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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 17:46:27 UTC
HMDB IDHMDB0000551
Secondary Accession Numbers
  • HMDB00551
Metabolite Identification
Common NameEtiocholanediol
DescriptionEtiocholanediol is one of the compounds tested to allow for the unequivocal identification of the presence of urinary anabolic steroids and metabolites banned for use in sport by athletes. In urine samples collected for anti-doping purposes with moderately elevated testosterone and epitestosterone ratio, or when a suspicion of manipulation of the sample occurs, Etiocholanediol is tested for further clarification. It is worth mentioning that the concentration parameters vary enormously according to the gender of the subjects, ethnic origin, the urine collection period (before or after effort, period of the day) and the hydration state of the athlete. Urinary steroid data using several methodologies are not appropriate for identification purposes and to an extent not unique to individuals. (PMID: 16337352 , 16338181 , 16337352 , 17260133 ).
Structure
Thumb
Synonyms
ValueSource
(3alpha,5beta,17beta)-Androstane-3,17-diolChEBI
3alpha,17beta-DihydroxyetiocholaneChEBI
(3a,5b,17b)-Androstane-3,17-diolGenerator
(3α,5β,17β)-androstane-3,17-diolGenerator
3a,17b-DihydroxyetiocholaneGenerator
3α,17β-dihydroxyetiocholaneGenerator
5b-Androstane-3a,17b-diolHMDB
b-Androstane-3a,17b-diolHMDB
beta-Androstane-3a,17b-diolHMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
Traditional Nameβ-androstane-3a,17b-diol
CAS Registry Number1851-23-6
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+/m1/s1
InChI KeyCBMYJHIOYJEBSB-GCXXXECGSA-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-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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m³·mol⁻¹ChemAxon
Polarizability35.2 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-0290000000-ef7ce05726cbec3a35bdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2237900000-35be1627cada18777db8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0090000000-ea970ea07cbd199d95caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0290000000-241c15d984d5502957c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-2790000000-1fb4fb943a8eb42cf30dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-7976b987ec10e61bdb4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0090000000-72251dd83cca96a12d44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r5-0190000000-8a798c89a6c57c153169View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000067 (0.000045-0.00012) uMAdult (>18 years old)MaleNormal details
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 IDFDB022111
KNApSAcK IDNot Available
Chemspider ID118551
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5535
PubChem Compound134494
PDB IDNot Available
ChEBI ID36714
References
Synthesis ReferenceBaulieu, Etienne Emile; Robel, Paul. Androst-5-ene-3b,17b-diol-17a-H3 to testosterone-17a-H3 and 5a- and 5b-androstane-3a,17b-diol-17a-H3 in vivo. Steroids (1963), 2(1), 111-18.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Saudan C, Kamber M, Barbati G, Robinson N, Desmarchelier A, Mangin P, Saugy M: Longitudinal profiling of urinary steroids by gas chromatography/combustion/isotope ratio mass spectrometry: diet change may result in carbon isotopic variations. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):324-7. Epub 2005 Dec 9. [PubMed:16338181 ]
  2. Robinson N, Castella V, Saudan C, Sottas PE, Schweizer C, Dimo-Simonin N, Mangin P, Saugy M: Elevated and similar urinary testosterone/epitestosterone ratio in all samples of a competition testing: suspicion of a manipulation. Forensic Sci Int. 2006 Nov 10;163(1-2):148-51. Epub 2005 Dec 6. [PubMed:16337352 ]
  3. Thevis M, Geyer H, Mareck U, Sigmund G, Henke J, Henke L, Schanzer W: Detection of manipulation in doping control urine sample collection: a multidisciplinary approach to determine identical urine samples. Anal Bioanal Chem. 2007 Aug;388(7):1539-43. Epub 2007 Jan 27. [PubMed:17260133 ]