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Record Information
Version3.6
Creation Date2013-07-09 16:18:00 UTC
Update Date2016-02-11 08:18:26 UTC
HMDB IDHMDB61096
Secondary Accession NumbersNone
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=1/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+/s2
InChI KeyInChIKey=AUDUMKPECIWTMB-HVOVEWBRNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenol ether
  • 4-chlorophenol
  • 2-chlorophenol
  • 2-halophenol
  • 4-halophenol
  • 1,3-dichlorobenzene
  • Phenol
  • Halobenzene
  • Chlorobenzene
  • Beta-hydroxy acid
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Secondary alcohol
  • Polyol
  • Guanidine
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.13 m3·mol-1ChemAxon
Polarizability39.7 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB61096
Metagene LinkHMDB61096
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