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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:43:28 UTC
HMDB IDHMDB0000554
Secondary Accession Numbers
  • HMDB00554
Metabolite Identification
Common NameDihydroandrosterone
DescriptionDihydroandrosterone is a major metabolite of testosterone. Dihydroandrosterone is the main steroid produced by the immature ovary; at puberty the synthesis of steroids shifts toward 4-ene-3-oxo steroids. testosterone 5a-reduced metabolites, including dihydrotestosterone are produced in the anterior pituitary and the central nervous system. Anabolic androgen steroid (AAS) are one of primary performance-enhancing substances abused by athletes. To defeat doping controls, athletes changed to take endogenous androgens from the application of synthetic AAS. testosterone was one candidate of endogenous androgens abused in sports. testosterone and its relevant steroids in urine is detected and monitored with GC/MS. The abuse of anabolic-androgenic steroids (AS) is a growing problem; however, the effects and mechanisms underlying their addictive effects are not well understood. (PMID: 17112575 , 6243214 , 491593 , 491592 ).
Structure
Thumb
Synonyms
ValueSource
(3alpha,5alpha,17beta)-Androstane-3,17-diolChEBI
3alpha,17beta-Dihydroxy-5alpha-androstaneChEBI
HombreolChEBI
(3a,5a,17b)-Androstane-3,17-diolGenerator
(3α,5α,17β)-androstane-3,17-diolGenerator
3a,17b-Dihydroxy-5a-androstaneGenerator
3α,17β-dihydroxy-5α-androstaneGenerator
AdiolHMDB
Etiocholane-3a,17b-diolHMDB
3a,5a-TetrahydrotestosteroneHMDB
5a-Androstane-3a,17b-diolHMDB
5alpha-Androstane-3alpha,17beta-androstanediolHMDB
5alpha-Androstane-3alpha,17beta-diolHMDB
Androstane-3a,17b-diolHMDB
Etiocholane-3alpha,17beta-diolHMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
Traditional Name5α-androstane-3α,17β-diol
CAS Registry Number1852-53-5
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyCBMYJHIOYJEBSB-KHOSGYARSA-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-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

  Molecular messenger:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point219 - 221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.56ALOGPS
logP3.2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m³·mol⁻¹ChemAxon
Polarizability35.39 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, Positivesplash10-03gi-0290000000-ef7ce05726cbec3a35bdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2226900000-73765a85fad7c004bde8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0090000000-22d60c19836ea8b4c291View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0390000000-edb0fb77b27575b4b729View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-2980000000-cd6eafa93f3164ed780aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-bc689c3cdfdf044c011eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0090000000-bfbc140857bbdb62bcffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vm-1290000000-bced1e06a8686f3501afView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Skin
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000475 (0.000352-0.000548) uMAdult (>18 years old)MaleNormal details
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 IDFDB022114
KNApSAcK IDNot Available
Chemspider ID15039
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5538
PubChem Compound15818
PDB IDNot Available
ChEBI ID36713
References
Synthesis ReferenceKieslich, Klaus. 5a-Androstane-3a,17b-diol. Ger. Offen. (1980), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Deslypere JP, Vermeulen A: Aging and tissue androgens. J Clin Endocrinol Metab. 1981 Aug;53(2):430-4. [PubMed:7251820 ]
  2. Rittmaster RS, Zwicker H, Thompson DL, Konok G, Norman RW: Androstanediol glucuronide production in human liver, prostate, and skin. Evidence for the importance of the liver in 5 alpha-reduced androgen metabolism. J Clin Endocrinol Metab. 1993 Apr;76(4):977-82. [PubMed:8473413 ]
  3. Frye CA: Some rewarding effects of androgens may be mediated by actions of its 5alpha-reduced metabolite 3alpha-androstanediol. Pharmacol Biochem Behav. 2007 Feb;86(2):354-67. Epub 2006 Nov 15. [PubMed:17112575 ]
  4. Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism. I--In the hypothalamus and in the anterior pituitary. J Steroid Biochem. 1979 Jul;11(1A):215-9. [PubMed:491592 ]
  5. Celotti F, Farina JM, Santaniello E, Martini L, Motta M: Effect of testosterone, its 5 alpha-reduced metabolites and the corresponding propionates on testosterone metabolism--II. In the ventral prostate and in the seminal vesicles. J Steroid Biochem. 1979 Jul;11(1A):221-5. [PubMed:491593 ]
  6. Eckstein B, Ravid R: Regulation of ovarian 17 beta-hydroxysteroid dehydrogenase activity by gonadotropin. Biochim Biophys Acta. 1980 Jan 17;627(2):165-71. [PubMed:6243214 ]