ESTRONE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC G03CA07 G03CC04
UNII X9XKA379T9
EPA CompTox DTXSID4022367

Structure

InChI Key DNXHEGUUPJUMQT-CBZIJGRNSA-N
Smiles C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O
InChI
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H22O2
Molecular Weight 270.37
AlogP 3.82
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 37.3
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 20.0

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 Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1B Cytochrome P450 1B1
- - - - 16-40
Enzyme Cytochrome P450 Cytochrome P450 family 19 Cytochrome P450 family 19A Cytochrome P450 19A1
- - - 2500 -
Enzyme Hydrolase
- 51000 - - -
Enzyme Oxidoreductase
- 109-810 - 3-9500 8-94
Secreted protein
- - 7 10000 -
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
1-480 29-210 - - -
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
1-1135 31-540 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 109
Unclassified protein
- 93100 - - -
Assay Description Organism Bioactivity Reference
Ability to activate estrogen receptor 1-mediated transcription. None 120.0 nM
Activation of estrogen response element in HeLa cells stably transfected with human Estrogen receptor alpha. None 0.7 nM
Inhibition of [3H]17-beta-estradiol binding to human recombinant Estrogen receptor alpha. None 480.0 nM
Binding affinity towards estrogen receptor alpha by [3H]17-beta-estradiol displacement. None 210.0 nM
Ability to activate estrogen receptor 2-mediated transcription. None 120.0 nM
Activation of estrogen response element in HeLa cells stably transfected with human Estrogen receptor beta. None 2.1 nM
Binding affinity towards estrogen receptor beta by [3H]17-beta-estradiol displacement. None 540.0 nM
Growth response in cultures of MCF-7 (human breast cancer cell line) cells Homo sapiens 0.0772 nM
Inhibition of 17-beta HSD1 in T47D cells Homo sapiens 330.0 nM
Displacement of [3H]estrone from ER beta Homo sapiens 31.0 nM
Displacement of [3H]estrone from ER alpha Homo sapiens 29.0 nM
Inhibition of ER beta-mediated transactivation of ERE in HeLa cell luciferase assay Homo sapiens 26.0 nM
Inhibition of ER beta-mediated transactivation of ERE in HeLa cell luciferase assay at 10 uM Homo sapiens 166.0 nM
Inhibition of 17beta-HSD1 overexpressed in homogenated HEK293 cells at 1 uM None 59.0 %
Inhibition of 17beta-HSD1 over-expressed in homogenated HEK293 cells at 0.1 uM None 19.0 %
Inhibition of 17beta-HSD1 over-expressed in intact HEK293 cells at 10 uM None 83.0 %
Inhibition of 17beta-HSD1 over-expressed in intact HEK293 cells at 1 uM None 38.0 %
Inhibition of 17beta-HSD1 over-expressed in intact HEK293 cells at 0.1 uM None 8.0 %
Inhibition of 17beta-HSD1 over-expressed in intact T47D cells at 10 uM None 93.0 %
Inhibition of 17beta-HSD1 over-expressed in intact T47D cells at 1 uM None 85.0 %
Inhibition of 17beta-HSD1 over-expressed in intact T47D cells at 0.1 uM None 36.0 %
Inhibition of 17beta-HSD7 over-expressed in intact HEK293 cells at 10 uM Homo sapiens 0.0 %
Inhibition of 17beta-HSD7 over-expressed in intact HEK293 cells at 1 uM Homo sapiens 0.0 %
Inhibition of 17beta-HSD12 over-expressed in intact HEK293 cells at 10 uM Homo sapiens 0.0 %
Inhibition of 17beta-HSD12 over-expressed in intact HEK293 cells at 1 uM Homo sapiens 0.0 %
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin Homo sapiens 6.607 nM
Inhibition of 17beta-HSD1 in human T47D cells assessed as inhibition of transformation of [14C]-estrone into [14C]estrogen at 0.1 uM after 24 hrs Homo sapiens 37.0 %
Inhibition of 17beta-HSD1 in human T47D cells assessed as inhibition of transformation of [14C]-estrone into [14C]-estrogen at 1 uM after 24 hrs Homo sapiens 85.0 %
