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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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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2013), EMA (2014))
Approved drug? Yes. FDA (2013)  |  EMA (2014)
Is prodrug? Yes
Active form monomethyl fumarate
IUPAC Name Click here for help
dimethyl (E)-but-2-enedioate
Synonyms Click here for help
BG-12 | BG00012 | fumaric acid | Tecfidera®
Database Links Click here for help
CAS Registry No. 624-49-7
ChEMBL Ligand CHEMBL2107333
DrugBank Ligand DB08908
DrugCentral Ligand 4757
GtoPdb PubChem SID 178103624
PubChem CID 637568
RCSB PDB Ligand EOU
Search Google for chemical match using the InChIKey LDCRTTXIJACKKU-ONEGZZNKSA-N
Search Google for chemicals with the same backbone LDCRTTXIJACKKU
UniChem Compound Search for chemical match using the InChIKey LDCRTTXIJACKKU-ONEGZZNKSA-N
UniChem Connectivity Search for chemical match using the InChIKey LDCRTTXIJACKKU-ONEGZZNKSA-N
Wikipedia Dimethyl_fumarate

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MedChemExpress
Dimethyl fumarate (links to external site)
Cat. No. HY-17363
Dimethyl fumarate (Standard) (links to external site)
Cat. No. HY-17363R