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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 04:33:58 UTC
Update Date2021-09-14 15:41:24 UTC
HMDB IDHMDB0003769
Secondary Accession Numbers
  • HMDB03769
Metabolite Identification
Common NameEtiocholanedione
DescriptionEtiocholanedione is a 5-beta metabolite product of the catabolism of androgens. Etiocholanedione has been identified as a ketosteroid and isolated from the urine of healthy and diseased persons. Etiocholanedione has been identified as a metabolite of an altered androgen metabolism that eventually leads hepatocellular carcinoma to impaired hormone responsiveness in human. Etiocholanedione has been identified as a metabolite of 17alpha-hydroxyprogesterone in some patients affected by congenital adrenal hyperplasia, although it doesn't appear to account for the masculinization observed in congenital hyperplasia. Etiocholanedione can be the product of microbial contamination of urine since a few organisms are able to synthesize it using endogenous steroids as substrates. Human axillary bacteria are able to produce small amounts of etiocholanedione from testosterone. (PMID: 12161001 , 13795320 , 11161304 , 2026727 ). Etiocholanedione has been found to be a metabolite of Corynebacterium (PMID: 11161304 ).
Structure
Data?1582752287
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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.64Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0074 g/LALOGPS
logP10(3.4) g/LALOGPS
logP10(3.97) g/LChemAxon
logS10(-4.6) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.30731661259
DarkChem[M-H]-165.59731661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Etiocholanedione EI-B (Non-derivatized)splash10-0079-2960000000-ea444704310ecd83d3ce2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Etiocholanedione GC-EI-TOF (Non-derivatized)splash10-052f-3921000000-17fcd3fbf7ce3dec6b0b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Etiocholanedione EI-B (Non-derivatized)splash10-0079-2960000000-ea444704310ecd83d3ce2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Etiocholanedione GC-EI-TOF (Non-derivatized)splash10-052f-3921000000-17fcd3fbf7ce3dec6b0b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0490000000-e4819053bc47c4809a6c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etiocholanedione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 10V, Positive-QTOFsplash10-000i-0190000000-274e4abb4afd97e047bd2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 20V, Positive-QTOFsplash10-05a9-0490000000-ea747ee7d3b074178ffe2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 40V, Positive-QTOFsplash10-0h04-2790000000-f49dc8e9045f408d36582015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 10V, Negative-QTOFsplash10-000i-0090000000-66fb88cf829fcdb74c4c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 20V, Negative-QTOFsplash10-000i-0090000000-dcc70e0ff918620e20dc2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 40V, Negative-QTOFsplash10-052f-3190000000-eb4a160989f10eb86d962015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 10V, Negative-QTOFsplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 20V, Negative-QTOFsplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 40V, Negative-QTOFsplash10-0f79-0090000000-0497207bd4a67a50d8d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 10V, Positive-QTOFsplash10-000i-0090000000-a3a5ee5e1cdb4d550aac2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 20V, Positive-QTOFsplash10-0h90-0970000000-66d8653b98d2df4aa3272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etiocholanedione 40V, Positive-QTOFsplash10-0a4i-1900000000-2a46c86775b66edae0182021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:11161304 ]
  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. [PubMed:12161001 ]
  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. [PubMed:13795320 ]
  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. [PubMed:2026727 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
Etiocholanolone + NAD → Etiocholanedione + NADH + Hydrogen Iondetails
Etiocholanolone + NADP → Etiocholanedione + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
Etiocholanedione + NADP → Hydrogen Ion + NADPH + Androstenedionedetails