NP-MRD: Showing NP-Card for 5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione (NP0303713)

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Record Information

Version

2.0

Created at

2022-09-10 18:18:13 UTC

Updated at

2022-09-10 18:18:13 UTC

NP-MRD ID

NP0303713

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione

Description

5,10-Dihydroxy-1,7-dimethoxy-3-methyl-1H,6H,9H-cyclohexa[g]isochromene-6,9-dione belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. 5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione is found in Fusarium solani. 5,10-Dihydroxy-1,7-dimethoxy-3-methyl-1H,6H,9H-cyclohexa[g]isochromene-6,9-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    5.8951    0.3475   -0.6140 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511   -0.7930   -0.3335 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7882   -0.8762   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8210   -2.2871    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3746   -3.4518    0.3496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9033   -1.1836    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4510   -1.3821    0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -2.5790    0.4114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127   -0.2627    0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926    0.9785   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5929    1.1663   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9969    2.4487   -0.4833 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4529    0.0917   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8857    0.2766   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706    1.4063   -0.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807    2.1409   -0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    2.0263    0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602    3.2473   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4884    0.7751    0.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7682   -0.4492    0.1698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1481   -1.2848    1.2007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9799   -2.2651    0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9743    0.0546   -0.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8224    1.1351    0.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6717    0.8281   -1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8844   -2.9562    0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7525   -3.4915    0.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8316    2.9096   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2566    3.1383   -0.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416    3.5805   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8071    2.9900    0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3977    4.0754    0.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -0.8562   -0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2651   -2.9634    1.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5930   -2.7433   -0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9242   -1.7249    0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 17  2  0
 17 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14  7  2  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  3 15  1  0
 15 16  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 21  1  0
 10 11  1  0
 15 14  1  0
 23 35  1  0
 23 36  1  0
 23 37  1  0
 21 34  1  6
 19 31  1  0
 19 32  1  0
 19 33  1  0
 17 30  1  0
 13 29  1  0
  4 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  9 28  1  0
M  END


  Mrv1533004191514012D          

 23 25  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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 C   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    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
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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
    6.4302   -0.4125    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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
 15 17  1  0  0  0  0
 10 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  3 20  1  0  0  0  0
  7 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303713

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1OC(C)=CC2=C(O)C3=C(C(=O)C=C(OC)C3=O)C(O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O7/c1-6-4-7-10(16(22-3)23-6)15(20)11-8(17)5-9(21-2)14(19)12(11)13(7)18/h4-5,16,18,20H,1-3H3

> <INCHI_KEY>
OKIWKPRHWNPATK-UHFFFAOYSA-N

> <FORMULA>
C16H14O7

> <MOLECULAR_WEIGHT>
318.281

> <EXACT_MASS>
318.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
31.093415223131586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,10-dihydroxy-1,7-dimethoxy-3-methyl-1H,6H,9H-cyclohexa[g]isochromene-6,9-dione

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
2.142943241666666

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.522549610902477

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.750788307841586

> <JCHEM_PKA_STRONGEST_BASIC>
-4.154773229367505

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
83.43360000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,10-dihydroxy-1,7-dimethoxy-3-methyl-1H-cyclohexa[g]isochromene-6,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   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       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    3    7                                                  
CONECT   21   13   22                                                       
CONECT   22   21                                                            
CONECT   23    5                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₇

Average Mass

318.2810 Da

Monoisotopic Mass

318.07395 Da

IUPAC Name

5,10-dihydroxy-1,7-dimethoxy-3-methyl-1H,6H,9H-cyclohexa[g]isochromene-6,9-dione

Traditional Name

5,10-dihydroxy-1,7-dimethoxy-3-methyl-1H-cyclohexa[g]isochromene-6,9-dione

CAS Registry Number

Not Available

SMILES

COC1OC(C)=CC2=C(O)C3=C(C(=O)C=C(OC)C3=O)C(O)=C12

InChI Identifier

InChI=1S/C16H14O7/c1-6-4-7-10(16(22-3)23-6)15(20)11-8(17)5-9(21-2)14(19)12(11)13(7)18/h4-5,16,18,20H,1-3H3

InChI Key

OKIWKPRHWNPATK-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, 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
Fusarium solani	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Not Available

Direct Parent

Isochromanequinones

Alternative Parents

Substituents

Isochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Isochromene
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Aryl ketone
Quinone
Pyranone
Benzenoid
Pyran
Vinylogous acid
Vinylogous ester
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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	2.03	ALOGPS
logP	2.14	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.43 m³·mol⁻¹	ChemAxon
Polarizability	31.09 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

14213580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione (NP0303713)

MOL for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

3D MOL for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

3D SDF for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

3D-SDF for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

PDB for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

3D PDB for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

SMILES for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

INCHI for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

Structure for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)

3D Structure for NP0303713 (5,10-dihydroxy-1,7-dimethoxy-3-methyl-1h-cyclohexa[g]isochromene-6,9-dione)