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Record Information
Version3.6
Creation Date2008-09-15 16:09:31 UTC
Update Date2013-06-10 16:57:22 UTC
HMDB IDHMDB10316
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetaminophen glucuronide
DescriptionAcetaminophen glucuronide is a natural human metabolite of Acetaminophen generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Structure
Thumb
Synonyms
  1. 4-(Acetylamino)phenyl beta-D-glucopyranosiduronic acid
  2. 4-(Acetylamino)phenyl beta-delta-glucopyranosiduronic acid
  3. 4-Acetamidophenol glucuronide
  4. 4-Acetamidophenyl b-D-glucopyranosiduronic acid
  5. 4-Acetamidophenyl b-delta-glucopyranosiduronic acid
  6. 4-Acetamidophenyl beta-D-glucopyranosiduronic acid
  7. 4-Acetamidophenyl beta-delta-glucopyranosiduronic acid
  8. p-Acetamidophenyl β-D-glucuronide
  9. Paracetamol glucuronide
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 IUPAC 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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassSugar Acids and Derivatives
Sub ClassGlucuronic Acid Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • Glucuronic Acid Derivatives
  • O-glycosyl Compounds
  • beta-D-glucosiduronic acid(ChEBI)
Substituents
  • 1,2 Diol
  • Acetal
  • Acetanilide
  • Beta Hydroxy Acid
  • Carboxamide Group
  • Carboxylic Acid
  • Hexose Monosaccharide
  • Oxane
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentGlucuronides
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
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
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 area145.55ChemAxon
rotatable bond count4ChemAxon
refractivity74.91ChemAxon
polarizability30.7ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified30.2 +/- 3.36 uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified33.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified43.7 +/- 4.5 uMAdult (>18 years old)Both
Beta-thalassemia
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
DrugBank Metabolite IDDBMET00580
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027468
KNApSAcK IDNot Available
Chemspider ID75744
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10316
Metagene LinkHMDB10316
METLIN IDNot Available
PubChem Compound83944
PDB IDNot Available
ChEBI ID32636
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

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