ESTRIOL

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Synonyms
Status
Molecule Category UNKNOWN
ATC G03CA04 G03CC06
UNII FB33469R8E
EPA CompTox DTXSID9022366

Structure

InChI Key PROQIPRRNZUXQM-ZXXIGWHRSA-N
Smiles C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1C[C@@H](O)[C@@H]2O
InChI
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H24O3
Molecular Weight 288.39
AlogP 2.58
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 0.0
Polar Surface Area 60.69
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
Estrogen receptor modulator MODULATOR PubMed Other PubMed
Protein: Estrogen receptor
Description: Estrogen receptor
Organism : Homo sapiens
P03372 ENSG00000091831
Protein: Estrogen receptor
Description: Estrogen receptor beta
Organism : Homo sapiens
Q92731 ENSG00000140009
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- - 100000 - -
Enzyme Oxidoreductase
- - - - 30
Secreted protein
- - 234 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
2 - - - -
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 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 103
Unclassified protein
- 20100 - - -
Assay Description Organism Bioactivity Reference
Growth response in cultures of MCF-7 (human breast cancer cell line) cells Homo sapiens 0.0483 nM
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin Homo sapiens 234.42 nM
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 29.5 %
DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 1.691 nM DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) None 0.483 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 110.17 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 102.73 %
Agonist activity at ER-beta (unknown origin) transfected in HEK293T cells after 24 hrs by Steady-Glo luciferase reporter gene assay Homo sapiens 0.1259 nM
Agonist activity at ER-alpha (unknown origin) transfected in HEK293T cells after 24 hrs by Steady-Glo luciferase reporter gene assay Homo sapiens 1.995 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 -5.72 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.75 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.77 %
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 0.04 % 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 0.18 % 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 0.04 % 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 0.18 %

Related Entries

Cross References

Resources Reference
ChEBI 27974
ChEMBL CHEMBL193482
DrugBank DB04573
DrugCentral 3187
FDA SRS FB33469R8E
Human Metabolome Database HMDB0000153
Guide to Pharmacology 2821
PDB ESL
PharmGKB PA164769104
PubChem 5756
SureChEMBL SCHEMBL78033
ZINC ZINC000003815418
CONTENTS