Inhibition of 17beta-HSD1 in human T47D cells assessed as inhibition of transformation of [14C]-estrone into [14C]estrogen at 10 uM after 24 hrs Homo sapiens 94.0 %
Inhibition of 17beta-HSD1 in human T47D cells assessed as inhibition of transformation of [14C]-estrone into [14C]estrogen Homo sapiens 218.0 nM
Inhibition of 17beta-HSD1 assessed as conversion of [14C]estradiol to [14C]estrone using NADP+ None 3.0 nM
Inhibition of 17beta-HSD1 expressed in HEK 293 cells assessed as conversion of [14C]estrone to [14C]estradiol using NADH None 810.0 nM
Inhibition of 17beta-HSD1 expressed in HEK 293 cells assessed as conversion of [14C]estrone to [14C]estradiol None 600.0 nM
Activity at human recombinant ERalpha by fluorescence polarization assay Homo sapiens 7.0 nM
Activity at human recombinant ERbeta by fluorescence polarization assay Homo sapiens 8.0 nM
Inhibition of His-tagged human 17beta-HSD1 expressed in Escherichia coli by scintillation counting Homo sapiens 109.0 nM
Displacement of [3H]17beta-estradiol from human ERalpha expressed in SF9 cells Homo sapiens 96.0 nM
Inhibition of His-tagged human 17beta-HSD1 expressed in Escherichia coli at 2 uM by scintillation counting Homo sapiens 90.0 %
Inhibition of human 17beta-HSD7 expressed in HEK293 cells assessed as inhibition of reduction of [14C]estrone into [14C]estradiol at 3 uM after 7 hrs Homo sapiens 10.1 %
DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 7.647 nM DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 2.185 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 280.11 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 109.27 %
Inhibition of VGLUT in rat brain assessed as [3H]-L-Glu uptake into synaptic vesicles at 250 uM relative to control Rattus norvegicus 98.0 %
Inhibition of recombinant human CYP1B1 expressed in bacterial microsomes co-expressing P450 reductase at 3 uM using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay relative to control Homo sapiens 40.0 %
Inhibition of recombinant human CYP1B1 expressed in supersomes coexpressing P450 reductase at 0.3 uM using 7-ethyl-O-resorufin as substrate after 45 mins in presence of NADPH by fluorescence assay relative to control Homo sapiens 16.0 %
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 3.39 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 21.04 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 15.96 %
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 0.1 % 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 0.06 % 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 0.1 %
Displacement of fluormone from GST-tagged ERbeta receptor LBD (unknown origin) measured after 60 mins by TR-FRET competitive binding assay Homo sapiens 0.94 nM
Agonist activity at full length human ERalpha receptor assessed as transcriptional activity incubated for 22 to 24 hrs by cell based luciferase reporter gene assay Homo sapiens 2.4 nM
Antagonist activity at full length human ERalpha receptor assessed as inhibition of estradiol-induced activation incubated for 22 to 24 hrs by cell based luciferase reporter gene assay Homo sapiens 50.0 nM
Antagonist activity at full length human ERbeta receptor assessed as inhibition of estradiol-induced activation incubated for 22 to 24 hrs by cell based luciferase reporter gene assay Homo sapiens 10.0 nM
Agonist activity at full length human ERbeta receptor assessed as transcriptional activity incubated for 22 to 24 hrs by cell based luciferase reporter gene assay Homo sapiens 0.5 nM

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Malaysia

Cross References

Resources Reference
ChEBI 17263
ChEMBL CHEMBL1405
DrugBank DB00655
DrugCentral 3188
FDA SRS X9XKA379T9
Human Metabolome Database HMDB0000145
Guide to Pharmacology 2818
KEGG C00468
PDB J3Z
PharmGKB PA449512
PubChem 5870
SureChEMBL SCHEMBL21702
ZINC ZINC000013509425
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