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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 19:41:24 UTC
Update Date2021-09-14 15:19:50 UTC
HMDB IDHMDB0004484
Secondary Accession Numbers
  • HMDB04484
Metabolite Identification
Common NameEtiocholanolone glucuronide
DescriptionEtiocholanolone glucuronide is a natural human metabolite of etiocholanolone generated in the liver by UDP glucuonyltransferase. Etiocholanolone (or 5-isoandrosterone) is a metabolite of testosterone. Classified a ketosteroid, it causes fever, immunostimulation and leukocytosis. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Data?1582752308
Synonyms
ValueSource
3alpha-Hydroxyetiocholan-17-one 3-glucosiduronic acidChEBI
3alpha-Hydroxyetiocholan-17-one 3-glucuronideChEBI
Etiocholan-3alpha-ol-17-one 3-glucuronideChEBI
Etiocholan-3alpha-ol-17-one 3-glucuronosideChEBI
3a-Hydroxyetiocholan-17-one 3-glucosiduronateGenerator
3a-Hydroxyetiocholan-17-one 3-glucosiduronic acidGenerator
3alpha-Hydroxyetiocholan-17-one 3-glucosiduronateGenerator
3Α-hydroxyetiocholan-17-one 3-glucosiduronateGenerator
3Α-hydroxyetiocholan-17-one 3-glucosiduronic acidGenerator
3a-Hydroxyetiocholan-17-one 3-glucuronideGenerator
3Α-hydroxyetiocholan-17-one 3-glucuronideGenerator
Etiocholan-3a-ol-17-one 3-glucuronideGenerator
Etiocholan-3α-ol-17-one 3-glucuronideGenerator
Etiocholan-3a-ol-17-one 3-glucuronosideGenerator
Etiocholan-3α-ol-17-one 3-glucuronosideGenerator
17-Oxoandrostan-3-yl hexopyranosiduronic acidHMDB
3alpha-Hydroxy-5beta-androstan-17-one 3-glucuronideHMDB
5Alpha.-androstan-3.alpha.-ol-17-one glucoronideHMDB
5beta-Androstan-3alpha-ol-17-one 3-glucuronideHMDB
Etiocholanolone 3-glucuronideHMDB
Androsterone glucosiduronateHMDB
Androsterone glucuronideHMDB
Androsterone glucuronide, (3beta,5alpha)-isomerHMDB
Androsterone glucuronide, (beta-D)-isomerHMDB
Androsterone glucuronide, sodium salt, (3alpha,5alpha)-isomerHMDB
Androsterone glucuronide, sodium salt, (3alpha,5beta)-isomerHMDB
(3alpha,5alpha)-17-Oxoandrostan-3-yl beta-D-glucopyranosiduronic acidHMDB
Chemical FormulaC25H38O8
Average Molecular Weight466.5644
Monoisotopic Molecular Weight466.256668192
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nameandrosterone glucuronide
CAS Registry Number3602-09-3
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13-,14+,15+,16+,18+,19+,20-,21+,23-,24+,25+/m1/s1
InChI KeyVFUIRAVTUVCQTF-SDHZCXLISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • Androstane-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Monosaccharide
  • Pyran
  • Oxane
  • Hydroxy acid
  • Ketone
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP2.06ALOGPS
logP2.32ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity116.09 m³·mol⁻¹ChemAxon
Polarizability50.37 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007a-6254900000-3224ce201f4200b35e4c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r7-0190600000-3fdda78a1e92f8b5b7b22016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0290000000-51d6fe94f1974c92c97f2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ec-0590000000-71f03526102b61380a882016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bi-1260900000-703dccf114629fa639b72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-1db7014540df9034a06e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4190000000-b2d4d7c7847df524456f2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-a63f64862ace09c4006b2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-5241900000-384ea6662fc4abc18a4b2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9032100000-351b0f7123639e6a74432021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-80c326e64042176a4be82021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-0792300000-a93b9d1cdd42d4c7cde22021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05bb-1904000000-0daa4e3ba6eed62c511b2021-09-07View Spectrum
MSMass Spectrum (Electron Ionization)splash10-007a-6254900000-3224ce201f4200b35e4c2021-09-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineDetected and Quantified0.70 (0.057-1.34) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.34 - 0.61 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023376
KNApSAcK IDNot Available
Chemspider ID391377
KEGG Compound IDC11136
BioCyc IDBeta-D-Glucuronides
BiGG ID2304848
Wikipedia LinkEtiocholanolone glucuronide
METLIN ID7064
PubChem Compound443078
PDB IDNot Available
ChEBI ID37451
Food Biomarker OntologyNot Available
VMH IDAHANDROSTANGLC
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nakazono T, Kashimura S, Hayashiba Y, Hisatomi T, Hara K: Identification of human urine stains by HPLC analysis of 17-ketosteroid conjugates. J Forensic Sci. 2002 May;47(3):568-72. [PubMed:12051338 ]

Only showing the first 10 proteins. There are 22 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
Reactions
Etiocholanolone + Uridine diphosphate glucuronic acid → Etiocholanolone glucuronide + Uridine 5'-diphosphatedetails

Only showing the first 10 proteins. There are 22 proteins in total.