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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL691
CHEMBL691
Compound Name ETHINYL ESTRADIOL
ChEMBL Synonyms FEMINONE | Ethinyl Estradiol | Ovulen-21 | Enovid-E | Norinyl | Ethynylestradiol | Ovulen-28 | LYNORAL | Enovid | ETHINYLOESTRADIOL | ETHINYLESTRADIOL | Etinestryl | ESTINYL | Ovulen | Ginestrene | Follicoral
Max Phase 4 (Approved)
Trade Names FEMINONE | LYNORAL | Etinestryl | Follicoral | ESTINYL
Molecular Formula C20H24O2

Additional synonyms for CHEMBL691 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1CC[C@@]2(O)C#C
Standard InChI InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7- ...
Download InChI
Standard InChI Key BFPYWIDHMRZLRN-SLHNCBLASA-N

Sources

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

Alternate Forms of Compound in ChEMBL


CHEMBL691

Molecule Features

CHEMBL691 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:Y Black Box:N Availability Type:Prescription-only

Mechanism of Action

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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Cystic FibrosisD003550Orphanet:586Cystic fibrosis1ClinicalTrials
Depressive DisorderD003866EFO:0003761unipolar depression2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection1ClinicalTrials
HemorrhageD006470MP:0001914hemorrhage2ClinicalTrials
Neural Tube DefectsD009436Orphanet:3388Neural tube defect3ClinicalTrials
Turner SyndromeD014424Orphanet:881Turner syndrome3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis1ClinicalTrials
Hidradenitis SuppurativaD017497EFO:1000710hidradenitis suppurativa2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
DysmenorrheaD0044123ClinicalTrials
Hepatitis CD006526EFO:0003047hepatitis C infection1ClinicalTrials
InfectionD007239EFO:0000544infection1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia1ClinicalTrials
Diabetes Mellitus, Type 2D003924EFO:0001360type II diabetes mellitus1ClinicalTrials
OsteoporosisD010024EFO:0003882osteoporosis2ClinicalTrials
PregnancyD011247EFO:0002950pregnancy3ClinicalTrials
Anorexia NervosaD000856EFO:0004215anorexia nervosa3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm2ClinicalTrials
Acne VulgarisD000152EFO:0003894acne3ClinicalTrials
AmenorrheaD0005683ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Polycystic Ovary SyndromeD011085EFO:0000660polycystic ovary syndrome3ClinicalTrials
Bone Diseases, MetabolicD001851HP:0000938osteopenia3ClinicalTrials
Hepatitis C, ChronicD019698EFO:0004220Chronic Hepatitis C infection1ClinicalTrials

Clinical Data

ClinicalTrials.gov ETHINYL ESTRADIOL
The Cochrane Collaboration ETHINYL ESTRADIOL

Metabolites for CHEMBL691

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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 CHEMBL691. 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
CHEMBL3559 Steryl-sulfatase Homo sapiens 1.000
CHEMBL4681 Aldo-keto-reductase family 1 member C3 Homo sapiens 1.000
CHEMBL206 Estrogen receptor alpha Homo sapiens 1.000
CHEMBL3181 Estradiol 17-beta-dehydrogenase 1 Homo sapiens 1.000
CHEMBL242 Estrogen receptor beta Homo sapiens 1.000
CHEMBL3072 Androgen Receptor Rattus norvegicus 1.000
CHEMBL2034 Glucocorticoid receptor Homo sapiens 1.000
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 1.000
CHEMBL208 Progesterone receptor Homo sapiens 1.000
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.999
CHEMBL1978 Cytochrome P450 19A1 Homo sapiens 0.999
CHEMBL1871 Androgen Receptor Homo sapiens 0.993
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.969
CHEMBL233 Mu opioid receptor Homo sapiens 0.837
CHEMBL3429 Estrogen-related receptor alpha Homo sapiens 0.779
CHEMBL3522 Cytochrome P450 17A1 Homo sapiens 0.633
CHEMBL4027 Neurokinin 1 receptor Rattus norvegicus 0.494
CHEMBL265 Dopamine D1 receptor Rattus norvegicus 0.493
CHEMBL3368 Glucocorticoid receptor Rattus norvegicus 0.473
CHEMBL4234 Estradiol 17-beta-dehydrogenase 3 Homo sapiens 0.333



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL3559 Steryl-sulfatase Homo sapiens 1.000
CHEMBL3072 Androgen Receptor Rattus norvegicus 1.000
CHEMBL3181 Estradiol 17-beta-dehydrogenase 1 Homo sapiens 1.000
CHEMBL206 Estrogen receptor alpha Homo sapiens 1.000
CHEMBL4681 Aldo-keto-reductase family 1 member C3 Homo sapiens 1.000
CHEMBL242 Estrogen receptor beta Homo sapiens 1.000
CHEMBL2034 Glucocorticoid receptor Homo sapiens 1.000
CHEMBL3394 Tubulin beta chain Bos taurus 1.000
CHEMBL3751 Estrogen-related receptor beta Homo sapiens 1.000
CHEMBL208 Progesterone receptor Homo sapiens 1.000
CHEMBL1978 Cytochrome P450 19A1 Homo sapiens 1.000
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 1.000
CHEMBL1871 Androgen Receptor Homo sapiens 0.999
CHEMBL4027 Neurokinin 1 receptor Rattus norvegicus 0.987
CHEMBL4729 Cytochrome P450 2B6 Homo sapiens 0.984
CHEMBL3522 Cytochrome P450 17A1 Homo sapiens 0.911
CHEMBL233 Mu opioid receptor Homo sapiens 0.886
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.845
CHEMBL237 Kappa opioid receptor Homo sapiens 0.822
CHEMBL4931 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase Homo sapiens 0.803

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
296.4 296.1776 3.61 0 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
10.24 - 4.11 4.11 1 22 0.72

Structural Alerts

There are 2 structural alerts for CHEMBL691. 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
G03CA - Natural and semisynthetic estrogens, plain
G03CA01 - ethinylestradiol

L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L02 - ENDOCRINE THERAPY
L02A - HORMONES AND RELATED AGENTS
L02AA - Estrogens
L02AA03 - ethinylestradiol

ChemSpider ChemSpider:BFPYWIDHMRZLRN-SLHNCBLASA-N
DailyMed ethinyl estradiol
PubChem SID: 144204698 SID: 144208489 SID: 144210731 SID: 170464983 SID: 26753042 SID: 76025

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL691



ACToR 406932-93-2
Atlas 17-alpha-ethynylestradiol 17 alpha-ethynylestradiol (EE2) ethinylestradiol 17a-ethynylestradiol
BindingDB 50187243
Brenda 90712 8464 34889 12525 11503 11603 114774 6789
ChEBI 4903
ChemicalBook CB1350377
DrugBank DB00977
DrugCentral 1082
eMolecules 475099
EPA CompTox Dashboard DTXSID5020576
FDA SRS 423D2T571U
Guide to Pharmacology 7071
Human Metabolome Database HMDB0001926
IBM Patent System 2CA2668E5C8F44D8E1479167C96C7D87
LINCS LSM-5593
LipidMaps LMST02010036
Mcule MCULE-5991854877
MolPort MolPort-001-794-636
NIH Clinical Collection SAM001247008
Nikkaji J2.803G
PDBe 3WF
PharmGKB PA449527
PubChem 5991
PubChem: Thomson Pharma 14922735 14898199
Rhea 4903
Selleck Ethinyl-Estradiol
SureChEMBL SCHEMBL4071
ZINC ZINC000003812897

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