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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:33 UTC

Update Date

2022-03-07 02:52:10 UTC

HMDB ID

HMDB0029462

Secondary Accession Numbers

HMDB29462

Metabolite Identification

Common Name

(E)-2,4,4'-Trihydroxychalcone

Description

(E)-2,4,4'-Trihydroxychalcone, also known as 562'6'-tetramethoxyflavone or ev-toxin, belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Based on a literature review very few articles have been published on (E)-2,4,4'-Trihydroxychalcone.

Structure

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

HMDB0029462
     RDKit          3D
(E)-2,4,4'-Trihydroxychalcone
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.2332   -2.0746   -1.2553 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -0.9716   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185   -0.3379   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150   -0.9331   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156   -0.3947   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219    0.8031    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759    1.3226    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290    0.6527    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1427    1.1917    0.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.5457   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882   -1.0918   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762   -2.2963   -1.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672   -0.3342   -0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470   -0.9704   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.4441   -0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912    0.7687    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3384    1.3194    0.3287 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    1.4299    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924    0.8746    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    0.6064    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692   -1.9059   -1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6307    1.3535    0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7740    2.2702    1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6430    1.8164    0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7197   -1.0884   -0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -2.7719   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6307   -1.9152   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8985   -0.9662   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1700    0.8497    0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0119    2.3657    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.4175    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  5  1  0
 19 13  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END


  Mrv0541 02241211232D          

 19 20  0  0  0  0            999 V2000
   -2.1441   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017   -2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017   -0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -1.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017   -3.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    3.0932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7417    3.0932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417    1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441    0.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  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
  5 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029462

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-12-5-1-10(2-6-12)14(18)8-4-11-3-7-13(17)9-15(11)19/h1-9,16-17,19H/b8-4+

> <INCHI_KEY>
VDYSHUXENHRSOO-XBXARRHUSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.650486714595523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.9796293439999997

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.737467337200343

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.809558455875417

> <JCHEM_PKA_STRONGEST_BASIC>
-6.047645286388479

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
72.8197

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029462
     RDKit          3D
(E)-2,4,4'-Trihydroxychalcone
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.2332   -2.0746   -1.2553 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -0.9716   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185   -0.3379   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150   -0.9331   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156   -0.3947   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219    0.8031    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759    1.3226    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290    0.6527    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1427    1.1917    0.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.5457   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882   -1.0918   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762   -2.2963   -1.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672   -0.3342   -0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470   -0.9704   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.4441   -0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912    0.7687    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3384    1.3194    0.3287 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    1.4299    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924    0.8746    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    0.6064    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692   -1.9059   -1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6307    1.3535    0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7740    2.2702    1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6430    1.8164    0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7197   -1.0884   -0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -2.7719   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6307   -1.9152   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8985   -0.9662   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1700    0.8497    0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0119    2.3657    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.4175    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  5  1  0
 19 13  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

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      -4.002  -3.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.617  -4.234   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.385  -3.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.385  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.617  -1.154   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.002  -1.924   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.617  -5.774   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.385   1.154   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.385   2.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.617   3.464   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.617   5.004   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.002   5.774   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.385   5.774   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.001   5.004   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.001   3.464   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.385   2.694   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.385   1.154   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.617   0.386   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.002   1.154   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    9                                                            
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15    9   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    5   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0029462
HETATM    1  O1  UNL     1       1.233  -2.075  -1.255  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.289  -0.972  -0.664  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.018  -0.338  -0.263  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.115  -0.933  -0.530  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.416  -0.395  -0.178  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.522   0.803   0.472  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.776   1.323   0.811  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.929   0.653   0.505  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.143   1.192   0.853  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.820  -0.546  -0.145  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.588  -1.092  -0.498  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.576  -2.296  -1.146  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.567  -0.334  -0.382  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.747  -0.970  -0.780  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.995  -0.444  -0.557  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.091   0.769   0.092  1.00  0.00           C  
HETATM   17  O4  UNL     1       6.338   1.319   0.329  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.932   1.430   0.502  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.692   0.875   0.262  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.030   0.606   0.245  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.069  -1.906  -1.055  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.631   1.353   0.726  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.774   2.270   1.321  1.00  0.00           H  
HETATM   24  H5  UNL     1      -6.643   1.816   0.207  1.00  0.00           H  
HETATM   25  H6  UNL     1      -5.720  -1.088  -0.395  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.761  -2.772  -1.441  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.631  -1.915  -1.283  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.898  -0.966  -0.880  1.00  0.00           H  
HETATM   29  H10 UNL     1       7.170   0.850   0.036  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.012   2.366   1.002  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.837   1.417   0.595  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   20
CONECT    4    5   21
CONECT    5    6    6   11
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24
CONECT   10   11   11   25
CONECT   11   12
CONECT   12   26
CONECT   13   14   14   19
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   18
CONECT   17   29
CONECT   18   19   19   30
CONECT   19   31
END

