3a,17a-Dihydroxy-5b-androstane (CHEM034833)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:15:42 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034833
Identification
Common Name3a,17a-Dihydroxy-5b-androstane
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass292.456 g/mol
Monoisotopic Mass292.240 g/mol
CAS Registry Number5856-10-0
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
SMILESC[C@]12CCC3C(CCC4C[C@H](O)CC[C@]34C)C1CC[C@H]2O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-3e8adedf0fc78f105180Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-3930000000-4565b95a3f4971c32c4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-016s-1900000000-d395cd752ea5bc7f6381Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-11452f48ce72555f1f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-11452f48ce72555f1f28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-befabe6e74d1b5abdfb4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000383
FooDB IDFDB022001
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5372
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID27727
PubChem Compound ID53477690
Kegg Compound IDC07632
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Miller, 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.
2. Uotila P, Hartiala J, Nienstedt W: The metabolism of testosterone by human, rabbit and rat kidney. Int J Biochem. 1980;12(3):345-51.
3. 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.
4. 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.
5. 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.