FENRETINIDE

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Synonyms
Status
Molecule Category UNKNOWN
UNII 187EJ7QEXL
EPA CompTox DTXSID2032005

Structure

InChI Key AKJHMTWEGVYYSE-FXILSDISSA-N
Smiles CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)Nc2ccc(O)cc2)C(C)(C)CCC1
InChI
InChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H33NO2
Molecular Weight 391.56
AlogP 6.86
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 49.33
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 29.0
Assay Description Organism Bioactivity Reference
Binding affinity against Retinoic acid receptor gamma Homo sapiens 400.0 nM
Dissociation constant with retinol binding protein was determined None 170.0 nM
Growth inhibition of human MCF7 cells after 6 days by MTT assay Homo sapiens 150.0 nM
Growth inhibition of human estrogen receptor expressing MCF7 cells at 4 uM after 68 hrs relative to control Homo sapiens 62.0 %
Growth inhibition of human estrogen receptor deficient adriamycin-resistant MCF7 cells at 4 uM after 68 hrs relative to control Homo sapiens 60.0 %
Growth inhibition of human HepG2 cells at 4 uM after 68 hrs relative to control Homo sapiens 27.0 %
Growth inhibition of human DU145 cells at 4 uM after 68 hrs relative to control Homo sapiens 41.0 %
Growth inhibition of human HL60 cells at 4 uM after 72 hrs relative to control Homo sapiens 55.0 %
Antiproliferative activity against mouse neural precursor cells by MTT assay Mus musculus 334.0 nM
Antiproliferative activity against mouse medulloblastoma cells harboring heterozygous ptch1 gene by MTT assay Mus musculus 204.0 nM
Binding affinity to His-tagged recombinant human sRBP expressed in Escherichia coli BL21(DE3) assessed as apparent dissociation constant after 5 mins by fluorescence spectrophotometric analysis Homo sapiens 156.0 nM
Inhibition of Akt phosphorylation in human MIAPaCa2 cells assessed as effect on phospho-ERK levels at 7 uM after 48 hrs by immunoblotting Homo sapiens 30.0 %
Inhibition of mouse Tdo2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 100 uM after 45 mins by spectrophotometric analysis relative to control Mus musculus 32.0 %
Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control Mus musculus 55.0 %
Inhibition of mushroom tyrosinase using L-tyrosine as substrate at 50 uM by spectrophotometry relative to control Agaricus bisporus 21.0 %
Inhibition of mushroom tyrosinase using L-DOPA as substrate at 50 uM by spectrophotometry relative to control Agaricus bisporus 20.0 %
Antiviral activity against Chikungunya virus LR2006-OPY1 infected in human Huh7.5 cells after 48 hrs by luciferase reporter gene assay Chikungunya virus 500.0 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 24.02 %
Antiviral activity against Dengue virus 1 infected in human PBMC assessed as reduction in viral titer after 48 hrs preincubated with cells prior to ADE-mediated viral infection by plaque assay Dengue virus 1 800.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.8 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 21.5 %
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 38.98 % 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 -0.33 % 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 -0.33 % 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 38.98 %

Cross References

Resources Reference
ChEBI 42588
ChEMBL CHEMBL7301
DrugBank DB05076
FDA SRS 187EJ7QEXL
PDB FEN
PubChem 5288209
SureChEMBL SCHEMBL11703
ZINC ZINC000003871023
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