NP-MRD: Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one (NP0052916)

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Record Information

Version

2.0

Created at

2022-04-27 23:47:57 UTC

Updated at

2022-04-27 23:47:57 UTC

NP-MRD ID

NP0052916

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one

Description

3,7-Dimethylquercetin, also known as DTHF, 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, 3,7-dimethylquercetin is considered to be a flavonoid lipid molecule. 3,7-Dimethylquercetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3,7-Dimethylquercetin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 3,7-Dimethylquercetin is found, on average, in the highest concentration within grape wines and beers. This could make 3,7-dimethylquercetin a potential biomarker for the consumption of these foods. 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one is found in Aeonium manriquiorum, Ageratina havanensis, Artemisia monosperma, Artemisia spp. , Baccharis pilularis, Blumea balsamifera, Calceolaria spp., Chrysothamnus viscidiflorus, Croton schiedeanus, Cyperus spp., Dioscorea bulbifera, Eirmocephala megaphylla, Eriodictyon trichocalyx, Eucryphia milliganii, Eucryphia moorei, Flourensia cernua, Grindelia tarapacana, Haplopappus taeda, Heliotropium pycnophyllum, Heliotropium stenophyllum, Holocarpha spp., Lantana camara , Larrea cuneifolia , Larrea divaricata , Larrea tridentata , Macaranga triloba, Wollastonia biflora, Mimulus cardinalis, Mirabilis viscosa, Nolana rostrata, Ozothamnus lycopodioides, Ozothamnus scutellifolius, Palafoxia sphacelata, Pelargonium fulgidum , Pelargonium quercifolium , Petunia surfinia, Rubus phoenicolasius , Salpiglossis sinuata, Siegesbeckia jorullensis, Siegesbeckia orientalis , Solanum pennellii, Taxus chinensis, Viscum album , Viscum cruciatum , Vitex agnus-castus, Vitis vinifera, Wallastonia bifora and Xanthocephalum gymnospermoides. 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one was first documented in 1989 (PMID: 2632060). A dimethoxyflavone that the 3,7-di-O-methyl derivative of quercetin (PMID: 19031255).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    5.0774   -1.6765    1.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1602   -0.4699    1.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    0.1183    0.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1240    1.3022   -0.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    1.8852   -0.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0844    3.0864   -1.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.2731   -0.6269 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6498    1.8532   -1.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7099    2.9389   -1.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5728    1.1876   -1.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6754    1.8081   -1.5800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4170    2.7950   -0.8511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6677    0.0134   -0.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8959   -0.7613   -0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.7616    0.8429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9282   -2.5078    1.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1175   -2.2755    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2632   -3.0043    0.8118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2019   -1.2876   -0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3864   -1.0194   -1.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0668   -0.5339   -0.7231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -0.4672    0.1649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262    0.0883    0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.4630    0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141   -1.8000    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0652   -2.5222    1.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2464   -1.7248    2.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1116    1.7667   -0.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9793    3.5453   -1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2588    2.6066    0.2145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932    3.8059   -1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5004    2.6940   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -1.9648    1.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8635   -3.3021    1.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2853   -3.7546    1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4265   -0.2859   -1.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1719    0.2104   -1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682   -1.3958    1.1356 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  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 22  1  0
 13 14  1  0
 14 21  2  0
 21 19  1  0
 19 20  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
  4  3  1  0
 15 14  1  0
 22 23  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 38  1  0
  6 29  1  0
  4 28  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 21 37  1  0
 20 36  1  0
 18 35  1  0
 16 34  1  0
 15 33  1  0
M  END


  Mrv0541 02241212092D          

 24 26  0  0  0  0            999 V2000
   -6.2609    1.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9754    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9754    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2609    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5465    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5465    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8320    1.7606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8320    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1175    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1175    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    2.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9741    2.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8320   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4031    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6899    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2609   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    3.8231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2597    2.9981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6886    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4043    1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  5  6  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
  8 17  2  0  0  0  0
  9 18  1  0  0  0  0
  2 19  1  0  0  0  0
  4 20  1  0  0  0  0
 12 21  1  0  0  0  0
 16 22  1  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052916

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-9-6-12(20)14-13(7-9)24-16(17(23-2)15(14)21)8-3-4-10(18)11(19)5-8/h3-7,18-20H,1-2H3

> <INCHI_KEY>
LUJAXSNNYBCFEE-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.496460919082196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.4150209093333332

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.770739872200133

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.144635514294771

> <JCHEM_PKA_STRONGEST_BASIC>
-4.567943663018915

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
86.09570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DTHF

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -11.687   3.286   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.021   2.516   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.021   0.976   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.687   0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.353   0.976   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.353   2.516   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -9.020   3.286   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -9.020   0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.686   0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.686   2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.352   3.286   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.019   5.596   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.352   4.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.019   2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.685   3.286   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.685   4.826   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -9.020  -1.334   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.352   0.206   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0     -14.354   3.286   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -11.687  -1.334   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.019   7.136   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.351   5.596   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.019   0.976   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.688   2.516   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   17                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9    7   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   21                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   22                                                  
CONECT   17    8                                                            
CONECT   18    9   23                                                       
CONECT   19    2   24                                                       
CONECT   20    4                                                            
CONECT   21   12                                                            
CONECT   22   16                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyrone	ChEBI
3,7-Di-O-methylquercetin	ChEBI
3,7-O-Dimethylquercetin	ChEBI
3',4',5-Trihydroxy-3,7-dimethoxyflavone	Kegg
5,3',4'-Trihydroxy-3,7-dimethoxyflavone	HMDB
DTHF	HMDB
Quercetin 3,7-dimethyl ether	HMDB
3,7-Dimethoxy-5,3',4'-trihydroxyflavone	HMDB

