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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

2012-09-11 18:34:43 UTC

Update Date

2023-02-21 17:23:38 UTC

HMDB ID

HMDB0033809

Secondary Accession Numbers

HMDB33809

Metabolite Identification

Common Name

Methyl hydrogen fumarate

Description

Methyl 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 Methyl 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
Methyl hydrogen fumaric acid	Generator
(2E)-4-Methoxy-4-oxo-2-butenoic acid	HMDB
2-Butenedioic acid (e)-, monomethyl ester	HMDB
Fumaric acid monomethyl ester	HMDB
Fumaric acid, methyl ester	HMDB
Fumaric acid, monomethyl ester	HMDB
mono-Methyl fumarate	HMDB
Monomethyl fumarate	HMDB

Chemical Formula

C₅H₆O₄

Average Molecular Weight

130.0987

Monoisotopic Molecular Weight

130.02660868

IUPAC Name

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

Traditional Name

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

CAS Registry Number

2756-87-8

SMILES

COC(=O)\C=C/C(O)=O

InChI Identifier

InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2-

InChI Key

NKHAVTQWNUWKEO-IHWYPQMZSA-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
Methyl 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: HMDB0033809)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033809)

Source

Exogenous

Exogenous (HMDB: HMDB0033809)

Food

Food (HMDB: HMDB0033809)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Endogenous (HMDB: HMDB0033809)

Plant

Plant (HMDB: HMDB0033809)

Animal

Animal (HMDB: HMDB0033809)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033809)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033809)

Lipid metabolism pathway (HMDB: HMDB0033809)

Cellular process

Cell signaling (HMDB: HMDB0033809)

Biochemical process

Lipid transport (HMDB: HMDB0033809)

Role

Biological role

Energy source (HMDB: HMDB0033809)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033809)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	144.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	36850 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	40.1 g/L	ALOGPS
logP	0.39	ALOGPS
logP	0.34	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	2.91	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	3	ChemAxon
Refractivity	29.38 m³·mol⁻¹	ChemAxon
Polarizability	11.31 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]+	129.457	31661259
DarkChem	[M-H]-	122.902	31661259
DeepCCS	[M+H]+	121.309	30932474
DeepCCS	[M-H]-	117.841	30932474
DeepCCS	[M-2H]-	154.639	30932474
DeepCCS	[M+Na]+	129.868	30932474
AllCCS	[M+H]+	130.3	32859911
AllCCS	[M+H-H2O]+	126.1	32859911
AllCCS	[M+NH4]+	134.2	32859911
AllCCS	[M+Na]+	135.3	32859911
AllCCS	[M-H]-	125.1	32859911
AllCCS	[M+Na-2H]-	127.8	32859911
AllCCS	[M+HCOO]-	130.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl hydrogen fumarate	COC(=O)\C=C/C(O)=O	2221.0	Standard polar	33892256
Methyl hydrogen fumarate	COC(=O)\C=C/C(O)=O	1149.3	Standard non polar	33892256
Methyl hydrogen fumarate	COC(=O)\C=C/C(O)=O	1189.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl hydrogen fumarate,1TMS,isomer #1	COC(=O)/C=C\C(=O)O[Si](C)(C)C	1193.3	Semi standard non polar	33892256
Methyl hydrogen fumarate,1TBDMS,isomer #1	COC(=O)/C=C\C(=O)O[Si](C)(C)C(C)(C)C	1439.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl hydrogen fumarate EI-B (Non-derivatized)	splash10-0w4i-9200000000-7ecdda048539e621b07d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl hydrogen fumarate EI-B (Non-derivatized)	splash10-0w4i-9200000000-7ecdda048539e621b07d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl hydrogen fumarate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-9100000000-a71e4aca283871539c13	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl hydrogen fumarate GC-MS (1 TMS) - 70eV, Positive	splash10-00dr-9600000000-8efaa5768632c7796b34	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl hydrogen fumarate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 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 - Methyl hydrogen fumarate 10V, Positive-QTOF	splash10-001j-9800000000-ee99c15b22a4380c2247	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 20V, Positive-QTOF	splash10-01qj-9400000000-0ec372c378315e5aedca	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 40V, Positive-QTOF	splash10-0a4i-9000000000-1050121173fb2950a861	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 10V, Negative-QTOF	splash10-004i-6900000000-5f7c980abbdf59d517e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 20V, Negative-QTOF	splash10-004j-9500000000-a9be74a48537ffa1d750	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 40V, Negative-QTOF	splash10-0udj-9000000000-9d252af084e5819ba8ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 10V, Negative-QTOF	splash10-0002-9300000000-54db977ec5b7475bbb34	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 20V, Negative-QTOF	splash10-0uxr-9000000000-3181d15ded39f2fedf50	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 40V, Negative-QTOF	splash10-0v4i-9000000000-702b29335347d8bb1ecb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 10V, Positive-QTOF	splash10-000i-9100000000-62bb6c6140de0869d984	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 20V, Positive-QTOF	splash10-0pbl-9000000000-72597347cc177bae0e65	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl hydrogen fumarate 40V, Positive-QTOF	splash10-0zfr-9000000000-9a7c01bcfdc820a529ee	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB011972

KNApSAcK ID

C00057320

Chemspider ID

4510649

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5354456

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1475371

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 Methyl hydrogen fumarate (HMDB0033809)

MOL for HMDB0033809 (Methyl hydrogen fumarate)

3D MOL for HMDB0033809 (Methyl hydrogen fumarate)

3D SDF for HMDB0033809 (Methyl hydrogen fumarate)

3D-SDF for HMDB0033809 (Methyl hydrogen fumarate)

PDB for HMDB0033809 (Methyl hydrogen fumarate)

3D PDB for HMDB0033809 (Methyl hydrogen fumarate)

SMILES for HMDB0033809 (Methyl hydrogen fumarate)

INCHI for HMDB0033809 (Methyl hydrogen fumarate)

Structure for HMDB0033809 (Methyl hydrogen fumarate)

3D Structure for HMDB0033809 (Methyl hydrogen fumarate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra