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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:56 UTC
Update Date2019-07-23 06:08:21 UTC
HMDB IDHMDB0031257
Secondary Accession Numbers
  • HMDB31257
Metabolite Identification
Common NameDimethyl fumarate
DescriptionDimethyl fumarate is a fungal growth inhibitor for tomato juice Dimethyl fumarate is an ester and an , -unsaturated electrophilic compound, undergoing reactions typical to them. It is also a diene acceptor in the ordinary Diels-Alder reaction, where the reactivity of its vinylidenic bond is enchanced by the two electron-withdrawing ester groups. Due to the geometry of the starting ester, the Diels-Alder product will have a trans configuration. Dimethyl fumarate is used to treat psoriasis. It is a lipophilic, highly mobile molecule in human tissue. However, as an , -unsaturated ester, dimethyl fumarate reacts rapidly with the detoxifying agent glutathione by Michael addition. When administered orally, it does not survive long enough to be absorbed into blood
Structure
Data?1563862101
Synonyms
ValueSource
2-Butenedioic acid (2Z)-, dimethyl esterChEBI
2-Butenedioic acid (Z)-, dimethyl esterChEBI
Dimethyl cis-ethylenedicarboxylateChEBI
Maleic acid, dimethyl esterChEBI
Methyl maleateChEBI
2-Butenedioate (2Z)-, dimethyl esterGenerator
2-Butenedioate (Z)-, dimethyl esterGenerator
Dimethyl cis-ethylenedicarboxylic acidGenerator
Maleate, dimethyl esterGenerator
Methyl maleic acidGenerator
Dimethyl fumaric acidGenerator
(e)-CH3OC(O)CH=chc(O)OCH3HMDB
1,2-Bis(methoxycarbonyl)-trans-ethyleneHMDB
2-Butenedioic acid (2E)-, 1,4-dimethyl esterHMDB
2-Butenedioic acid (2E)-, dimethyl esterHMDB
2-Butenedioic acid (e)-, dimethyl esterHMDB
2-Butenedioic acid, dimethyl esterHMDB
Allomaleic acid dimethyl esterHMDB
BG 12 CompoundHMDB
Boletic acid dimethyl esterHMDB
But-2-enedioic acid, dimethyl esterHMDB
Dimethyl (2E)-2-butenedioateHMDB
Dimethyl (2E)-but-2-enedioateHMDB
Dimethyl (e)-but-2-enedioateHMDB
Dimethyl but-2-enedioateHMDB
Dimethyl ester(2E)-2-butenedioic acidHMDB
Dimethyl ester(e)-2-butenedioic acidHMDB
Dimethyl trans-ethylenedicarboxylateHMDB
Dimethylester kyseliny fumaroveHMDB
DimethylfumarateHMDB
FumadermHMDB
Fumaric acid dimethyl esterHMDB
Fumaric acid, dimethyl esterHMDB
Fumaric acid, dimethyl ester (8ci)HMDB
Methyl fumarateHMDB
trans-1, 2-Ethylenedicarboxylic acid dimethyl esterHMDB
trans-1,2-Ethylenedicarboxylic acid dimethyl esterHMDB
trans-Butenedioic acid dimethyl esterHMDB
Dimethyl maleic acidGenerator
Chemical FormulaC6H8O4
Average Molecular Weight144.1253
Monoisotopic Molecular Weight144.042258744
IUPAC Name1,4-dimethyl (2Z)-but-2-enedioate
Traditional Namedimethyl maleate
CAS Registry Number624-49-7
SMILES
COC(=O)\C=C/C(=O)OC
InChI Identifier
InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-
InChI KeyLDCRTTXIJACKKU-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point102 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.74Not Available
Predicted Properties
PropertyValueSource
Water Solubility12.9 g/LALOGPS
logP0.45ALOGPS
logP0.72ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.15 m³·mol⁻¹ChemAxon
Polarizability13.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-7900000000-6c17ce0137a98251d821Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-cf4bc8e74198c9d1fbe2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9800000000-9b43ca980ebe24e7dd08Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-155805a1d757b9c0e41bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-7995ee86e999e5109520Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-7900000000-6c17ce0137a98251d821Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-cf4bc8e74198c9d1fbe2Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9800000000-9b43ca980ebe24e7dd08Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-5900000000-155805a1d757b9c0e41bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-1900000000-7995ee86e999e5109520Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ql-9600000000-9b7e4e9fb1429b084be5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0900000000-52a1c7b06f3e21edf137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-3900000000-2c7c53ab39a3c1688bacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06sr-9200000000-509f89775c164df76c24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-40c63012b9511f8490e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-2900000000-c0fd047df97ddf890ee1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-89cb0515dab9e09d5146Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003290
KNApSAcK IDNot Available
Chemspider ID4436352
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDimethyl_maleate
METLIN IDNot Available
PubChem Compound5271565
PDB IDNot Available
ChEBI ID35460
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.