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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:52 UTC
Update Date2023-02-21 17:30:16 UTC
HMDB IDHMDB0060946
Secondary Accession Numbers
  • HMDB60946
Metabolite Identification
Common NameNAPQI
DescriptionNAPQI, also known as acetimidoquinone or NABQ, belongs to the class of organic compounds known as secondary ketimines. These are ketimines where the nitrogen of the ketimine group is linked to an alkyl or aryl group. NAPQI is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, NAPQI participates in a number of enzymatic reactions. In particular, NAPQI can be biosynthesized from acetaminophen through the action of the enzymes cytochrome P450 2E1, cytochrome P450 1A2, cytochrome P450 2D6, cytochrome P450 3A4, and cytochrome P450 2A6. In addition, NAPQI and glutathione can be converted into acetaminophen cystein; which is mediated by the enzymes glutathione S-transferase p and glutathione S-transferase theta-1. In humans, NAPQI is involved in acetaminophen metabolism pathway. It is normally produced only in small amounts, and then almost immediately detoxified in the liver. NAPQI is a metabolite of acetaminophen. NAPQI (N-acetyl-p-benzoquinone imine) is a toxic byproduct produced during the xenobiotic metabolism of the analgesic paracetamol (acetaminophen). However, under some conditions in which NAPQI is not effectively detoxified (usually in case of paracetamol overdose), it causes severe damage to the liver.
Structure
Thumb
Synonyms
ValueSource
4-Acetylimino-2,5-cyclohexadien-1-oneChEBI
AcetimidoquinoneChEBI
N-Acetyl-4-benzoquinoneimineChEBI
N-Acetyl-p-benzoquinone imineChEBI
N-AcetylbenzoquinoneimineChEBI
N-Acetyl-4-benzoquinone imineHMDB
N-Acetyl-4-benzoquinoneimine, 3,5-(14)C-labeled CPDHMDB
N-Acetyl-p-benzoquinoneimineHMDB
NABQHMDB
Chemical FormulaC8H7NO2
Average Molecular Weight149.1467
Monoisotopic Molecular Weight149.047678473
IUPAC NameN-(4-oxocyclohexa-2,5-dien-1-ylidene)acetamide
Traditional NameN-acetyl-p-benzoquinone
CAS Registry NumberNot Available
SMILES
CC(=O)N=C1C=CC(=O)C=C1
InChI Identifier
InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
InChI KeyURNSECGXFRDEDC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as secondary ketimines. These are ketimines where the nitrogen of the ketimine group is linked to an alkyl or aryl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassImines
Direct ParentSecondary ketimines
Alternative Parents
Substituents
  • Secondary ketimine
  • Azomethine
  • Cyclic ketone
  • N-acylimine
  • Ketone
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNAPQI
METLIN IDNot Available
PubChem Compound39763
PDB IDNot Available
ChEBI ID29132
Food Biomarker OntologyNot Available
VMH IDNAPQI
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available