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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:52 UTC
Update Date2019-07-23 07:15:26 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
Data?1563866126
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
Disposition

Biological location

Process

Naturally occurring process

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
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
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]+134.19831661259
DarkChem[M-H]-129.5431661259
DeepCCS[M+H]+131.94730932474
DeepCCS[M-H]-128.90830932474
DeepCCS[M-2H]-165.88230932474
DeepCCS[M+Na]+141.36330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NAPQICC(=O)N=C1C=CC(=O)C=C12332.8Standard polar33892256
NAPQICC(=O)N=C1C=CC(=O)C=C11358.6Standard non polar33892256
NAPQICC(=O)N=C1C=CC(=O)C=C11645.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - NAPQI GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-26d4378e16051e29f3a02017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAPQI GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - NAPQI GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 10V, Positive-QTOFsplash10-0udi-0900000000-ac4176497e66953d40c02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 20V, Positive-QTOFsplash10-0pb9-0900000000-742d4824d6c715e26f222017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 40V, Positive-QTOFsplash10-002f-9000000000-6e485c18c7bf55922b572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 10V, Negative-QTOFsplash10-0002-0900000000-2a0e88975df639fa01542017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 20V, Negative-QTOFsplash10-0a4j-0900000000-d205478121975decd1e62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 40V, Negative-QTOFsplash10-0a4i-5900000000-069af19709609ef10b8d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 10V, Positive-QTOFsplash10-0zfr-0900000000-7770a7a758395a5aeeee2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 20V, Positive-QTOFsplash10-0a59-4900000000-c817f1a34bce822d981d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 40V, Positive-QTOFsplash10-0a59-9500000000-1dabf7d69b9d1c2251142021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 10V, Negative-QTOFsplash10-0002-0900000000-d32a0a3b410ab42005862021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 20V, Negative-QTOFsplash10-0002-0900000000-017594813fe14d2bf2a92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - NAPQI 40V, Negative-QTOFsplash10-056r-9500000000-376138408404ae9cf5172021-10-12Wishart LabView Spectrum
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