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Human Metabolome Database Version 3.5

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Showing metabocard for Acetaminophen glucuronide (HMDB10316)

Record Information
Version 3.5
Creation Date 2008-09-15 10:09:31 -0600
Update Date 2013-06-10 10:57:22 -0600
HMDB ID HMDB10316
Secondary Accession Numbers None
Metabolite Identification
Common Name Acetaminophen glucuronide
Description Acetaminophen 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C14H17NO8
Average Molecular Weight 327.2867
Monoisotopic Molecular Weight 327.095416525
IUPAC Name (2S,3S,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name acetaminophen glucuronide
CAS Registry Number 16110-10-4
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 Key IPROLSVTVHAQLE-BYNIDDHOSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Acids and Derivatives
Sub Class Glucuronic 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 Parent Glucuronides
Ontology
Status Detected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 27.7 g/L ALOGPS
LogP -0.68 ALOGPS
LogP -1 ChemAxon
LogS -1.07 ALOGPS
pKa (strongest acidic) 3.17 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 145.55 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 74.91 ChemAxon
Polarizability 30.7 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
30.2 +/- 3.36 uM Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
33.4 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Bouatra, S. ...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Male Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 43.7 +/- 4.5 uM Adult (>18 years old) Both Comment Beta-thalassemia
Associated Disorders and Diseases
Disease References
Beta-thalassemia
  • 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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB027468
    KNApSAcK ID Not Available
    Chemspider ID 75744 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Beta-D-Glucuronides Link_out
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB10316 Link_out
    Metagene Link HMDB10316 Link_out
    METLIN ID Not Available
    PubChem Compound 83944 Link_out
    PDB ID Not Available
    ChEBI ID 32636 Link_out
    References
    Synthesis Reference Not 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 Link_out
    Enzymes
    Name: UDP-glucuronosyltransferase 2B4
    Reactions: Not Available
    Gene Name: UGT2B4
    Uniprot ID: P06133 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-4
    Reactions: Not Available
    Gene Name: UGT1A4
    Uniprot ID: P22310 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 2B7
    Reactions: Not Available
    Gene Name: UGT2B7
    Uniprot ID: P16662 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-1
    Reactions: Not Available
    Gene Name: UGT1A1
    Uniprot ID: P22309 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-9
    Reactions: Not Available
    Gene Name: UGT1A9
    Uniprot ID: O60656 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: UDP-glucuronosyltransferase 1-6
    Reactions: Not Available
    Gene Name: UGT1A6
    Uniprot ID: P19224 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Beta-glucuronidase
    Reactions: Not Available
    Gene Name: GUSB
    Uniprot ID: P08236 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA