Record Information
Version1.0
Creation date2015-10-09 22:31:14 UTC
Update date2017-01-19 02:36:27 UTC
FoodComEx IDPC000537
FoodDB RecordFDB022072
Chemical Information
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). [HMDB]
CAS Number53-42-9
Structure
Thumb
Synonyms
SynonymSource
(3a,5b)-3-Hydroxyandrostan-17-oneGenerator
(3alpha,5beta)-3-Hydroxyandrostan-17-oneChEBI
(3α,5β)-3-hydroxyandrostan-17-oneGenerator
3a-Etiocholanolonehmdb
3a-Hydroxy-5b-androstan-17-oneGenerator
3a-Hydroxy-5b-androstane-17-onehmdb
3a-Hydroxyetiocholan-17-oneGenerator
3alpha-EtiocholanoloneChEBI
3alpha-Hydroxy-5beta-androstan-17-onehmdb
3alpha-Hydroxyetiocholan-17-onehmdb
3α-etiocholanoloneGenerator
3α-hydroxy-5β-androstan-17-oneGenerator
3α-hydroxyetiocholan-17-oneGenerator
5 beta Androsteronehmdb
5-Isoandrosteronehmdb
5b-Androstan-3a-ol-17-onehmdb
5b-Androstane-3a-ol-17-onehmdb
5b-Androsteronehmdb
5beta-Androstan-3alpha-ol-17-oneChEBI
5beta-AndrosteroneChEBI
5β-androstan-3α-ol-17-oneGenerator
5β-androsteroneGenerator
a-Etiocholanolonehmdb
Aetiocholanolonehmdb
alpha-Etiocholanolonehmdb
Etiocholan-3a-ol-17-oneGenerator
Etiocholan-3alpha-ol-17-oneChEBI
Etiocholan-3α-ol-17-oneGenerator
Chemical FormulaC19H30O2
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 20 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals A637630