Hexestrol
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Also known as ErythrohexestrolMeso-hexestrolMesohexestrolNSC-9894(+/-)-hexestrolSID11112224SID26748324SID56463535SID144203928SID144211773SID174006924SID170466031rel-Hexestrol
Summary
Hexestrol (CHEMBL9225) is an approved small molecule targeting ESR1.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Targets: 1 (ESR1)
- Chemistry: 270.4 Da · C18H22O2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL9225 |
| Name | Hexestrol |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 192197 |
| Molecular formula | C18H22O2 |
| Molecular weight | 270.4 |
| InChIKey | PBBGSZCBWVPOOL-HDICACEKSA-N |
SMILES: CC[C@H](C1=CC=C(C=C1)O)[C@@H](CC)C2=CC=C(C=C2)O
IUPAC name: 4-[(3S,4R)-4-(4-hydroxyphenyl)hexan-3-yl]phenol
Also known as: Erythrohexestrol, Hexestrol, Meso-hexestrol, Mesohexestrol, NSC-9894, (+/-)-hexestrol, SID11112224, SID26748324, SID56463535, SID144203928, HEXESTROL, SID144211773
Patent coverage: 956 distinct patent families (2,912 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| ESR1 | Estrogen receptor-α | Antagonist | 10.3 | 1.7% | P03372 |
Broader ChEMBL bioactivity targets: 27 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Microtubule-associated protein tau, Prelamin-A/C, 4’-phosphopantetheinyl transferase ffp, Ferritin light chain, Androgen receptor, Beta-lactamase, D(1A) dopamine receptor, Estrogen receptor, Thromboxane A2 receptor.
Bioactivity
ChEMBL activities: 17 potent at pChembl ≥ 5 of 35 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P06211 | 8.7 | IC50 | 2 | nM | CHEMBL_ACT_1178531 |
| ESR1 | 7.6 | AC50 | 25.2 | nM | CHEMBL_ACT_25138913 |
| LMNA | 6.5 | Potency | 316.2 | nM | CHEMBL_ACT_3648934 |
| TDP1 | 6.3 | Potency | 501.2 | nM | CHEMBL_ACT_3936972 |
| PGR | 5.73 | AC50 | 1848 | nM | CHEMBL_ACT_25204346 |
| CYP2C19 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4016336 |
| CYP2C19 | 5.5 | AC50 | 3162 | nM | CHEMBL_ACT_6008402 |
| SLC6A3 | 5.48 | AC50 | 3305 | nM | CHEMBL_ACT_25125014 |
| P00811 | 5.4 | Potency | 3981 | nM | CHEMBL_ACT_4664754 |
| CYP3A4 | 5.3 | Potency | 5012 | nM | CHEMBL_ACT_4949221 |
| CYP2C9 | 5.3 | Potency | 5012 | nM | CHEMBL_ACT_5073219 |
| CYP3A4 | 5.3 | Potency | 5012 | nM | CHEMBL_ACT_5078570 |
| CYP3A4 | 5.3 | AC50 | 5012 | nM | CHEMBL_ACT_6005260 |
| CYP2C9 | 5.3 | AC50 | 5012 | nM | CHEMBL_ACT_6023870 |
| AR | 5.16 | AC50 | 6946 | nM | CHEMBL_ACT_25203413 |
| ADORA3 | 5.07 | AC50 | 8466 | nM | CHEMBL_ACT_25198761 |
| SLC6A2 | 5.06 | AC50 | 8771 | nM | CHEMBL_ACT_25146055 |
Target pathways
Aggregated over 1 target gene(s): ESR1.
