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Compound Detail

CHEMBL9225

HEXESTROL
💊 Approved Drug
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💊 Approved Drug
CC[C@H](c1ccc(O)cc1)[C@@H](CC)c1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL9225
Name HEXESTROL
Phase Approved
Structure Type MOL
InChI Key PBBGSZCBWVPOOL-HDICACEKSA-N

Known Names

Erythrohexestrol Hexestrol Meso-hexestrol Mesohexestrol NSC-9894
3
Targets
3
Activities
2
Assay Types
1
PK Parameters
20
Publications
5
Known Names

Molecular Properties

270.4
MW (Da)
4.79
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.82
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product
USAN Stem -estr-

Extended Properties

Molecular Formula C18H22O2
MW 270.37
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness 0.25

Drug Warnings

Withdrawn
carcinogenicity
suspected carcinogenicity in newborns following prenatal exposure.
Country: Italy   Year: 1979

Activity Summary

IC50 2 meas. best 8.7
EC50 1 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Ishikawa
CHEMBL614649
 EC50 10.0 10.0 0.1 1
Estrogen receptor
CHEMBL2094114
 IC50 8.7 8.7 2.0 1
Unchecked
CHEMBL612545
 IC50 5.16 5.16 6880.5 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 830000000.0 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Ishikawa EC50 = 0.1 nM 10.0 Agonist activity in Ishikawa human endometrial cells -
Estrogen receptor IC50 = 2.0 nM 8.7 Binding affinity for rat estrogen receptor -
Unchecked IC50 = 6880.5 nM 5.16 PubChem BioAssay. GLP1 secretion from STC-1 cells-IC50. (Class of assay: confi... -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
2995668 10.1021/jm00148a022 Estrogen receptor 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
9873709 10.1016/s0960-894x(98)00592-7 Estrogen receptor 4
19394116 10.1016/j.ejmech.2009.03.013 Estrogen receptor 3
19394116 10.1016/j.ejmech.2009.03.013 Estrogen receptor beta 3
2296033 10.1021/jm00163a066 Estrogen receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
19286283 10.1016/j.ejmech.2009.02.006 Estrogen receptor beta 3
19286283 10.1016/j.ejmech.2009.02.006 Estrogen receptor 3
19286283 10.1016/j.ejmech.2009.02.006 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
15501051 10.1016/j.bmcl.2004.09.048 Estrogen receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.1016/0960-894X(96)00165-5 Estrogen receptor 2
6809943 10.1021/jm00349a013 MCF7 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine