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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-04-12 15:51:51 UTC
Update Date2017-12-07 01:55:33 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 month is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women. (PMID: 15808000 , 15103700 , 10638382 , 15370836 ).
Structure
Thumb
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
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-diol
Traditional Name4-androstenediol
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
DescriptionThis compound 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
Polarizability34.52 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-0290000000-7d52fa98e687764c22a2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-066r-3236900000-b524811a4353b5996ed1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-f4b512d07e8fa29cf8beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0290000000-7a460a768fecd3e1cea3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01oy-3890000000-8177324a0ce9fde3f678View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7318adfbaee2ca1f4eefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0090000000-ea1dd5bd96f621180cc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-1190000000-355691f711b0faad45c2View 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 IDDB01526
Phenol Explorer Compound IDNot Available
FoodDB 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 ID428213
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 ]