NP-MRD: Showing NP-Card for 5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0290217)

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Record Information

Version

2.0

Created at

2022-09-09 20:47:54 UTC

Updated at

2022-09-09 20:47:54 UTC

NP-MRD ID

NP0290217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

Description

5-Hydroxy-7,8-dimethoxyflavanone belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, 5-hydroxy-7,8-dimethoxyflavanone is considered to be a flavonoid lipid molecule. 5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one is found in Andrographis affinis, Andrographis lineata, Andrographis paniculata, Isodon oresbius, Miliusa balansae and Uvaria scheffleri. 5-Hydroxy-7,8-dimethoxyflavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    4.9950    1.3089   -0.9829 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8242    1.4722   -0.2079 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8187    0.5237   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478   -0.5380   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -1.4915   -1.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0713   -2.5464   -2.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8108   -1.2909   -0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815   -0.2114    0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    0.7185    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    1.7957    1.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9829    1.7754    2.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513   -0.0303    1.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6024   -0.8669    1.0046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7336   -0.1393    0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -0.6148   -0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888    0.1231   -1.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8551    1.3907   -0.6828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0471    1.8986    0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0138    1.1573    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3263   -2.2023    0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3144   -2.1919   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513   -2.9740   -1.5942 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5398    0.4400   -0.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7605    1.1754   -2.0567 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5726    2.2550   -0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8445   -0.6767   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5389   -3.2990   -2.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0316    0.6908    2.9293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069    2.1640    2.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340    2.2326    3.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978   -1.0056    2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3961   -1.5912   -1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2033   -0.2945   -1.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6696    1.9765   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2639    2.9066    0.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3791    1.5657    1.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2265   -2.6996    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8980   -2.9065    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9 10  1  0
 10 11  1  0
  9  8  1  0
  8  7  2  0
  7 21  1  0
 21 22  2  0
 21 20  1  0
 20 13  1  0
 13 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 12  8  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 20 37  1  0
 20 38  1  0
 13 31  1  1
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
  6 27  1  0
  4 26  1  0
M  END

  Mrv1533004241518432D          

 22 24  0  0  0  0            999 V2000
   -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 O   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 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
    0.7145   -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
    1.4289    0.8250    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    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 C   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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 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  2  0  0  0  0
 12 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
  3 19  1  0  0  0  0
 18 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C2=C(C(=O)CC(O2)C2=CC=CC=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-20-14-9-12(19)15-11(18)8-13(10-6-4-3-5-7-10)22-17(15)16(14)21-2/h3-7,9,13,19H,8H2,1-2H3

> <INCHI_KEY>
VPGMCCIECGDASG-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.31

> <EXACT_MASS>
300.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.115161339295334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7,8-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
3.126896162333333

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.772517805768228

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.190388661809436

> <JCHEM_PKA_STRONGEST_BASIC>
-4.488025677541112

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
80.25440000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-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      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    6   19   20                                                  
CONECT   19   18    3                                                       
CONECT   20   18                                                            
CONECT   21    4   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₅

Average Mass

300.3100 Da

Monoisotopic Mass

300.09977 Da

IUPAC Name

5-hydroxy-7,8-dimethoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C2=C(C(=O)CC(O2)C2=CC=CC=C2)C(O)=C1

InChI Identifier

InChI=1S/C17H16O5/c1-20-14-9-12(19)15-11(18)8-13(10-6-4-3-5-7-10)22-17(15)16(14)21-2/h3-7,9,13,19H,8H2,1-2H3

InChI Key

VPGMCCIECGDASG-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
Andrographis affinis	LOTUS Database	35616633
Andrographis lineata	LOTUS Database	35616633
Andrographis paniculata	LOTUS Database	35616633
Isodon oresbius	LOTUS Database	35616633
Miliusa balansae	LOTUS Database	35616633
Uvaria scheffleri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140659 )

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	ALOGPS
logP	3.13	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.25 m³·mol⁻¹	ChemAxon
Polarizability	31.12 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

13963770

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one (NP0290217)

MOL for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D MOL for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D SDF for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D-SDF for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

PDB for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D PDB for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

SMILES for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

INCHI for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

Structure for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)

3D Structure for NP0290217 (5-hydroxy-7,8-dimethoxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one)