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Showing NP-Card for 4-phenyl-but-3-en-2-one (NP0145941)

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Record Information
Version2.0
Created at2022-09-02 01:14:43 UTC
Updated at2022-09-02 01:14:43 UTC
NP-MRD IDNP0145941
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-phenyl-but-3-en-2-one
Description4-Phenylbut-3-en-2-one, also known as BENZ or methyl styryl ketone, belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. 4-phenyl-but-3-en-2-one is found in Basella alba and Polygala senega. 4-phenyl-but-3-en-2-one was first documented in 1985 (PMID: 3918942). 4-Phenylbut-3-en-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 15476972) (PMID: 18330113) (PMID: 21112333) (PMID: 25441446).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0145941 (4-phenyl-but-3-en-2-one)


  Mrv1652308231921272D          

 11 11  0  0  0  0            999 V2000
   -0.7145    3.7125    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
    0.0000    0.8250    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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    3.7125    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  4  2  0  0  0  0
  8  7  2  0  0  0  0
  9  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
  8 10  1  4  0  0  0
 11  9  2  0  0  0  0
M  END
Download

3D MOL for NP0145941 (4-phenyl-but-3-en-2-one)

     RDKit          3D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -4.0524    0.0206    0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8669   -0.6264   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0199   -1.6650   -0.7021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5107   -0.0874    0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793   -0.6865   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8820   -0.2028   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418    0.9201    0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5732    1.3462    0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851    0.6453   -0.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.4791   -0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219   -0.8938   -0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    1.1256    0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646   -0.2675    1.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9453   -0.2743    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    0.8081    0.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6570   -1.5758   -0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4551    1.4874    0.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7936    2.2421    1.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6061    0.9899    0.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037   -1.0409   -1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6415   -1.7859   -1.4401 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
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
M  END
Download

3D SDF for NP0145941 (4-phenyl-but-3-en-2-one)


  Mrv1652308231921272D          

 11 11  0  0  0  0            999 V2000
   -0.7145    3.7125    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
    0.0000    0.8250    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    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    3.7125    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  4  2  0  0  0  0
  8  7  2  0  0  0  0
  9  1  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
  8 10  1  4  0  0  0
 11  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0145941

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3

> <INCHI_KEY>
BWHOZHOGCMHOBV-UHFFFAOYSA-N

> <FORMULA>
C10H10O

> <MOLECULAR_WEIGHT>
146.189

> <EXACT_MASS>
146.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.585602757129326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-phenylbut-3-en-2-one

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.4657117826666664

> <ALOGPS_LOGS>
-2.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.68292834586809

> <JCHEM_PKA_STRONGEST_BASIC>
-4.800398655053069

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
46.61100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-phenyl-but-3-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0145941 (4-phenyl-but-3-en-2-one)

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PDB for NP0145941 (4-phenyl-but-3-en-2-one)
HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   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       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    8    9                                                       
CONECT    8    7   10                                                       
CONECT    9    1    7   11                                                  
CONECT   10    5    6    8                                                  
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0145941 (4-phenyl-but-3-en-2-one)
Download
SMILES for NP0145941 (4-phenyl-but-3-en-2-one)
CC(=O)C=CC1=CC=CC=C1
Download
INCHI for NP0145941 (4-phenyl-but-3-en-2-one)
InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3
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View in JSmol
Synonyms
ValueSource
2-Phenylvinyl methyl ketoneChEBI
4-Phenyl-3-buten-2-oneChEBI
AcetocinnamoneChEBI
BENZChEBI
BenzalacetonChEBI
BenzalacetoneChEBI
Benzilidene acetoneChEBI
BenzilideneacetoneChEBI
Benzylidene acetoneChEBI
Methyl 2-phenylvinyl ketoneChEBI
Methyl beta-styryl ketoneChEBI
Methyl styryl ketoneChEBI
Styryl methyl ketoneChEBI
Methyl b-styryl ketoneGenerator
Methyl β-styryl ketoneGenerator
Chemical FormulaC10H10O
Average Mass146.1890 Da
Monoisotopic Mass146.07316 Da
IUPAC Name4-phenylbut-3-en-2-one
Traditional Name4-phenyl-but-3-en-2-one
CAS Registry NumberNot Available
SMILES
CC(=O)C=CC1=CC=CC=C1
InChI Identifier
InChI=1S/C10H10O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8H,1H3
InChI KeyBWHOZHOGCMHOBV-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
Basella albaLOTUS Database
Polygala senegaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassStyrenes  
Direct ParentStyrenes  
Alternative Parents
Substituents
  • Styrene
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Enone
    • 

  • Acryloyl-group
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP2.23ALOGPS
logP2.47ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)19.68ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.61 m³·mol⁻¹ChemAxon
Polarizability16.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0141081  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB093249  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzylideneacetone  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID217301  
Good Scents IDNot Available
References
General References
  1. Ji D, Yi Y, Kang GH, Choi YH, Kim P, Baek NI, Kim Y: Identification of an antibacterial compound, benzylideneacetone, from Xenorhabdus nematophila against major plant-pathogenic bacteria. FEMS Microbiol Lett. 2004 Oct 15;239(2):241-8. doi: 10.1016/j.femsle.2004.08.041. [PubMed:15476972  ] 
  2. Kwon B, Kim Y: Benzylideneacetone, an immunosuppressant, enhances virulence of Bacillus thuringiensis against beet armyworm (Lepidoptera: Noctuidae). J Econ Entomol. 2008 Feb;101(1):36-41. doi:  10.1603/0022-0493(2008)101[36:baievo]2.0.co;2. [PubMed:18330113  ] 
  3. Kim J, Kim Y: Benzylideneacetone, an eicosanoid biosynthesis inhibitor enhances baculovirus pathogenicity in the diamondback moth, Plutella xylostella. J Invertebr Pathol. 2011 Feb;106(2):308-13. doi: 10.1016/j.jip.2010.11.006. Epub  2010 Nov 26. [PubMed:21112333  ] 
  4. Liu X, Jia YL, Chen JW, Liang G, Guo HY, Hu YH, Shi Y, Zhou HT, Chen QX: Inhibition effects of benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol on the activity of mushroom tyrosinase. J Biosci Bioeng. 2015 Mar;119(3):275-9. doi: 10.1016/j.jbiosc.2014.08.014. Epub  2014 Nov 14. [PubMed:25441446  ] 
  5. Polak L: Antigenic competition in the induction of contact sensitivity in the guinea pig. Int Arch Allergy Appl Immunol. 1985;76(3):275-81. doi: 10.1159/000233705. [PubMed:3918942  ] 
  6. LOTUS database [Link]