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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:40 UTC
Update Date2018-05-20 20:24:56 UTC
HMDB IDHMDB0003193
Secondary Accession Numbers
  • HMDB03193
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 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 glucuronateMeSH
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 KeyNIKZPECGCSUSBV-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
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002s-7374900000-df9fd1c0a23d7096cf26View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1606029000-ace2748138aab320b602View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rj-0190600000-c12508c47c05623543aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0390000000-6967a132771292eb3775View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-0690000000-83b24c8c2b8d988ca1bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1260900000-8a8bad65d00272674fb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-4ea1e726f18e48a97877View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-b41d42aa036b4867d7fcView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Semen
  • Urine
Tissue Locations
  • Brain
  • Hypothalamus
  • Kidney
  • Liver
  • Muscle
  • Sperm
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    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
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB023122
    KNApSAcK IDNot Available
    Chemspider ID97270
    KEGG Compound IDC11134
    BioCyc IDNot Available
    BiGG ID2304840
    Wikipedia LinkNot Available
    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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:8327267 ]
    7. Sayo H, Hosokawa M: [Spin immunoassay of urinary testosterone (author's transl)]. Yakugaku Zasshi. 1980 Jan;100(1):56-60. [PubMed: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. [PubMed: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. [PubMed:947290 ]

    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
    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

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