Human Metabolome Database Version 3.5

Showing metabocard for Etiocholanediol (HMDB00551)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:27:34 -0600
HMDB ID HMDB00551
Secondary Accession Numbers None
Metabolite Identification
Common Name Etiocholanediol
Description Etiocholanediol 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 Link_out, 16338181 Link_out, 16337352 Link_out, 17260133 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5b-Androstane-3a,17b-diol
  2. (3a,5b,17b)-Androstane-3,17-diol
  3. 3a,17b-Dihydroxyetiocholane
  4. b-Androstane-3a,17b-diol
  5. beta-Androstane-3a,17b-diol
Chemical Formula C19H32O2
Average Molecular Weight 292.4562
Monoisotopic Molecular Weight 292.240230268
IUPAC Name (1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional IUPAC Name 5β-androstane-3α,17β-diol
CAS Registry Number 1851-23-6
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 Key CBMYJHIOYJEBSB-GCXXXECGSA-N
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)
Substituents
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct Parent Androgens and Derivatives
Ontology
Status Detected 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
  • Cytoplasm
  • 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 35.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.000067 (0.000045-0.00012) uM Adult (>18 years old) Male Normal
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 FDB022111
KNApSAcK ID Not Available
Chemspider ID 118551 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00551 Link_out
Metagene Link HMDB00551 Link_out
METLIN ID 5535 Link_out
PubChem Compound 134494 Link_out
PDB ID Not Available
ChEBI ID 36714 Link_out
References
Synthesis Reference Baulieu, 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. 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 Link_out
  2. 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 Link_out
  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 Link_out