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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:33 UTC
HMDB IDHMDB0001250
Secondary Accession Numbers
  • HMDB01250
Metabolite Identification
Common NameN-Acetylarylamine
DescriptionN-Acetylarylamine is an odourless solid chemical of leaf or flake-like appearance. It is also known as acetanilide, N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin. N-Acetylarylamine has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study.
Structure
Data?1676999733
Synonyms
ValueSource
AcetamidobenzeneChEBI
AcetanilChEBI
AcetanilidChEBI
AcetanilideChEBI
Acetic acid anilideChEBI
N-AcetylaminobenzeneChEBI
N-PhenylacetamideKegg
Acetate anilideGenerator
AntifebrinHMDB
N-AcetylarylamineChEBI
Chemical FormulaC8H9NO
Average Molecular Weight135.1632
Monoisotopic Molecular Weight135.068413915
IUPAC NameN-phenylacetamide
Traditional Nameacetanilide
CAS Registry Number55576-55-1
SMILES
CC(=O)NC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
InChI KeyFZERHIULMFGESH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • 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 effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.39 mg/mL at 25 °CNot Available
LogP1.16HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg124.16730932474
[M-H]-Not Available124.167http://allccs.zhulab.cn/database/detail?ID=AllCCS00000296
[M+H]+Not Available124.994http://allccs.zhulab.cn/database/detail?ID=AllCCS00000296
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.03 g/LALOGPS
logP1.05ALOGPS
logP1.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.92 m³·mol⁻¹ChemAxon
Polarizability14.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.26231661259
DarkChem[M-H]-124.74531661259
AllCCS[M+H]+127.92632859911
AllCCS[M-H]-126.72632859911
DeepCCS[M+H]+128.0130932474
DeepCCS[M-H]-124.66430932474
DeepCCS[M-2H]-161.71730932474
DeepCCS[M+Na]+137.11230932474
AllCCS[M+H]+127.932859911
AllCCS[M+H-H2O]+123.332859911
AllCCS[M+NH4]+132.332859911
AllCCS[M+Na]+133.532859911
AllCCS[M-H]-126.732859911
AllCCS[M+Na-2H]-128.432859911
AllCCS[M+HCOO]-130.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcetylarylamineCC(=O)NC1=CC=CC=C11828.2Standard polar33892256
N-AcetylarylamineCC(=O)NC1=CC=CC=C11337.1Standard non polar33892256
N-AcetylarylamineCC(=O)NC1=CC=CC=C11378.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylarylamine,1TMS,isomer #1CC(=O)N(C1=CC=CC=C1)[Si](C)(C)C1305.0Semi standard non polar33892256
N-Acetylarylamine,1TMS,isomer #1CC(=O)N(C1=CC=CC=C1)[Si](C)(C)C1380.0Standard non polar33892256
N-Acetylarylamine,1TMS,isomer #1CC(=O)N(C1=CC=CC=C1)[Si](C)(C)C1672.9Standard polar33892256
N-Acetylarylamine,1TBDMS,isomer #1CC(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1519.7Semi standard non polar33892256
N-Acetylarylamine,1TBDMS,isomer #1CC(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1586.7Standard non polar33892256
N-Acetylarylamine,1TBDMS,isomer #1CC(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C1823.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine EI-B (Non-derivatized)splash10-000f-9000000000-62d570000b48b08370732017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine GC-EI-TOF (Non-derivatized)splash10-0006-9100000000-4122036cecde322748ea2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-5b4e4f73d383d9139de82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-2293bbd44d7f9fc8077c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine EI-B (Non-derivatized)splash10-000f-9000000000-62d570000b48b08370732018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine GC-EI-TOF (Non-derivatized)splash10-0006-9100000000-4122036cecde322748ea2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-5b4e4f73d383d9139de82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylarylamine GC-EI-TOF (Non-derivatized)splash10-00dr-4900000000-2293bbd44d7f9fc8077c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylarylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-2bd7881947c0c62f2a312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylarylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-7eb05e193f729f0e27112017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , negative-QTOFsplash10-000x-9700000000-e7d678f13a1e17c9ed992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-1d77cc60e4a023d4dd222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-8877ad97a3992f9131132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-71ff77e29eb7281376052017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , positive-QTOFsplash10-014r-4900000000-7f8d10f07700a193e6222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , positive-QTOFsplash10-014u-9300000000-f975b8216fe43fc1d9cc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , positive-QTOFsplash10-0006-9200000000-12e9d1610beecb011c9d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , positive-QTOFsplash10-004l-9200000000-2d487e012ca3b59d0a9b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine LC-ESI-QQ , positive-QTOFsplash10-004l-9000000000-e50ad2b0e89696e088512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylarylamine 35V, Positive-QTOFsplash10-0006-9000000000-46f47c26afc8877cc2f12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 10V, Positive-QTOFsplash10-000l-5900000000-61578dc3c9789feb5f8a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 20V, Positive-QTOFsplash10-0006-9300000000-299ec76356db162d42592016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 