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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:52 UTC
Update Date2018-05-20 20:31:53 UTC
HMDB IDHMDB0060946
Secondary Accession Numbers
  • HMDB60946
Metabolite Identification
Common NameNAPQI
DescriptionNAPQI 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). It is normally produced only in small amounts, and then almost immediately detoxified in the liver. However, under some conditions in which NAPQI is not effectively detoxified (usually in case of paracetamol overdose), it causes severe damage to the liver. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
4-acetylimino-2,5-Cyclohexadien-1-oneChEBI
AcetimidoquinoneChEBI
N-Acetyl-4-benzoquinoneimineChEBI
N-Acetyl-P-benzoquinone imineChEBI
N-Acetyl-4-benzoquinone imineMeSH
N-Acetyl-4-benzoquinoneimine, 3,5-(14)C-labeled CPDMeSH
N-Acetyl-P-benzoquinoneimineMeSH
NABQMeSH
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
DescriptionThis compound 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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.99 g/LALOGPS
logP0.53ALOGPS
logP0.57ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)19.14ChemAxon
pKa (Strongest Basic)-0.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area46.5 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.45 m³·mol⁻¹ChemAxon
Polarizability14.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-26d4378e16051e29f3a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-ac4176497e66953d40c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-0900000000-742d4824d6c715e26f22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-6e485c18c7bf55922b57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-2a0e88975df639fa0154View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0900000000-d205478121975decd1e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-069af19709609ef10b8dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound39763
      PDB IDNot Available
      ChEBI ID29132
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available