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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0961000000-dcaaa03ec12ac3e8bc7bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0961000000-dcaaa03ec12ac3e8bc7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9352000000-77fed48f2ac24b73fab8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0udi-4100349000-5176b6b37f6857b7f999View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03k9-0900000000-5e02cd6d491f4b1cf8f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00di-0900000000-acce7f7634727584b435View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0922000000-d3ea032d2b2a786b49a4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-7bb565a0815d9e8681c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0w29-2900000000-8029b9ba6317a5c7bacbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1902000000-63bf36b7f8481253b041View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-3901000000-ac725135cde5a222d64aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0udi-9800000000-d0386babb34ac3708373View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014l-9200000000-dc0cedc02a918704f9c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0udi-0907000000-cc6b4eeb1854a02b091eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ik9-2900000000-f45589acb1254525eedcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-8f1b83b451250f90fa5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0xxr-3900000000-560c53f10968963e3a63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0udi-0907000000-ab44d212f9ebe70f73e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0zfr-9800000000-16b1e116a6a82ae143a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-7900000000-0106d7d985bdfc7ce4aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0902000000-232646fdc95c354d8ef2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0901000000-24d1372940103501af9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-6900000000-65f843147decea0cfc44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w4i-0946000000-4049f1415ff9576f5924View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-0910000000-a1b732d82b46888499a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc0-2900000000-7fe5c0cbd17367744596View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fc0-2968000000-a253cd8c945d814768e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2931000000-8678b1c192068d44639bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc0-3900000000-6e974e4924ffcc0ae778View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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