ponesimod   

GtoPdb Ligand ID: 9320

Synonyms: ACT-128800 | ACT128800 | Compound 8bo [PMID:20446681]
Compound class: Synthetic organic
Comment: Ponesimod (ACT-128800) is an orally active sphingosine-1-phosphate (S1P) receptor modulator [1] in development as a disease-modifying therapy (DMT) for multiple sclerosis (MS). The compound is reported as a partial S1P4 and S1P5 receptor agonist, with maximum activity 18% and 42% of that induced by the endogenous ligand S1P (at 10μM ACT-128800) [1].
The INN record for ponesimod stipulates the (2R) stereoisomer ((2Z,5Z)-5-{3-chloro-4-[(2R)-2,3-dihydroxypropoxy]phenylmethylidene}-3-(2-methylphenyl)-2-(propylimino)-1,3-thiazolidin-4-one).
Selective SIP1 receptor agonists are being developed and investigated for immunomodulatory/immunosuppresant potential in autoimmune diseases.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 107.66
Molecular weight 460.12
XLogP 3.55
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCCN=C1SC(=Cc2ccc(c(c2)Cl)OCC(CO)O)C(=O)N1c1ccccc1C
Isomeric SMILES CCCN=C1S/C(=C\c2ccc(c(c2)Cl)OC[C@@H](CO)O)/C(=O)N1c1ccccc1C
InChI InChI=1S/C23H25ClN2O4S/c1-3-10-25-23-26(19-7-5-4-6-15(19)2)22(29)21(31-23)12-16-8-9-20(18(24)11-16)30-14-17(28)13-27/h4-9,11-12,17,27-28H,3,10,13-14H2,1-2H3/b21-12-,25-23?/t17-/m1/s1
InChI Key LPAUOXUZGSBGDU-ULCCENQXSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(5Z)-5-[[3-chloro-4-[(2R)-2,3-dihydroxypropoxy]phenyl]methylidene]-3-(2-methylphenyl)-2-propylimino-1,3-thiazolidin-4-one
International Nonproprietary Names
INN number INN
9150 ponesimod
Synonyms
ACT-128800 | ACT128800 | Compound 8bo [PMID:20446681]
Database Links
CAS Registry No. 854107-55-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL1096146
GtoPdb PubChem SID 318164839
PubChem CID 11363176
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