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Showing NP-Card for 4'-Methylacetophenone (NP0001343)

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Record Information
Version2.0
Created at2012-09-11 17:50:45 UTC
Updated at2024-09-03 04:22:24 UTC
NP-MRD IDNP0001343
Natural Product DOIhttps://doi.org/10.57994/2848
Secondary Accession NumbersNone
Natural Product Identification
Common Name4'-Methylacetophenone
Description4'-Methylacetophenone, also known as melilot or sweet clover, 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. 4'-Methylacetophenone is a sweet, acetophenone, and bitter almond tasting compound. 4'-Methylacetophenone has been detected, but not quantified, in several different foods, such as citrus, garden tomato, pepper (spice), garden tomato (var.), And milk and milk products. This could make 4'-methylacetophenone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0001343 (4'-Methylacetophenone)


  Mrv1652303202019002D          

 10 10  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    0.0000    0.8250    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
    0.7145    2.0625    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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
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3D MOL for NP0001343 (4'-Methylacetophenone)

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3D SDF for NP0001343 (4'-Methylacetophenone)

  Mrv1652303202019002D          

 10 10  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    0.0000    0.8250    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
    0.7145    2.0625    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
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001343

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3

> <INCHI_KEY>
GNKZMNRKLCTJAY-UHFFFAOYSA-N

> <FORMULA>
C9H10O

> <MOLECULAR_WEIGHT>
134.1751

> <EXACT_MASS>
134.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.245736080257778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(4-methylphenyl)ethan-1-one

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
2.0443147240000004

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.24068782709233

> <JCHEM_PKA_STRONGEST_BASIC>
-7.379150115231225

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
41.502

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-methylacetophenone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0001343 (4'-Methylacetophenone)
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PDB for NP0001343 (4'-Methylacetophenone)
HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7    1    3    4                                                  
CONECT    8    2    9   10                                                  
CONECT    9    5    6    8                                                  
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0001343 (4'-Methylacetophenone)
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SMILES for NP0001343 (4'-Methylacetophenone)
CC(=O)C1=CC=C(C)C=C1
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INCHI for NP0001343 (4'-Methylacetophenone)
InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3
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View in JSmol
Synonyms
ValueSource
1-p-TolylethanoneHMDB
(4-Methylphenyl) methyl ketoneHMDB
(4-Methylphenyl)ethanoneHMDB
1-(4-Methylphenyl)-ethanoneHMDB
1-(4-Methylphenyl)ethanoneHMDB
1-(4-Methylphenyl)ethanone, 9ciHMDB
1-Acetyl-4-methylbenzeneHMDB
1-Methyl-4-acetylbenzeneHMDB
4'-Methyl-acetophenoneHMDB
4-AcetyltolueneHMDB
4-MethylacetophenoneHMDB
4-Methylphenyl methyl ketoneHMDB
EsberivenHMDB
FEMA 2677HMDB
MelilotHMDB
MelilotalHMDB
Methyl p-tolyl ketoneHMDB
Nchem.328-comp4aHMDB
p-AcetotolueneHMDB
p-AcetyltolueneHMDB
p-Methyl acetophenoneHMDB
p-MethylacetophenoneHMDB
p-Tolyl methyl ketoneHMDB
Para-methyl-acetophenoneHMDB
Sweet cloverHMDB
Yellow melilotHMDB
Yellow sweet cloverHMDB
Chemical FormulaC9H10O
Average Mass134.1751 Da
Monoisotopic Mass134.07316 Da
IUPAC Name1-(4-methylphenyl)ethan-1-one
Traditional NameP-methylacetophenone
CAS Registry Number122-00-9
SMILES
CC(=O)C1=CC=C(C)C=C1
InChI Identifier
InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3
InChI KeyGNKZMNRKLCTJAY-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 800, CD3OD, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-06-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Apium graveolens var. dulceFooDB
    • Alexander J. MacLeod, Glesni MacLeod, G. Subramanian. Volatile aroma constituents of celery. Phyt...
Aspalathus linearis
Baccharis dracunculifolia
Cannabis sativaCannabisDB
      Not Available
Capsicum annuum var. annuumFooDB
Cichorium endivia
Citrus aurantium
Citrus limonPlant
Citrus medica
Evernia prunastri
Mangifera indica
Myrocarpus fastigiatus
Petroselinum crispumFooDB
Piper nigrum L.FooDB
Prunus dulcis
Sarcodontia uda
Senecio vulgarisPlant
Solanum lycopersicumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Solanum tuberosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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
    • 

  • Aryl alkyl ketone
    • 

  • Benzoyl
    • 

  • Toluene
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.37 mg/mL at 15 °CNot Available
LogP2.10Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP2.11ALOGPS
logP2.04ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)16.24ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.5 m³·mol⁻¹ChemAxon
Polarizability15.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0032608  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010549  
KNApSAcK IDNot Available
Chemspider ID8186  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8500  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .