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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-15 16:09:31 UTC
Update Date2021-09-14 14:57:35 UTC
HMDB IDHMDB0010316
Secondary Accession Numbers
  • HMDB10316
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). Within humans, acetaminophen glucuronide participates in a number of enzymatic reactions. In particular, acetaminophen glucuronide and uridine 5'-diphosphate can be biosynthesized from acetaminophen and uridine diphosphate glucuronic acid through its interaction with the enzymes UDP-glucuronosyltransferase 1-9, UDP-glucuronosyltransferase 2B15, UDP-glucuronosyltransferase 1-1, and UDP-glucuronosyltransferase 1-6. In addition, acetaminophen glucuronide can be converted into acetaminophen glucuronide through its interaction with the enzyme ATP-binding cassette sub-family g member 2. In humans, acetaminophen glucuronide is involved in acetaminophen metabolism pathway. Acetaminophen glucuronide, with regard to humans, has been linked to the inborn metabolic disorder beta-thalassemia. A beta-D-glucosiduronic acid that is the O-glucuronide of paracetamol (acetaminophen).
Structure
Data?1582752813
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
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility27.7 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.12131661259
DarkChem[M-H]-176.40731661259
DeepCCS[M+H]+175.29230932474
DeepCCS[M-H]-172.89630932474
DeepCCS[M-2H]-205.83830932474
DeepCCS[M+Na]+181.20430932474
AllCCS[M+H]+175.732859911
AllCCS[M+H-H2O]+172.632859911
AllCCS[M+NH4]+178.532859911
AllCCS[M+Na]+179.332859911
AllCCS[M-H]-172.632859911
AllCCS[M+Na-2H]-172.632859911
AllCCS[M+HCOO]-172.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Acetaminophen glucuronideCC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C14515.5Standard polar33892256
Acetaminophen glucuronideCC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C12850.2Standard non polar33892256
Acetaminophen glucuronideCC(=O)NC1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C13193.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acetaminophen glucuronide,1TMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=C12983.7Semi standard non polar33892256
Acetaminophen glucuronide,1TMS,isomer #2CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=C12982.8Semi standard non polar33892256
Acetaminophen glucuronide,1TMS,isomer #3CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=C12983.7Semi standard non polar33892256
Acetaminophen glucuronide,1TMS,isomer #4CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=C12983.4Semi standard non polar33892256
Acetaminophen glucuronide,1TMS,isomer #5CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C2822.8Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=C13011.7Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #10CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C2784.6Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #2CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C=C13016.7Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #3CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=C13004.0Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #4CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C2787.4Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #5CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=C13000.4Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #6CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C13010.2Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #7CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C2796.6Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #8CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=C12993.2Semi standard non polar33892256
Acetaminophen glucuronide,2TMS,isomer #9CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2790.9Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C=C13030.4Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #10CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2815.1Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #2CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=C13017.5Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #3CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C2821.4Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #4CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C13017.3Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #5CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C2825.1Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #6CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2832.8Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #7CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C13009.5Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #8CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C2819.7Semi standard non polar33892256
Acetaminophen glucuronide,3TMS,isomer #9CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2828.4Semi standard non polar33892256
Acetaminophen glucuronide,4TMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C13062.4Semi standard non polar33892256
Acetaminophen glucuronide,4TMS,isomer #2CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C2863.6Semi standard non polar33892256
Acetaminophen glucuronide,4TMS,isomer #3CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2880.8Semi standard non polar33892256
Acetaminophen glucuronide,4TMS,isomer #4CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2887.2Semi standard non polar33892256
Acetaminophen glucuronide,4TMS,isomer #5CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2863.6Semi standard non polar33892256
Acetaminophen glucuronide,5TMS,isomer #1CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2922.5Semi standard non polar33892256
Acetaminophen glucuronide,5TMS,isomer #1CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2678.3Standard non polar33892256
Acetaminophen glucuronide,5TMS,isomer #1CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C=C1)[Si](C)(C)C2988.7Standard polar33892256
Acetaminophen glucuronide,1TBDMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C=C13269.7Semi standard non polar33892256
Acetaminophen glucuronide,1TBDMS,isomer #2CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13272.5Semi standard non polar33892256
Acetaminophen glucuronide,1TBDMS,isomer #3CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13281.1Semi standard non polar33892256
Acetaminophen glucuronide,1TBDMS,isomer #4CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=C13307.0Semi standard non polar33892256
Acetaminophen glucuronide,1TBDMS,isomer #5CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3056.4Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C=C13534.0Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #10CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3243.8Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #2CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13507.6Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #3CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13506.9Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #4CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3255.5Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #5CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13515.5Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #6CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13508.6Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #7CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3266.3Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #8CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13530.1Semi standard non polar33892256
Acetaminophen glucuronide,2TBDMS,isomer #9CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3258.6Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13713.1Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #10CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3462.5Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #2CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13728.9Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #3CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3465.5Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #4CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13727.2Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #5CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3460.6Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #6CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3472.0Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #7CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13697.3Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #8CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3459.8Semi standard non polar33892256
Acetaminophen glucuronide,3TBDMS,isomer #9CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3463.6Semi standard non polar33892256
Acetaminophen glucuronide,4TBDMS,isomer #1CC(=O)NC1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13917.5Semi standard non polar33892256
Acetaminophen glucuronide,4TBDMS,isomer #2CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3661.2Semi standard non polar33892256
Acetaminophen glucuronide,4TBDMS,isomer #3CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3694.5Semi standard non polar33892256
Acetaminophen glucuronide,4TBDMS,isomer #4CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3675.9Semi standard non polar33892256
Acetaminophen glucuronide,4TBDMS,isomer #5CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3663.1Semi standard non polar33892256
Acetaminophen glucuronide,5TBDMS,isomer #1CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3871.4Semi standard non polar33892256
Acetaminophen glucuronide,5TBDMS,isomer #1CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3493.9Standard non polar33892256
Acetaminophen glucuronide,5TBDMS,isomer #1CC(=O)N(C1=CC=C(O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3459.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acetaminophen glucuronide GC-EI-TOF (Non-derivatized)splash10-00kb-0961000000-dcaaa03ec12ac3e8bc7b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acetaminophen glucuronide GC-EI-TOF (Non-derivatized)splash10-00kb-0961000000-dcaaa03ec12ac3e8bc7b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetaminophen glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9352000000-77fed48f2ac24b73fab82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetaminophen glucuronide GC-MS (4 TMS) - 70eV, Positivesplash10-0udi-4100349000-5176b6b37f6857b7f9992017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetaminophen glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acetaminophen glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide Linear Ion Trap , negative-QTOFsplash10-03k9-0900000000-5e02cd6d491f4b1cf8f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide Linear Ion Trap , positive-QTOFsplash10-00di-0900000000-acce7f7634727584b4352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide Linear Ion Trap , positive-QTOFsplash10-000i-0922000000-d3ea032d2b2a786b49a42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 20V, Positive-QTOFsplash10-0udi-0900000000-7bb565a0815d9e8681c42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 30V, Positive-QTOFsplash10-0w29-2900000000-8029b9ba6317a5c7bacb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 10V, Positive-QTOFsplash10-0udi-1902000000-63bf36b7f8481253b0412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 10V, Negative-QTOFsplash10-03di-3901000000-ac725135cde5a222d64a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 20V, Negative-QTOFsplash10-0udi-9800000000-d0386babb34ac37083732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 30V, Positive-QTOFsplash10-014l-9200000000-dc0cedc02a918704f9c22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 0V, Positive-QTOFsplash10-0udi-0907000000-cc6b4eeb1854a02b091e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 35V, Negative-QTOFsplash10-0ik9-2900000000-f45589acb1254525eedc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 40V, Positive-QTOFsplash10-03di-4900000000-8f1b83b451250f90fa5f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 35V, Positive-QTOFsplash10-0xxr-3900000000-560c53f10968963e3a632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 0V, Positive-QTOFsplash10-0udi-0907000000-ab44d212f9ebe70f73e62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 30V, Negative-QTOFsplash10-0zfr-9800000000-16b1e116a6a82ae143a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 40V, Negative-QTOFsplash10-0pb9-7900000000-0106d7d985bdfc7ce4ae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 10V, Positive-QTOFsplash10-0udi-0902000000-232646fdc95c354d8ef22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 10V, Positive-QTOFsplash10-0udi-0901000000-24d1372940103501af9d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acetaminophen glucuronide 30V, Positive-QTOFsplash10-0udi-6900000000-65f843147decea0cfc442021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetaminophen glucuronide 10V, Positive-QTOFsplash10-0w4i-0946000000-4049f1415ff9576f59242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetaminophen glucuronide 20V, Positive-QTOFsplash10-0zfr-0910000000-a1b732d82b46888499a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetaminophen glucuronide 40V, Positive-QTOFsplash10-0pc0-2900000000-7fe5c0cbd173677445962016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetaminophen glucuronide 10V, Negative-QTOFsplash10-0fc0-2968000000-a253cd8c945d814768e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetaminophen glucuronide 20V, Negative-QTOFsplash10-0udi-2931000000-8678b1c192068d44639b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acetaminophen glucuronide 40V, Negative-QTOFsplash10-0pc0-3900000000-6e974e4924ffcc0ae7782016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30.2 +/- 3.36 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified33.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified43.7 +/- 4.5 uMAdult (>18 years old)Both
Beta-thalassemia
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Beta-thalassemia
  1. Tankanitlert J, Howard TA, Temsakulphong A, Sirankapracha P, Morales NP, Sanvarinda Y, Fucharoen P, Ware RE, Fucharoen S, Chantharaksri U: A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. Eur J Clin Pharmacol. 2006 Sep;62(9):743-8. Epub 2006 Jul 15. [PubMed:16845508 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDACMPGLU
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aw TY, Jones DP: Intracellular inhibition of UDP-glucose dehydrogenase during ethanol oxidation. Chem Biol Interact. 1983 Mar;43(3):283-8. [PubMed:6825201 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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 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. 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:
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
References
  1. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. [PubMed:11714888 ]
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
References
  1. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. [PubMed:11714888 ]
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:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
References
  1. Court MH: Acetaminophen UDP-glucuronosyltransferase in ferrets: species and gender differences, and sequence analysis of ferret UGT1A6. J Vet Pharmacol Ther. 2001 Dec;24(6):415-22. [PubMed:11903872 ]
  2. Court MH, Duan SX, von Moltke LL, Greenblatt DJ, Patten CJ, Miners JO, Mackenzie PI: Interindividual variability in acetaminophen glucuronidation by human liver microsomes: identification of relevant acetaminophen UDP-glucuronosyltransferase isoforms. J Pharmacol Exp Ther. 2001 Dec;299(3):998-1006. [PubMed:11714888 ]
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name:
GUSB
Uniprot ID:
P08236
Molecular weight:
74731.46