NP-MRD: Showing NP-Card for 4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside (NP0060693)

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Record Information

Version

2.0

Created at

2022-04-28 05:41:56 UTC

Updated at

2022-04-28 05:41:56 UTC

NP-MRD ID

NP0060693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside

Description

CHEMBL463197 belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, CHEMBL463197 is considered to be a flavonoid. 4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside is found in Bidens andicola . Based on a literature review very few articles have been published on CHEMBL463197.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207412D          

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M  END

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M  END


  Mrv1652304282207412D          

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    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 14 17  1  0  0  0  0
  3 18  1  0  0  0  0
  2 19  1  0  0  0  0
  1 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
 24 39  1  6  0  0  0
 23 40  1  1  0  0  0
 22 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@H](OC2=C(O)C(O)=C(C=C2)C(=O)\C=C\C2=CC=C(O)C=C2)O[C@H](COC(=O)\C=C\C2=CC=CC=C2)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C32H30O12/c1-18(33)42-31-30(40)29(39)25(17-41-26(36)16-10-19-5-3-2-4-6-19)44-32(31)43-24-15-13-22(27(37)28(24)38)23(35)14-9-20-7-11-21(34)12-8-20/h2-16,25,29-32,34,37-40H,17H2,1H3/b14-9+,16-10+/t25-,29-,30+,31-,32-/m1/s1

> <INCHI_KEY>
SBEYXFRVWXXGPA-KHVJMIKNSA-N

> <FORMULA>
C32H30O12

> <MOLECULAR_WEIGHT>
606.58

> <EXACT_MASS>
606.173726406

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
61.09642142499882

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-{2,3-dihydroxy-4-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4-dihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.533012057333334

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.043534540101009

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3186716791813495

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649832467418861

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
155.66419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-{2,3-dihydroxy-4-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4-dihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667 -12.320   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.338  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      14.670   2.310   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14                                                            
CONECT   18    3                                                            
CONECT   19    2                                                            
CONECT   20    1   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   41                                                  
CONECT   23   22   24   40                                                  
CONECT   24   23   25   39                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39   24                                                            
CONECT   40   23                                                            
CONECT   41   22   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₃₀O₁₂

Average Mass

606.5800 Da

Monoisotopic Mass

606.17373 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-{2,3-dihydroxy-4-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4-dihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

Traditional Name

[(2R,3S,4S,5R,6S)-5-(acetyloxy)-6-{2,3-dihydroxy-4-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]phenoxy}-3,4-dihydroxyoxan-2-yl]methyl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@H](OC2=C(O)C(O)=C(C=C2)C(=O)\C=C\C2=CC=C(O)C=C2)O[C@H](COC(=O)\C=C\C2=CC=CC=C2)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C32H30O12/c1-18(33)42-31-30(40)29(39)25(17-41-26(36)16-10-19-5-3-2-4-6-19)44-32(31)43-24-15-13-22(27(37)28(24)38)23(35)14-9-20-7-11-21(34)12-8-20/h2-16,25,29-32,34,37-40H,17H2,1H3/b14-9+,16-10+/t25-,29-,30+,31-,32-/m1/s1

InChI Key

SBEYXFRVWXXGPA-KHVJMIKNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Bidens andicola	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxychalcone
Phenolic glycoside
Linear 1,3-diarylpropanoid
Cinnamylphenol
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Benzoyl
Catechol
Phenoxy compound
Phenol ether
Styrene
Aryl ketone
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Alpha,beta-unsaturated ketone
Enone
Vinylogous acid
Acryloyl-group
Secondary alcohol
Ketone
1,2-diol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	4.06	ALOGPS
logP	4.53	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	155.66 m³·mol⁻¹	ChemAxon
Polarizability	61.1 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

8754941

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10579559

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside (NP0060693)

MOL for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

3D MOL for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

3D SDF for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

3D-SDF for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

PDB for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

3D PDB for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

SMILES for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

INCHI for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

Structure for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)

3D Structure for NP0060693 (4,2',3',4'-Tetrahydroxychalcone 4'-O-(2''-O-acetyl-6''-O-cinnamoyl)glucoside)