NP-MRD: Showing NP-Card for (2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate (NP0322100)

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Record Information

Version

2.0

Created at

2022-09-12 00:40:53 UTC

Updated at

2022-09-12 00:40:54 UTC

NP-MRD ID

NP0322100

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate

Description

(2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate is found in Vigna radiata.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202402D          

 44 48  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 40 43  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309122202402D          

 44 48  0  0  1  0            999 V2000
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   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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
   -2.1434   -1.2375    0.0000 O   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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  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
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  4  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 30 38  1  0  0  0  0
 16 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 13 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0322100

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(=O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](OC(=O)C=CC2=CC=C(O)C=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O14/c31-12-23-26(39)29(44-24(37)6-3-13-1-4-15(32)5-2-13)27(40)30(43-23)42-22-11-17-18(34)9-16(33)10-21(17)41-28(22)14-7-19(35)25(38)20(36)8-14/h1-11,23,26-27,29-33,35-36,38-40H,12H2/t23-,26-,27-,29+,30-/m1/s1

> <INCHI_KEY>
DJOVFIDNLBVHAM-XMIMKILASA-N

> <FORMULA>
C30H26O14

> <MOLECULAR_WEIGHT>
610.524

> <EXACT_MASS>
610.132255517

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
59.26045028434144

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)-5H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
1.14260414

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.169022219744246

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.397635604309851

> <JCHEM_PKA_STRONGEST_BASIC>
2.5444165566728465

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999995

> <JCHEM_REFRACTIVITY>
154.886

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.336  11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   43                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   39                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   20   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   18   30                                                  
CONECT   30   29   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   30                                                       
CONECT   39   16   40                                                       
CONECT   40   39   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   13   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₁₄

Average Mass

610.5240 Da

Monoisotopic Mass

610.13226 Da

IUPAC Name

(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)-5H-chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(=O)C3=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@@H](OC(=O)C=CC2=CC=C(O)C=C2)[C@@H]1O

InChI Identifier

InChI=1S/C30H26O14/c31-12-23-26(39)29(44-24(37)6-3-13-1-4-15(32)5-2-13)27(40)30(43-23)42-22-11-17-18(34)9-16(33)10-21(17)41-28(22)14-7-19(35)25(38)20(36)8-14/h1-11,23,26-27,29-33,35-36,38-40H,12H2/t23-,26-,27-,29+,30-/m1/s1

InChI Key

DJOVFIDNLBVHAM-XMIMKILASA-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

Species Name	Source	Reference
Vigna radiata	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	1.14	ChemAxon
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	2.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	232.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	154.89 m³·mol⁻¹	ChemAxon
Polarizability	59.26 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate (NP0322100)

MOL for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0322100 ((2s,3r,4s,5r,6r)-3,5-dihydroxy-2-{[7-hydroxy-5-oxo-2-(3,4,5-trihydroxyphenyl)chromen-3-yl]oxy}-6-(hydroxymethyl)oxan-4-yl 3-(4-hydroxyphenyl)prop-2-enoate)