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Showing NP-Card for o-aminoacetophenone (NP0311829)

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Record Information
Version2.0
Created at2022-09-11 08:05:48 UTC
Updated at2022-09-11 08:05:48 UTC
NP-MRD IDNP0311829
Secondary Accession NumbersNone
Natural Product Identification
Common Nameo-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. An aromatic ketone that is acetophenone in which one of the ortho hydrogens of the phenyl group has been replaced by an amino group. 2'-Aminoacetophenone is a moderately basic compound (based on its pKa). 2'-Aminoacetophenone is a sweet, foxy, and grape tasting compound. Outside of the human body, 2'-Aminoacetophenone has been detected, but not quantified in, fruits and milk and milk products. o-aminoacetophenone is found in Castanopsis cuspidata and Vitis vinifera. o-aminoacetophenone was first documented in 1971 (PMID: 11946045). This could make 2'-aminoacetophenone a potential biomarker for the consumption of these foods (PMID: 110829) (PMID: 21054900) (PMID: 25043228) (PMID: 25047450) (PMID: 25488497) (PMID: 25614099).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0311829 (o-aminoacetophenone)


  Mrv0541 05061306362D          

 10 10  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
M  END
Download

3D MOL for NP0311829 (o-aminoacetophenone)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.6221   -0.7273   -0.5792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582    0.2249    0.0313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1517    1.2381    0.5931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2134   -0.0068   -0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2929   -1.1274   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6437   -1.3897   -0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5125   -0.4906   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336    0.6492    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6574    0.8932    0.5555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080    2.0702    1.2167 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221   -0.5942   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -1.7694   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390   -0.5963   -0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465   -1.8086   -1.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0222   -2.2694   -1.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5759   -0.6717   -0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7387    1.3421    0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099    3.0048    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3160    2.0287    2.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9  4  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 10 18  1  0
 10 19  1  0
M  END
Download

3D SDF for NP0311829 (o-aminoacetophenone)


  Mrv0541 05061306362D          

 10 10  0  0  0  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  1  1  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  5  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0311829

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
GTDQGKWDWVUKTI-UHFFFAOYSA-N

> <FORMULA>
C8H9NO

> <MOLECULAR_WEIGHT>
135.1632

> <EXACT_MASS>
135.068413915

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
14.383575507840265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(2-aminophenyl)ethan-1-one

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
1.3519673806666668

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.257319766020704

> <JCHEM_PKA_STRONGEST_BASIC>
2.564505851071787

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
41.16120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-aminoacetophenone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0311829 (o-aminoacetophenone)

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PDB for NP0311829 (o-aminoacetophenone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    8                                                       
CONECT    6    1    7   10                                                  
CONECT    7    4    6    8                                                  
CONECT    8    5    7    9                                                  
CONECT    9    8                                                            
CONECT   10    6                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0311829 (o-aminoacetophenone)
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SMILES for NP0311829 (o-aminoacetophenone)
CC(=O)C1=CC=CC=C1N
Download
INCHI for NP0311829 (o-aminoacetophenone)
InChI=1S/C8H9NO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,9H2,1H3
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View in JSmol
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'-AminoacetophenoneChEBI
2-Aminoacetophenone hydrochlorideMeSH
O-AminoacetophenoneMeSH
Chemical FormulaC8H9NO
Average Mass135.1632 Da
Monoisotopic Mass135.06841 Da
IUPAC Name1-(2-aminophenyl)ethan-1-one
Traditional NameO-aminoacetophenone
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Castanopsis cuspidataLOTUS Database
Vitis viniferaLOTUS Database
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
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
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
HMDB IDHMDB0032630  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Cox CD, Parker J: Use of 2-aminoacetophenone production in identification of Pseudomonas aeruginosa. J Clin Microbiol. 1979 Apr;9(4):479-84. doi: 10.1128/jcm.9.4.479-484.1979. [PubMed:110829  ] 
  2. Frydman RB, Tomaro ML, Frydman B: Pyrrolooxygenases: The biosynthesis of 2-aminoacetophenone. FEBS Lett. 1971 Oct 1;17(2):273-276. doi: 10.1016/0014-5793(71)80163-1. [PubMed:11946045  ] 
  3. Scott-Thomas AJ, Syhre M, Pattemore PK, Epton M, Laing R, Pearson J, Chambers ST: 2-Aminoacetophenone as a potential breath biomarker for Pseudomonas aeruginosa in the cystic fibrosis lung. BMC Pulm Med. 2010 Nov 7;10:56. doi: 10.1186/1471-2466-10-56. [PubMed:21054900  ] 
  4. Kapsetaki SE, Tzelepis I, Avgousti K, Livadaras I, Garantonakis N, Varikou K, Apidianakis Y: The bacterial metabolite 2-aminoacetophenone promotes association of pathogenic bacteria with flies. Nat Commun. 2014 Jul 21;5:4401. doi: 10.1038/ncomms5401. [PubMed:25043228  ] 
  5. Horlacher N, Schwack W: Photooxidation of tryptophan leading to 2-aminoacetophenone--a possible reason for the untypical aging off-flavor in wine. Photochem Photobiol. 2014 Nov-Dec;90(6):1257-63. doi: 10.1111/php.12321. Epub  2014 Aug 18. [PubMed:25047450  ] 
  6. Zhao G, Sun W, Wang J: Purification and characterization of a novel NADPH-dependent 2-aminoacetophenone reductase from Arthrobacter sulfureus. J Biosci Bioeng. 2015 Jun;119(6):648-51. doi: 10.1016/j.jbiosc.2014.11.004. Epub  2014 Dec 6. [PubMed:25488497  ] 
  7. Kviatkovski I, Chernin L, Yarnitzky T, Frumin I, Sobel N, Helman Y: Pseudomonas aeruginosa activates the quorum sensing LuxR response regulator through secretion of 2-aminoacetophenone. Chem Commun (Camb). 2015 Feb 21;51(15):3258-61. doi: 10.1039/c4cc10393a. [PubMed:25614099  ] 
  8. Horlacher N, Schwack W: Determination of 2-Aminoacetophenone in wine by high-performance thin-layer chromatography-fluorescence detection. J Chromatogr A. 2016 Feb 5;1432:140-4. doi: 10.1016/j.chroma.2015.12.081. Epub  2015 Dec 31. [PubMed:26777086  ] 
  9. Gerlach C, Elsinghorst PW, Schmarr HG, Wust M: 2-Aminoacetophenone Is the Main Volatile Phase I Skatole Metabolite in Pietrain x Baden-Wurttemberg Hybrid Type Boars. J Agric Food Chem. 2016 Feb 10;64(5):1158-63. doi: 10.1021/acs.jafc.5b05729. Epub  2016 Jan 29. [PubMed:26804051  ] 
  10. Bandyopadhaya A, Constantinou C, Psychogios N, Ueki R, Yasuhara S, Martyn JA, Wilhelmy J, Mindrinos M, Rahme LG, Tzika AA: Bacterial-excreted small volatile molecule 2-aminoacetophenone induces oxidative stress and apoptosis in murine skeletal muscle. Int J Mol Med. 2016 Apr;37(4):867-78. doi: 10.3892/ijmm.2016.2487. Epub 2016 Feb  12. [PubMed:26935176  ] 
  11. Dollmann B, Wichmann D, Schmitt A, Koehler H, Schreier P: Quantitative analysis of 2-aminoacetophenone in off-flavored wines by stable isotope dilution assay. J AOAC Int. 1996 Mar-Apr;79(2):583-6. [PubMed:8920148  ] 
  12. LOTUS database [Link]