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CHEBI:167450 - monomethyl fumarate

ChEBI IDCHEBI:167450
ChEBI Namemonomethyl fumarate
Stars
DefinitionA dicarboxylic acid monoester resulting from the formal condensation of one of the carboxy groups of fumaric acid with methanol. Is is a metabolite of dimethyl fumarate and used for the the treatment of patients with relapsing multiple sclerosis (MS). It also induces the NFE2L2 (Nrf2) transcription factor by binding to KEAP1.
Last Modified25 February 2021
SubmitterR. Stephan
DownloadsMolfile
FormulaC5H6O4
Net Charge0
Average Mass130.099
Monoisotopic Mass130.02661
SMILESCOC(=O)/C=C/C(=O)O
InChIInChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
InChIKeyNKHAVTQWNUWKEO-NSCUHMNNSA-N
Wikipedia
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
Application:
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
ChEBI Ontology
Outgoing Relation(s)
monomethyl fumarate (CHEBI:167450) has functional parent fumaric acid (CHEBI:18012)
monomethyl fumarate (CHEBI:167450) has role antioxidant (CHEBI:22586)
monomethyl fumarate (CHEBI:167450) has role drug metabolite (CHEBI:49103)
monomethyl fumarate (CHEBI:167450) has role immunomodulator (CHEBI:50846)
monomethyl fumarate (CHEBI:167450) is a dicarboxylic acid monoester (CHEBI:36244)
monomethyl fumarate (CHEBI:167450) is a enoate ester (CHEBI:51702)
monomethyl fumarate (CHEBI:167450) is a methyl ester (CHEBI:25248)
IUPAC Name 
(2E)-4-methoxy-4-oxobut-2-enoic acid
INNs  Source
fumarate de monométhyleWHO MedNet
monomethyl fumarateWHO MedNet
monomethylis fumarasWHO MedNet
fumarato de monometiloWHO MedNet
Synonyms  Source
MMFSUBMITTER
monomethylfumarateSUBMITTER
(E)-4-methoxy-4-oxobut-2-enoic acidChEBI
methyl hydrogen fumarateChemIDplus
fumaric acid monomethyl esterDrugBank
mono-methyl fumarateChEBI
Brand Name  Source
BafiertamKEGG DRUG
Manual XrefsDatabases
FDB011972FooDB
DB14219DrugBank
HMDB0033809HMDB
D11492KEGG DRUG
Monomethyl_fumarateWikipedia
4520322ChemSpider
Registry NumbersSources
Reaxys:1722673Reaxys
CAS:2756-87-8ChemIDplus
Citations