NP-MRD: Showing NP-Card for 2-Hydroxy-4,5,6-trimethoxydihydrochalcone (NP0060779)

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Record Information

Version

2.0

Created at

2022-04-28 05:46:10 UTC

Updated at

2022-04-28 05:46:10 UTC

NP-MRD ID

NP0060779

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxy-4,5,6-trimethoxydihydrochalcone

Description

2-Hydroxy-4,5,6-trimethoxydihydrochalcone belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, 2-hydroxy-4,5,6-trimethoxydihydrochalcone is considered to be a flavonoid lipid molecule. 2-Hydroxy-4,5,6-trimethoxydihydrochalcone is found in Uvaria mocali and Uvaria mocoli . 2-Hydroxy-4,5,6-trimethoxydihydrochalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -4.7524   -1.3195   -2.4769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901   -0.2086   -1.6845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2134   -0.2660   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4197   -1.3837   -1.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2362   -1.4750   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480   -2.6142   -0.4186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -0.3916    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957   -0.4959    1.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5181   -0.2901    0.1726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8133   -0.3832    0.8625 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8684   -0.6043    2.1137 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0614   -0.2223    0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2841   -0.3058    0.7456 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4296   -0.1488    0.0045 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3754    0.0903   -1.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1563    0.1785   -2.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0212    0.0162   -1.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335    0.7548    0.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835    1.8467    1.3206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    2.0265    2.6576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    0.8131   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6545    1.9179   -0.1398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6885    2.0050    0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7214   -1.1728   -2.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9513   -1.4395   -3.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7508   -2.2222   -1.8282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7150   -2.2184   -1.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7446   -3.3706   -0.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697    0.2270    2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -1.5161    1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839    0.7231   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -1.0071   -0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2820   -0.4950    1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3760   -0.2237    0.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3254    0.2008   -1.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1254    0.3665   -3.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    0.0863   -1.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422    2.7984    2.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7278    2.4166    3.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9575    1.1241    3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5638    1.2127    1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6851    1.9714    0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5473    2.9985    1.3382 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  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  7 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
M  END

  Mrv1533004191520542D          

 23 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
    2.8579   -1.6500    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   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
  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
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(CCC(=O)C2=CC=CC=C2)C(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O5/c1-21-16-11-15(20)13(17(22-2)18(16)23-3)9-10-14(19)12-7-5-4-6-8-12/h4-8,11,20H,9-10H2,1-3H3

> <INCHI_KEY>
XXHGGLKQZUXJDI-UHFFFAOYSA-N

> <FORMULA>
C18H20O5

> <MOLECULAR_WEIGHT>
316.353

> <EXACT_MASS>
316.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.741254422711606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(6-hydroxy-2,3,4-trimethoxyphenyl)-1-phenylpropan-1-one

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
3.0332227006666668

> <ALOGPS_LOGS>
-4.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.69566905995921

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.77505780020808

> <JCHEM_PKA_STRONGEST_BASIC>
-4.452191304615841

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
87.1542

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(6-hydroxy-2,3,4-trimethoxyphenyl)-1-phenylpropan-1-one

> <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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
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    7   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₅

Average Mass

316.3530 Da

Monoisotopic Mass

316.13107 Da

IUPAC Name

3-(6-hydroxy-2,3,4-trimethoxyphenyl)-1-phenylpropan-1-one

Traditional Name

3-(6-hydroxy-2,3,4-trimethoxyphenyl)-1-phenylpropan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(CCC(=O)C2=CC=CC=C2)C(OC)=C1OC

InChI Identifier

InChI=1S/C18H20O5/c1-21-16-11-15(20)13(17(22-2)18(16)23-3)9-10-14(19)12-7-5-4-6-8-12/h4-8,11,20H,9-10H2,1-3H3

InChI Key

XXHGGLKQZUXJDI-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
Uvaria mocali	Plant	KNApSAcK
Uvaria mocoli	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retro-dihydrochalcones

Alternative Parents

Substituents

Retro-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Methoxyphenol
4-alkoxyphenol
Phenylketone
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Benzoyl
Phenoxy compound
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Ether
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120610 )

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	2.95	ALOGPS
logP	3.03	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.78	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	7	ChemAxon
Refractivity	87.15 m³·mol⁻¹	ChemAxon
Polarizability	33.74 Å³	ChemAxon
Number of Rings	2	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

15380424

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-Hydroxy-4,5,6-trimethoxydihydrochalcone (NP0060779)

MOL for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

3D MOL for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

3D SDF for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

3D-SDF for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

PDB for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

3D PDB for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

SMILES for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

INCHI for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

Structure for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)

3D Structure for NP0060779 (2-Hydroxy-4,5,6-trimethoxydihydrochalcone)