Top Reactome pathways
17 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Nuclear signaling by ERBB4 | 1 | ESR1 |
| PIP3 activates AKT signaling | 1 | ESR1 |
| Constitutive Signaling by Aberrant PI3K in Cancer | 1 | ESR1 |
| Nuclear Receptor transcription pathway | 1 | ESR1 |
| SUMOylation of intracellular receptors | 1 | ESR1 |
| Ovarian tumor domain proteases | 1 | ESR1 |
| PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling | 1 | ESR1 |
| TFAP2 (AP-2) family regulates transcription of growth factors and their receptors | 1 | ESR1 |
| RUNX1 regulates estrogen receptor mediated transcription | 1 | ESR1 |
| ESR-mediated signaling | 1 | ESR1 |
| RUNX1 regulates transcription of genes involved in WNT signaling | 1 | ESR1 |
| Regulation of RUNX2 expression and activity | 1 | ESR1 |
| Extra-nuclear estrogen signaling | 1 | ESR1 |
| Estrogen-dependent gene expression | 1 | ESR1 |
| Mitochondrial unfolded protein response (UPRmt) | 1 | ESR1 |
| Developmental Lineage of Mammary Gland Luminal Epithelial Cells | 1 | ESR1 |
| Developmental Lineage of Mammary Gland Alveolar Cells | 1 | ESR1 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| negative regulation of transcription by RNA polymerase II | 1 |
| antral ovarian follicle growth | 1 |
| epithelial cell development | 1 |
| chromatin remodeling | 1 |
| regulation of DNA-templated transcription | 1 |
| regulation of transcription by RNA polymerase II | 1 |
| signal transduction | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| positive regulation of cytosolic calcium ion concentration | 1 |
| androgen metabolic process | 1 |
| male gonad development | 1 |
| negative regulation of gene expression | 1 |
| nuclear receptor-mediated steroid hormone signaling pathway | 1 |
| estrogen receptor signaling pathway | 1 |
| response to estradiol | 1 |
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
Clinical trials
Total trials: 0.
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
173 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| FULVESTRANT | ChEMBL + PubChem | Phase 4 (approved) | ESR1 |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | ESR1 |
| ALECTINIB | ChEMBL | Phase 4 (approved) | ESR1 |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | ESR1 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | ESR1 |
| ASPIRIN | ChEMBL | Phase 4 (approved) | ESR1 |
| AZTREONAM | ChEMBL | Phase 4 (approved) | ESR1 |
| BAZEDOXIFENE | ChEMBL | Phase 4 (approved) | ESR1 |
| BELINOSTAT | ChEMBL | Phase 4 (approved) | ESR1 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | ESR1 |
| BEXAROTENE | ChEMBL | Phase 4 (approved) | ESR1 |
| BISACODYL | ChEMBL | Phase 4 (approved) | ESR1 |
| BITHIONOL | ChEMBL | Phase 4 (approved) | ESR1 |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | ESR1 |
| BUTOCONAZOLE | ChEMBL | Phase 4 (approved) | ESR1 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | ESR1 |
| CASPOFUNGIN | ChEMBL | Phase 4 (approved) | ESR1 |
| CEFADROXIL | ChEMBL | Phase 4 (approved) | ESR1 |
| CEFEPIME | ChEMBL | Phase 4 (approved) | ESR1 |
