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Record Information
Version1.0
Creation Date2016-09-30 23:06:04 UTC
Update Date2020-04-22 15:12:44 UTC
BMDB IDBMDB0003769
Secondary Accession Numbers
  • BMDB03769
Metabolite Identification
Common NameEtiocholanedione
DescriptionEtiocholanedione , also known as Etiocholanedione or etiocholanedione, 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, etiocholanedione is considered to be a steroid lipid molecule. Etiocholanedione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Etiocholanedione exists in all living organisms, ranging from bacteria to humans. Etiocholanedione participates in a number of enzymatic reactions, within cattle. In particular, Etiocholanedione can be biosynthesized from androstenedione through its interaction with the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, Etiocholanedione can be converted into etiocholanolone; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In cattle, etiocholanedione is involved in the metabolic pathway called the androstenedione metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
Etiocholane-3,17-dioneChEBI
EtiocholanedioneChEBI
(5b)-Androstane-3,17-dioneHMDB
5b-Androstane-3,17-dioneHMDB
5b-AndrostanedioneHMDB
5beta-Androstane-3,17-dioneHMDB
Etiochola-3,17-dioneHMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC Name(1S,2S,7R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-dione
Traditional Name5-β-androstane-3,17-dione
CAS Registry Number1229-12-5
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14+,15+,16+,18+,19+/m1/s1
InChI KeyRAJWOBJTTGJROA-QJISAEMRSA-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-oxo-5-beta-steroid
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.64Not Available
Predicted Properties
PropertyValueSource
logP3.4ALOGPS
logP3.97ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.78ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.78 m³·mol⁻¹ChemAxon
Polarizability33.79 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-2960000000-ea444704310ecd83d3ceView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-3921000000-17fcd3fbf7ce3dec6b0bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-2960000000-ea444704310ecd83d3ceView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-3921000000-17fcd3fbf7ce3dec6b0bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0490000000-e4819053bc47c4809a6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-274e4abb4afd97e047bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-0490000000-ea747ee7d3b074178ffeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h04-2790000000-f49dc8e9045f408d3658View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-66fb88cf829fcdb74c4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-dcc70e0ff918620e20dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3190000000-eb4a160989f10eb86d96View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003769
DrugBank IDDB07375
Phenol Explorer Compound IDNot Available
FooDB IDFDB023225
KNApSAcK IDNot Available
Chemspider ID389114
KEGG Compound IDC03772
BioCyc ID5-BETA-ANDROSTANE-317-DIONE
BiGG IDNot Available
Wikipedia LinkEtiocholanedione
METLIN IDNot Available
PubChem Compound440114
PDB IDNot Available
ChEBI ID16985
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available