40V, Positive-QTOFsplash10-00kf-9000000000-f918e8f5428211fb9a252016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 10V, Negative-QTOFsplash10-001i-2900000000-9def162dfa4b1400554c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 20V, Negative-QTOFsplash10-0006-9500000000-137a2164ab31a33087922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 40V, Negative-QTOFsplash10-0006-9100000000-63a8773b99832a19d5e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 10V, Negative-QTOFsplash10-0006-9400000000-753f541f128c751917c72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 20V, Negative-QTOFsplash10-0006-9100000000-5df9abaffe7f5bdbe5d72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 40V, Negative-QTOFsplash10-0006-9000000000-e621b748b2a107ee39e82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 10V, Positive-QTOFsplash10-000l-4900000000-b549e531b7dd15d51b672021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 20V, Positive-QTOFsplash10-0006-9000000000-60ecfd1f5d15dfbcfb812021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylarylamine 40V, Positive-QTOFsplash10-014l-9000000000-df32423a180287f625672021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022512
KNApSAcK IDNot Available
Chemspider ID880
KEGG Compound IDC07565
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Phenylacetamide
METLIN ID6107
PubChem Compound904
PDB IDNot Available
ChEBI ID28884
Food Biomarker OntologyNot Available
VMH IDM01251
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ogino M, Nakada Y, Negoro N, Itokawa S, Nishimura S, Sanada T, Satomi T, Kita S, Kubo K, Marui S: Discovery of a novel acyl-CoA: cholesterol acyltransferase inhibitor: the synthesis, biological evaluation, and reduced adrenal toxicity of (4-phenylcoumarin)acetanilide derivatives with a carboxylic acid moiety. Chem Pharm Bull (Tokyo). 2011;59(11):1369-75. [PubMed:22041073 ]
  2. Poraj-Kobielska M, Kinne M, Ullrich R, Scheibner K, Kayser G, Hammel KE, Hofrichter M: Preparation of human drug metabolites using fungal peroxygenases. Biochem Pharmacol. 2011 Oct 1;82(7):789-96. doi: 10.1016/j.bcp.2011.06.020. Epub 2011 Jun 23. [PubMed:21723855 ]
  3. Wu Y, Choy PY, Mao F, Kwong FY: Toluene derivatives as simple coupling precursors for cascade palladium-catalyzed oxidative C-H bond acylation of acetanilides. Chem Commun (Camb). 2013 Jan 25;49(7):689-91. doi: 10.1039/c2cc37352a. [PubMed:23230572 ]
  4. Yan GF, Wang Q, Wei BL, Sun XC, Chen GQ, Gao SM: [Photophysical properties of novel organic europium (III) complexes]. Guang Pu Xue Yu Guang Pu Fen Xi. 2010 Oct;30(10):2606-10. [PubMed:21137382 ]
  5. Chen CZ, Yan CT, Kumar PV, Huang JW, Jen JF: Determination of alachlor and its metabolite 2,6-diethylaniline in microbial culture medium using online microdialysis enriched-sampling coupled to high-performance liquid chromatography. J Agric Food Chem. 2011 Aug 10;59(15):8078-85. doi: 10.1021/jf201129j. Epub 2011 Jul 11. [PubMed:21707080 ]
  6. Liang HQ, Tao YP, Han LG, Han YX, Mo YJ: [Raman, FTIR spectra and normal mode analysis of acetanilide]. Guang Pu Xue Yu Guang Pu Fen Xi. 2012 Oct;32(10):2706-9. [PubMed:23285870 ]
  7. Sun L, Zhang S, Song Q: (4-Chloro-acetanilido-kappa(2)N,O)bis-[2-(pyridin-2-yl)phenyl-kappa(2)C(1),N]irid ium(III). Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 1;69(Pt 2):m98. doi: 10.1107/S1600536813000433. Epub 2013 Jan 12. [PubMed:23424440 ]
  8. Bouchonnet S, Bourcier S, Souissi Y, Genty C, Sablier M, Roche P, Boireau V, Ingrand V: GC-MS(n) and LC-MS/MS couplings for the identification of degradation products resulting from the ozonation treatment of Acetochlor. J Mass Spectrom. 2012 Apr;47(4):439-52. doi: 10.1002/jms.2056. [PubMed:22689619 ]
  9. Kalkhoff SJ, Vecchia AV, Capel PD, Meyer MT: Eleven-year trend in acetanilide pesticide degradates in the Iowa River, Iowa. J Environ Qual. 2012 Sep-Oct;41(5):1566-79. doi: 10.2134/jeq2011.0426. [PubMed:23099949 ]
  10. Weiler M, Nakamura T, Sekiya H, Dopfer O, Miyazaki M, Fujii M: Ionization-induced solvent migration in acetanilide-methanol clusters inferred from isomer-selective infrared spectroscopy. Chemphyschem. 2012 Dec 7;13(17):3875-81. doi: 10.1002/cphc.201200704. Epub 2012 Oct 30. [PubMed:23112069 ]
  11. Fu YY, Yang CX, Yan XP: Metal-organic framework MIL-100(Fe) as the stationary phase for both normal-phase and reverse-phase high performance liquid chromatography. J Chromatogr A. 2013 Jan 25;1274:137-44. doi: 10.1016/j.chroma.2012.12.015. Epub 2012 Dec 17. [PubMed:23290359 ]
  12. Ogino M, Fukui S, Nakada Y, Tokunoh R, Itokawa S, Kakoi Y, Nishimura S, Sanada T, Fuse H, Kubo K, Wada T, Marui S: Discovery of a potent and orally available acyl-CoA: cholesterol acyltransferase inhibitor as an anti-atherosclerotic agent: (4-phenylcoumarin)acetanilide derivatives. Chem Pharm Bull (Tokyo). 2011;59(10):1268-73. [PubMed:21963637 ]
  13. Lu C, Markina NA, Larock RC: Synthesis of N-acylcarbazoles through palladium-catalyzed aryne annulation of 2-haloacetanilides. J Org Chem. 2012 Dec 21;77(24):11153-60. doi: 10.1021/jo3021727. Epub 2012 Dec 5. [PubMed:23214463 ]

Enzymes

General function:
Involved in acetyltransferase activity
Specific function:
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivate several known carcinogens.
Gene Name:
NAT1
Uniprot ID:
P18440
Molecular weight:
33898.445
General function:
Involved in acetyltransferase activity
Specific function:
Not Available
Gene Name:
NAT2
Uniprot ID:
A4Z6T7
Molecular weight:
33570.2