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Showing Compound Dimethyl fumarate (FDB003290)

Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2018-05-28 22:43:56 UTC
Primary IDFDB003290
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDimethyl fumarate
DescriptionFungal 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.
CAS Number624-49-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
Chemical FormulaC6H8O4
IUPAC name1,4-dimethyl (2Z)-but-2-enedioate
InChI IdentifierInChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3-
InChI KeyLDCRTTXIJACKKU-ARJAWSKDSA-N
Isomeric SMILESCOC(=O)\C=C/C(=O)OC
Average Molecular Weight144.1253
Monoisotopic Molecular Weight144.042258744
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-6c17ce0137a98251d821Spectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-8900000000-cf4bc8e74198c9d1fbe2Spectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-9800000000-9b43ca980ebe24e7dd08Spectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-5900000000-155805a1d757b9c0e41bSpectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-7995ee86e999e5109520Spectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-7900000000-6c17ce0137a98251d821Spectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-8900000000-cf4bc8e74198c9d1fbe2Spectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-9800000000-9b43ca980ebe24e7dd08Spectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-5900000000-155805a1d757b9c0e41bSpectrum
GC-MSDimethyl fumarate, non-derivatized, GC-MS Spectrumsplash10-03di-1900000000-7995ee86e999e5109520Spectrum
Predicted GC-MSDimethyl fumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ql-9600000000-9b7e4e9fb1429b084be5Spectrum
Predicted GC-MSDimethyl fumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0900000000-52a1c7b06f3e21edf1372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-3900000000-2c7c53ab39a3c1688bac2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06sr-9200000000-509f89775c164df76c242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-40c63012b9511f8490e32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-2900000000-c0fd047df97ddf890ee12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9200000000-89cb0515dab9e09d51462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-9500000000-33bc0abdab46b5a42b1f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9l-9000000000-12b87d2f6c05d60479162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-9000000000-cc19a5706e05ef5eb3482021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-1d56ae91abb29a4fba912021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gx0-9300000000-13e505571c984fd1ebfb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066r-9000000000-494ce88adb3552f6a3302021-09-22View Spectrum
NMRNot Available
ChemSpider ID4436352
ChEMBL IDCHEMBL2259700
KEGG Compound IDNot Available
Pubchem Compound ID5271565
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB31257
CRC / DFC (Dictionary of Food Compounds) IDCVQ85-P:CVQ78-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDimethyl_fumarate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
No data available in table
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference