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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 15:42:17 UTC
NP-MRD IDNP0000565
Secondary Accession NumbersNone
Natural Product Identification
Common NameEtiocholanolone
DescriptionEtiocholanolone is the 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine and is androgenically inactive. Classified a ketosteroid, it causes fever (it is a pyrogen), immunostimulation and leukocytosis. The pyrogenic effect of Etiocholanolone has been shown to be due to the release of interleukin-1 (IL-1) from the leukocytes that are mobilized in response to its production or injection. Etiocholanolone has anticonvulsant activity and may be an endogenous modulator of seizure susceptibility. Significantly increased values of etiocholanolone (along with testoterone and androsterone) an be detected in the urine of men with androgenic alopecia (male pattern baldness).
Structure
Thumb
Synonyms
ValueSource
(3alpha,5beta)-3-Hydroxyandrostan-17-oneChEBI
3alpha-EtiocholanoloneChEBI
3alpha-Hydroxyetiocholan-17-oneChEBI
5-IsoandrosteroneChEBI
5beta-Androstan-3alpha-ol-17-oneChEBI
5beta-AndrosteroneChEBI
AETIOCHOLANOLONEChEBI
Etiocholan-3alpha-ol-17-oneChEBI
3alpha-Hydroxy-5beta-androstan-17-oneKegg
(3a,5b)-3-Hydroxyandrostan-17-oneGenerator
(3Α,5β)-3-hydroxyandrostan-17-oneGenerator
3a-EtiocholanoloneGenerator
3Α-etiocholanoloneGenerator
3a-Hydroxyetiocholan-17-oneGenerator
3Α-hydroxyetiocholan-17-oneGenerator
5b-Androstan-3a-ol-17-oneGenerator
5Β-androstan-3α-ol-17-oneGenerator
5b-AndrosteroneGenerator
5Β-androsteroneGenerator
Etiocholan-3a-ol-17-oneGenerator
Etiocholan-3α-ol-17-oneGenerator
3a-Hydroxy-5b-androstan-17-oneGenerator
3Α-hydroxy-5β-androstan-17-oneGenerator
3a-Hydroxy-5b-androstane-17-oneHMDB
5 beta AndrosteroneHMDB
5b-Androstane-3a-ol-17-oneHMDB
a-EtiocholanoloneHMDB
alpha-EtiocholanoloneHMDB
3-alpha-Hydroxy-5-beta-androstan-17-oneHMDB
5-beta-AndrosteroneHMDB
3 alpha Hydroxy 5 beta androstan 17 oneHMDB
Chemical FormulaC19H30O2
Average Mass290.4403 Da
Monoisotopic Mass290.22458 Da
IUPAC Name(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
CAS Registry Number53-42-9
SMILES
[H][C@@]12CCC(=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/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1
InChI KeyQGXBDMJGAMFCBF-BNSUEQOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Apiocrea chrysosperma Ap101KNApSAcK Database
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
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point152 - 154 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.36 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000490
DrugBank IDDB02854
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022072
KNApSAcK IDC00016580
Chemspider ID5669
KEGG Compound IDC04373
BioCyc IDNot Available
BiGG ID43684
Wikipedia LinkEtiocholanolone
METLIN ID5477
PubChem Compound5880
PDB IDNot Available
ChEBI ID28195
Good Scents IDNot Available
References
General References
  1. Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27. [PubMed:15946323 ]
  2. Poor V, Juricskay S, Telegdy E: Urinary steroids in men with male-pattern alopecia. J Biochem Biophys Methods. 2002 Oct-Nov;53(1-3):123-30. [PubMed:12406594 ]
  3. George JM, Wolff SM, Diller E, Bartter FC: Recurrent fever of unknown etiology: failure to demonstrate association between fever and plasma unconjugated etiocholanolone. J Clin Invest. 1969 Mar;48(3):558-63. [PubMed:4886315 ]
  4. Kecskes L, Juricskay Z: Steroid spectrum in human urine as revealed by gas chromatography. I. Qualitative analysis of C19--C2102-3 steroids. Acta Biochim Biophys Acad Sci Hung. 1975;10(1-2):37-49. [PubMed:1146492 ]