AFIMOXIFENE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category UNKNOWN
UNII 95K54647BZ
EPA CompTox DTXSID7022384

Structure

InChI Key TXUZVZSFRXZGTL-QPLCGJKRSA-N
Smiles CC/C(=C(\c1ccc(O)cc1)c1ccc(OCCN(C)C)cc1)c1ccccc1
InChI
InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H29NO2
Molecular Weight 387.52
AlogP 5.7
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 32.7
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Estrogen receptor modulator MODULATOR KEGG Wikipedia
Protein: Estrogen receptor
Description: Estrogen receptor
Organism : Homo sapiens
P03372 ENSG00000091831
Protein: Estrogen-related receptor gamma
Description: Estrogen-related receptor gamma
Organism : Homo sapiens
P62508 ENSG00000196482
Protein: Estrogen receptor
Description: Estrogen receptor beta
Organism : Homo sapiens
Q92731 ENSG00000140009
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 1
- 1-70 - - -
Assay Description Organism Bioactivity Reference
Antagonist activity at luciferase-fused ERalpha in human HEK293 cells expressing eYFP assessed as reduction of E2-induced estrogenic activity after 2 hrs by BRET assay Homo sapiens 70.0 nM
Antagonist activity at ERalpha in human T47D-KBLuc cells assessed as inhibition of E2-induced transcriptional activity by luciferase reporter gene assay Homo sapiens 10.0 nM
Antiproliferative activity against human MCF7 cells treated for 48 hrs followed by refreshed every 96 hrs measured on day 10 by Lowry assay Homo sapiens 150.0 nM
Displacement of fluormone-labeled ES2 from recombinant full length human ERalpha ligand binding domain expressed in insect cells after 2 hrs by TR-FRET assay Homo sapiens 0.53 nM
Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 5 days by Coulter counting method Homo sapiens 3.4 nM
Induction of selective estrogen receptor alpha degradation in human MCF7 cells harboring TK-ERE-Luc assessed as reduction in estradiol-induced transcriptional activity after 24 hrs by luciferase reporter gene assay Homo sapiens 3.0 nM
Antiproliferative activity against human MCF7 cells after 6 days in presence of estradiol by CellTiter-Glo assay Homo sapiens 9.9 nM
Induction of selective estrogen receptor alpha degradation in human MCF7 cells harboring TK-ERE-Luc assessed as reduction in estradiol-induced GREB1 mRNA expression after 24 hrs by TaqMan assay Homo sapiens 10.2 nM
Displacement of Fluormone ES2 Green from full-length untagged human ERalpha expressed in insect cells after 2 hrs by fluorescence polarization assay Homo sapiens 5.6 nM
Inhibition of estradiol-induced proliferation in human Ishikawa cells after 72 hrs by Cell-titer-Glo assay Homo sapiens 3.57 ug.mL-1
Inhibition of estradiol-induced proliferation in human MCF7 cells after 72 hrs by Cell-titer-Glo assay Homo sapiens 0.95 ug.mL-1
Inhibition of estradiol-induced proliferation in human MDA-MB-231 cells after 72 hrs by Cell-titer-Glo assay Homo sapiens 6.51 ug.mL-1
Inhibition of NFkappaB in mouse RAW 264.7 cells assessed as reduction in LPS induced NO production at 10 uM after 24 hrs by Griess assay relative to control Mus musculus 21.51 %
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 0.19 %
Binding affinity to GST-tagged human ER alpha ligand-binding domain by TR-FRET assay Homo sapiens 2.1 nM
Antagonist activity at FLAG-tagged ERalpha (unknown origin) expressed in HEK293 cells assessed as reduction in E2-induced ER-alpha-mediated transcriptional activity by luciferase reporter gene assay Homo sapiens 0.79 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 0.28 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.96 %
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 -0.31 % 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 -0.24 % 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 -0.31 % 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 -0.24 %
Antagonist activity at estrogen receptor in human T47D cells incubated for 18 hrs by ultra high sensitivity luminescence reporter gene assay Homo sapiens 1.36 nM
Antiproliferative activity against human MCF-7 cells incubated for 72 hrs by Cell-titer Glo assay Homo sapiens 3.5 nM
Displacement of fluorescent-labeled E2 from LBD of ERalpha (unknown origin) by TR-FRET assay Homo sapiens 2.24 nM
Displacement of fluorescent-labeled E2 from LBD of ERbeta (unknown origin) by TR-FRET assay Homo sapiens 1.68 nM
Antagonist activity at ERalpha (unknown origin) expressed in human U2OS cells assessed as inhibition of E2-induced transactivation by dual luciferase reporter gene assay Homo sapiens 2.3 nM
Antagonist activity at ERbeta (unknown origin) expressed in human U2OS cells assessed as inhibition of E2-induced transactivation by dual luciferase reporter gene assay Homo sapiens 1.0 nM
Displacement of fluorescent labeled-ligand from ERalpha (unknown origin) by competitive binding assay Homo sapiens 7.5 nM

Related Entries

Cross References

Resources Reference
ChEBI 44616
ChEMBL CHEMBL489
DrugBank DB04468
FDA SRS 95K54647BZ
Human Metabolome Database HMDB0060530
KEGG C05011
PDB OHT
SureChEMBL SCHEMBL9189
ZINC ZINC000000902197
CONTENTS