DIETHYLSTILBESTROL

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC G03CB02 G03CC05 L02AA01
UNII 731DCA35BT
EPA CompTox DTXSID3020465

Structure

InChI Key RGLYKWWBQGJZGM-ISLYRVAYSA-N
Smiles CC/C(=C(/CC)c1ccc(O)cc1)c1ccc(O)cc1
InChI
InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H20O2
Molecular Weight 268.36
AlogP 4.83
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 40.46
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 20.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action Action Reference
Estrogen receptor alpha agonist AGONIST PubMed
Protein: Estrogen receptor alpha
Description: Estrogen receptor
Organism : Homo sapiens
P03372 ENSG00000091831
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 14000 - - -
Enzyme Isomerase
- 75000 - - -
Enzyme Oxidoreductase
- 460 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 30
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
- 14600 - - -
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
0-12 0-770 - 0-0
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 2
0-9 4-610 - 0-0 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group B Nuclear hormone receptor subfamily 3 group B member 3
630 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 14125 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 31-46
Transporter Primary active transporter P-type ATPase Calcium ATPase
- 14000 - - -
Assay Description Organism Bioactivity Reference
Inhibition of estradiol binding to estrogen receptor in Human Breast cancer cytosol (3.3% ethanol) Homo sapiens 0.126 nM
Apparent inhibition constant for estrogen receptor in Human uterine cytosol in 3.3%ethanol Homo sapiens 0.128 nM
In vitro displacement of 0.5 nM [3H]17-beta-estradiol from human Estrogen receptor alpha Homo sapiens 0.49 nM
In vitro inhibition of [3H]17-beta-estradiol binding to human estrogen receptor alpha Homo sapiens 3.0 nM
In vitro displacement of 0.5 nM [3H]17-beta-estradiol from human Estrogen receptor beta Homo sapiens 0.63 nM
In vitro inhibitory concentration against [3H]17-beta-estradiol binding to human estrogen receptor 2 Homo sapiens 4.0 nM
Activation of estrogen response element in HeLa cells stably transfected with human Estrogen receptor alpha. None 0.06 nM
Inhibition of [3H]17-beta-estradiol binding to human recombinant Estrogen receptor alpha. None 12.0 nM
Displacement of radioligand from Estrogen receptor alpha None 0.33 nM
Activation of estrogen response element in HeLa cells stably transfected with human Estrogen receptor beta. None 0.02 nM
Inhibition of [3H]17-beta-estradiol binding to human recombinant Estrogen receptor beta. None 9.0 nM
In vitro agonist effect on estrogen receptor alpha transcriptional activation in MCF-7 cells at 10 pM Homo sapiens 0.007 nM
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 30.1 %
Estrogen-Related Receptor gamma activity in FRET assay Homo sapiens 630.0 nM
Inhibition of Trypanosoma brucei GalE at 50 uM Trypanosoma brucei 75.0 %
Inhibition of human aldehyde oxidase Homo sapiens 460.0 nM
DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole) None 958.0 nM
DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) Bos taurus 611.0 nM
DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) None 851.0 nM
DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 0.915 nM DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 0.261 nM
TP_TRANSPORTER: drug resistance(SN-38) in BCRP-expressing K562 cells None 500.0 nM
TP_TRANSPORTER: drug resistance(Mitoxantrone) in BCRP-expressing K562 cells None 500.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 62.1 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 31.1 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 68.1 %
Displacement of [3H]-estradiol from human recombinant ERalpha expressed in Sf21 cells after 2 hrs Homo sapiens 770.0 nM
Displacement of [3H]-estradiol from human recombinant ERbeta expressed in Sf21 cells after 2 hrs Homo sapiens 610.0 nM
Displacement of [3H]Estradiol from human recombinant estrogen receptor alpha expressed in Sf9 cells after 2 hrs Homo sapiens 0.22 nM Displacement of [3H]Estradiol from human recombinant estrogen receptor alpha expressed in Sf9 cells after 2 hrs Homo sapiens 0.77 nM
Displacement of [3H]Estradiol from human recombinant estrogen receptor alpha expressed in Sf9 cells at 10 uM after 2 hrs relative to control Homo sapiens -6.0 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 45.56 %
Inhibition of human recombinant TTR Y78F mutant-mediated fibrillogenesis at 40 uM after 30 mins by turbidimetric assay relative to control Homo sapiens 67.0 %
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 30.69 %
Agonist activity at FLAG-tagged ERalpha (unknown origin) expressed in HEK293 cells assessed as induction of ER-alpha-mediated transcriptional activity by luciferase reporter gene assay Homo sapiens 0.2 nM
Selective estrogen receptor down-regulator activity at FLAG-tagged ERalpha (unknown origin) expressed in HEK293 cells assessed as induction of ERalpha degradation by luciferase reporter gene assay Homo sapiens 0.11 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 1.74 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.04 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 11.4 %
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 1.42 % 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 0.02 % 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 0.02 % 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 1.42 % 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 0.02 % 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 0.02 %

Cross References

Resources Reference
ChEBI 41922
ChEMBL CHEMBL411
DrugBank DB00255
DrugCentral 875
FDA SRS 731DCA35BT
Guide to Pharmacology 2801
KEGG C07620
PDB DES
PharmGKB PA449307
PubChem 448537
SureChEMBL SCHEMBL9223
ZINC ZINC000000001290
CONTENTS