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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:07 UTC
HMDB IDHMDB0000383
Secondary Accession Numbers
  • HMDB00383
Metabolite Identification
Common Name3a,17a-Dihydroxy-5b-androstane
Description3a,17a-Dihydroxy-5b-androstane, also known as 5b-androstane-3a,17a-diol or 3,7-dharn-17-one, 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. 3a,17a-Dihydroxy-5b-androstane is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752127
Synonyms
ValueSource
3 alpha,5 beta,7 alpha-3,7-Dihydroxyandrostan-17-oneHMDB
5b-Androstane-3a,17a-diolHMDB
3,7-DHARN-17-oneHMDB
3,7-Dihydroxyandrostan-17-one, (3beta,5beta,7beta)-isomerHMDB
3,7-Dihydroxyandrostan-17-one, (3beta,5alpha,7alpha)-isomerHMDB
3,7-Dihydroxyandrostan-17-oneHMDB
3,7-Dihydroxyandrostan-17-one, (3beta,5alpha,7beta)-isomerHMDB
3 alpha,7 alpha-5 beta-3,7-Dihydroxyandrostan-17-oneHMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
Traditional Name(2S,5R,14R,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
CAS Registry Number5856-10-0
SMILES
C[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@H]2O
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-CRQQDORFSA-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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
Polarizability35.28 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-0290000000-2102975bd891dd587151Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2227900000-87cd967afbbb2453594fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0090000000-f273d079c7767f673ac4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0290000000-241c15d984d5502957c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-2790000000-1cfe15a3e20555af8c99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-7976b987ec10e61bdb4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0090000000-72251dd83cca96a12d44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r5-0190000000-1da2626be2ffb7cb7813Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022001
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07632
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5372
PubChem Compound53477690
PDB IDNot Available
ChEBI ID27727
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceMiller, A. M.; Dorfman, Ralph I. Metabolism of the steroid hormones: Isolation of etiocholane-3(a),17(a)-diol from human urine. Endocrinology (1948), 42 174-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Uotila P, Hartiala J, Nienstedt W: The metabolism of testosterone by human, rabbit and rat kidney. Int J Biochem. 1980;12(3):345-51. [PubMed:7418937 ]
  2. Eriksson H, Gustafsson JA, Sjovall J: Excretion of steroid hormones in adults. C19 and C21 steroids in faeces from pregnant women. Eur J Biochem. 1970 Feb;12(3):520-6. [PubMed:5440628 ]
  3. Shackleton CH, Roitman E, Phillips A, Chang T: Androstanediol and 5-androstenediol profiling for detecting exogenously administered dihydrotestosterone, epitestosterone, and dehydroepiandrosterone: potential use in gas chromatography isotope ratio mass spectrometry. Steroids. 1997 Oct;62(10):665-73. [PubMed:9381514 ]
  4. Peng TC, Munson PL: The isolation of 5-beta-androstane-3-alpha,17-alpha-diol from normal human urine. Steroids. 1968 Feb;11(2):105-12. [PubMed:5636704 ]