Showing metabocard for Acetaminophen glucuronide (BMDB0010316)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:04:12 UTC
Update Date2020-05-11 20:42:04 UTC
BMDB IDBMDB0010316
Secondary Accession Numbers
  • BMDB10316
Metabolite Identification
Common NameAcetaminophen glucuronide
DescriptionAcetaminophen glucuronide, also known as 4-glucuronosidoacetanilide or deethylphenacetin glucuronide, 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. Acetaminophen glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetaminophen glucuronide, with regard to humans, has been linked to the inborn metabolic disorder beta-thalassemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Paracetamol glucuronideChEBI
4-(Acetylamino)phenyl beta-D-glucopyranosiduronic acidHMDB
4-(Acetylamino)phenyl beta-delta-glucopyranosiduronic acidHMDB
4-Acetamidophenol glucuronideHMDB
4-Acetamidophenyl b-D-glucopyranosiduronic acidHMDB
4-Acetamidophenyl b-delta-glucopyranosiduronic acidHMDB
4-Acetamidophenyl beta-D-glucopyranosiduronic acidHMDB
4-Acetamidophenyl beta-delta-glucopyranosiduronic acidHMDB
p-Acetamidophenyl β-D-glucuronideHMDB
4-(Acetylamino)phenyl β-D-glucopyranosiduronic acidHMDB
4-GlucuronosidoacetanilideHMDB
4-Hydroxyacetanilide glucuronideHMDB
Acetanilide glucuronideHMDB
4'-(Glucuronosyloxy)-acetanilideHMDB
Deethylphenacetin glucuronideHMDB
N-Acetyl-4-aminophenol glucuronideHMDB
N-Acetyl-4-glucuronosidoanilineHMDB
N-Acetyl-p-aminophenyl glucuronideHMDB
Paracetamol O-glucuronideHMDB
Paracetamol β-glucuronideHMDB
Paracetamol beta-glucuronideHMDB
p-Acetamidophenyl D-glucosiduronic acidHMDB
p-Acetamidophenyl glucosiduronic acidHMDB
p-Acetamidophenyl glucuronideHMDB
PCM-gHMDB
p-AcetamidophenylglucuronideHMDB
Acetaminophen glucuronideHMDB
Chemical FormulaC14H17NO8
Average Molecular Weight327.2867
Monoisotopic Molecular Weight327.095416525
IUPAC Name(2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nameacetaminophen glucuronide
CAS Registry Number16110-10-4
SMILES
CC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1
InChI Identifier
InChI=1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21)/t9-,10-,11+,12-,14+/m0/s1
InChI KeyIPROLSVTVHAQLE-BYNIDDHOSA-N
Chemical Taxonomy
Description 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 ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Pyran
  • Oxane
  • Secondary alcohol
  • Acetal
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.68ALOGPS
logP-1ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.55 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.91 m³·mol⁻¹ChemAxon
Polarizability30.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010316
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027468
KNApSAcK IDNot Available
Chemspider ID75744
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound83944
PDB IDNot Available
ChEBI ID32636
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available