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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 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
Data?1582752139
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
5Β-androstane-3α,17β-diolHMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5R,7R,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-diol
Traditional 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
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
Description 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

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.99631661259
DarkChem[M-H]-165.68431661259
AllCCS[M+H]+177.23432859911
AllCCS[M-H]-179.13632859911
DeepCCS[M-2H]-208.67130932474
DeepCCS[M+Na]+183.30530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Etiocholanediol[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@]12C2433.3Standard polar33892256
Etiocholanediol[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@]12C2438.1Standard non polar33892256
Etiocholanediol[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@]12C2611.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Etiocholanediol,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC[C@@H]2O[Si](C)(C)C2563.9Semi standard non polar33892256
Etiocholanediol,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC[C@@H]2O2552.9Semi standard non polar33892256
Etiocholanediol,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]34C)[C@@H]1CC[C@@H]2O[Si](C)(C)C2573.3Semi standard non polar33892256
Etiocholanediol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2857.1Semi standard non polar33892256
Etiocholanediol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@@H](O)CC[C@H]4[C@@H]3CC[C@@H]2C12820.7Semi standard non polar33892256
Etiocholanediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3133.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-0290000000-ef7ce05726cbec3a35bd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2237900000-35be1627cada18777db82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanediol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 10V, Positive-QTOFsplash10-004l-0090000000-ea970ea07cbd199d95ca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 20V, Positive-QTOFsplash10-056r-0290000000-241c15d984d5502957c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 40V, Positive-QTOFsplash10-00mk-2790000000-1fb4fb943a8eb42cf30d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 10V, Negative-QTOFsplash10-0006-0090000000-7976b987ec10e61bdb4c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 20V, Negative-QTOFsplash10-006x-0090000000-72251dd83cca96a12d442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 40V, Negative-QTOFsplash10-01r5-0190000000-8a798c89a6c57c1531692017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 10V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 20V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 40V, Negative-QTOFsplash10-000l-0090000000-ac9e93370094e8aebfa12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 10V, Positive-QTOFsplash10-002f-0090000000-36f4d97265b0d994d6282021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 20V, Positive-QTOFsplash10-052b-3940000000-b87bad8b672cc5fb32b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanediol 40V, Positive-QTOFsplash10-0aos-3900000000-0f8ce10c286f165d6e0f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB022111
KNApSAcK IDNot Available
Chemspider ID118551
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtiocholanediol
METLIN ID5535
PubChem Compound134494
PDB IDNot Available
ChEBI ID36714
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]