Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:05:25 UTC
Update Date2021-09-14 15:40:19 UTC
HMDB IDHMDB0060580
Secondary Accession Numbers
  • HMDB60580
Metabolite Identification
Common NameEthisterone
DescriptionEthisterone is a metabolite of danazol. Ethisterone is a progestogen hormone. The first orally active progestin, ethisterone (pregneninolone, 17α-ethynyltestosterone or 19–norandrostane), the 17α-ethynyl analog of testosterone, was synthesized in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at Schering AG in Berlin and marketed in Germany in 1939 as Proluton C and by Schering in the U.S. in 1945 as Pranone. Ethisterone was also marketed in the U.S. (Wikipedia )
Structure
Data?1563866078
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 Weight312.4458
Monoisotopic Molecular Weight312.20893014
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
CAS Registry NumberNot Available
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@]2(O)C#C
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.09331661259
DarkChem[M-H]-171.44131661259
DeepCCS[M-2H]-216.90230932474
DeepCCS[M+Na]+192.37230932474
AllCCS[M+H]+180.032859911
AllCCS[M+H-H2O]+177.032859911
AllCCS[M+NH4]+182.832859911
AllCCS[M+Na]+183.632859911
AllCCS[M-H]-185.932859911
AllCCS[M+Na-2H]-186.132859911
AllCCS[M+HCOO]-186.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EthisteroneC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@]2(O)C#C3806.9Standard polar33892256
EthisteroneC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@]2(O)C#C2692.7Standard non polar33892256
EthisteroneC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@]2(O)C#C2767.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethisterone,1TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C2857.0Semi standard non polar33892256
Ethisterone,1TMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2721.1Semi standard non polar33892256
Ethisterone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2816.6Semi standard non polar33892256
Ethisterone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2846.0Standard non polar33892256
Ethisterone,2TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3132.9Standard polar33892256
Ethisterone,1TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3120.6Semi standard non polar33892256
Ethisterone,1TBDMS,isomer #2C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C2996.9Semi standard non polar33892256
Ethisterone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3321.6Semi standard non polar33892256
Ethisterone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3316.0Standard non polar33892256
Ethisterone,2TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C3348.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ethisterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0490000000-70da7a36790d59e5aec12017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethisterone GC-MS (1 TMS) - 70eV, Positivesplash10-0aou-1259000000-15d6bab9887e263c62732017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethisterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 10V, Positive-QTOFsplash10-03di-0169000000-c3a3859c9249ba72e6622017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 20V, Positive-QTOFsplash10-0btj-0291000000-04631559fd3d6eeaf96d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 40V, Positive-QTOFsplash10-0v4r-2490000000-b96a17af7ffa84b61a5e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 10V, Negative-QTOFsplash10-03di-0009000000-714673f1ccbbef0d107a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 20V, Negative-QTOFsplash10-03di-0039000000-edc9d17d6776c137fae12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 40V, Negative-QTOFsplash10-052g-0090000000-09a994bdce08144c9cb62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 10V, Positive-QTOFsplash10-0292-0092000000-87469d8eaf22bca0423c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 20V, Positive-QTOFsplash10-01dj-0950000000-872492e74ef79726b1fc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 40V, Positive-QTOFsplash10-00xr-3940000000-1fb184dfb1c47b20c9272021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 10V, Negative-QTOFsplash10-03di-0009000000-152b659b4891e36b54f32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 20V, Negative-QTOFsplash10-03di-0009000000-2fd97457f6fe96a074b42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethisterone 40V, Negative-QTOFsplash10-0a59-0394000000-326a8e9cae724f94ba3a2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC14487
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthisterone
METLIN IDNot Available
PubChem Compound5284557
PDB IDNot Available
ChEBI ID34749
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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. [PubMed:16902246 ]
  3. 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. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. MACGREGOR TN: Progesterone and ethisterone. Practitioner. 1958 Jan;180(1075):83-7. [PubMed:13494335 ]
  6. Dmowski WP: Endocrine properties and clinical application of danazol. Fertil Steril. 1979 Mar;31(3):237-51. [PubMed:374128 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.