2-METHOXYESTRADIOL

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Synonyms
Status
Molecule Category UNKNOWN
UNII 6I2QW73SR5
EPA CompTox DTXSID3040938

Structure

InChI Key CQOQDQWUFQDJMK-SSTWWWIQSA-N
Smiles COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
InChI
InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H26O3
Molecular Weight 302.41
AlogP 3.62
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 49.69
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 22.0
Assay Description Organism Bioactivity Reference
In vitro inhibition of primary human umbilical vein endothelial cell (HUVEC) proliferation at 0.01 uM Homo sapiens 100.0 %
IIn vitro inhibition of primary human umbilical vein endothelial cell (HUVEC) proliferation at 0.1 uM Homo sapiens 100.0 %
In vitro inhibition of primary human umbilical vein endothelial cell (HUVEC) proliferation at 1 uM Homo sapiens 60.0 %
In vitro inhibition of primary human umbilical vein endothelial cell (HUVEC) proliferation at 3 uM Homo sapiens 25.0 %
In vitro inhibition of primary human umbilical vein endothelial cell (HUVEC) proliferation in presence of bFGF Homo sapiens 100.0 %
Inhibition of estrogen receptor negative MDA-MB 231 breast cancer cell proliferation at 1 uM Homo sapiens 250.0 nM
Compound was evaluated for inhibition of colchicine binding to tubulin in experiment I. Bos taurus 19.0 %
Compound was evaluated for inhibition of colchicine binding to tubulin in experiment II. Bos taurus 60.0 %
Evaluated for % inhibition of colchicine binding to tubulin. None 19.0 %
Percentage inhibition of colchicine binding to tubulin. None 38.0 %
Inhibition of colchicine binding to tubulin None 44.0 %
Growth inhibitory concentration against MDA-MB-231 cancer cell line Homo sapiens 840.0 nM
Antiproliferative activity against human LNCaP cell line Homo sapiens 500.0 nM
Antiproliferative activity against human HUVECs after 48 hrs Homo sapiens 840.0 nM
Antiangiogenic activity against HUVEC cells assessed as inhibition of proliferation Homo sapiens 523.0 nM
Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin Homo sapiens 0.8318 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 74.3 %
Antiangiogenic activity against HUVECs by Brdu incorporation assay Homo sapiens 840.0 nM
Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by WST1 assay Homo sapiens 790.0 nM
Antiangiogenic activity against HUVEC assessed as growth inhibition after 48 hrs by WST1 assay Homo sapiens 680.0 nM
Antiproliferative activity against human MDA-MB-231 cells Homo sapiens 790.0 nM
Antiangiogenic activity in HUVEC assessed as inhibition of cell proliferation Homo sapiens 680.0 nM
Antiproliferative activity against human MCF7 cells after 72 hrs by crystal violet biomass reduction assay Homo sapiens 842.0 nM
Displacement of [3H]colchicine from bovine brain tubulin at 5 uM after 10 mins Bos taurus 17.0 %
Cytotoxicity against vincristine-resistant human HL60 cells after 72 hrs MTS assay Homo sapiens 900.0 nM
Antiproliferative activity against human SKOV3 cells by sulforhodamine B assay Homo sapiens 867.0 nM
Antiproliferative activity against human HeLa cells by sulforhodamine B assay Homo sapiens 608.0 nM
Antiproliferative activity against human HeLa cells expressing tubulin 3beta by sulforhodamine B assay Homo sapiens 586.0 nM
Anticancer activity against human K562 cells assessed as cell growth inhibition after 5 days by MTT assay Homo sapiens 800.0 nM
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 4.4 %
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 -3.78 %
Cytotoxicity against human PC3 cells after 72 hrs by CellTiter one aqueous solution assay Homo sapiens 82.0 ug.mL-1
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 20.72 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 0.1 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 22.54 %
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 0.75 % 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 0.5 % 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 0.53 % 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 0.5 % 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 0.53 % 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 0.75 %

Related Entries

Cross References

Resources Reference
ChEBI 28955
ChEMBL CHEMBL299613
DrugBank DB02342
FDA SRS 6I2QW73SR5
Human Metabolome Database HMDB0000405
KEGG C05302
PDB ESM
PubChem 66414
SureChEMBL SCHEMBL8796
ZINC ZINC000003818826
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