Testosterone glucuronide (CHEM021798)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:12:46 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021798
Identification
Common NameTestosterone glucuronide
ClassSmall Molecule
DescriptionTestosterone 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, testosterone glucuronide is considered to be a steroid conjugate lipid molecule. Testosterone glucuronide exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Testosterone glucuronide can be biosynthesized from testosterone; which is catalyzed by the enzyme UDP-glucuronosyltransferase 2B17. In cattle, testosterone glucuronide is involved in the metabolic pathway called the androgen and estrogen metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Testosterone 17beta-(beta-D-glucuronide)ChEBI
Testosterone glucuronosideChEBI
Testosterone 17b-(b-D-glucuronide)Generator
Testosterone 17β-(β-D-glucuronide)Generator
(17b)-3-Oxoandrost-4-en-17-yl b-D-glucopyranosiduronic acidHMDB
b-D-3-Oxoandrost-4-en-17b-yl glucopyranosiduronic acidHMDB
b-D-Androstane glucopyranosiduronic acidHMDB
Epitestosterone glucuronideHMDB
Testosterone 17-glucosiduronateHMDB
Testosterone 17-glucuronideHMDB
Testosterone glucopyranuronosideHMDB
Testosterone glucosiduronideHMDB
Testosterone glucuronateHMDB
Testosterone-glucuronideHMDB
(alpha)-Isomer OF testosterone glucuronateHMDB
Chemical FormulaC25H36O8
Average Molecular Mass464.549 g/mol
Monoisotopic Mass464.241 g/mol
CAS Registry Number1180-25-2
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nametestosterone glucuronide
SMILES[H][C@@]12CC[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C25H36O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h11,14-21,23,27-29H,3-10H2,1-2H3,(H,30,31)/t14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1
InChI KeyNIKZPECGCSUSBV-HMAFJQTKSA-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
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • Delta-4-steroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexenone
  • Beta-hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Pyran
  • Oxane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.26 g/LALOGPS
logP1.83ALOGPS
logP1.91ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity116.71 m³·mol⁻¹ChemAxon
Polarizability49.29 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002s-7374900000-df9fd1c0a23d7096cf26Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1606029000-ace2748138aab320b602Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rj-0190600000-c12508c47c05623543aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0390000000-6967a132771292eb3775Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-0690000000-83b24c8c2b8d988ca1bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1260900000-8a8bad65d00272674fb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-4ea1e726f18e48a97877Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-b41d42aa036b4867d7fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-bd3da6f548433d38332dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0571-9621300000-3022d77647816a41cad4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9034100000-4cb79673d1b5b82c353cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190500000-35f41b813389a2ebb839Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0301-0963500000-58248b539c8cea653977Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdl-1931000000-98e24f4d12e60e585a9cSpectrum
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 IDHMDB0003193
FooDB IDFDB023122
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2304840
BioCyc IDNot Available
METLIN ID2794
PDB IDNot Available
Wikipedia LinkTestosterone glucuronide
Chemspider ID97270
ChEBI ID28835
PubChem Compound ID108192
Kegg Compound IDC11134
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. van de Kerkhof DH, de Boer D, Thijssen JH, Maes RA: Evaluation of testosterone/epitestosterone ratio influential factors as determined in doping analysis. J Anal Toxicol. 2000 Mar;24(2):102-15.
2. Perera DM, McGarrigle HH, Lawrence DM, Lucas M: Amniotic fluid testosterone and testosterone glucuronide levels in the determination of foetal sex. J Steroid Biochem. 1987 Feb;26(2):273-7.
3. Jimenez C, de la Torre R, Segura J, Ventura R: Stability studies of testosterone and epitestosterone glucuronides in urine. Rapid Commun Mass Spectrom. 2006;20(5):858-64.
4. de Boer D, de Jong EG, van Rossum JM, Maes RA: Doping control of testosterone and human chorionic gonadotrophin: a case study. Int J Sports Med. 1991 Feb;12(1):46-51.
5. Raynaud E, Audran M, Pages JC, Brun JF, Fedou C, Chanal JL, Orsetti A: [Study of urinary excretion of testosterone and epitestosterone glucuronides in children and adolescents]. Pathol Biol (Paris). 1993 Feb;41(2):159-63.
6. Sayo H, Hosokawa M: [Spin immunoassay of urinary testosterone (author's transl)]. Yakugaku Zasshi. 1980 Jan;100(1):56-60.
7. Jones MK, Ramsay ID, Collins WP: Concentration of testosterone glucuronide in urine from women with breast tumours. Br J Cancer. 1977 Jun;35(6):885-7.
8. Purvis K, Saksena SK, Landgren BM, Cekan Z, Diczfalusy E: Steroid conjugates in human seminal plasma. Clin Endocrinol (Oxf). 1976 May;5(3):253-61.
9. Krawczynska H, Zachmann M, Prader A: Urinary testosterone glucuronide and sulphate in newborns and young infants. Acta Endocrinol (Copenh). 1976 Aug;82(4):842-50.
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225