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Showing Compound Testosterone glucuronide (FDB023122)

Record Information
Version1.0
Creation date2011-09-21 00:25:01 UTC
Update date2015-07-21 06:57:31 UTC
Primary IDFDB023122
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number1180-25-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC25H36O8
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
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
Isomeric 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
Average Molecular Weight464.5485
Monoisotopic Molecular Weight464.241018128
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTestosterone glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002s-7374900000-df9fd1c0a23d7096cf26Spectrum
Predicted GC-MSTestosterone glucuronide, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-1606029000-ace2748138aab320b602Spectrum
Predicted GC-MSTestosterone glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rj-0190600000-c12508c47c05623543ae2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0390000000-6967a132771292eb37752016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-0690000000-83b24c8c2b8d988ca1bf2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1260900000-8a8bad65d00272674fb82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-4ea1e726f18e48a978772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-b41d42aa036b4867d7fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-bd3da6f548433d38332d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0571-9621300000-3022d77647816a41cad42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-9034100000-4cb79673d1b5b82c353c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190500000-35f41b813389a2ebb8392021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0301-0963500000-58248b539c8cea6539772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdl-1931000000-98e24f4d12e60e585a9c2021-09-22View Spectrum
NMRNot Available
ChemSpider ID97270
ChEMBL IDCHEMBL2074651
KEGG Compound IDC11134
Pubchem Compound ID108192
Pubchem Substance IDNot Available
ChEBI ID28835
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03193
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2304840
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTestim
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference