mocravimod   Click here for help

GtoPdb Ligand ID: 9727

Synonyms: compound 2 [PMID: 23124563] | KRP-203 | KRP203
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Mocravimod (KRP203) is a sphingosine 1-phosphate receptor type 1 (S1P1R) agonist with immunomodulatory potential [6]. Structurally mocravimod is a highly modified analogue of the approved multiple sclerosis drug fingolimod. Like fingolimod it is a prodrug that is phosphorylated in vivo by sphingosine kinase 2 (SPHK2), with mocravimod-phosphate (+KRP203-phosphate) being the active entity.
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 3
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 101.01
Molecular weight 443.13
XLogP 4.71
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 OCC(CCc1ccc(cc1Cl)Sc1cccc(c1)OCc1ccccc1)(CO)N
Isomeric SMILES OCC(CCc1ccc(cc1Cl)Sc1cccc(c1)OCc1ccccc1)(CO)N
InChI InChI=1S/C24H26ClNO3S/c25-23-14-22(10-9-19(23)11-12-24(26,16-27)17-28)30-21-8-4-7-20(13-21)29-15-18-5-2-1-3-6-18/h1-10,13-14,27-28H,11-12,15-17,26H2
InChI Key IINUNQPYJGJCJI-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/)
Bioactivity Comments
There is evidence to support mocravimod's action as a partial (low potency) agonist at the S1P3R [4]. The selectivity for S1P1R over S1P3R is proposed to reduce S1P3R-driven bradycardia that is observed as a side effect with the non-selective S1PR modulator fingolimod (FTY720) [5].