NP-MRD: Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one (NP0059762)

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Record Information

Version

2.0

Created at

2022-04-28 04:57:36 UTC

Updated at

2022-04-28 04:57:36 UTC

NP-MRD ID

NP0059762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one

Description

2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-chromen-4-one belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one is found in Dalbergia odorifera . 2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    4.8562    1.6620   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8052    0.3101   -0.0167 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6210   -0.4089    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871    0.1876    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -0.5219    0.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0521    0.0210    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1167   -0.5909    0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458    0.1507    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6230   -0.3161    0.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616    0.4550   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6183    1.7744   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7437    2.5702   -0.5333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3732    2.3043   -0.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2672    3.6578   -0.8089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2681    1.5134   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812   -1.9078    0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1975   -2.6750    0.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1557   -2.5576    0.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2239   -3.7735    0.9965 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3245   -1.8568    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -2.4782    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7284   -1.7510    0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547   -2.3376    0.6295 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044    2.0117   -0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852    1.8724   -1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    2.2496    0.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573    1.2356   -0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806   -1.3323    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7542    0.0218    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6859    3.5318   -0.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314    4.0272   -0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2780    1.9228   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1131   -3.6429    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6244   -3.5283    0.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7906   -1.8006    0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 20 18  1  0
 18 19  2  0
 18 16  1  0
 16 17  1  0
 16  7  2  0
  7  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 22  3  1  0
 15  8  1  0
  6  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
 21 34  1  0
 23 35  1  0
 17 33  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
M  END

  Mrv1533004241511322D          

 23 25  0  0  0  0            999 V2000
   -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 O   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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
    0.0000   -1.6500    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
  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
 10 12  1  0  0  0  0
  5 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 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
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 16 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0059762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1O)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-22-13-6-12-8(5-11(13)19)14(20)15(21)16(23-12)7-2-3-9(17)10(18)4-7/h2-6,17-19,21H,1H3

> <INCHI_KEY>
DZMMKNCBWCZLDC-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.67064460642756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.65219352

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.413488937217197

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.323637478897295

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8906111971995356

> <JCHEM_POLAR_SURFACE_AREA>
116.45

> <JCHEM_REFRACTIVITY>
81.34450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-7-methoxychromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   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       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003   2.310   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  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
CONECT   16    7   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2650 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-3,6-dihydroxy-7-methoxychromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1O)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C16H12O7/c1-22-13-6-12-8(5-11(13)19)14(20)15(21)16(23-12)7-2-3-9(17)10(18)4-7/h2-6,17-19,21H,1H3

InChI Key

DZMMKNCBWCZLDC-UHFFFAOYSA-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
Dalbergia odorifera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
3-hydroxyflavone
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
6-hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Catechol
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111595 )

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	2	ALOGPS
logP	1.65	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.32	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.34 m³·mol⁻¹	ChemAxon
Polarizability	30.67 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one (NP0059762)

MOL for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D MOL for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D SDF for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D-SDF for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

PDB for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D PDB for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

SMILES for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

INCHI for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

Structure for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)

3D Structure for NP0059762 (2-(3,4-Dihydroxyphenyl)-3,6-dihydroxy-7-methoxy-4H-1-benzopyran-4-one)