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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:26:50 UTC

Update Date

2022-03-07 02:53:49 UTC

HMDB ID

HMDB0033691

Secondary Accession Numbers

HMDB33691

Metabolite Identification

Common Name

2'-Hydroxy-4',6'-dimethoxychalcone

Description

2'-Hydroxy-4',6'-dimethoxychalcone, also known as 4',6'-dimethoxy-2'-hydroxychalcone, belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 2'-hydroxy-4',6'-dimethoxychalcone is considered to be a flavonoid. 2'-Hydroxy-4',6'-dimethoxychalcone has been detected, but not quantified in, beverages. This could make 2'-hydroxy-4',6'-dimethoxychalcone a potential biomarker for the consumption of these foods. 2'-Hydroxy-4',6'-dimethoxychalcone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2'-Hydroxy-4',6'-dimethoxychalcone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033691
     RDKit          3D
2'-Hydroxy-4',6'-dimethoxychalcone
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.5083    0.9768    2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746    0.0714    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613   -0.0785    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.6359    1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    0.4723    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.2370    1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804   -0.4129   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383   -0.6368   -0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841   -1.5006   -1.6357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    0.0141   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -0.2801   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829    0.3489   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9506   -0.0594   -1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1903    0.4344   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2986    1.3896    0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1749    1.8193    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    1.2954    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2493   -1.1362   -0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9905   -2.0476   -1.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -2.7984   -2.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.9729   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0601    0.6094    3.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940    1.9801    1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6033    1.0086    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0459    1.3428    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    1.8988    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    0.7638    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -1.0254   -1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -0.8153   -1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0718    0.0843   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2854    1.7878    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    2.5741    1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.6465    1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6959   -2.1469   -2.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384   -3.6421   -2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -3.2881   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3668   -1.5498   -0.7721 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  2  0
  8 10  1  0
 10 11  2  0
 11 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  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv0541 05061307172D          

 21 22  0  0  0  0            999 V2000
    2.1434    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   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    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    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
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    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
   -1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
 21  2  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033691

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+

> <INCHI_KEY>
QKQLSQLKXBHUSO-CMDGGOBGSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.3065

> <EXACT_MASS>
284.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.543866084250624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.921417456

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.98074607071105

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.189677877742016

> <JCHEM_PKA_STRONGEST_BASIC>
-4.575932460949793

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
81.7843

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flavokavain B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033691
     RDKit          3D
2'-Hydroxy-4',6'-dimethoxychalcone
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.5083    0.9768    2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746    0.0714    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613   -0.0785    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.6359    1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    0.4723    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.2370    1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804   -0.4129   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383   -0.6368   -0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841   -1.5006   -1.6357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    0.0141   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -0.2801   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829    0.3489   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9506   -0.0594   -1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1903    0.4344   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2986    1.3896    0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1749    1.8193    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    1.2954    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2493   -1.1362   -0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9905   -2.0476   -1.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -2.7984   -2.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.9729   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0601    0.6094    3.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940    1.9801    1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6033    1.0086    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0459    1.3428    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    1.8988    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    0.7638    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -1.0254   -1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -0.8153   -1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0718    0.0843   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2854    1.7878    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    2.5741    1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.6465    1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6959   -2.1469   -2.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384   -3.6421   -2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -3.2881   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3668   -1.5498   -0.7721 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  2  0
  8 10  1  0
 10 11  2  0
 11 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  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
M  END

