Monomethyl Fumarate
(E)-4-methoxy-4-oxobut-2-enoic acid
Molecular Identity
Monomethyl Fumarate
(E)-4-methoxy-4-oxobut-2-enoic acid
PubChem CID: 5369209
Monomethyl fumarate is 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. It has a role as an antioxidant, a drug metabolite and an immunomodulator. It is a methyl ester, a dicarboxylic acid monoester and an enoate ester. It is functionally related to a fumaric acid.
2D Structure
Properties
C5H6O4
Molecular Formula
130.10
Molecular Weight
g/mol
130.0266
Exact Mass
Da
0.4
XLogP
Drug-like (Lipinski: < 5)
63.6
TPSA
Good oral absorption (< 140 A²)
1
H-Bond Donors
4
H-Bond Acceptors
147
Complexity
SMILES
Canonical SMILES
SMILES: COC(=O)C=CC(=O)OIsomeric SMILES
SMILES: COC(=O)/C=C/C(=O)OSynonyms(20)
Monomethyl fumarate2756-87-8Fumaric acid monomethyl esterBafiertam45IUB1PX8RmethylhydrogenfumarateCHEBI:167450NSC-523835DTXSID801016498RefChem:55666DTXCID30209463220-412-6Methyl FumaratemonomethylfumarateMethyl hydrogen fumarate
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Monomethyl Fumarate
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