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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 22:34:37 UTC
Update Date2019-01-11 19:18:06 UTC
HMDB IDHMDB0004626
Secondary Accession Numbers
  • HMDB04626
Metabolite Identification
Common NameTetrahydrogestrinone
DescriptionThe identification of tetrahydrogestrinone (THG), the first true "designer androgen," as a sports doping agent reflects both an alarmingly sophisticated illicit manufacturing facility and an underground network of androgen abusers in elite sports, as well as the still untapped potential for designer androgens in medicine. Never marketed, THG was apparently developed as a potent androgen that was undetectable by conventional International Olympic Committee-mandated urinary sports doping tests. As a potent androgen and progestin with unspecified contaminants, its distribution for use at high doses without any prior biological or toxicological evaluation poses significant health risks. Yet this diversion of science also highlights the prospect of designer androgens for use in human medicine. Designer androgens also offer the possibility of tissue-specific effects enhancing the beneficial effects of androgens while mitigating the undesirable ones. Further developments require better understanding of the post receptor tissue selectivity of androgens, comparable to the mechanism underlying that of partial estrogen agonists (SERMs). This experience highlights the ongoing need for vigilance to detect novel drug doping strategies in order to maintain fairness and safety in elite sports. This will require the deployment of generic catch-all tests, such as sensitive and specific in vitro androgen bioassays, coupled with the development of mass spectrometry-based tests for specific doping agents. Starting from gestrinone, chemists can synthesize THG in one reaction step. (PMID: 15934041 , 15292520 ).
Structure
Data?1547234286
Synonyms
ValueSource
(17a)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,9,11-trien-3-oneHMDB
THGHMDB
Chemical FormulaC21H28O2
Average Molecular Weight312.4458
Monoisotopic Molecular Weight312.20893014
IUPAC Name(10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one
Traditional Nametetrahydrogestrinone
CAS Registry Number618903-56-3
SMILES
[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h9,11,13,18-19,23H,3-8,10,12H2,1-2H3/t18-,19+,20+,21+/m1/s1
InChI KeyOXHNQTSIKGHVBH-ANULTFPQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-oxosteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.95ALOGPS
logP3.5ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.9ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.42 m³·mol⁻¹ChemAxon
Polarizability37.02 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1190000000-df8a155fb516cec4576aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2029000000-895175c474d195f98cc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0095000000-8cbb62095c5e14373a79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-0191000000-e69b0d42106f07a3727cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-1490000000-96c8e821e03405188c49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0029000000-c002fd210563a9508a67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0089000000-1b89e06ba01d60280bddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0090000000-e424a28e9a87e909dcf0View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06870
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023385
KNApSAcK IDNot Available
Chemspider ID5257020
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrogestrinone
METLIN IDNot Available
PubChem Compound6857686
PDB ID17H
ChEBI IDNot Available
References
Synthesis ReferenceLabrie, Fernand; Luu-The, Van; Calvo, Ezequiel; Martel, Celine; Cloutier, Julie; Gauthier, Sylvain; Belleau, Pascal; Morissette, Jean; Levesque, Marie-Helene; Labrie, Claude. Tetrahydrogestrinone induces a genomic signature typical of a potent anabolic steroid. J Endocrinol. 2005 Feb;184(2):427-33. Pubmed: 15684350
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thevis M, Geyer H, Mareck U, Schanzer W: Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. J Mass Spectrom. 2005 Jul;40(7):955-62. [PubMed:15934041 ]
  2. Handelsman DJ: Designer androgens in sport: when too much is never enough. Sci STKE. 2004 Jul 27;2004(244):pe41. [PubMed:15292520 ]