TARANABANT

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII X9U622S114
EPA CompTox DTXSID60220464

Structure

InChI Key QLYKJCMUNUWAGO-GAJHUEQPSA-N
Smiles C[C@H](NC(=O)C(C)(C)Oc1ccc(C(F)(F)F)cn1)[C@@H](Cc1ccc(Cl)cc1)c1cccc(C#N)c1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C27H25ClF3N3O2
Molecular Weight 515.96
AlogP 6.31
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 75.01
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 36.0

Bioactivity

Mechanism of Action Action Reference
Cannabinoid CB1 receptor inverse agonist INVERSE AGONIST PubMed
Protein: Cannabinoid CB1 receptor
Description: Cannabinoid receptor 1
Organism : Homo sapiens
P21554 ENSG00000118432
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 1 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 1 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 14200 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Cannabinoid receptor
2-2 0-22 - 0 -
Assay Description Organism Bioactivity Reference
Inhibition of [3H]CP-55940 binding to human recombinant CB1 receptor in CHO cells Homo sapiens 0.3 nM
Inhibition of [3H]CP-55940 binding to human recombinant CB2 receptor in CHO cells Homo sapiens 290.0 nM
Inverse agonist activity at human recombinant CB1 receptor assessed as inhibition of forskolin-induced cAMP production in CHO cells Homo sapiens 2.4 nM
Displacement of [3H]CP-55940 from human recombinant CB1R expressed in CHO cells Homo sapiens 0.3 nM
Displacement of [3H]CP-55940 from human wild type CB1R expressed in CHO cells Homo sapiens 0.74 nM
Displacement of [3H]CP-55940 from human CB1R F200L mutant expressed in CHO cells Homo sapiens 5.0 nM
Displacement of [3H]CP-55940 from human CB1R W279A mutant expressed in CHO cells Homo sapiens 4.9 nM
Displacement of [3H]CP-55940 from human CB1R K192L mutant expressed in CHO cells Homo sapiens 1.2 nM
Displacement of [3H]SR-141716 from human CBR1 S383A mutant expressed in CHO cells Homo sapiens 19.0 nM
Displacement of [3H]CP-55940 from human CB1R F170L mutant expressed in CHO cells Homo sapiens 22.0 nM
Displacement of [3H]SR-141716 from human wild type CB1R expressed in CHO cells Homo sapiens 0.094 nM
Displacement of [3H]CP-55940 from human CB1R expressed in HEK293 cells Homo sapiens 0.3 nM
Displacement of [3H]CP-55940 from human CB1 receptor expressed in CHO cells Homo sapiens 0.29 nM
Displacement of [3H]CP-55940 from CB1 receptor in Sprague-Dawley rat cerebellum by liquid scintillation spectrometry Rattus norvegicus 0.86 nM
Inverse agonist activity at cannabinoid CB1 receptor None 0.3 nM
Displacement of [3H]rimonabant from human CB1 receptor expressed in HEK293 cells by liquid scintillation counting Homo sapiens 0.3 nM
Displacement of [3H]rimonabant from human CB2 receptor expressed in HEK293 cells by liquid scintillation counting Homo sapiens 290.0 nM
Displacement of [3H]CP-55940 from recombinant human CB1 receptor expressed in CHO cells Homo sapiens 0.3 nM
Inverse agonist activity at human CB1 receptor assessed as forskolin-induced cAMP level by adenylyl cyclase activation flash plate assay Homo sapiens 2.4 nM
Displacement of [3H]CP-55940 from recombinant human CB2 receptor expressed in CHO cell Homo sapiens 285.0 nM
Inhibition of human CB1 receptor Homo sapiens 0.3 nM
Inhibition of cannabinoid CB1 receptor None 0.3 nM
Inhibition of cannabinoid CB2 receptor None 290.0 nM
Binding affinity to human CB1 receptor Homo sapiens 0.3 nM
Displacement of [3H]CP55490 from human recombinant cannabinoid CB1 receptor expressed in CHO cells Homo sapiens 0.74 nM
Inhibition of CYP1A2 in human liver microsomes after 30 mins Homo sapiens 20.0 nM
Inhibition of CYP2C9 in human liver microsomes after 30 mins Homo sapiens 0.93 nM
Inhibition of CYP3A4 in human liver microsomes after 30 mins Homo sapiens 20.0 nM
Inhibition of CYP2D6 in human liver microsomes after 30 mins Homo sapiens 0.59 nM
Displacement of [3H]SR141716A from rat brain CB1 receptor at pH 7.4 after 1 hr by liquid scintillation counting Rattus norvegicus 0.3 nM
Inhibition of CB1 receptor (unknown origin) Homo sapiens 0.3 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 1.94 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 16.77 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.7 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.25 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.0 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.0 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.25 %
Inhibition of radiolabeled CP5549 binding to human Cannabinoid receptor 1 expressed in CHO cells by competition assay Homo sapiens 0.3 nM

Cross References

Resources Reference
ChEMBL CHEMBL220360
DrugBank DB06624
FDA SRS X9U622S114
Guide to Pharmacology 9231
PDB 7DY
PubChem 11226090
SureChEMBL SCHEMBL304925
ZINC ZINC000028701758
CONTENTS