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Record Information
Version1.0
Creation Date2016-09-30 23:09:38 UTC
Update Date2020-05-11 20:23:50 UTC
BMDB IDBMDB0004484
Secondary Accession Numbers
  • BMDB04484
Metabolite Identification
Common NameEtiocholanolone glucuronide
DescriptionEtiocholanolone glucuronide, also known as etiocholanolone glucuronide, 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. Thus, etiocholanolone glucuronide is considered to be a steroid conjugate lipid molecule. Etiocholanolone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, etiocholanolone glucuronide is involved in the metabolic pathway called the androstenedione metabolism pathway.
Structure
Thumb
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
StatusDetected 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007a-6254900000-3224ce201f4200b35e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r7-0190600000-3fdda78a1e92f8b5b7b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0290000000-51d6fe94f1974c92c97fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ec-0590000000-71f03526102b61380a88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bi-1260900000-703dccf114629fa639b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-1db7014540df9034a06eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4190000000-b2d4d7c7847df524456fView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
Biospecimen Locations
  • Kidney
  • Liver
  • Urine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Treated with steroids
details
HMDB IDHMDB0004484
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available