firategrast   Click here for help

GtoPdb Ligand ID: 11486

Synonyms: SB-683699 | SB683699
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Firategrast (SB-683699) is an orally bioavailable, short-acting small molecule α4-integrin antagonist. It was designed to reduce α4β1/α4β7 integrin-mediated trafficking of lymphocytes into the central nervous system (CNS). Anti-α4-integrin natalizumab is currently approved to treat MS, but its long half-life is problematic, and it has to be administered by infusion. This short acting small molecule was developed as an alternative to antibody therapy.
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 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.

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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 12
Topological polar surface area 94.09
Molecular weight 499.18
XLogP 5
No. Lipinski's rules broken 2
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.

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Canonical SMILES CCOCc1cc(OC)c(c(c1)OC)c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)c1c(F)cccc1F
Isomeric SMILES CCOCc1cc(OC)c(c(c1)OC)c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)c1c(F)cccc1F
InChI InChI=1S/C27H27F2NO6/c1-4-36-15-17-13-22(34-2)24(23(14-17)35-3)18-10-8-16(9-11-18)12-21(27(32)33)30-26(31)25-19(28)6-5-7-20(25)29/h5-11,13-14,21H,4,12,15H2,1-3H3,(H,30,31)(H,32,33)/t21-/m0/s1
InChI Key YLFZHHDVRSYTKT-NRFANRHFSA-N
Classification Click here for help
Compound class Synthetic organic
International Nonproprietary Names Click here for help
INN number INN
8755 firategrast
Synonyms Click here for help
SB-683699 | SB683699
Database Links Click here for help
CAS Registry No. 402567-16-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL2104967
DrugBank Ligand DB12732
GtoPdb PubChem SID 440816854
PubChem CID 9935681
Search Google for chemical match using the InChIKey YLFZHHDVRSYTKT-NRFANRHFSA-N
Search Google for chemicals with the same backbone YLFZHHDVRSYTKT
Search PubMed clinical trials firategrast
Search PubMed titles firategrast
Search PubMed titles/abstracts firategrast
UniChem Compound Search for chemical match using the InChIKey YLFZHHDVRSYTKT-NRFANRHFSA-N
UniChem Connectivity Search for chemical match using the InChIKey YLFZHHDVRSYTKT-NRFANRHFSA-N