HMDB0029462
     RDKit          3D
(E)-2,4,4'-Trihydroxychalcone
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.2332   -2.0746   -1.2553 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2890   -0.9716   -0.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0185   -0.3379   -0.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1150   -0.9331   -0.5295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4156   -0.3947   -0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219    0.8031    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7759    1.3226    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9290    0.6527    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1427    1.1917    0.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8203   -0.5457   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882   -1.0918   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5762   -2.2963   -1.1463 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672   -0.3342   -0.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470   -0.9704   -0.7804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.4441   -0.5565 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912    0.7687    0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3384    1.3194    0.3287 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    1.4299    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924    0.8746    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0299    0.6064    0.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692   -1.9059   -1.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6307    1.3535    0.7255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7740    2.2702    1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6430    1.8164    0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7197   -1.0884   -0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -2.7719   -1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6307   -1.9152   -1.2833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8985   -0.9662   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1700    0.8497    0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0119    2.3657    1.0021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    1.4175    0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 11  5  1  0
 19 13  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
562'6'-Tetramethoxyflavone	HMDB
2',5,6,6'-Tetramethoxyflavone	HMDB
5,6,2',6'-Tetramethoxyflavone	HMDB
Ev-toxin	HMDB

Chemical Formula

C₁₅H₁₂O₄

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

IUPAC Name

(2E)-3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-3-(2,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C15H12O4/c16-12-5-1-10(2-6-12)14(18)8-4-11-3-7-13(17)9-15(11)19/h1-9,16-17,19H/b8-4+

InChI Key

VDYSHUXENHRSOO-XBXARRHUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones 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

Retrochalcones

Alternative Parents

Substituents

Retrochalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Benzoyl
Resorcinol
Styrene
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Enone
Acryloyl-group
Alpha,beta-unsaturated ketone
Ketone
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029462)
Cell membrane (HMDB: HMDB0029462)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029462)

Source

Endogenous

Endogenous (HMDB: HMDB0029462)

Plant

Plant (HMDB: HMDB0029462)

Exogenous

Food

Food (HMDB: HMDB0029462)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029462)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	3	ALOGPS
logP	2.98	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.82 m³·mol⁻¹	ChemAxon
Polarizability	26.65 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]+	157.032	30932474
DeepCCS	[M-H]-	154.674	30932474
DeepCCS	[M-2H]-	187.654	30932474
DeepCCS	[M+Na]+	163.125	30932474
AllCCS	[M+H]+	159.3	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	163.0	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	158.6	32859911
AllCCS	[M+Na-2H]-	158.1	32859911
AllCCS	[M+HCOO]-	157.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.51 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0471 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1826.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	274.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	542.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	408.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	968.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	377.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1127.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	391.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	242.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	91.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-2,4,4'-Trihydroxychalcone	OC1=CC=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1O	4735.8	Standard polar	33892256
(E)-2,4,4'-Trihydroxychalcone	OC1=CC=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1O	2759.1	Standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone	OC1=CC=C(C=C1)C(=O)\C=C\C1=CC=C(O)C=C1O	3087.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-2,4,4'-Trihydroxychalcone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2O)C=C1	2928.1	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2)C(O)=C1	2910.5	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=CC=C1/C=C/C(=O)C1=CC=C(O)C=C1	2838.1	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2O)C=C1	2897.3	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2O[Si](C)(C)C)C=C1	2868.4	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2)C(O[Si](C)(C)C)=C1	2885.5	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C=C1	2902.8	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2O)C=C1	3183.1	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2)C(O)=C1	3183.3	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1/C=C/C(=O)C1=CC=C(O)C=C1	3123.7	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C=C1	3457.1	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3435.8	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)C2=CC=C(O)C=C2)C(O[Si](C)(C)C(C)(C)C)=C1	3450.5	Semi standard non polar	33892256
(E)-2,4,4'-Trihydroxychalcone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C=C1	3688.5	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 - (E)-2,4,4'-Trihydroxychalcone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-2960000000-0cd325a2855ef9ebf655	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2,4,4'-Trihydroxychalcone GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-2106900000-91581430299c75da05c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 10V, Positive-QTOF	splash10-0a4i-0190000000-96074e6138bf47204857	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 20V, Positive-QTOF	splash10-0abi-0980000000-74253cadc1109f8eb8ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 40V, Positive-QTOF	splash10-00y3-8920000000-746b44e18cc848dcb992	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 10V, Negative-QTOF	splash10-0a4i-0290000000-008f125e4eb2ec153b59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 20V, Negative-QTOF	splash10-0a4i-1490000000-7317a7c4d578e10671c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 40V, Negative-QTOF	splash10-066u-6930000000-0af17ed60b5158858890	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 10V, Negative-QTOF	splash10-0a4i-0090000000-82e226df9342cd67d796	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 20V, Negative-QTOF	splash10-0a4r-3890000000-a36eb7f8aa12a177051d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 40V, Negative-QTOF	splash10-000f-6910000000-2c352da4c8b1c3006218	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 10V, Positive-QTOF	splash10-0a4i-0490000000-cd8ef27d0fec9abf0b6c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 20V, Positive-QTOF	splash10-05fr-1910000000-120f5904292e970be8c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-2,4,4'-Trihydroxychalcone 40V, Positive-QTOF	splash10-014i-8900000000-e2b33f77f8bbf1556933	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

FDB000583

KNApSAcK ID

Not Available

Chemspider ID

4479640

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5322052

PDB ID

Not Available

ChEBI ID

174359

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 (E)-2,4,4'-Trihydroxychalcone (HMDB0029462)

MOL for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

3D MOL for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

3D SDF for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

3D-SDF for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

PDB for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

3D PDB for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

SMILES for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

INCHI for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

Structure for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

3D Structure for HMDB0029462 ((E)-2,4,4'-Trihydroxychalcone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra