040207 (Ethyl hydrogen fumarate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra