NP-MRD: Showing NP-Card for (2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one (NP0197070)

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Record Information

Version

2.0

Created at

2022-09-04 15:16:00 UTC

Updated at

2022-09-04 15:16:00 UTC

NP-MRD ID

NP0197070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

Description

Galluflavanone belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. (2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one is found in Semecarpus anacardium. (2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one was first documented in 2021 (PMID: 34655900). Based on a literature review very few articles have been published on Galluflavanone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217162D          

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M  END


  Mrv1652309042217162D          

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  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 21 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  2  0  0  0  0
 11 33  2  0  0  0  0
  5 33  1  0  0  0  0
  4 34  1  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  1  0  0  0  0
 37 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
  2 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C(=O)C[C@H](OC2=C1)C1=CC(O)=C(O)C(=C1)C1=C(O)C=CC2=C1O[C@@H](CC2=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O11/c31-14-1-2-15-19(33)10-24(40-26(15)9-14)12-5-17(28(38)21(35)6-12)27-18(32)4-3-16-20(34)11-25(41-30(16)27)13-7-22(36)29(39)23(37)8-13/h1-9,24-25,31-32,35-39H,10-11H2/t24-,25-/m0/s1

> <INCHI_KEY>
IDDFUPQGTOMEGV-DQEYMECFSA-N

> <FORMULA>
C30H22O11

> <MOLECULAR_WEIGHT>
558.495

> <EXACT_MASS>
558.116211528

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
52.625965876474346

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-8-{2,3-dihydroxy-5-[(2S)-7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
3.7406303249999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.867721506748542

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.260015929727124

> <JCHEM_PKA_STRONGEST_BASIC>
-6.010584526714557

> <JCHEM_POLAR_SURFACE_AREA>
194.20999999999998

> <JCHEM_REFRACTIVITY>
143.63869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-8-{2,3-dihydroxy-5-[(2S)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -13.337  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -14.670  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -14.670   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.336   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.003   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0     -14.670   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0     -16.004   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -17.338   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -17.338   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -18.672   1.540   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -18.672  -0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -20.005   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -21.339   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -20.005   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -21.339   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -18.672   4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -16.004   6.160   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -14.670   6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -14.670   8.470   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   41                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   31                                                  
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21                                                       
CONECT   30   20   31                                                       
CONECT   31   30   17   32                                                  
CONECT   32   31                                                            
CONECT   33   11    5                                                       
CONECT   34    4   35                                                       
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   35    2                                                  
MASTER        0    0    0    0    0    0    0    0   41    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₁

Average Mass

558.4950 Da

Monoisotopic Mass

558.11621 Da

IUPAC Name

(2S)-8-{2,3-dihydroxy-5-[(2S)-7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S)-8-{2,3-dihydroxy-5-[(2S)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C(=O)C[C@H](OC2=C1)C1=CC(O)=C(O)C(=C1)C1=C(O)C=CC2=C1O[C@@H](CC2=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C30H22O11/c31-14-1-2-15-19(33)10-24(40-26(15)9-14)12-5-17(28(38)21(35)6-12)27-18(32)4-3-16-20(34)11-25(41-30(16)27)13-7-22(36)29(39)23(37)8-13/h1-9,24-25,31-32,35-39H,10-11H2/t24-,25-/m0/s1

InChI Key

IDDFUPQGTOMEGV-DQEYMECFSA-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
Semecarpus anacardium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

Bi- and polyflavonoid skeleton
3'-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Biphenol
Chromone
Chromane
Benzopyran
1-benzopyran
Pyrogallol derivative
Benzenetriol
Aryl ketone
Aryl alkyl ketone
Catechol
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Ether
Organoheterocyclic compound
Polyol
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.74	ChemAxon
pKa (Strongest Acidic)	7.26	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	194.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	143.64 m³·mol⁻¹	ChemAxon
Polarizability	52.63 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006521

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101326873

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tahir Ul Qamar M, Ahmad S, Khan A, Mirza MU, Ahmad S, Abro A, Chen LL, Almatroudi A, Wei DQ: Structural probing of HapR to identify potent phytochemicals to control Vibrio cholera through integrated computational approaches. Comput Biol Med. 2021 Nov;138:104929. doi: 10.1016/j.compbiomed.2021.104929. Epub 2021 Oct 9. [PubMed:34655900 ]
LOTUS database [Link]

Showing NP-Card for (2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one (NP0197070)

MOL for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0197070 ((2s)-8-{2,3-dihydroxy-5-[(2s)-7-hydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl]phenyl}-7-hydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one)