taranabant   

GtoPdb Ligand ID: 9231

Synonyms: MK 0364 | MK-0364
Compound class: Synthetic organic
Comment: Taranabant is a cannabinoid CB1 receptor antagonist/inverse agonist [2-3], with anorectic action. It was investigated for its potential as a novel weight management therapeutic in obese and overweight patients.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 75.01
Molecular weight 515.16
XLogP 6.56
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES N#Cc1cccc(c1)C(C(NC(=O)C(Oc1ccc(cn1)C(F)(F)F)(C)C)C)Cc1ccc(cc1)Cl
Isomeric SMILES N#Cc1cccc(c1)[C@@H]([C@@H](NC(=O)C(Oc1ccc(cn1)C(F)(F)F)(C)C)C)Cc1ccc(cc1)Cl
InChI InChI=1S/C27H25ClF3N3O2/c1-17(34-25(35)26(2,3)36-24-12-9-21(16-33-24)27(29,30)31)23(14-18-7-10-22(28)11-8-18)20-6-4-5-19(13-20)15-32/h4-13,16-17,23H,14H2,1-3H3,(H,34,35)/t17-,23+/m0/s1
InChI Key QLYKJCMUNUWAGO-GAJHUEQPSA-N
Classification
Compound class Synthetic organic
IUPAC Name
N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
International Nonproprietary Names
INN number INN
8848 taranabant
Synonyms
MK 0364 | MK-0364
Database Links
BindingDB Ligand 50200841
CAS Registry No. 701977-09-5 (source: WHO INN record)
ChEMBL Ligand CHEMBL220360
GtoPdb PubChem SID 315661306
PubChem CID 11226090
RCSB PDB Ligand 7DY
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