You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2007-04-12 18:45:57 UTC
Update Date2017-03-02 21:28:04 UTC
HMDB IDHMDB05962
Secondary Accession NumbersNone
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
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.66 m3·mol-1ChemAxon
Polarizability33.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB05962
Metagene LinkHMDB05962
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. [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. [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. [10774538 ]