General Information of the Compound
Compound ID
CP0106737
Compound Name
N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[5-(trifluoromethyl)pyridin-2-yl]oxypropanamide
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Synonyms
L]-2-methyl-2-[(5-(trifluoromethyl)pyridin-2-yl)oxy]propanamide
MK 0364
MK-0364
MK-0634
MK0364
N-((1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl)-2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanamide
N-(3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl)-2-methyl-2-((5-(trifluoromethyl)pyridin-2-yl)oxy)propanamide
N-[(1S,2S)-3-(4-Chlorophenyl)-2-(3-cyanophenyl)-1-methylpropy
N-[(1S,2S)-3-(4-Chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[[5-(trifluoromethyl)pyridin-2-yl]oxy]propanamide
Taranabant
Taranabant (INN/USAN)
Taranabant [USAN]
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Structure
Formula
C27H25ClF3N3O2
Molecular Weight
515.963
Canonical SMILES
C[C@H](NC(=O)C(C)(C)Oc1ccc(cn1)C(F)(F)F)[C@@H](Cc1ccc(Cl)cc1)c1cccc(c1)C#N
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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
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InChIKey
QLYKJCMUNUWAGO-GAJHUEQPSA-N
CAS
701977-09-5
Physicochemical Property
logP
6.31408
Rotatable Bonds
8
Heavy Atom Count
36
Polar Areas
75.01
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Complexity
36

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 11226090
SID: 50086932
ChEMBL ID
CHEMBL220360
DrugBank ID
DB06624
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT01298, Cannabinoid receptor 1
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO
 Cell Line Info 
Cricetulus griseus (Chinese hamster)  4
1
EC50 = 2.4 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
IC50 = 0.29 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
IC50 = 0.3 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
4
IC50 = 0.74 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000006 HEK293
 Cell Line Info 
Homo sapiens (Human)  2
1
IC50 = 0.3 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
Ki = 0.3 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 0.3 nM
Protein ID: PT00834, Cannabinoid receptor 2
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO
 Cell Line Info 
Cricetulus griseus (Chinese hamster)  2
1
IC50 = 285 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
IC50 = 290 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000026 CHO-K1
 Cell Line Info 
Cricetulus griseus (Chinese hamster)  1
1
IC50 = 1170 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000006 HEK293
 Cell Line Info 
Homo sapiens (Human)  1
1
Ki = 290 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 290 nM
Clinical Information about the Compound
Drug 1 ( Taranabant )
Drug Name Taranabant
Company Merck
Indication
Obesity
Discontinued in Phase 3
Target(s)
Cannabinoid receptor 1 (CB1)
 Target Info 
Antagonist