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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:26:11 UTC
HMDB IDHMDB00383
Secondary Accession NumbersNone
Metabolite Identification
Common Name3a,17a-Dihydroxy-5b-androstane
DescriptionThe unspecified form of the steroid, normally a major metabolite of testosterone with androgenic activity. It has been implicated as a regulator of gonadotropin secretion.3a,17a-Dihydroxy-5b-androstane is a metabolite of natural androgens (testosterone, epitestosterone, dihydrotestosterone, and dehydroepiandrosterone) present in small amount in the urine of normal individuals (PMID 9381514 ).
Structure
Thumb
Synonyms
  1. 3 alpha,5 beta,7 alpha-3,7-Dihydroxyandrostan-17-one
  2. 3a,17a-Dihydroxy-5b-androstane
  3. 5b-Androstane-3a,17a-diol
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional IUPAC Name(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
CAS Registry Number5856-10-0
SMILES
C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@H]2O
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+/m1/s1
InChI KeyCBMYJHIOYJEBSB-CRQQDORFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassAndrogens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • C19 steroids (androgens) and derivatives(Lipidmaps)
  • Hydroxysteroids
  • androstane-3alpha,17beta-diol(ChEBI)
Substituents
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct ParentAndrogens and Derivatives
Ontology
StatusExpected and 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 PointNot AvailableNot 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 area40.46ChemAxon
rotatable bond count0ChemAxon
refractivity84.63ChemAxon
polarizability35.28ChemAxon
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 IDFDB022001
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07632
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00383
Metagene LinkHMDB00383
METLIN ID5372
PubChem Compound53477690
PDB IDNot Available
ChEBI ID27727
References
Synthesis ReferenceMiller, A. M.; Dorfman, Ralph I. Metabolism of the steroid hormones: Isolation of etiocholane-3(a),17(a)-diol from human urine. Endocrinology (1948), 42 174-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Uotila P, Hartiala J, Nienstedt W: The metabolism of testosterone by human, rabbit and rat kidney. Int J Biochem. 1980;12(3):345-51. Pubmed: 7418937
  2. Eriksson H, Gustafsson JA, Sjovall J: Excretion of steroid hormones in adults. C19 and C21 steroids in faeces from pregnant women. Eur J Biochem. 1970 Feb;12(3):520-6. Pubmed: 5440628
  3. Shackleton CH, Roitman E, Phillips A, Chang T: Androstanediol and 5-androstenediol profiling for detecting exogenously administered dihydrotestosterone, epitestosterone, and dehydroepiandrosterone: potential use in gas chromatography isotope ratio mass spectrometry. Steroids. 1997 Oct;62(10):665-73. Pubmed: 9381514
  4. Peng TC, Munson PL: The isolation of 5-beta-androstane-3-alpha,17-alpha-diol from normal human urine. Steroids. 1968 Feb;11(2):105-12. Pubmed: 5636704