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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:52 UTC
Update Date2023-02-21 17:22:33 UTC
HMDB IDHMDB0032630
Secondary Accession Numbers
  • HMDB32630
Metabolite Identification
Common Name2'-Aminoacetophenone
Description2'-Aminoacetophenone, also known as O-acetylaniline or 1-acetyl-2-aminobenzene, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2'-Aminoacetophenone exists as a solid, slightly soluble (in water), and an extremely weak acidic (essentially neutral) compound (based on its pKa). Within the cell, 2'-aminoacetophenone is primarily located in the cytoplasm. 2'-Aminoacetophenone is a sweet, foxy, and grape tasting compound that can be found in fruits and milk and milk products. This makes 2'-aminoacetophenone a potential biomarker for the consumption of these food products.
Structure
Data?1677000153
Synonyms
ValueSource
1-Acetyl-2-aminobenzeneChEBI
2-AcetylanilineChEBI
2-AcetylphenylamineChEBI
2-AminoacetophenoneChEBI
5 KaalChEBI
O-AcetylanilineChEBI
O-AminoacetylbenzeneChEBI
O-Aminophenyl methyl ketoneChEBI
Ortho-aminoacetophenoneChEBI
1-(2-Aminophenyl)-ethanoneHMDB
1-(2-Aminophenyl)ethanone, 9ciHMDB
1-(Aminophenyl)-ethanoneHMDB
2'-AmonioacetophenoneHMDB
FEMA 3906HMDB
2-Aminoacetophenone hydrochlorideHMDB
O-AminoacetophenoneHMDB
2'-AminoacetophenoneChEBI
Chemical FormulaC8H9NO
Average Molecular Weight135.1632
Monoisotopic Molecular Weight135.068413915
IUPAC Name1-(2-aminophenyl)ethan-1-one
Traditional NameO-aminoacetophenone
CAS Registry Number551-93-9
SMILES
CC(=O)C1=CC=CC=C1N
InChI Identifier
InChI=1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3
InChI KeyGTDQGKWDWVUKTI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Benzoyl
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Amine
  • Primary amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point20 °CNot Available
Boiling Point85.00 to 90.00 °C. @ 0.50 mm HgThe Good Scents Company Information System
Water Solubility3555 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.63Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.7 g/LALOGPS
logP0.98ALOGPS
logP1.35ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)16.26ChemAxon
pKa (Strongest Basic)2.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.16 m³·mol⁻¹ChemAxon
Polarizability14.38 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]+129.07731661259
DarkChem[M-H]-123.6531661259
DeepCCS[M+H]+129.83130932474
DeepCCS[M-H]-127.29230932474
DeepCCS[M-2H]-163.33730932474
DeepCCS[M+Na]+138.18830932474
AllCCS[M+H]+127.832859911
AllCCS[M+H-H2O]+123.132859911
AllCCS[M+NH4]+132.232859911
AllCCS[M+Na]+133.532859911
AllCCS[M-H]-126.532859911
AllCCS[M+Na-2H]-128.232859911
AllCCS[M+HCOO]-130.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2'-AminoacetophenoneCC(=O)C1=CC=CC=C1N2261.7Standard polar33892256
2'-AminoacetophenoneCC(=O)C1=CC=CC=C1N1279.1Standard non polar33892256
2'-AminoacetophenoneCC(=O)C1=CC=CC=C1N1331.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2'-Aminoacetophenone,1TMS,isomer #1CC(=O)C1=CC=CC=C1N[Si](C)(C)C1450.3Semi standard non polar33892256
2'-Aminoacetophenone,1TMS,isomer #1CC(=O)C1=CC=CC=C1N[Si](C)(C)C1515.9Standard non polar33892256
2'-Aminoacetophenone,2TMS,isomer #1CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1507.5Semi standard non polar33892256
2'-Aminoacetophenone,2TMS,isomer #1CC(=O)C1=CC=CC=C1N([Si](C)(C)C)[Si](C)(C)C1662.3Standard non polar33892256
2'-Aminoacetophenone,1TBDMS,isomer #1CC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C1695.9Semi standard non polar33892256
2'-Aminoacetophenone,1TBDMS,isomer #1CC(=O)C1=CC=CC=C1N[Si](C)(C)C(C)(C)C1741.0Standard non polar33892256
2'-Aminoacetophenone,2TBDMS,isomer #1CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1940.9Semi standard non polar33892256
2'-Aminoacetophenone,2TBDMS,isomer #1CC(=O)C1=CC=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2045.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2'-Aminoacetophenone EI-B (Non-derivatized)splash10-00y3-8900000000-5b770b73f4fd1d3c31b62017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2'-Aminoacetophenone EI-B (Non-derivatized)splash10-00y3-8900000000-5b770b73f4fd1d3c31b62018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Aminoacetophenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00y3-9800000000-87de04cb36dec199538d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Aminoacetophenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Aminoacetophenone 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 - 2'-Aminoacetophenone 10V, Positive-QTOFsplash10-000i-0900000000-390dd0a9927907e2e6652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Positive-QTOFsplash10-000i-2900000000-ba632cb2c303bfdf5ad12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Positive-QTOFsplash10-0gbc-9300000000-05733141b0e2d5c6345b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 10V, Negative-QTOFsplash10-001i-0900000000-97c834df79371be37b1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Negative-QTOFsplash10-001l-6900000000-f8a3d865b06a13af1cd82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Negative-QTOFsplash10-0006-9300000000-cac192025ffacc504db82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 10V, Negative-QTOFsplash10-001i-2900000000-e2fa340834ceeb9524382021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Negative-QTOFsplash10-0006-9400000000-72b13192818d590429782021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Negative-QTOFsplash10-00kf-9300000000-ec964628a8bc2468c3192021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 10V, Positive-QTOFsplash10-00kr-0900000000-bf06926af58b9dc8bf282021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 20V, Positive-QTOFsplash10-00kf-9800000000-294904f564e143ece6b42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Aminoacetophenone 40V, Positive-QTOFsplash10-0fr6-9100000000-9986bebd23c9773439172021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB010574
KNApSAcK IDNot Available
Chemspider ID13859235
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11086
PDB IDVNJ
ChEBI ID91110
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1062161
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .