Etiocholanedione (CHEM035568)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:53:31 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035568
Identification
Common NameEtiocholanedione
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass288.424 g/mol
Monoisotopic Mass288.209 g/mol
CAS Registry Number1229-12-5
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
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 IdentifierInChI=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
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 Solubility0.0074 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-2960000000-ea444704310ecd83d3ceSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-3921000000-17fcd3fbf7ce3dec6b0bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-2960000000-ea444704310ecd83d3ceSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-3921000000-17fcd3fbf7ce3dec6b0bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0490000000-e4819053bc47c4809a6cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-274e4abb4afd97e047bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05a9-0490000000-ea747ee7d3b074178ffeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h04-2790000000-f49dc8e9045f408d3658Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-66fb88cf829fcdb74c4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-dcc70e0ff918620e20dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-3190000000-eb4a160989f10eb86d96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-0090000000-0497207bd4a67a50d8d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-a3a5ee5e1cdb4d550aacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h90-0970000000-66d8653b98d2df4aa327Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1900000000-2a46c86775b66edae018Spectrum
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 IDDB07375
HMDB IDHMDB0003769
FooDB IDFDB023225
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID5-BETA-ANDROSTANE-317-DIONE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEtiocholanedione
Chemspider ID389114
ChEBI ID16985
PubChem Compound ID440114
Kegg Compound IDC03772
YMDB IDNot Available
ECMDB IDECMDB24084
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. de la Torre R, de la Torre X, Alia C, Segura J, Baro T, Torres-Rodriguez JM: Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control. Anal Biochem. 2001 Feb 15;289(2):116-23.
2. Granata OM, Carruba G, Montalto G, Miele M, Bellavia V, Modica G, Blomquist CH, Castagnetta LA: Altered androgen metabolism eventually leads hepatocellular carcinoma to an impaired hormone responsiveness. Mol Cell Endocrinol. 2002 Jul 31;193(1-2):51-8.
3. AXELROD LR, GOLDZIEHER JW: The metabolism of 17alpha-hydroxyprogesterone and its relation to congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1960 Feb;20:238-52.
4. Mallet AI, Holland KT, Rennie PJ, Watkins WJ, Gower DB: Applications of gas chromatography-mass spectrometry in the study of androgen and odorous 16-androstene metabolism by human axillary bacteria. J Chromatogr. 1991 Jan 2;562(1-2):647-58.