2-Acetamidophenol (CHEM016506)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:35:01 UTC
Update Date2016-11-09 01:15:24 UTC
Accession NumberCHEM016506
Identification
Common Name2-Acetamidophenol
ClassSmall Molecule
DescriptionA member of the class of phenols that is 2-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group. A positional isomer of paracetamol which possesses anti-inflammatory, anti-arthritic and anti-platelet aggregation properties.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(Acetylamino)phenolChEBI
2-(N-Acetylamino)phenolChEBI
2-AcetaminophenolChEBI
2-HydroxyacetanilideChEBI
Acet-O-aminofenolChEBI
N-(2-Hydroxyphenyl)acetamideChEBI
N-Acetyl-2-aminophenolChEBI
N-Acetyl-O-aminophenolChEBI
O-(Acetylamino)phenolChEBI
O-AcetamidophenolChEBI
O-AcetaminophenolChEBI
O-AcetylaminofenolChEBI
O-HydroxyacetanilideChEBI
2-AcetamidophenolHMDB
2’-hydroxyacetanilideHMDB
HPAAHMDB
2'-HydroxyacetanilideHMDB, ChEBI
Chemical FormulaC8H9NO2
Average Molecular Mass151.163 g/mol
Monoisotopic Mass151.063 g/mol
CAS Registry Number614-80-2
IUPAC NameN-(2-hydroxyphenyl)ethanimidic acid
Traditional NameN-(2-hydroxyphenyl)ethanimidic acid
SMILESCC(O)=NC1=CC=CC=C1O
InChI IdentifierInChI=1S/C8H9NO2/c1-6(10)9-7-4-2-3-5-8(7)11/h2-5,11H,1H3,(H,9,10)
InChI KeyADVGKWPZRIDURE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAcetanilides
Alternative Parents
Substituents
  • Acetanilide
  • N-acetylarylamine
  • N-arylamide
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.06 g/LALOGPS
logP1.06ALOGPS
logP2.28ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.44ChemAxon
pKa (Strongest Basic)-0.032ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.66 m³·mol⁻¹ChemAxon
Polarizability15.45 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3900000000-4d9102b66c05fcde72e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-8970000000-90bf32dc54b96f2ac02cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0w29-0900000000-af77e021f255b3b8fac0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0w29-0900000000-fef297ff805f8db233f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-0900000000-d43684d0a48bdabe138eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-03di-1900000000-f3793f07afce760fff06Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-03di-0900000000-c9d1b55ac09e031197f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-75bb3fca4fa6220b174cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-0900000000-f6d6bd9ad3bc874fabd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0900000000-ab0e2f7e82eb134f3b0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-03xr-9700000000-4704f18c2b30e7d4b4f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03di-4900000000-d59f856eb2831dfe2eefSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-0900000000-149c09f49abe5f9581f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0900000000-1876114b794275814876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0900000000-fc4c73f9baccb46248d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-ab81b53931ce6ab0f825Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9500000000-15d739304f54ad540f65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-1086be7b11354178c768Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-d009c4036acd34f5b83aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-90fe96bd72602d40b92bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b065bf14e56bbaed60a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-2bbceee473f22d15a64dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-4a2a4932ca605186545aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-d3551e9940af66c88a11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-3a0fa5be1ac01e1e12c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w30-9100000000-7088c0fee50a79c98570Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0061919
FooDB IDFDB093735
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID143107
PubChem Compound ID11972
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20452462
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23971042
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24186846
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24370547
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24846408
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25663820
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=28474155
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29790115
9. Cohen SM, Bryan GT: Effect of p-hydroxyacetanilide, sodium sulfate, and L-methionine on the leukemogenicity of N-[4-(5-nitro-2-furyl)-2-thiazolyl]acetamide. Cancer Res. 1978 May;38(5):1398-405.
10. Mohan LC, Grantham PH, Weisburger EK, Weisburger JH, Idoine JB: Mechanisms of the inhibitory action of p-hydroxyacetanilide on carcinogenesis by N-2-fluorenylacetamide or N-hydroxy-N-2-fluorenylacetamide. J Natl Cancer Inst. 1976 Apr;56(4):763-8.
11. Mancilla J, Valdes E, Gil L: A novel isocratic HPLC method to separate and quantify acetanilide and its hydroxy aromatic derivatives: 2-, 3- and 4-hydroxyacetanilide (paracetamol or acetaminophen). Eur J Drug Metab Pharmacokinet. 1989 Jul-Sep;14(3):241-4.
12. Hamilton M, Kissinger PT: The metabolism of 2- and 3-hydroxyacetanilide. Determination of metabolic products by liquid chromatography/electrochemistry. Drug Metab Dispos. 1986 Jan-Feb;14(1):5-12.
13. Rottero AE, Kissinger P: Detection and identification of three thioether conjugates of 2-hydroxyacetanilide by liquid chromatography/electrochemistry. Biomed Chromatogr. 1987 Feb;2(1):24-9.
14. Streeter AJ, Baillie TA: 2-Acetamido-p-benzoquinone: a reactive arylating metabolite of 3'-hydroxyacetanilide. Biochem Pharmacol. 1985 Aug 15;34(16):2871-6.
15. Yamamoto RS, Williams GM, Richardson HL, Weisburger EK, Weisburger JH: Effect of p-hydroxyacetanilide on liver cancer induction by N hydroxy-N-2-fluorenylacetamide. Cancer Res. 1973 Mar;33(3):454-7.
16. Weisburger JH, Weisburger EK, Madison RM, Wenk ML, Klein DS: Effect of acetanilide and p-hydroxyacetanilide on the carcinogenicity of N-2-fluorenylacetamide and N-hydroxy-N-2-fluorenylacetamide in mice, hamsters, and female rats. J Natl Cancer Inst. 1973 Jul;51(1):235-40.
17. Theriault RJ, Longfield TH: Microbial conversion of acetanilide to 2'-hydroxyacetanilide and 4'-hydroxyacetanilide. Appl Microbiol. 1967 Nov;15(6):1431-6.
18. Zhu Y, Wang P, Sha W, Sang S: Urinary Biomarkers of Whole Grain Wheat Intake Identified by Non-targeted and Targeted Metabolomics Approaches. Sci Rep. 2016 Nov 2;6:36278. doi: 10.1038/srep36278.
19. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510
20. Sheikh Saeed, Shahazad Saeed, 'Therapeutic applications of 2-hydroxyacetanilide.' U.S. Patent US20050049229, issued March 03, 2005.: http://www.google.ca/patents/US20050049229