ethisterone (CHEM044273)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:59:12 UTC
Update Date2016-11-09 01:23:05 UTC
Accession NumberCHEM044273
Identification
Common Nameethisterone
ClassSmall Molecule
DescriptionA 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17-beta-Hydroxy-17-alpha-ethynyl-4-androsten-3-oneChEBI
17-Ethynyl-17beta-hydroxyandrost-4-en-3-oneChEBI
17-Hydroxy-17alpha-pregn-4-en-20-yn-3-oneChEBI
17alpha-EthinyltestosteroneChEBI
17alpha-Ethynyl-17beta-hydroxyandrost-4-en-3-oneChEBI
17alpha-EthynyltestosteroneChEBI
AethisteronChEBI
AethisteronumChEBI
AnhydrohydroxyprogesteroneChEBI
AnhydroxyprogesteroneChEBI
EthisteronumChEBI
EthynyltestosteroneChEBI
EtisteronaChEBI
LutocylolChEBI
NugestoralChEBI
Ora-lutinChEBI
PranoneChEBI
ProdroxanChEBI
ProduxanChEBI
ProgestabChEBI
ProgestoralChEBI
SyngestrotabsChEBI
TrosinoneChEBI
17alpha-Ethinyl testosteroneKegg
ProgestoletsKegg
17-b-Hydroxy-17-a-ethynyl-4-androsten-3-oneGenerator
17-Β-hydroxy-17-α-ethynyl-4-androsten-3-oneGenerator
17-Ethynyl-17b-hydroxyandrost-4-en-3-oneGenerator
17-Ethynyl-17β-hydroxyandrost-4-en-3-oneGenerator
17-Hydroxy-17a-pregn-4-en-20-yn-3-oneGenerator
17-Hydroxy-17α-pregn-4-en-20-yn-3-oneGenerator
17a-EthinyltestosteroneGenerator
17Α-ethinyltestosteroneGenerator
17a-Ethynyl-17b-hydroxyandrost-4-en-3-oneGenerator
17Α-ethynyl-17β-hydroxyandrost-4-en-3-oneGenerator
17a-EthynyltestosteroneGenerator
17Α-ethynyltestosteroneGenerator
17a-Ethinyl testosteroneGenerator
17Α-ethinyl testosteroneGenerator
17 alpha EthynyltestosteroneHMDB
17 alpha-EthynyltestosteroneHMDB
PregneninoloneHMDB
Chemical FormulaC21H28O2
Average Molecular Mass312.446 g/mol
Monoisotopic Mass312.209 g/mol
CAS Registry Number434-03-7
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Nameethisterone
SMILESC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@]2(O)C#C
InChI IdentifierInChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
InChI KeyCHNXZKVNWQUJIB-CEGNMAFCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Acetylide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0091 g/LALOGPS
logP3.44ALOGPS
logP3.52ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.9 m³·mol⁻¹ChemAxon
Polarizability36.45 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0490000000-70da7a36790d59e5aec1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0aou-1259000000-15d6bab9887e263c6273Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0169000000-c3a3859c9249ba72e662Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btj-0291000000-04631559fd3d6eeaf96dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4r-2490000000-b96a17af7ffa84b61a5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-714673f1ccbbef0d107aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0039000000-edc9d17d6776c137fae1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-0090000000-09a994bdce08144c9cb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0292-0092000000-87469d8eaf22bca0423cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01dj-0950000000-872492e74ef79726b1fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-3940000000-1fb184dfb1c47b20c927Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-152b659b4891e36b54f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0009000000-2fd97457f6fe96a074b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-0394000000-326a8e9cae724f94ba3aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060580
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEthisterone
Chemspider IDNot Available
ChEBI ID34749
PubChem Compound ID5284557
Kegg Compound IDC14487
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=13494335
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=374128
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=8327560
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. MACGREGOR TN: Progesterone and ethisterone. Practitioner. 1958 Jan;180(1075):83-7.
9. Dmowski WP: Endocrine properties and clinical application of danazol. Fertil Steril. 1979 Mar;31(3):237-51.
10. The lipid handbook with CD-ROM