tepilamide fumarate   Click here for help

GtoPdb Ligand ID: 9770

Synonyms: XP 23829 | XP-23829 | XP23829
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Tepilamide fumarate (XP23829) is a small-molecule fumaric acid ester prodrug of monomethyl fumarate (MMF). It is being developed by Arbor Pharmaceuticals (formerly XenoPort) as a potential treatment for autoinflammatory diseases.

tepilamide fumarate 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 6
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 72.91
Molecular weight 243.11
XLogP 0.39
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 CCN(C(=O)COC(=O)C=CC(=O)OC)CC
Isomeric SMILES CCN(C(=O)COC(=O)/C=C/C(=O)OC)CC
InChI InChI=1S/C11H17NO5/c1-4-12(5-2)9(13)8-17-11(15)7-6-10(14)16-3/h6-7H,4-5,8H2,1-3H3/b7-6+
InChI Key AKUGRXRLHCCENI-VOTSOKGWSA-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
Is prodrug? Yes
Active form monomethyl fumarate
IUPAC Name Click here for help
4-O-[2-(diethylamino)-2-oxoethyl] 1-O-methyl (E)-but-2-enedioate
International Nonproprietary Names Click here for help
INN number INN
10672 tepilamide fumarate
Synonyms Click here for help
XP 23829 | XP-23829 | XP23829
Database Links Click here for help
GtoPdb PubChem SID 354702243
PubChem CID 46179632
Search Google for chemical match using the InChIKey AKUGRXRLHCCENI-VOTSOKGWSA-N
Search Google for chemicals with the same backbone AKUGRXRLHCCENI
Search PubMed clinical trials tepilamide fumarate
Search PubMed titles tepilamide fumarate
Search PubMed titles/abstracts tepilamide fumarate
UniChem Compound Search for chemical match using the InChIKey AKUGRXRLHCCENI-VOTSOKGWSA-N
UniChem Connectivity Search for chemical match using the InChIKey AKUGRXRLHCCENI-VOTSOKGWSA-N

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MedChemExpress
Tepilamide fumarate (links to external site)
Cat. No. HY-109105