NP-MRD: Showing NP-Card for (2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one (NP0316369)

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Record Information

Version

2.0

Created at

2022-09-11 15:31:17 UTC

Updated at

2022-09-11 15:31:18 UTC

NP-MRD ID

NP0316369

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

Description

CHEMBL1926699 belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. Based on a literature review very few articles have been published on CHEMBL1926699.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112217312D          

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    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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   -0.4125    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
    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 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 22 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316369

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(\C=C\CC(O)CCC2=CC=CC=C2)C2=CC=C(O)C=C2)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H34O7/c1-42-32-22-31(40)33(35(41)34(32)30(39)21-13-24-11-17-27(37)18-12-24)29(25-14-19-28(38)20-15-25)9-5-8-26(36)16-10-23-6-3-2-4-7-23/h2-7,9,11-15,17-22,26,29,36-38,40-41H,8,10,16H2,1H3/b9-5+,21-13+

> <INCHI_KEY>
VIHJUBYCOAJPQW-OGGKTOENSA-N

> <FORMULA>
C35H34O7

> <MOLECULAR_WEIGHT>
566.65

> <EXACT_MASS>
566.230453435

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
63.283634447135626

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-1-{2,4-dihydroxy-3-[(2E)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_LOGP>
7.599781659

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.398668727020285

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.942598070277532

> <JCHEM_PKA_STRONGEST_BASIC>
-2.713204390005961

> <JCHEM_POLAR_SURFACE_AREA>
127.45

> <JCHEM_REFRACTIVITY>
166.0367

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-{2,4-dihydroxy-3-[(2E)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   29                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22    8   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22                                                       
CONECT   29    7   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    3   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   42                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₄O₇

Average Mass

566.6500 Da

Monoisotopic Mass

566.23045 Da

IUPAC Name

(2E)-1-{2,4-dihydroxy-3-[(2E)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1-{2,4-dihydroxy-3-[(2E)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(\C=C\CC(O)CCC2=CC=CC=C2)C2=CC=C(O)C=C2)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C35H34O7/c1-42-32-22-31(40)33(35(41)34(32)30(39)21-13-24-11-17-27(37)18-12-24)29(25-14-19-28(38)20-15-25)9-5-8-26(36)16-10-23-6-3-2-4-7-23/h2-7,9,11-15,17-22,26,29,36-38,40-41H,8,10,16H2,1H3/b9-5+,21-13+

InChI Key

VIHJUBYCOAJPQW-OGGKTOENSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Bis-desmethoxycurcumin
2'-hydroxychalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Diphenylmethane
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Methoxyphenol
Fatty alcohol
Anisole
Methoxybenzene
Aryl ketone
Phenol ether
Styrene
Phenoxy compound
Resorcinol
Benzoyl
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated ketone
Vinylogous acid
Enone
Acryloyl-group
Ketone
Secondary alcohol
Ether
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.6	ChemAxon
pKa (Strongest Acidic)	6.94	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	166.04 m³·mol⁻¹	ChemAxon
Polarizability	63.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28490661

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57390523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one (NP0316369)

MOL for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D MOL for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D SDF for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D-SDF for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

PDB for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D PDB for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

SMILES for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

INCHI for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

Structure for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)

3D Structure for NP0316369 ((2e)-1-{2,4-dihydroxy-3-[(2e)-5-hydroxy-1-(4-hydroxyphenyl)-7-phenylhept-2-en-1-yl]-6-methoxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one)