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       4.001  17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  15.400   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.667  13.860   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  16.170   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8    9   12                                                       
CONECT    9    8   14                                                       
CONECT   10   13   15                                                       
CONECT   11   13   16                                                       
CONECT   12    6    7    8                                                  
CONECT   13   10   11   20                                                  
CONECT   14    9   17   18                                                  
CONECT   15   10   17   19                                                  
CONECT   16   11   17   21                                                  
CONECT   17   14   15   16                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    1   13                                                       
CONECT   21    2   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0033691
HETATM    1  C1  UNL     1      -5.508   0.977   2.097  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.175   0.071   1.084  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.861  -0.079   0.669  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.817   0.636   1.211  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.514   0.472   0.783  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.549   1.237   1.394  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.180  -0.413  -0.209  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.138  -0.637  -0.703  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.284  -1.501  -1.636  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.361   0.014  -0.262  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.544  -0.280  -0.803  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.783   0.349  -0.388  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.951  -0.059  -1.045  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.190   0.434  -0.773  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.299   1.390   0.206  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.175   1.819   0.877  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.917   1.295   0.576  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.249  -1.136  -0.756  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.991  -2.048  -1.761  1.00  0.00           O  
HETATM   20  C16 UNL     1      -3.012  -2.798  -2.345  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.545  -0.973  -0.330  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.060   0.609   3.054  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.094   1.980   1.923  1.00  0.00           H  
HETATM   24  H3  UNL     1      -6.603   1.009   2.242  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.046   1.343   1.996  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.745   1.899   2.125  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.429   0.764   0.509  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.555  -1.025  -1.585  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.886  -0.815  -1.824  1.00  0.00           H  
HETATM   30  H9  UNL     1       7.072   0.084  -1.312  1.00  0.00           H  
HETATM   31  H10 UNL     1       7.285   1.788   0.429  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.320   2.574   1.638  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.070   1.646   1.110  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.696  -2.147  -2.941  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.638  -3.642  -2.959  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.609  -3.288  -1.521  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.367  -1.550  -0.772  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   17
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   33
CONECT   18   19   21   21
CONECT   19   20
CONECT   20   34   35   36
CONECT   21   37
END

HMDB0033691
     RDKit          3D
2'-Hydroxy-4',6'-dimethoxychalcone
 37 38  0  0  0  0  0  0  0  0999 V2000
   -5.5083    0.9768    2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1746    0.0714    1.0839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8613   -0.0785    0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173    0.6359    1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    0.4723    0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.2370    1.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804   -0.4129   -0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383   -0.6368   -0.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2841   -1.5006   -1.6357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3612    0.0141   -0.2621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -0.2801   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7829    0.3489   -0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9506   -0.0594   -1.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1903    0.4344   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2986    1.3896    0.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1749    1.8193    0.8770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9171    1.2954    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2493   -1.1362   -0.7557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9905   -2.0476   -1.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119   -2.7984   -2.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5453   -0.9729   -0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0601    0.6094    3.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0940    1.9801    1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6033    1.0086    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0459    1.3428    1.9959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7454    1.8988    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294    0.7638    0.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -1.0254   -1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865   -0.8153   -1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0718    0.0843   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2854    1.7878    0.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    2.5741    1.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0700    1.6465    1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6959   -2.1469   -2.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6384   -3.6421   -2.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6085   -3.2881   -1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3668   -1.5498   -0.7721 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  2  0
  8 10  1  0
 10 11  2  0
 11 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  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 20 34  1  0
 20 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',6'-Dimethoxy-2'-hydroxychalcone	ChEBI
CHALCONE,2-hydroxy-4,6-dimethyl	HMDB
Flavokawain b	HMDB
Flavokawin b	HMDB
2'-Hydroxy-4',6'-dimethoxychalcone	ChEBI
Flavokavin b	MeSH
Flavokavain b	MeSH

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.3065

Monoisotopic Molecular Weight

284.104859

IUPAC Name

(2E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

Traditional Name

flavokavain B

CAS Registry Number

1775-97-9

SMILES

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

InChI Identifier

InChI=1S/C17H16O4/c1-20-13-10-15(19)17(16(11-13)21-2)14(18)9-8-12-6-4-3-5-7-12/h3-11,19H,1-2H3/b9-8+

