3,17-Androstanediol glucuronide (CHEM022536)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:51 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022536
Identification
Common Name3,17-Androstanediol glucuronide
ClassSmall Molecule
Description3,17-Androstanediol glucuronide is a natural human metabolite of 3,17-Androstanediol generated in the liver by UDP glucuonyltransferase. 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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-alpha-Androstanediol glucuronideMeSH
Androstane-3,17-diol glucuronide, (3beta,5alpha,17beta)-isomerMeSH
3-Hydroxyandrostan-17-yl-glucopyranosiduronic acidMeSH
5-alpha-Androstane-3 alpha,17 beta-diol glucuronideMeSH
Androstane-3,17-diol glucuronide, (3alpha,5beta,17beta)-isomerMeSH
3 alpha-Diol gMeSH
Androstane-3,17-diol glucuronideMeSH
(1S,2S,5R,7S,10R,11S,14S,15S)-14-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acidGenerator
3,17-Androstanediol glucuronideMeSH
Chemical FormulaC25H40O8
Average Molecular Mass468.580 g/mol
Monoisotopic Mass468.272 g/mol
CAS Registry NumberNot Available
IUPAC Name(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
Traditional Name(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)OC(=O)[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C25H40O8/c1-24-9-7-13(32-23(31)21-19(28)18(27)20(29)22(30)33-21)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-22,26-30H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,22+,24-,25-/m0/s1
InChI KeyTWDCYBTXSUNASK-WGGIPMEBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androstane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Glucuronic acid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Cyclic alcohol
  • Hemiacetal
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.46 g/LALOGPS
logP1.53ALOGPS
logP1.26ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)11.28ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity116.93 m³·mol⁻¹ChemAxon
Polarizability51.3 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufr-2252900000-e8b21ec4c59fa25430abSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01c0-2172009000-a4958380a87f863237f7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0v00-0150900000-0da9bc97749253b33683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0390300000-769869c73d90594fb8faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-0390000000-ab30d939b842834b10a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bc-2381900000-ddd548b54c8a4bf88f9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1190100000-744b9dc5e79d1a3e4f64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2090000000-057254cc12d8b9c61a33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0310900000-517b004bcf83a149c60aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1955700000-9ec79c9a2db226eff76aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2619100000-3ed5b3c0d176a46e5643Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0010900000-7ee483c9728f56ae4d62Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3311900000-b3c084f686634bed1729Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0l06-9235300000-443959a6b86b8cc3bd06Spectrum
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 IDNot Available
HMDB IDHMDB0010321
FooDB IDFDB027473
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDBeta-D-Glucuronides
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID116053
ChEBI ID172699
PubChem Compound ID3034755
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available