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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL411
CHEMBL411
Compound Name DIETHYLSTILBESTROL
ChEMBL Synonyms ESTROBENE | DISTILBENE | APSTIL | FONATOL | STILBOESTROL | SYNESTRIN | STILBETIN | NEW-ESTRANOL 1 | TAMPOVAGAN | ESTROGENINE | STILBESTROFORM | Stilboesterol | ESTROMENIN | PALESTROL | CYREN A | DIETHYLSTILBESTROL | STILBESTROL | SYNTHESTRIN
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names DIETHYLSTILBESTROL | STILBESTROL | APSTIL | DISTILBENE | STILBETIN | TAMPOVAGAN | Stilboesterol
Molecular Formula C18H20O2

Additional synonyms for CHEMBL411 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC\C(=C(\CC)/c1ccc(O)cc1)\c2ccc(O)cc2
Standard InChI InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-1 ...
Download InChI
Standard InChI Key RGLYKWWBQGJZGM-ISLYRVAYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL411

Molecule Features

CHEMBL411 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year
Country United States
Reason
Class

Mechanism of Action

Mechanism of Action ChEMBL Target References
Estrogen receptor alpha agonist Estrogen receptor alpha PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
NeoplasmsD009369EFO:0000616neoplasm4ATC
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov DIETHYLSTILBESTROL
The Cochrane Collaboration DIETHYLSTILBESTROL

Metabolites for CHEMBL411

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Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL411. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL206 Estrogen receptor alpha Homo sapiens 1.000
CHEMBL242 Estrogen receptor beta Homo sapiens 1.000
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.697
CHEMBL3318 Tyrosinase Agaricus bisporus 0.666
CHEMBL3222 Delta opioid receptor Mus musculus 0.625
CHEMBL2858 Mu opioid receptor Mus musculus 0.530
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.519
CHEMBL3530 Dual specificity mitogen-activated protein kinase kinase 7 Homo sapiens 0.331
CHEMBL2938 Protein kinase C gamma Homo sapiens 0.204



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL206 Estrogen receptor alpha Homo sapiens 1.000
CHEMBL242 Estrogen receptor beta Homo sapiens 1.000
CHEMBL4245 Estrogen-related receptor gamma Homo sapiens 1.000
CHEMBL270 Mu opioid receptor Rattus norvegicus 0.675
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.660
CHEMBL3318 Tyrosinase Agaricus bisporus 0.622
CHEMBL2693 Cystinyl aminopeptidase Homo sapiens 0.595
CHEMBL1978 Cytochrome P450 19A1 Homo sapiens 0.505
CHEMBL3222 Delta opioid receptor Mus musculus 0.471
CHEMBL2858 Mu opioid receptor Mus musculus 0.357
CHEMBL236 Delta opioid receptor Homo sapiens 0.252

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
268.4 268.1463 4.83 4 40.46 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 2 0 2 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
10.19 - 5.33 5.33 2 20 0.78

Structural Alerts

There are 2 structural alerts for CHEMBL411. To view alerts please click here.

Compound Cross References

ATC G - GENITO URINARY SYSTEM AND SEX HORMONES
G03 - SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03C - ESTROGENS
G03CC - Estrogens, combinations with other drugs
G03CC05 - diethylstilbestrol

G - GENITO URINARY SYSTEM AND SEX HORMONES
G03 - SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
G03C - ESTROGENS
G03CB - Synthetic estrogens, plain
G03CB02 - diethylstilbestrol

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L02 - ENDOCRINE THERAPY
L02A - HORMONES AND RELATED AGENTS
L02AA - Estrogens
L02AA01 - diethylstilbestrol

ChemSpider ChemSpider:RGLYKWWBQGJZGM-ISLYRVAYSA-N
PubChem SID: 11532921 SID: 144209605 SID: 144210844 SID: 17389919 SID: 26747240 SID: 26752777
Wikipedia Diethylstilbestrol

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL411



ACToR 22610-99-7
Atlas diethylstilbestrol
BindingDB 20625
Brenda 44833
ChEBI 41922
ChemicalBook CB9751457
DrugCentral 875
eMolecules 489194
EPA CompTox Dashboard DTXSID3020465
FDA SRS 731DCA35BT
Guide to Pharmacology 2801
KEGG Ligand C07620
LINCS LSM-42960
Mcule MCULE-3156396266
MolPort MolPort-001-785-868 MolPort-005-933-652
Nikkaji J113.282B J2.801K
NMRShiftDB 20200150
PDBe DES
PharmGKB PA449307
PubChem 448537
PubChem: Drugs of the Future 56310572
PubChem: Thomson Pharma 14848307
Selleck Diethylstilbestrol(Stilbestrol)
SureChEMBL SCHEMBL9223
ZINC ZINC000000001290

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/RGLYKWWBQGJZGM-ISLYRVAYSA-N spacer
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