InChI Key

QKQLSQLKXBHUSO-CMDGGOBGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Methoxybenzene
Anisole
Benzoyl
Aryl ketone
Phenoxy compound
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:65899 )
dimethoxybenzene (CHEBI:65899 )
chalcones (CHEBI:65899 )
Chalcones and dihydrochalcones (LMPK12120246 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033691)

Cellular substructure

Membrane (HMDB: HMDB0033691)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033691)

Source

Exogenous

Food

Food (HMDB: HMDB0033691)

Beverage

Beverages (FooDB: FOOD00870)

Endogenous

Plant

Plant (HMDB: HMDB0033691)

Not Available

Nutrient (HMDB: HMDB0033691)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	91 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	3.9	ALOGPS
logP	3.92	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.19	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.78 m³·mol⁻¹	ChemAxon
Polarizability	30.54 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	168.689	30932474
DeepCCS	[M-H]-	166.331	30932474
DeepCCS	[M-2H]-	199.217	30932474
DeepCCS	[M+Na]+	174.782	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.5	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	167.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2'-Hydroxy-4',6'-dimethoxychalcone	COC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C1	3760.4	Standard polar	33892256
2'-Hydroxy-4',6'-dimethoxychalcone	COC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C1	2476.5	Standard non polar	33892256
2'-Hydroxy-4',6'-dimethoxychalcone	COC1=CC(O)=C(C(=O)\C=C\C2=CC=CC=C2)C(OC)=C1	2653.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2'-Hydroxy-4',6'-dimethoxychalcone,1TMS,isomer #1	COC1=CC(OC)=C(C(=O)/C=C/C2=CC=CC=C2)C(O[Si](C)(C)C)=C1	2517.6	Semi standard non polar	33892256
2'-Hydroxy-4',6'-dimethoxychalcone,1TBDMS,isomer #1	COC1=CC(OC)=C(C(=O)/C=C/C2=CC=CC=C2)C(O[Si](C)(C)C(C)(C)C)=C1	2784.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2790000000-55c54509736fc2799cd6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone GC-MS (1 TMS) - 70eV, Positive	splash10-006x-6449000000-886bb5f544d421c5c1c5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone LC-ESI-qTof , Positive-QTOF	splash10-00lr-0900000000-887bb7e62bbec731a8f7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone , positive-QTOF	splash10-001i-0900000000-f456ae52791e208e7a0e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Negative-QTOF	splash10-001i-0390000000-d17368362a50f3779299	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Negative-QTOF	splash10-0ue9-1960000000-077f2945d8d4fb663330	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Negative-QTOF	splash10-0kvt-4930000000-f1b41017e8bbdc9e5730	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Negative-QTOF	splash10-001i-0290000000-49df8bccba954e251b61	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Negative-QTOF	splash10-00lr-0690000000-151e1951cbdb6b0cb17d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Negative-QTOF	splash10-0f9f-7940000000-0032eeb54416d6c7298e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Positive-QTOF	splash10-000i-0190000000-d2b945cda2c651f98204	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Positive-QTOF	splash10-001r-0890000000-3c934b149da6c66eacc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Positive-QTOF	splash10-0udi-1920000000-34edd66b5dda77a0b65e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 10V, Positive-QTOF	splash10-000i-0390000000-bd10f8d7e501a32ab8cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 20V, Positive-QTOF	splash10-001i-0900000000-05e1177b781e4c2c1129	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-Hydroxy-4',6'-dimethoxychalcone 40V, Positive-QTOF	splash10-0udi-2900000000-9657eea0d14d444ffe8a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011797

KNApSAcK ID

C00006936

Chemspider ID

4511912

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5356121

PDB ID

Not Available

ChEBI ID

65899

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2'-Hydroxy-4',6'-dimethoxychalcone (HMDB0033691)

MOL for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

3D MOL for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

3D SDF for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

3D-SDF for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

PDB for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

3D PDB for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

SMILES for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

INCHI for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

Structure for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

3D Structure for HMDB0033691 (2'-Hydroxy-4',6'-dimethoxychalcone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra