dimethyl fumarate   Click here for help

GtoPdb Ligand ID: 7045

Synonyms: BG-12 | BG00012 | fumaric acid | Tecfidera®
Approved drug PDB Ligand Immunopharmacology Ligand
dimethyl fumarate is an approved drug (FDA (2013), EMA (2014))
Compound class: Synthetic organic
Comment: The active metabolite of dimethyl fumarate is monomethyl fumarate.
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 52.6
Molecular weight 144.04
XLogP 0.23
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COC(=O)C=CC(=O)OC
Isomeric SMILES COC(=O)/C=C/C(=O)OC
InChI InChI=1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+
InChI Key LDCRTTXIJACKKU-ONEGZZNKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Blewett MM, Xie J, Zaro BW, Backus KM, Altman A, Teijaro JR, Cravatt BF. (2016)
Chemical proteomic map of dimethyl fumarate-sensitive cysteines in primary human T cells.
Sci Signal, 9 (445): rs10. [PMID:27625306]
2. Diebold M, Sievers C, Bantug G, Sanderson N, Kappos L, Kuhle J, Lindberg RLP, Derfuss T. (2018)
Dimethyl fumarate influences innate and adaptive immunity in multiple sclerosis.
J Autoimmun, 86: 39-50. [PMID:28958667]
3. Kornberg MD, Bhargava P, Kim PM, Putluri V, Snowman AM, Putluri N, Calabresi PA, Snyder SH. (2018)
Dimethyl fumarate targets GAPDH and aerobic glycolysis to modulate immunity.
Science, 360 (6387): 449-453. [PMID:29599194]
4. Lee CF, Lo YC, Cheng CH, Furtmüller GJ, Oh B, Andrade-Oliveira V, Thomas AG, Bowman CE, Slusher BS, Wolfgang MJ et al.. (2015)
Preventing Allograft Rejection by Targeting Immune Metabolism.
Cell Rep, 13 (4): 760-770. [PMID:26489460]
5. Li W, Kong AN. (2009)
Molecular mechanisms of Nrf2-mediated antioxidant response.
Mol Carcinog, 48 (2): 91-104. [PMID:18618599]
6. Linker RA, Lee DH, Ryan S, van Dam AM, Conrad R, Bista P, Zeng W, Hronowsky X, Buko A, Chollate S et al.. (2011)
Fumaric acid esters exert neuroprotective effects in neuroinflammation via activation of the Nrf2 antioxidant pathway.
Brain, 134 (Pt 3): 678-92. [PMID:21354971]
7. Schuiveling M, Vazirpanah N, Radstake TRDJ, Zimmermann M, Broen JCA. (2018)
Metformin, A New Era for an Old Drug in the Treatment of Immune Mediated Disease?.
Curr Drug Targets, 19 (8): 945-959. [PMID:28606032]