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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 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
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional Name(1S,2S,5R,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-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
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-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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point219 - 221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB01530
Phenol Explorer Compound IDNot Available
FooDB IDFDB022114
KNApSAcK IDNot Available
Chemspider ID15039
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3%CE%B1-Androstanediol
METLIN ID5538
PubChem Compound15818
PDB IDNot Available
ChEBI ID36713
Food Biomarker OntologyNot Available
VMH IDCE2209
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]
  7. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]