mosedipimod   Click here for help

GtoPdb Ligand ID: 9771

Synonyms: EC-18 | Plag, (+/-)
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Mosedipimod (EC-18) is a monoacetyldiglyceride that is being investigated for anti-inflammatory potential [1]. It is a synthetic form of a major constituent isolated from the antlers of Sika deer. In preclinical studies the anti-inflammatory effects were determined to be associated with iNOS suppression [3]. EC-18 has also been shown to attenuate IL-4 production [4]. We show the chemical structure without specified stereochemisrty to represent the racemic mixture. Note that CHEMBL157366 represents a specific stereoisomer of this compound.
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 36
Topological polar surface area 78.9
Molecular weight 634.52
XLogP 15.94
No. Lipinski's rules broken 2

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 CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)C
Isomeric SMILES CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)C
InChI InChI=1S/C39H70O6/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-39(42)45-37(34-43-36(3)40)35-44-38(41)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2/h12,14,18-19,37H,4-11,13,15-17,20-35H2,1-3H3
InChI Key GAKUNXBDVGLOFS-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
(1-acetyloxy-3-hexadecanoyloxypropan-2-yl) (9Z,12Z)-octadeca-9,12-dienoate
International Nonproprietary Names Click here for help
INN number INN
10702 mosedipimod
Synonyms Click here for help
EC-18 | Plag, (+/-)
Database Links Click here for help
CAS Registry No. 221139-79-3 (source: WHO INN record)
GtoPdb PubChem SID 354702244
PubChem CID 9960925
Search Google for chemical match using the InChIKey GAKUNXBDVGLOFS-UHFFFAOYSA-N
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UniChem Compound Search for chemical match using the InChIKey GAKUNXBDVGLOFS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey GAKUNXBDVGLOFS-UHFFFAOYSA-N