monomethyl fumarate (CHEBI:167450)

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CHEBI:167450 - monomethyl fumarate

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ChEBI ID	CHEBI:167450
ChEBI Name	monomethyl fumarate
Stars
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.
Last Modified	25 February 2021
Submitter	R. Stephan
Downloads	Molfile

Formula	C5H6O4
Net Charge	0
Average Mass	130.099
Monoisotopic Mass	130.02661
SMILES	COC(=O)/C=C/C(=O)O
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

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:	drug metabolite immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
Applications:	immunomodulator Biologically active substance whose activity affects or plays a role in the functioning of the immune system. immunosuppressive agent An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.

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) has role immunosuppressive agent (CHEBI:35705)
	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 fatty acid ester (CHEBI:35748)
	monomethyl fumarate (CHEBI:167450) is a methyl ester (CHEBI:25248)
	monomethyl fumarate (CHEBI:167450) is a organic molecular entity (CHEBI:50860)

IUPAC Name
(2E)-4-methoxy-4-oxobut-2-enoic acid

INNs	Source
fumarate de monométhyle	WHO MedNet
fumarato de monometilo	WHO MedNet
monomethyl fumarate	WHO MedNet
monomethylis fumaras	WHO MedNet

Synonyms	Source
fumaric acid monomethyl ester	DrugBank
(E)-4-methoxy-4-oxobut-2-enoic acid	ChEBI
methyl hydrogen fumarate	ChemIDplus
MMF	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

Registry Numbers	Sources
Reaxys:1722673	Reaxys
CAS:2756-87-8	ChemIDplus

Citations