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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-15 17:02:34 UTC
Update Date2018-05-20 20:35:02 UTC
HMDB IDHMDB0010327
Secondary Accession Numbers
  • HMDB10327
Metabolite Identification
Common NameDehydroisoandrosterone 3-glucuronide
DescriptionDehydroisoandrosterone 3-glucuronide is a natural human metabolite of Dehydroisoandrosterone 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.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H36O8
Average Molecular Weight464.5485
Monoisotopic Molecular Weight464.241018128
IUPAC Name(3S,4S,5R,6R)-6-({2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(3S,4S,5R,6R)-6-({2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC12CCC3C(CC=C4CC(CCC34C)O[C@@H]3OC([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C1CCC2=O
InChI Identifier
InChI=1S/C25H36O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h3,13-16,18-21,23,27-29H,4-11H2,1-2H3,(H,30,31)/t13?,14?,15?,16?,18-,19-,20+,21?,23+,24?,25?/m0/s1
InChI KeyGLONBVCUAVPJFV-CLIRWHJISA-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
  • Androstane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Delta-5-steroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Pyran
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.09ALOGPS
logP1.91ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity116.94 m³·mol⁻¹ChemAxon
Polarizability49.91 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-5264900000-e350fddca64a2b86632bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-3117019000-d73bbab241b09ed812afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rj-0190600000-5a501cb9f2f64d24a28bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0290000000-de6f2a0f1b8c12b6ab98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rl-0490000000-d30c89e988b3cafb1d50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1260900000-ad0963b4f8cf5df4a6feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-e4a4467f431a4e95469bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4190000000-b0f801fe14114db9c2e4View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB027479
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC03033
      BioCyc IDBeta-D-Glucuronides
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound53480448
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available

      Only showing the first 10 proteins. There are 19 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
      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
      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
      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
      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
      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
      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
      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
      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
      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

      Only showing the first 10 proteins. There are 19 proteins in total.