NP-MRD: Showing NP-Card for 2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one (NP0053280)

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Record Information

Version

2.0

Created at

2022-04-27 23:59:35 UTC

Updated at

2022-04-27 23:59:35 UTC

NP-MRD ID

NP0053280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one

Description

Demethoxykanugin belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, demethoxykanugin is considered to be a flavonoid lipid molecule. 2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one is found in Millettia leucantha, Millettia pinnata, Rhus chinensis and Suregada multiflora. Demethoxykanugin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
    5.9921    2.3854    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764    2.4269    0.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8059    1.2872   -0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    0.0606   -0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512   -1.0460   -0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826   -0.8794   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3760   -1.9683   -0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8480   -3.1248   -0.5565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0134   -1.7848   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572   -2.9398   -0.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0457   -3.6438    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641   -0.5545   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9751   -0.2287   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9285   -1.1350   -0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2817   -0.7556   -0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6211    0.5188   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632    1.4411    0.2287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618    1.0677    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205    2.6239    0.5692 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5986    2.5364   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8777    1.1444   -0.0249 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2988    0.4568   -0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    0.3493   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364    1.4441   -0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3610    1.8517    0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3831    3.4216    0.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3860    1.9034   -0.8886 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4631   -0.0870   -0.2585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210   -2.0107   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2082   -2.8805    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2050   -4.2863    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9964   -4.1962    0.5594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7340   -2.1321   -0.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280   -1.4938   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688    1.7664    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3648    3.1280    0.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4997    2.9232   -1.0637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600    2.4102    0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 24  2  0
 24 23  1  0
 23  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
 12 22  1  0
 12 13  1  0
 13 18  2  0
 18 17  1  0
 17 16  2  0
 16 21  1  0
 21 20  1  0
 20 19  1  0
 16 15  1  0
 15 14  2  0
  4  3  1  0
 14 13  1  0
 22 23  1  0
 19 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 38  1  0
  5 29  1  0
  4 28  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 18 35  1  0
 20 36  1  0
 20 37  1  0
 15 34  1  0
 14 33  1  0
M  END


  Mrv0541 05061309522D          

 24 27  0  0  0  0            999 V2000
   10.4970    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   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
    9.0681    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15  7  1  0  0  0  0
 15 13  2  0  0  0  0
 16 12  1  0  0  0  0
 17 10  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21  2  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 22 13  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 14  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0053280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C(=O)C(OC)=C(O2)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O6/c1-20-11-4-5-12-14(8-11)24-17(18(21-2)16(12)19)10-3-6-13-15(7-10)23-9-22-13/h3-8H,9H2,1-2H3

> <INCHI_KEY>
UBKPBGYXBIXFFC-UHFFFAOYSA-N

> <FORMULA>
C18H14O6

> <MOLECULAR_WEIGHT>
326.3002

> <EXACT_MASS>
326.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.191651807849595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-3,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.2989503419999995

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3439675735941865

> <JCHEM_POLAR_SURFACE_AREA>
63.22000000000001

> <JCHEM_REFRACTIVITY>
85.9199

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demethoxykanugin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      19.594   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.927   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.593   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.593   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.221   5.153   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.927   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.926   1.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.926  -0.237   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      18.261   4.383   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.127   6.399   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.127   3.907   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.926   4.383   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    6   10                                                       
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6    3   13                                                       
CONECT    7   10   15                                                       
CONECT    8   11   14                                                       
CONECT    9   22   23                                                       
CONECT   10    3    7   17                                                  
CONECT   11    4    8   20                                                  
CONECT   12    5   14   16                                                  
CONECT   13    6   15   22                                                  
CONECT   14    8   12   24                                                  
CONECT   15    7   13   23                                                  
CONECT   16   12   18   19                                                  
CONECT   17   10   18   24                                                  
CONECT   18   16   17   21                                                  
CONECT   19   16                                                            
CONECT   20    1   11                                                       
CONECT   21    2   18                                                       
CONECT   22    9   13                                                       
CONECT   23    9   15                                                       
CONECT   24   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one	HMDB
3,7-Dimethoxy-3',4'-methylenedioxyflavone	HMDB
Desmethoxykanugin	HMDB

Chemical Formula

C₁₈H₁₄O₆

Average Mass

326.3002 Da

Monoisotopic Mass

326.07904 Da

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-3,7-dimethoxy-4H-chromen-4-one

Traditional Name

demethoxykanugin

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C(=O)C(OC)=C(O2)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C18H14O6/c1-20-11-4-5-12-14(8-11)24-17(18(21-2)16(12)19)10-3-6-13-15(7-10)23-9-22-13/h3-8H,9H2,1-2H3

InChI Key

UBKPBGYXBIXFFC-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
Millettia leucantha	Plant	KNApSAcK
Pongamia pinnata	Plant	KNApSAcK
Rhus chinensis	Plant	KNApSAcK
Suregada multiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

3-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Flavone
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Benzodioxole
Anisole
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Acetal
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111572 )

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	2.64	ALOGPS
logP	2.3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	63.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	85.92 m³·mol⁻¹	ChemAxon
Polarizability	33.19 Å³	ChemAxon
Number of Rings	4	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

HMDB0037570

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016658

KNApSAcK ID

C00005045

Chemspider ID

8557152

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10381709

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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Showing NP-Card for 2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one (NP0053280)

MOL for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D MOL for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D SDF for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D-SDF for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

PDB for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D PDB for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

SMILES for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

INCHI for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

Structure for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D Structure for NP0053280 (2-(1,3-Benzodioxol-5-yl)-3,7-dimethoxy-4H-1-benzopyran-4-one)