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2889 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-chromen-4-one

Traditional Name

DTHF

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H14O7/c1-22-9-6-12(20)14-13(7-9)24-16(17(23-2)15(14)21)8-3-4-10(18)11(19)5-8/h3-7,18-20H,1-2H3

InChI Key

LUJAXSNNYBCFEE-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
Aeonium manriquiorum	Plant	KNApSAcK
Ageratina havanensis	Plant	KNApSAcK
Artemisia monosperma	LOTUS Database	35616633
Artemisia spp.	Plant	KNApSAcK
Baccharis pilularis	Plant	KNApSAcK
Blumea balsamifera	LOTUS Database	35616633
Calceolaria spp.	Plant	KNApSAcK
Chrysothamnus viscidiflorus	Plant	KNApSAcK
Croton schiedeanus	LOTUS Database	35616633
Cyperus spp.	Plant	KNApSAcK
Dioscorea bulbifera	LOTUS Database	35616633
Eirmocephala megaphylla	Plant	KNApSAcK
Eriodictyon trichocalyx	Plant	KNApSAcK
Eucryphia milliganii	Plant	KNApSAcK
Eucryphia moorei	Plant	KNApSAcK
Flourensia cernua	Plant	KNApSAcK
Grindelia tarapacana	Plant	KNApSAcK
Haplopappus taeda	Plant	KNApSAcK
Heliotropium pycnophyllum	Plant	KNApSAcK
Heliotropium stenophyllum	Plant	KNApSAcK
Holocarpha spp.	Plant	KNApSAcK
Lantana camara	Plant	KNApSAcK
Larrea cuneifolia	Plant	KNApSAcK
Larrea divaricata	Plant	KNApSAcK
Larrea tridentata	Plant	KNApSAcK
Macaranga triloba	Plant	KNApSAcK
Melanthera biflora	LOTUS Database	35616633
Mimulus cardinalis	Plant	KNApSAcK
Mirabilis viscosa	Plant	KNApSAcK
Nolana rostrata	LOTUS Database	35616633
Ozothamnus lycopodioides	Plant	KNApSAcK
Ozothamnus scutellifolius	Plant	KNApSAcK
Palafoxia sphacelata	Plant	KNApSAcK
Pelargonium fulgidum	Plant	KNApSAcK
Pelargonium quercifolium	Plant	KNApSAcK
Petunia surfinia	Plant	KNApSAcK
Rubus phoenicolasius	Plant	KNApSAcK
Salpiglossis sinuata	Plant	KNApSAcK
Siegesbeckia jorullensis	-	KNApSAcK
Sigesbeckia orientalis	-	KNApSAcK
Solanum pennellii	Plant	KNApSAcK
Taxus chinensis	Plant	KNApSAcK
Viscum album	Plant	KNApSAcK
Viscum cruciatum	Plant	KNApSAcK
Vitex agnus-castus	LOTUS Database	35616633
Vitis vinifera	LOTUS Database	35616633
Wallastonia bifora	-	KNApSAcK
Xanthocephalum gymnospermoides	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

7-methoxyflavonoid-skeleton
3-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
Hydroxyflavonoid
4'-hydroxyflavonoid
Flavone
5-hydroxyflavonoid
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Anisole
Catechol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:18010 )
dimethoxyflavone (CHEBI:18010 )
flavonols (C01265 )
Flavones and Flavonols (LMPK12112731 )
a flavonol derivative (345-TRIHYDROXY-37-DIMETHOXYFLAVONE )

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	2.42	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.14	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	86.1 m³·mol⁻¹	ChemAxon
Polarizability	32.5 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

HMDB0029263

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

345-TRIHYDROXY-37-DIMETHOXYFLAVONE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280417

PDB ID

Not Available

ChEBI ID

18010

Good Scents ID

Not Available

References

General References

Qiu YK, Kang TG, Dou DQ, Liang L, Dong F: Three novel compounds from the leaves of Smallanthus sonchifolius. J Asian Nat Prod Res. 2008 Nov-Dec;10(11-12):1109-15. doi: 10.1080/10286020802361230. [PubMed:19031255 ]
Komoda Y: Isolation of flavonoids from Populus nigra as delta 4-3-ketosteroid (5 alpha) reductase inhibitors. Chem Pharm Bull (Tokyo). 1989 Nov;37(11):3128-30. doi: 10.1248/cpb.37.3128. [PubMed:2632060 ]

Showing NP-Card for 2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one (NP0052916)

MOL for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D MOL for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D SDF for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D-SDF for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

PDB for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D PDB for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

SMILES for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

INCHI for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

Structure for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)

3D Structure for NP0052916 (2-(3,4-Dihydroxyphenyl)-5-hydroxy-3,7-dimethoxy-4H-1-benzopyran-4-one)