Human Metabolome Database Version 3.5

Showing metabocard for 3a,17a-Dihydroxy-5b-androstane (HMDB00383)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:26:11 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name 3a,17a-Dihydroxy-5b-androstane
Description The 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  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 Formula C19H32O2
Average Molecular Weight 292.4562
Monoisotopic Molecular Weight 292.240230268
IUPAC Name (2S,5R,14R,15S)-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional IUPAC Name (2S,5R,14R,15S)-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadecane-5,14-diol
CAS Registry Number 5856-10-0
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
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Androgens and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • C19 steroids (androgens) and derivatives(Lipidmaps)
  • Hydroxysteroids
  • androstane-3alpha,17beta-diol(ChEBI)
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct Parent Androgens and Derivatives
Status Expected and Not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.019 g/L ALOGPS
LogP 3.56 ALOGPS
LogP 3.2 ChemAxon
LogS -4.18 ALOGPS
pKa (strongest acidic) 18.3 ChemAxon
pKa (strongest basic) -0.76 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 40.46 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 84.63 ChemAxon
Polarizability 35.28 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022001
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C07632 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00383 Link_out
Metagene Link HMDB00383 Link_out
METLIN ID 5372 Link_out
PubChem Compound 53477690 Link_out
PDB ID Not Available
ChEBI ID 27727 Link_out
Synthesis Reference Miller, 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out