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/)
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form mocravimod-phosphate
IUPAC Name Click here for help
2-Amino-2-(2-(2-chloro-4-(3-benzyloxyphenylthio)phenyl)ethyl)-1,3-propanediol
International Nonproprietary Names Click here for help
INN number INN
10472 mocravimod
Synonyms Click here for help
compound 2 [PMID: 23124563] | KRP-203 | KRP203
Database Links Click here for help
CAS Registry No. 509092-16-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL2137148
GtoPdb PubChem SID 354702203
PubChem CID 11155874
Search Google for chemical match using the InChIKey IINUNQPYJGJCJI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IINUNQPYJGJCJI
Search PubMed clinical trials mocravimod
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UniChem Compound Search for chemical match using the InChIKey IINUNQPYJGJCJI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IINUNQPYJGJCJI-UHFFFAOYSA-N