NP-MRD: Showing NP-Card for 6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione (NP0243878)

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Record Information

Version

2.0

Created at

2022-09-07 04:31:38 UTC

Updated at

2022-09-07 04:31:38 UTC

NP-MRD ID

NP0243878

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione

Description

SCHEMBL846752 belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione is found in Trichophyton violaceum. SCHEMBL846752 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521222D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161521222D          

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    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -3.4914    0.0000 O   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  2  0  0  0  0
  5  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
  4 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
 28 40  1  0  0  0  0
 40 41  1  0  0  0  0
 22 41  1  0  0  0  0
 41 42  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0243878

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C(=O)C2=C(O)C=C3CC(C)OC(=O)C3=C2C1=O)C1=C(OC)C(=O)C2=C3C(=O)OC(C)CC3=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H22O12/c1-9-5-11-7-13(31)17-19(15(11)29(37)41-9)25(35)27(39-3)21(23(17)33)22-24(34)18-14(32)8-12-6-10(2)42-30(38)16(12)20(18)26(36)28(22)40-4/h7-10,31-32H,5-6H2,1-4H3

> <INCHI_KEY>
AVJBJCCXUSFJHP-UHFFFAOYSA-N

> <FORMULA>
C30H22O12

> <MOLECULAR_WEIGHT>
574.494

> <EXACT_MASS>
574.111126148

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
56.97516323869348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-1H,3H,4H,7H,10H-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-1H,3H,4H,7H,10H-naphtho[1,2-c]pyran-1,7,10-trione

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.8279634099999997

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.115598724094008

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5135085229524465

> <JCHEM_PKA_STRONGEST_BASIC>
-4.664055707809852

> <JCHEM_POLAR_SURFACE_AREA>
179.79999999999998

> <JCHEM_REFRACTIVITY>
146.98279999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3H,4H-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3H,4H-naphtho[1,2-c]pyran-1,7,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -2.516   0.151   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.746  -1.183   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.516  -2.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -5.184   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.746  -6.517   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.056  -5.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.826  -6.517   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.056  -7.851   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.366  -6.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.136  -5.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.676  -5.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.446  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -10.986  -3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.676  -2.516   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -7.136  -2.516   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.366  -1.183   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.366  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.826  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.056  -2.516   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.826  -1.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.206  -1.183   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564   0.151   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.874  -1.183   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.414  -1.183   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.724  -2.516   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.104  -7.851   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -0.206  -6.517   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18    7   20                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22    4   23   41                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   40                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   29   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   28   41                                                  
CONECT   41   40   22   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₂O₁₂

Average Mass

574.4940 Da

Monoisotopic Mass

574.11113 Da

IUPAC Name

6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-1H,3H,4H,7H,10H-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-1H,3H,4H,7H,10H-naphtho[1,2-c]pyran-1,7,10-trione

Traditional Name

6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3H,4H-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3H,4H-naphtho[1,2-c]pyran-1,7,10-trione

CAS Registry Number

Not Available

SMILES

COC1=C(C(=O)C2=C(O)C=C3CC(C)OC(=O)C3=C2C1=O)C1=C(OC)C(=O)C2=C3C(=O)OC(C)CC3=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C30H22O12/c1-9-5-11-7-13(31)17-19(15(11)29(37)41-9)25(35)27(39-3)21(23(17)33)22-24(34)18-14(32)8-12-6-10(2)42-30(38)16(12)20(18)26(36)28(22)40-4/h7-10,31-32H,5-6H2,1-4H3

InChI Key

AVJBJCCXUSFJHP-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
Trichophyton violaceum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthoquinone
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Benzenoid
Pyran
Vinylogous ester
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	3.17	ALOGPS
logP	2.83	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	6.51	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	179.8 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.98 m³·mol⁻¹	ChemAxon
Polarizability	56.98 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

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

12444969

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione (NP0243878)

MOL for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

3D MOL for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

3D SDF for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

3D-SDF for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

PDB for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

3D PDB for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

SMILES for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

INCHI for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

Structure for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)

3D Structure for NP0243878 (6-hydroxy-8-{6-hydroxy-9-methoxy-3-methyl-1,7,10-trioxo-3h,4h-naphtho[1,2-c]pyran-8-yl}-9-methoxy-3-methyl-3h,4h-naphtho[1,2-c]pyran-1,7,10-trione)