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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:26:52 UTC
HMDB IDHMDB00458
Secondary Accession NumbersNone
Metabolite Identification
Common Name5a-Androstane-3a,17a-diol
Description5a-Androstane-3a,17a-diol is an steroid found in feces from pregnant women (PMID 5440628 ), primarily in the monosulfate and disulfate fractions from normal human (PMID 4245755 ), and glucuronide and mono- and disulphate conjugates of neutral steroids in human bile (PMID 5493463 ).
Structure
Thumb
Synonyms
  1. 3a,17a-Dihydroxy-5a-androstane
  2. 5a-Androstane-3a,17a-diol
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5R,7S,10R,11S,14R,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,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
CAS Registry Number6165-21-5
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-CUZKMJQKSA-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
  • Cytoplasm
  • 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
  • Cytoplasm
  • 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 IDFDB022056
KNApSAcK IDNot Available
Chemspider ID8032954
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00458
Metagene LinkHMDB00458
METLIN ID5446
PubChem Compound9857254
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceMcDermott, Ian R.; Robinson, Cecil H. Novel synthesis of 5a-androstane-3a,17a-diol. Journal of the Chemical Society, Chemical Communications (1979), (1), 28-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. Laatikainen T, Vihko R: Identification of C19O2 and C21O2 steroids in the mono- and disulphate fractions of human faeces. Eur J Biochem. 1970 Apr;13(3):534-8. Pubmed: 4245755
  3. Laatikainen T: Quantitative studies on the excretion of glucuronide and mono- and disulphate conjugates of neutral steroids in human bile. Ann Clin Res. 1970 Dec;2(4):338-49. Pubmed: 5493463