TAMIBAROTENE

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Synonyms
Status
Molecule Category Free-form
UNII 08V52GZ3H9
EPA CompTox DTXSID5046853

Structure

InChI Key MUTNCGKQJGXKEM-UHFFFAOYSA-N
Smiles CC1(C)CCC(C)(C)c2cc(NC(=O)c3ccc(C(=O)O)cc3)ccc21
InChI
InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H25NO3
Molecular Weight 351.45
AlogP 4.99
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 66.4
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 26.0

Bioactivity

Mechanism of Action Action Reference
Retinoic acid receptor alpha agonist AGONIST PubMed PubMed
Protein: Retinoic acid receptor alpha
Description: Retinoic acid receptor alpha
Organism : Homo sapiens
P10276 ENSG00000131759
Protein: Retinoic acid receptor beta
Description: Retinoic acid receptor beta
Organism : Homo sapiens
P10826 ENSG00000077092
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 1
45 78 - 7 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 2
235 - - 30 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 3
591 - - - -
Assay Description Organism Bioactivity Reference
Agonistic activity towards retinoic acid receptor-beta Homo sapiens 30.0 nM
Binding affinity for Retinoic Acid Receptor alpha (RAR alpha) Homo sapiens 78.0 nM
Agonistic activity towards retinoic acid receptor-alpha None 6.5 nM
Agonist activity at RARalpha None 45.0 nM
Agonist activity at RARbeta None 235.0 nM
Agonist activity at RARgamma None 591.0 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 67.6 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 28.79 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 13.97 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 1.046 %
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 0.06 % 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 -0.12 % 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 -0.21 % 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 -0.21 % 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 0.06 % 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 -0.12 %

Cross References

Resources Reference
ChEBI 32181
ChEMBL CHEMBL25202
DrugBank DB04942
DrugCentral 3580
FDA SRS 08V52GZ3H9
Human Metabolome Database HMDB0015605
Guide to Pharmacology 2648
KEGG C12864
PDB A80
PharmGKB PA164743464
PubChem 108143
SureChEMBL SCHEMBL36207
ZINC ZINC000000538415
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