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Record Information
Version1.0
Creation Date2016-09-30 22:31:30 UTC
Update Date2020-04-22 15:03:49 UTC
BMDB IDBMDB0000490
Secondary Accession Numbers
  • BMDB00490
Metabolite Identification
Common NameEtiocholanolone
DescriptionEtiocholanolone, also known as Etiocholanolone, 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. Thus, etiocholanolone is considered to be a steroid lipid molecule. Etiocholanolone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Etiocholanolone exists in all living organisms, ranging from bacteria to humans. Etiocholanolone can be biosynthesized from etiocholanedione through the action of the enzyme aldo-keto reductase family 1 member C4. In cattle, etiocholanolone is involved in the metabolic pathway called the androstenedione metabolism pathway.
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 Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number53-42-9
SMILESNot Available
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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point152 - 154 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000490
DrugBank IDDB02854
Phenol Explorer Compound IDNot Available
FooDB IDFDB022072
KNApSAcK IDNot Available
Chemspider ID5669
KEGG Compound IDC04373
BioCyc IDNot Available
BiGG ID43684
Wikipedia LinkEtiocholanolone
METLIN ID5477
PubChem Compound5880
PDB IDNot Available
ChEBI ID28195
References
Synthesis ReferencePelli, Beatrice; Traldi, Pietro; Gargano, Michele; Ravasio, Nicoletta; Rossi, Michele. Easy determination of epimeric androsterones by collision spectroscopy: the molar ratio of 5b-androstan-3a-ol-17-one and 5b-androstan-3b-ol-17-one obtained by hydrogenation of 5b-androstane-3,17-dione on copper/alumina. Organic Mass Spectrometry (1987), 22(3), 183-5.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available