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Record Information
Version4.0
Creation Date2013-07-09 16:18:00 UTC
Update Date2017-09-27 08:44:01 UTC
HMDB IDHMDB0061096
Secondary Accession Numbers
  • HMDB61096
Metabolite Identification
Common Name3-hydroxyguanfacine glucuronide
Description3-hydroxyguanfacine glucuronide is a metabolite of guanfacine. Guanfacine (brand name Tenex, and the extended release Intuniv) is a sympatholytic. It is a selective α2A receptor agonist. These receptors are concentrated heavily in the prefrontal cortex and the locus coeruleus, with the potential to improve attention abilities via modulating post-synaptic α2A receptors in the prefrontal cortex. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H17Cl2N3O9
Average Molecular Weight454.216
Monoisotopic Molecular Weight453.034184571
IUPAC Name(2R,3R,4R,5S,6R)-6-{3-[(carbamimidoyl-C-hydroxycarbonimidoyl)methyl]-2,4-dichloro-5-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S,6R)-6-{3-[(carbamimidoyl-C-hydroxycarbonimidoyl)methyl]-2,4-dichloro-5-hydroxyphenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
NC(=N)N=C(O)CC1=C(Cl)C(O)=CC(O[C@H]2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)=C1Cl
InChI Identifier
InChI=1S/C15H17Cl2N3O9/c16-7-3(1-6(22)20-15(18)19)8(17)5(2-4(7)21)28-14-11(25)9(23)10(24)12(29-14)13(26)27/h2,9-12,14,21,23-25H,1H2,(H,26,27)(H4,18,19,20,22)/t9-,10-,11+,12-,14+/m1/s1
InChI KeyAUDUMKPECIWTMB-DIACKHNESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • 1,3-dichlorobenzene
  • 4-halophenol
  • 2-halophenol
  • Phenoxy compound
  • 2-chlorophenol
  • 4-chlorophenol
  • Phenol ether
  • Beta-hydroxy acid
  • Chlorobenzene
  • Halobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Oxane
  • Pyran
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Aryl chloride
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Carboximidamide
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Imine
  • Organohalogen compound
  • Organochloride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP0.15ALOGPS
logP-2.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)-0.0028ChemAxon
pKa (Strongest Basic)15.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area219.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.13 m³·mol⁻¹ChemAxon
Polarizability39.7 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fbi-2070900000-42589e2b6123d3df5519View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1190000000-523efd8f6bbc09d99537View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5950000000-eeba26081a7705e174a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zir-3142900000-a6cb0cfc34b2969ac3c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7i-6194400000-bf12e444a82b2bf3c61aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9030000000-58478e751925330400b3View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
      DrugBank Metabolite IDDBMET00456
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available