dimethyl itaconate   Click here for help

GtoPdb Ligand ID: 9939

Synonyms: dimethylitaconate | itaconic acid dimethyl ester
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Dimethyl itaconate is a membrane-permeable derivative of the immunoregulatory metabolite itaconate. Itaconate is one of the most highly induced metabolites produced when activated macrophages undergo metabolic remodeling. Itaconate acts as a major physiological regulator of metabolic switching and effector functions of inflammatory macrophages. Itaconate and dimethyl itaconate inhibit production of IL-6 and IL-12 (secondary transcriptional response), but not TNF (a primary transcriptional response) following Toll-like receptor stimulation [4].

Itaconate has been found to promote an electrophilic stress response (i.e. a rapid adaptive defense response) [1]. An electrophilic stress response involves various mechanisms, including the nuclear translocation of the redox-sensitive transcription factor Nrf2 (nuclear factor E2-related factor 2), which senses electrophilic and oxidative stresses and protects against cellular damage via Kelch-like ECH-associated protein 1 (Keap1) [2-3,5]. Both itaconate and dimethyl itaconate induce Nrf2-dependent and -independent responses, the Nrf2-independent response being that which involves regulation of IκBζ [1].

dimethyl itaconate is commercially available from our sponsors

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 5
Topological polar surface area 52.6
Molecular weight 158.06
XLogP 0.24
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)CC(=C)C(=O)OC
Isomeric SMILES COC(=O)CC(=C)C(=O)OC
InChI InChI=1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3
InChI Key ZWWQRMFIZFPUAA-UHFFFAOYSA-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
IUPAC Name Click here for help
dimethyl 2-methylidenebutanedioate
Synonyms Click here for help
dimethylitaconate | itaconic acid dimethyl ester
Database Links Click here for help
CAS Registry No. 617-52-7 (source: PubChem)
GtoPdb PubChem SID 363894233
PubChem CID 69240
Search Google for chemical match using the InChIKey ZWWQRMFIZFPUAA-UHFFFAOYSA-N
Search Google for chemicals with the same backbone ZWWQRMFIZFPUAA
UniChem Compound Search for chemical match using the InChIKey ZWWQRMFIZFPUAA-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey ZWWQRMFIZFPUAA-UHFFFAOYSA-N

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MedChemExpress
Dimethyl itaconate (links to external site)
Cat. No. HY-W041892