| CEFTAZIDIME | ChEMBL | Phase 4 (approved) | ESR1 |
| CERIVASTATIN | ChEMBL | Phase 4 (approved) | ESR1 |
| CHLOROTRIANISENE | ChEMBL | Phase 4 (approved) | ESR1 |
| CISPLATIN | ChEMBL | Phase 4 (approved) | ESR1 |
| CLOFAZIMINE | ChEMBL | Phase 4 (approved) | ESR1 |
| CLOMIPHENE | ChEMBL | Phase 4 (approved) | ESR1 |
| CYCLOFENIL | ChEMBL | Phase 4 (approved) | ESR1 |
| DANAZOL | ChEMBL | Phase 4 (approved) | ESR1 |
| DAUNORUBICIN | ChEMBL | Phase 4 (approved) | ESR1 |
| DEQUALINIUM | ChEMBL | Phase 4 (approved) | ESR1 |
| DESOGESTREL | ChEMBL | Phase 4 (approved) | ESR1 |
| DIENESTROL | ChEMBL | Phase 4 (approved) | ESR1 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | ESR1 |
| DINOPROSTONE | ChEMBL | Phase 4 (approved) | ESR1 |
| DOXORUBICIN | ChEMBL | Phase 4 (approved) | ESR1 |
| DRONEDARONE | ChEMBL | Phase 4 (approved) | ESR1 |
| ELACESTRANT | ChEMBL | Phase 4 (approved) | ESR1 |
| ERGOCALCIFEROL | ChEMBL | Phase 4 (approved) | ESR1 |
| ERTAPENEM | ChEMBL | Phase 4 (approved) | ESR1 |
| ESTETROL | ChEMBL | Phase 4 (approved) | ESR1 |
| ESTRADIOL | ChEMBL | Phase 4 (approved) | ESR1 |
| ESTRADIOL CYPIONATE | ChEMBL | Phase 4 (approved) | ESR1 |
| ESTRADIOL VALERATE | ChEMBL | Phase 4 (approved) | ESR1 |
| ESTRAMUSTINE | ChEMBL | Phase 4 (approved) | ESR1 |
| ESTRIOL | ChEMBL | Phase 4 (approved) | ESR1 |
| ESTRONE | ChEMBL | Phase 4 (approved) | ESR1 |
| ETHINYL ESTRADIOL | ChEMBL | Phase 4 (approved) | ESR1 |
| ETHYLESTRENOL | ChEMBL | Phase 4 (approved) | ESR1 |
| ETHYNODIOL DIACETATE | ChEMBL | Phase 4 (approved) | ESR1 |
| ETONOGESTREL | ChEMBL | Phase 4 (approved) | ESR1 |
| ETRAVIRINE | ChEMBL | Phase 4 (approved) | ESR1 |
| FLUPIRTINE | ChEMBL | Phase 4 (approved) | ESR1 |
| HEXACHLOROPHENE | ChEMBL | Phase 4 (approved) | ESR1 |
| IBUPROFEN | ChEMBL | Phase 4 (approved) | ESR1 |
| ISOCONAZOLE | ChEMBL | Phase 4 (approved) | ESR1 |
| LASOFOXIFENE | ChEMBL | Phase 4 (approved) | ESR1 |
| LENVATINIB | ChEMBL | Phase 4 (approved) | ESR1 |
| LEVONORGESTREL | ChEMBL | Phase 4 (approved) | ESR1 |
| LUSUTROMBOPAG | ChEMBL | Phase 4 (approved) | ESR1 |
| LYMECYCLINE | ChEMBL | Phase 4 (approved) | ESR1 |
| MASOPROCOL | ChEMBL | Phase 4 (approved) | ESR1 |
Related Atlas pages
- Genes: ESR1
- Drugs: Fulvestrant, Acetophenazine, Alectinib, Apomorphine, Aripiprazole, Aspirin, Aztreonam, Bazedoxifene, Belinostat, Benzbromarone, Bexarotene, Bisacodyl, Bithionol, Bromocriptine, Butoconazole, Candesartan Cilexetil, Caspofungin, Cefadroxil, Cefepime, Ceftazidime, Cerivastatin, Chlorotrianisene, Cisplatin, Clofazimine, Clomiphene, Cyclofenil, Danazol, Daunorubicin, Dequalinium, Desogestrel, Dienestrol, Diethylstilbestrol, Dinoprostone, Doxorubicin, Dronedarone, Elacestrant, Ergocalciferol, Ertapenem, Estetrol, Estradiol, Estradiol Cypionate, Estradiol Valerate, Estramustine, Estriol, Estrone, Ethinyl Estradiol, Ethylestrenol, Ethynodiol Diacetate, Etonogestrel, Etravirine, Flupirtine, Hexachlorophene, Ibuprofen, Isoconazole, Lasofoxifene, Lenvatinib, Levonorgestrel, Lusutrombopag, Lymecycline, Masoprocol