APD668   Click here for help

GtoPdb Ligand ID: 12151

Synonyms: APD-668 | compound 3k [PMID: 21444206] | compound A129 [WO2005007658A2] [2] | JNJ-28630368 | JNJ28630368
PDB Ligand
Compound class: Synthetic organic
Comment: APD668 (also known as JNJ-28630368) is a synthetic small molecule agonist of the orphan G protein-coupled receptor GPR119 [1,3]. Its in vitro profile and in vivo actions as a GLP-1 secretagogue, reducing triglyceride uptake and hepatic lipogenesis suggests the potential of GPR119 agonists for the treatment of dyslipidemia and non-alcoholic steatohepatitis. However, clinical development of both this compound and the structurally related lead JNJ-38431055 has been terminated.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 124.37
Molecular weight 477.15
XLogP 3.52
No. Lipinski's rules broken 0
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Canonical SMILES CC(OC(=O)N1CCC(CC1)Oc1ncnc2c1cnn2c1ccc(cc1F)S(=O)(=O)C)C
Isomeric SMILES CC(C)OC(=O)N1CCC(CC1)Oc1ncnc2c1cnn2c1c(cc(cc1)S(=O)(=O)C)F
InChI InChI=1S/C21H24FN5O5S/c1-13(2)31-21(28)26-8-6-14(7-9-26)32-20-16-11-25-27(19(16)23-12-24-20)18-5-4-15(10-17(18)22)33(3,29)30/h4-5,10-14H,6-9H2,1-3H3
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
propan-2-yl 4-[1-(2-fluoro-4-methylsulfonylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]oxypiperidine-1-carboxylate
Synonyms Click here for help
APD-668 | compound 3k [PMID: 21444206] | compound A129 [WO2005007658A2] [2] | JNJ-28630368 | JNJ28630368
Database Links Click here for help
Specialist databases
GPCRdb Ligand APD668
Other databases
BindingDB Ligand 50343442
CAS Registry No. 832714-46-2 (source: PubChem)
ChEMBL Ligand CHEMBL1775179
GtoPdb PubChem SID 472319273
PubChem CID 11705608
RCSB PDB Ligand I7J, I7J
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UniChem Connectivity Search for chemical match using the InChIKey XTRUQJBVQBUKSQ-UHFFFAOYSA-N