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Record Information
Version4.0
Creation Date2007-04-12 18:45:57 UTC
Update Date2017-09-27 08:24:39 UTC
HMDB IDHMDB0005962
Secondary Accession Numbers
  • HMDB05962
Metabolite Identification
Common NameDehydroandrosterone
DescriptionDehydroandrosterone is a normal human androgen. It has been found dehydroandrosterone and other androgens excretion is affected by seasonal rhythms changes. In a study of patients with peptic ulcer in the stage of remission, their androgen levels were higher both in summer and winter, but in the spring their levels are higher in normal subjects. There is a high correlation between Dehydroandrosterone excretion and testosterone; this ratio is also used as an aid for a better discrimination between physiologically high and pharmacologically high ratios of testosterone in sports. (PMID: 3157236 , 9001956 , 10774538 ).
Structure
Thumb
Synonyms
ValueSource
3a-Hydroxy-5-androsten-17-oneHMDB
3a-Hydroxy-androst-5-en-17-oneHMDB
Androst-5-en-3a-ol-17-oneHMDB
D5-Androstene-3a-ol-17-oneHMDB
IsoandrostenoloneHMDB
AndrostenoloneMeSH
DehydroisoandrosteroneMeSH
5 Androsten 3 beta hydroxy 17 oneMeSH
5 Androsten 3 ol 17 oneMeSH
5-Androsten-3-ol-17-oneMeSH
DHEAMeSH
DehydroepiandrosteroneMeSH
5-Androsten-3-beta-hydroxy-17-oneMeSH
PrasteroneMeSH
Prasterone, 3 alpha isomerMeSH
Prasterone, 3 alpha-isomerMeSH
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC Name(1S,2R,5R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Namedehydroandrosterone
CAS Registry Number2283-82-1
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O2/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/h3,13-16,20H,4-11H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1
InChI KeyFMGSKLZLMKYGDP-HKQXQEGQSA-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
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP3.53ALOGPS
logP3.36ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.66 m³·mol⁻¹ChemAxon
Polarizability33.96 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, Positivesplash10-08pl-0290000000-e7c57e64082ba630bb86View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001m-1069000000-c5bd759bc6149ac932eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-a667a243a4d1f4d5e402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0290000000-03f40d327c70daf5361aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-3590000000-254aaa59cce970705502View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-8b01497a25c81d375b42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-41c2d6ae909fbc17a1bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2090000000-5e1c69e4cc1018242a56View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023792
KNApSAcK IDNot Available
Chemspider ID118560
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDehydroandrosterone
METLIN IDNot Available
PubChem Compound134506
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceButenandt, Adolf; Dannenbaum, Hans; Hanisch, Gunter; Kudszus, Helmut. Dehydroandrosterone. Z. physiol. Chem. (1935), 237 57-74.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Eil'bart VL: [Seasonal and circadian rhythms of the excretion of androgens and their fractions in peptic ulcer patients in the remission phase in the markedly continental climate of Transbaikalia]. Ter Arkh. 1985;57(1):80-4. [PubMed:3157236 ]
  2. Dehennin L, Lafarge P, Dailly P, Bailloux D, Lafarge JP: Combined profile of androgen glucuro- and sulfoconjugates in post-competition urine of sportsmen: a simple screening procedure using gas chromatography-mass spectrometry. J Chromatogr B Biomed Appl. 1996 Dec 6;687(1):85-91. [PubMed:9001956 ]
  3. Uralets VP, Gillette PA: Over-the-counter delta5 anabolic steroids 5-androsen-3,17-dione; 5-androsten-3beta, 17beta-diol; dehydroepiandrosterone; and 19-nor-5-androsten-3,17-dione: excretion studies in men. J Anal Toxicol. 2000 Apr;24(3):188-93. [PubMed:10774538 ]