monomethyl fumarate   

GtoPdb Ligand ID: 5786

Synonyms: methyl hydrogen fumarate
Compound class: Synthetic organic
Comment: Monomethyl fumarate (MMF) is the active metabolite of the approved drug dimethyl fumarate (DMF).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 63.6
Molecular weight 130.03
XLogP -0.1
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COC(=O)C=CC(=O)O
Isomeric 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+
InChI Key NKHAVTQWNUWKEO-NSCUHMNNSA-N
References
1. Tang H, Lu JY, Zheng X, Yang Y, Reagan JD. (2008)
The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist.
Biochem. Biophys. Res. Commun., 375 (4): 562-5. [PMID:18722346]
2. van Veldhoven JP, Blad CC, Artsen CM, Klopman C, Wolfram DR, Abdelkadir MJ, Lane JR, Brussee J, Ijzerman AP. (2011)
Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A).
Bioorg. Med. Chem. Lett., 21 (9): 2736-9. [PMID:21167710]