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Showing Compound Acetaminophen (FDB022713)

Record Information
Version1.0
Creation date2011-09-21 00:18:21 UTC
Update date2019-11-26 03:21:06 UTC
Primary IDFDB022713
Secondary Accession Numbers
  • FDB021663
Chemical Information
FooDB NameAcetaminophen
DescriptionThe excellent tolerability of therapeutic doses of paracetamol (acetaminophen) is a major factor in the very wide use of the drug. The major problem in the use of paracetamol is its hepatotoxicity after an overdose. Hepatotoxicity has also been reported after therapeutic doses, but critical analysis indicates that most patients with alleged toxicity from therapeutic doses have taken overdoses. Importantly, prospective studies indicate that therapeutic doses of paracetamol are an unlikely cause of hepatotoxicity in patients who ingest moderate to large amounts of alcohol. (PMID 15733027) Single doses of paracetamol are effective analgesics for acute postoperative pain and give rise to few adverse effects. (PMID 14974073) Acetaminophen (AAP) overdose and the resulting hepatotoxicity is an important clinical problem. In addition, AAP is widely used as a prototype hepatotoxin to study mechanisms of chemical-induced cell injury and to test the hepatoprotective potential of new drugs and herbal medicines. Because of its importance, the mechanisms of AAP-induced liver cell injury have been extensively investigated and controversially discussed for many years. (PMID 16863451) [HMDB]
CAS Number103-90-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility4.15 g/LALOGPS
logP0.51ALOGPS
logP0.91ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.9 m³·mol⁻¹ChemAxon
Polarizability15.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H9NO2
IUPAC nameN-(4-hydroxyphenyl)acetamide
InChI IdentifierInChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
InChI KeyRZVAJINKPMORJF-UHFFFAOYSA-N
Isomeric SMILESCC(=O)NC1=CC=C(O)C=C1
Average Molecular Weight151.1626
Monoisotopic Molecular Weight151.063328537
Classification
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-4900000000-ffdd0f8a1e6e450fc1622014-09-20View Spectrum
GC-MSUkonan D, 2 TMS, GC-MS Spectrumsplash10-0a4i-4971200000-17e6e1373f10ba4ec138Spectrum
GC-MSUkonan D, non-derivatized, GC-MS Spectrumsplash10-0a4i-1900000000-df97f74a81da3a46a697Spectrum
GC-MSUkonan D, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-ef277124e1b50b5f010eSpectrum
GC-MSUkonan D, non-derivatized, GC-MS Spectrumsplash10-0udi-0900000000-7aa6a54b74b345d91e37Spectrum
GC-MSUkonan D, non-derivatized, GC-MS Spectrumsplash10-0a4i-4971200000-17e6e1373f10ba4ec138Spectrum
Predicted GC-MSUkonan D, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-3900000000-070b8ab49f93898e0aa4Spectrum
Predicted GC-MSUkonan D, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05gl-8930000000-76d6dca6afdf5945dba1Spectrum
Predicted GC-MSUkonan D, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0zfr-0900000000-125e44ce332576a1e1552017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-7e46df4b4b653c90c2582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-bb6e34d2d574a249d7212017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-2f45dd7efce38361f8062017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0pb9-0900000000-e48b48d64b6b985ab4552017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-b72b0e33fd35512fe6de2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-97bcaa95f26159307d032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-c50b4b79792e2c2e68f92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-7e46df4b4b653c90c2582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-2b07cd2813d3f23e88f12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0pb9-0900000000-5b92f09589afe838f23a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0900000000-f0ca5ff6526b9f0050342017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-7e45ef71674dcdde90682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-0900000000-f6d6bd9ad3bc874fabd52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-7ec733f46e03a5a79fc42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udi-0900000000-bb6e34d2d574a249d7212021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0udi-0900000000-2f45dd7efce38361f8062021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0udi-0900000000-7e46df4b4b653c90c2582021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0zfr-0900000000-125e44ce332576a1e1552021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0pb9-0900000000-e48b48d64b6b985ab4552021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-b72b0e33fd35512fe6de2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0udi-0900000000-2b07cd2813d3f23e88f12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-0900000000-97bcaa95f26159307d032021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0pb9-0900000000-5b92f09589afe838f23a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-f0ca5ff6526b9f0050342021-09-20View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, 5%_DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID1906
ChEMBL IDCHEMBL112
KEGG Compound IDC06804
Pubchem Compound ID1983
Pubchem Substance IDNot Available
ChEBI ID2386
Phenol-Explorer IDNot Available
DrugBank IDDB00316
HMDB IDHMDB01859
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDTYL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAcetaminophen
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Milk (Cow)Expected but not quantifiedNot Available29291809
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference