amiselimod   

GtoPdb Ligand ID: 9319

Synonyms: Example 1 [US20090137530] | MT-1303 | MT1303
Compound class: Synthetic organic
Comment: Amiselimod (MT-1303) is claimed in patent US20090137530 (Compound 1-3 is the hydrochloride used experimentally) as a potential immunomodulatory agent [1]. It is a sphingosine-1-phosphate (SIP) receptor prodrug agonist, similar in action to the approved MS drug fingolimod, but with improved receptor subtype selectivity [3].
Selective SIP1 receptor agonists are being investigated for immunomodulatory/immunosuppresant action in MS and other autoimmune conditions [2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 13
Topological polar surface area 75.71
Molecular weight 377.22
XLogP 4.17
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCOc1ccc(cc1C(F)(F)F)CCC(CO)(CO)N
Isomeric SMILES CCCCCCCOc1ccc(cc1C(F)(F)F)CCC(CO)(CO)N
InChI InChI=1S/C19H30F3NO3/c1-2-3-4-5-6-11-26-17-8-7-15(12-16(17)19(20,21)22)9-10-18(23,13-24)14-25/h7-8,12,24-25H,2-6,9-11,13-14,23H2,1H3
InChI Key JVCPIJKPAKAIIP-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Is prodrug? Yes
Active form amiselimod phosphate
IUPAC Name
2-amino-2-[2-[4-heptoxy-3-(trifluoromethyl)phenyl]ethyl]propane-1,3-diol
International Nonproprietary Names
INN number INN
10021 amiselimod
Synonyms
Example 1 [US20090137530] | MT-1303 | MT1303
Database Links
CAS Registry No. 942399-20-4 (source: WHO INN record)
GtoPdb PubChem SID 318164838
PubChem CID 16129483
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