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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2007-04-12 15:51:51 UTC
Update Date2020-02-26 21:26:08 UTC
HMDB IDHMDB0005849
Secondary Accession Numbers
  • HMDB05849
Metabolite Identification
Common Name4-Androstenediol
Description4-Androstenediol is a metabolite of testosterone. Conversely, the conversion of 4-androstenediol to testosterone has been demonstrated to occur in homogenates of hyperplastic human female adrenal glands. 4-Androstenediol is an anabolic agent that has been found in increased concentration in athletes suspected of doping. 4-Androstenediol has also been found in aqueous and solid nutritional supplements that are commercially available. Studies showing that non-hormonal supplements such as vitamins, minerals, and amino acids can contain anabolic androgenic steroids not declared on the labels of the products have been published. These undeclared substances (often prohormones of testosterone) can cause health risks to consumers and might lead to positive results in sports doping control. It has been demonstrated that 4-androstenediol taken by mouth is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women (PMID: 15808000 , 15103700 , 10638382 , 15370836 ).
Structure
Data?1582752368
Synonyms
ValueSource
Androst-4-ene-3beta,17beta-diolKegg
Androst-4-ene-3b,17b-diolGenerator
Androst-4-ene-3β,17β-diolGenerator
(3b,17b)-Androst-4-ene-3,17-diolHMDB
3b,17b-Dihydroxy-4-androsteneHMDB
4-Androstene-3b,17b-diolHMDB
Androst-4-en-3b,17b-diolHMDB
D4-Androstene-3b,17b-diolHMDB
(3beta,17beta)-Androst-4-ene-3,17-diolHMDB
(3β,17β)-Androst-4-ene-3,17-diolHMDB
3beta,17beta-Dihydroxy-4-androsteneHMDB
3β,17β-Dihydroxy-4-androsteneHMDB
4-AndrostenediolHMDB
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol
Traditional Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol
CAS Registry Number1156-92-9
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyBTTWKVFKBPAFDK-LOVVWNRFSA-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
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-4-steroid
  • Delta-4-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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 Solubility0.048 g/LALOGPS
logP3.1ALOGPS
logP2.95ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.5ChemAxon
pKa (Strongest Basic)-0.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.33 m³·mol⁻¹ChemAxon
Polarizability34.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-0290000000-7d52fa98e687764c22a2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-066r-3236900000-b524811a4353b5996ed1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-f4b512d07e8fa29cf8beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0290000000-7a460a768fecd3e1cea3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01oy-3890000000-8177324a0ce9fde3f678Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7318adfbaee2ca1f4eefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0090000000-ea1dd5bd96f621180cc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-1190000000-355691f711b0faad45c2Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01526
Phenol Explorer Compound IDNot Available
FooDB IDFDB023781
KNApSAcK IDNot Available
Chemspider ID120071
KEGG Compound IDC14210
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Androstenediol
METLIN IDNot Available
PubChem Compound136297
PDB IDNot Available
ChEBI ID34386
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thuyne WV, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements. J Chromatogr Sci. 2005 Jan;43(1):2-6. [PubMed:15808000 ]
  2. Van Thuyne W, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in solid nutritional supplements. Biomed Chromatogr. 2004 Apr;18(3):155-9. [PubMed:15103700 ]
  3. Earnest CP, Olson MA, Broeder CE, Breuel KF, Beckham SG: In vivo 4-androstene-3,17-dione and 4-androstene-3 beta,17 beta-diol supplementation in young men. Eur J Appl Physiol. 2000 Feb;81(3):229-32. [PubMed:10638382 ]
  4. Parr MK, Geyer H, Reinhart U, Schanzer W: Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. Food Addit Contam. 2004 Jul;21(7):632-40. [PubMed:15370836 ]