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Record Information
Version3.6
Creation Date2006-05-22 15:12:40 UTC
Update Date2016-05-13 21:10:25 UTC
HMDB IDHMDB03193
Secondary Accession NumbersNone
Metabolite Identification
Common NameTestosterone glucuronide
DescriptionTestosterone glucuronide is a natural human metabolite of testosterone. Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted in the testes of males and the ovaries of females although small amounts are secreted by the adrenal glands. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. There is a sex difference in the median values of testosterone glucuronide in the amniotic fluid specimens 15-19 wk gestation between female (median 160 pM, range 64-465 pM) and male (median 817 pM, range 68-3707 pM). This difference, when used in conjunction with amniotic fluid unconjugated testosterone values, increase the predictive accuracy of fetal sexing from 95.4 to 98.9%. In human newborns and young infants, urinary testosterone sulfate is higher than glucuronide. The high sulfokinase activity in fetal and neonatal testes is more likely responsible for this phenomenon than an impaired glucuronizing capacity of the liver. Urinary excretion of testosterone glucuronide increases significantly during puberty. The level of testosterone glucuronide exceeds the level of unconjugated testosterone in human seminal plasma. Urinary testosterone glucuronide excretion is increased in women with virilizing adrenocortical tumors. Concentration of testosterone glucuronide in urine from women with breast tumor in urine samples is not different from patients with benign or malignant breast disease, either before or after the menopause. (PMID: 8327267 , 3560942 , 6246233 , 871373 , 133773 , 947290 ).
Structure
Thumb
Synonyms
ValueSource
Testosterone 17beta-(beta-D-glucuronide)ChEBI
Testosterone glucuronideChEBI
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
Chemical FormulaC25H36O8
Average Molecular Weight464.5485
Monoisotopic Molecular Weight464.241018128
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
CAS Registry Number1180-25-2
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 Identifier
InChI=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 KeyInChIKey=NIKZPECGCSUSBV-HMAFJQTKSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Saccharide
  • Cyclic ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 - 156 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.26 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity116.71 m3·mol-1ChemAxon
Polarizability49.29 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Semen
  • Urine
Tissue Location
  • Brain
  • Hypothalamus
  • Kidney
  • Liver
  • Muscle
  • Sperm
  • Testes
Pathways
NameSMPDB LinkKEGG Link
17-Beta Hydroxysteroid Dehydrogenase III DeficiencySMP00356Not Available
Androgen and Estrogen MetabolismSMP00068map00150
Aromatase deficiencySMP00565Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
SemenDetected and Quantified0.0388 (0.0297 - 0.0506) uMAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0092 (0.00015-0.019) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0059 - 0.013 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00562
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023122
KNApSAcK IDNot Available
Chemspider ID97270
KEGG Compound IDC11134
BioCyc IDNot Available
BiGG ID2304840
Wikipedia LinkTestim
NuGOwiki LinkHMDB03193
Metagene LinkHMDB03193
METLIN ID2794
PubChem Compound108192
PDB IDNot Available
ChEBI ID28835
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [10732948 ]
  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. [3560942 ]
  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. [16470578 ]
  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. [2030059 ]
  5. 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. [133773 ]
  6. 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. [8327267 ]
  7. Sayo H, Hosokawa M: [Spin immunoassay of urinary testosterone (author's transl)]. Yakugaku Zasshi. 1980 Jan;100(1):56-60. [6246233 ]
  8. 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. [871373 ]
  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. [947290 ]

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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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:
UGT1A3
Uniprot ID:
P35503
Molecular weight:
60337.835
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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:
UGT1A10
Uniprot ID:
Q9HAW8
Molecular weight:
59809.075
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:
UGT2B17
Uniprot ID:
O75795
Molecular weight:
61094.915
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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:
UGT1A5
Uniprot ID:
P35504
Molecular weight:
60070.565
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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:
UGT2B11
Uniprot ID:
O75310
Molecular weight:
61037.8
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone 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:
UGT1A7
Uniprot ID:
Q9HAW7
Molecular weight:
59818.315
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name:
GUSB
Uniprot ID:
P08236
Molecular weight:
74731.46
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 (By similarity).
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Molecular weight:
60253.94
Reactions
Testosterone + Uridine diphosphate glucuronic acid → Testosterone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Not Available
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Molecular weight:
59809.1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Not Available
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6
Molecular weight:
59741.0
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Not Available
Gene Name:
UGT1A7
Uniprot ID:
Q5DSZ7
Molecular weight:
59818.3