CHEBI:167450 - monomethyl fumarate

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ChEBI Name monomethyl fumarate
ChEBI ID CHEBI:167450
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
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Formula C5H6O4
Net Charge 0
Average Mass 130.099
Monoisotopic Mass 130.02661
InChI InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+
InChIKey NKHAVTQWNUWKEO-NSCUHMNNSA-N
SMILES COC(=O)\C=C\C(O)=O
Roles Classification
Chemical Role(s): 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 (Bronsted base).
(via oxoacid )
Biological Role(s): drug metabolite

immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
Application(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
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ChEBI Ontology
Outgoing 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 Sources
fumarate de monométhyle WHO MedNet
fumarato de monometilo WHO MedNet
monomethyl fumarate WHO MedNet
monomethylis fumaras WHO MedNet
Synonyms Sources
(E)-4-methoxy-4-oxobut-2-enoic acid ChEBI
fumaric acid monomethyl ester DrugBank
methyl hydrogen fumarate ChemIDplus
MMF
Note: (2021-02-25) Used as an abbreviation.
 SUBMITTER
mono-methyl fumarate ChEBI
monomethylfumarate SUBMITTER
Brand Name Source
Bafiertam KEGG DRUG
Manual Xrefs Databases
4520322 ChemSpider
D11492 KEGG DRUG
DB14219 DrugBank
FDB011972 FooDB
HMDB0033809 HMDB
Monomethyl_fumarate Wikipedia
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Registry Numbers Types Sources
1722673 Reaxys Registry Number Reaxys
2756-87-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
25 February 2021