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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-10-19 22:53:58 UTC
HMDB IDHMDB00493
Secondary Accession NumbersNone
Metabolite Identification
Common Name5a-Androstane-3b,17b-diol
DescriptionAndrostane-3,17-diol is a metabolite of dihydrotestosterone. It doesn't bind androgen receptors, but efficiently binds the estrogen receptor beta and inhibits prostate cancer cell migration through the activation of estrogen receptor beta. (PMID 15958594 ).
Structure
Thumb
Synonyms
ValueSource
(3beta,5alpha,17beta)-Androstane-3,17-diolChEBI
3beta,17beta-Dihydroxy-5alpha-androstaneChEBI
5-ALPHA-ANDROSTANE-3-BETA,17BETA-diolChEBI
5alpha-Androstan-3beta,17beta-diolChEBI
(3b,5a,17b)-Androstane-3,17-diolGenerator
(3β,5α,17β)-androstane-3,17-diolGenerator
3b,17b-Dihydroxy-5a-androstaneGenerator
3β,17β-dihydroxy-5α-androstaneGenerator
5-a-ANDROSTANE-3-b,17b-diolGenerator
5-α-androstane-3-β,17β-diolGenerator
5a-Androstan-3b,17b-diolGenerator
5α-androstan-3β,17β-diolGenerator
3b,17b-AndrostanediolHMDB
5alpha-Androstane-3beta,17beta-diolHMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
Traditional Name5-α-androstane-3-β,17β-diol
CAS Registry Number571-20-0
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 KeyInChIKey=CBMYJHIOYJEBSB-YSZCXEEOSA-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-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and 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 (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.019 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m3·mol-1ChemAxon
Polarizability35.52 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0feb-0910000000-95c33219e21fca1431b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006t-9621000000-2bf4147f35ce4e2b858aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aos-9851000000-65b418ed0598e7d18552View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.000149 (0.000057-0.00025) uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableAdult (>18 years old)Female
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [22944140 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022073
KNApSAcK IDNot Available
Chemspider ID211834
KEGG Compound IDC12525
BioCyc IDALPHA-ANDROSTAN-3BETA17BETA-DIOL
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00493
Metagene LinkHMDB00493
METLIN ID5479
PubChem Compound242332
PDB IDAOM
ChEBI ID18329
References
Synthesis ReferenceMerlani, M. I.; Amiranashvili, L. Sh.; Men'shova, N. I.; Kemertelidze, E. P. Synthesis of 5a-androstan-3b,17b-diol from tigogenin. Chemistry of Natural Compounds (2007), 43(1), 97-99.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Stewart ME, Pochi PE, Strauss JS, Wotiz HH, Clark SJ: In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol. J Endocrinol. 1977 Mar;72(3):385-90. [856929 ]
  2. Guerini V, Sau D, Scaccianoce E, Rusmini P, Ciana P, Maggi A, Martini PG, Katzenellenbogen BS, Martini L, Motta M, Poletti A: The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype. Cancer Res. 2005 Jun 15;65(12):5445-53. [15958594 ]