| 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 manipliation 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(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 Formlia |
C19H32O2
| Average Molecliar Weight |
292.4562
| Monoisotopic Molecliar Weight |
292.240230268
| 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 Name |
β-androstane-3a,17b-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 |
| Classification |
Not classified
| 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 Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Polarizability35.2 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Blood
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.000067 (0.000045-0.00012) uMAdlit (>18 years old)MaleNormal
17716701
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| 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
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00551
| Metagene Link |
HMDB00551
| METLIN ID |
5535
| PubChem Compound |
134494
| PDB ID |
Not Available
| ChEBI ID |
36714
Product: Ibrutinib-biotin
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 |
- 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 ]
- 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 ]
- 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 ]
|
PMID: 15175384