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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:57:20 UTC
Update Date2019-10-24 15:55:17 UTC
HMDB IDHMDB0061919
Secondary Accession Numbers
  • HMDB61919
Metabolite Identification
Common Name2'-Hydroxyacetanilide
Description2'-Hydroxyacetanilide, also known as N-(2-hydroxyphenyl)acetamide (HPAA), belongs to the class of organic compounds known as aminophenols. These are organic compounds containing an amino group attached to a phenol. HPAA is a benzoxazinoid metabolite. It is a potential urinary biomarker of whole grain intake (PMID: 27805021 ).
Structure
Data?1563866247
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 Weight151.1626
Monoisotopic Molecular Weight151.063328537
IUPAC NameN-(2-hydroxyphenyl)ethanimidic acid
Traditional NameN-(2-hydroxyphenyl)ethanimidic acid
CAS Registry Number614-80-2
SMILES
CC(=O)NC1=CC=CC=C1O
InChI Identifier
InChI=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
Ontology
Disposition

Biological location:

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 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093735
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11972
PDB IDNot Available
ChEBI ID143107
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:639067 ]
  2. 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. [PubMed:815562 ]
  3. 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. [PubMed:2612521 ]
  4. 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. [PubMed:2868865 ]
  5. 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. [PubMed:3508090 ]
  6. Streeter AJ, Baillie TA: 2-Acetamido-p-benzoquinone: a reactive arylating metabolite of 3'-hydroxyacetanilide. Biochem Pharmacol. 1985 Aug 15;34(16):2871-6. [PubMed:4026876 ]
  7. 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. [PubMed:4347712 ]
  8. 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. [PubMed:4720874 ]
  9. Theriault RJ, Longfield TH: Microbial conversion of acetanilide to 2'-hydroxyacetanilide and 4'-hydroxyacetanilide. Appl Microbiol. 1967 Nov;15(6):1431-6. [PubMed:16349759 ]
  10. 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. [PubMed:27805021 ]
  11. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]
  12. Sheikh Saeed, Shahazad Saeed, 'Therapeutic applications of 2-hydroxyacetanilide.' U.S. Patent US20050049229, issued March 03, 2005. [Link]