amiselimod   Click here for help

GtoPdb Ligand ID: 9319

Synonyms: Example 1 [US20090137530] | MT-1303 | MT1303
Immunopharmacology Ligand
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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. 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.

✖
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
Click here for help

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.

✖
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
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel