NP-MRD: Showing NP-Card for 5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol (NP0252326)

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Record Information

Version

2.0

Created at

2022-09-07 15:47:52 UTC

Updated at

2022-09-07 15:47:52 UTC

NP-MRD ID

NP0252326

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol

Description

90989-33-6 Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol is found in Morus macroura. Based on a literature review very few articles have been published on 90989-33-6.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217472D          

 43 48  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072217472D          

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    4.7812    3.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 11 19  2  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 34 43  1  0  0  0  0
  2 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@H]([C@@H]([C@H](C1)C1=CC=C(O)C=C1O)C(=O)C1=CC=C(O)C=C1O)C1=C(O)C=C2OC(=CC2=C1O)C1=CC=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H28O9/c1-16-9-23(21-7-5-19(36)12-26(21)38)31(33(41)22-8-6-20(37)13-27(22)39)25(10-16)32-28(40)15-30-24(34(32)42)14-29(43-30)17-3-2-4-18(35)11-17/h2-8,10-15,23,25,31,35-40,42H,9H2,1H3/t23-,25-,31-/m1/s1

> <INCHI_KEY>
OPMAIQOGIRTPOM-DGYRLYMOSA-N

> <FORMULA>
C34H28O9

> <MOLECULAR_WEIGHT>
580.589

> <EXACT_MASS>
580.173332482

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
61.0080382868687

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(1R,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol

> <JCHEM_LOGP>
6.618873940000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.093070069945748

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.539970864343151

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9107581036725145

> <JCHEM_POLAR_SURFACE_AREA>
171.82

> <JCHEM_REFRACTIVITY>
160.06989999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1R,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.400   5.510   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.726   6.854   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.427   8.864   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.222   8.834   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.222  10.374   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.258  11.313   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.258  12.853   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.924  10.543   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.590   8.233   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.925  11.313   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.925  12.853   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   43                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12                                                       
CONECT   19   11   20                                                       
CONECT   20   19    9   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21                                                            
CONECT   23    4   24   34                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   26   33                                                  
CONECT   33   32                                                            
CONECT   34   23   35   43                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35   42                                                  
CONECT   42   41                                                            
CONECT   43   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₂₈O₉

Average Mass

580.5890 Da

Monoisotopic Mass

580.17333 Da

IUPAC Name

5-[(1R,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol

Traditional Name

5-[(1R,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol

CAS Registry Number

Not Available

SMILES

CC1=C[C@H]([C@@H]([C@H](C1)C1=CC=C(O)C=C1O)C(=O)C1=CC=C(O)C=C1O)C1=C(O)C=C2OC(=CC2=C1O)C1=CC=CC(O)=C1

InChI Identifier

InChI=1S/C34H28O9/c1-16-9-23(21-7-5-19(36)12-26(21)38)31(33(41)22-8-6-20(37)13-27(22)39)25(10-16)32-28(40)15-30-24(34(32)42)14-29(43-30)17-3-2-4-18(35)11-17/h2-8,10-15,23,25,31,35-40,42H,9H2,1H3/t23-,25-,31-/m1/s1

InChI Key

OPMAIQOGIRTPOM-DGYRLYMOSA-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
Morus laevigata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Linear 1,7-diphenylheptane skeleton
2-phenylbenzofuran
Phenylbenzofuran
Alkyl-phenylketone
Phenylketone
Benzofuran
Benzoyl
Aryl alkyl ketone
Aryl ketone
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Furan
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	6.62	ChemAxon
pKa (Strongest Acidic)	7.54	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	171.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	160.07 m³·mol⁻¹	ChemAxon
Polarizability	61.01 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

C00008102

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

101366716

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol (NP0252326)

MOL for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

3D MOL for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

3D SDF for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

3D-SDF for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

PDB for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

3D PDB for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

SMILES for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

INCHI for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

Structure for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)

3D Structure for NP0252326 (5-[(1r,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2-(3-hydroxyphenyl)-1-benzofuran-4,6-diol)