MiMeDB: Showing metabocard for Isoliquiritigenin (MMDBc0053372)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:22:28 UTC

Update Date

2025-01-16 04:50:01 UTC

Metabolite ID

MMDBc0053372

Metabolite Identification

Common Name

Isoliquiritigenin

Description

Isoliquiritigenin is found in pulses. Isoliquiritigenin is isolated from Medicago specie

Structure

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

HMDB0037316
     RDKit          3D
Isoliquiritigenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.8321   -2.5744    0.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267   -1.3074    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440   -0.4674    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -1.0117    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -0.2483    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6348    1.1079   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8622    1.7699   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0671    1.1036    0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2677    1.8160   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.2663    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092   -0.9283    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094   -0.8617    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -1.8489    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7254   -1.4850    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1137   -0.1616   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4480    0.1749   -0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    0.7890   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902    0.4568   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8128    1.4600   -0.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    0.5877   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -2.0967    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747    1.7259   -0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    2.8482   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7535    2.0290   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9300   -0.8170    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -2.0059    0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -2.9138    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4927   -2.2721    0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7301    1.1397   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    1.8496   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293    2.4080   -0.2207 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
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 11  5  1  0
 18 12  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
 11 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
M  END


  Mrv1652306222023492D          

 21 22  0  0  0  0            999 V2000
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   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
    5.0013   -2.8875    0.0000 O   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
    5.7158   -1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  7  6  2  0  0  0  0
  8  3  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20  3  1  0  0  0  0
 21  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053372

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1=C(O)C=C(O)C=C1

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

> <INCHI_KEY>
DXDRHHKMWQZJHT-FPYGCLRLSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.656339568424237

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.6296293439999996

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.573677969309692

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.110975707565281

> <JCHEM_PKA_STRONGEST_BASIC>
-6.352946961329956

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
72.8197

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoliquiritigenin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037316
     RDKit          3D
Isoliquiritigenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.8321   -2.5744    0.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267   -1.3074    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440   -0.4674    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -1.0117    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -0.2483    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6348    1.1079   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8622    1.7699   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0671    1.1036    0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2677    1.8160   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.2663    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092   -0.9283    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094   -0.8617    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -1.8489    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7254   -1.4850    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1137   -0.1616   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4480    0.1749   -0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    0.7890   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902    0.4568   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8128    1.4600   -0.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    0.5877   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -2.0967    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747    1.7259   -0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    2.8482   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7535    2.0290   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9300   -0.8170    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -2.0059    0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -2.9138    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4927   -2.2721    0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7301    1.1397   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    1.8496   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293    2.4080   -0.2207 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
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 11  5  1  0
 18 12  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
 11 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0      10.669  -3.080   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.668  -2.310   0.000  0.00  0.00           H+0
CONECT    1    4   10                                                       
CONECT    2    5   10                                                       
CONECT    3    8   10   20                                                  
CONECT    4    1   11                                                       
CONECT    5    2   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   13                                                       
CONECT    8    3   14   21                                                  
CONECT    9   12   15                                                       
CONECT   10    1    2    3                                                  
CONECT   11    4    5   16                                                  
CONECT   12    6    9   17                                                  
CONECT   13    7   14   15                                                  
CONECT   14    8   13   18                                                  
CONECT   15    9   13   19                                                  
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    3                                                            
CONECT   21    8                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0037316
HETATM    1  O1  UNL     1      -0.832  -2.574   0.180  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.027  -1.307   0.081  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.144  -0.467   0.041  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.378  -1.012   0.107  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.592  -0.248   0.074  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.635   1.108  -0.028  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.862   1.770  -0.053  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.067   1.104   0.021  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.268   1.816  -0.008  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.018  -0.266   0.124  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.809  -0.928   0.149  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.409  -0.862   0.020  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.405  -1.849   0.074  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.725  -1.485   0.020  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.114  -0.162  -0.087  1.00  0.00           C  
HETATM   16  O3  UNL     1      -6.448   0.175  -0.139  1.00  0.00           O  
HETATM   17  C14 UNL     1      -4.127   0.789  -0.139  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.790   0.457  -0.087  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.813   1.460  -0.143  1.00  0.00           O  
HETATM   20  H1  UNL     1       0.152   0.588  -0.038  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.421  -2.097   0.189  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.775   1.726  -0.091  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.915   2.848  -0.133  1.00  0.00           H  
HETATM   24  H5  UNL     1       6.754   2.029  -0.884  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.930  -0.817   0.183  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.845  -2.006   0.231  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.119  -2.914   0.160  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.493  -2.272   0.064  1.00  0.00           H  
HETATM   29  H10 UNL     1      -6.730   1.140  -0.217  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.403   1.850  -0.224  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.129   2.408  -0.221  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
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   26
CONECT   12   13   13   18
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   17
CONECT   16   29
CONECT   17   18   18   30
CONECT   18   19
CONECT   19   31
END

HMDB0037316
     RDKit          3D
Isoliquiritigenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -0.8321   -2.5744    0.1803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0267   -1.3074    0.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1440   -0.4674    0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3780   -1.0117    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5924   -0.2483    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6348    1.1079   -0.0276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8622    1.7699   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0671    1.1036    0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2677    1.8160   -0.0082 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.2663    0.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092   -0.9283    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4094   -0.8617    0.0199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4050   -1.8489    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7254   -1.4850    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1137   -0.1616   -0.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4480    0.1749   -0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1268    0.7890   -0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7902    0.4568   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8128    1.4600   -0.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1521    0.5877   -0.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -2.0967    0.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7747    1.7259   -0.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146    2.8482   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7535    2.0290   -0.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9300   -0.8170    0.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8447   -2.0059    0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -2.9138    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4927   -2.2721    0.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7301    1.1397   -0.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4032    1.8496   -0.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1293    2.4080   -0.2207 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
  2 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 11  5  1  0
 18 12  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
 11 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 19 31  1  0
M  END

Synonyms

Value	Source
(e)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenone	ChEBI
(e)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propene-1-one	ChEBI
2',4,4'-Trihydroxychalcone	ChEBI
4,2',4'-Trihydroxychalcone	ChEBI
trans-2',4,4'-Trihydroxychalcone	ChEBI
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one	HMDB
2',4',4-Trihydroxychalcone	HMDB, MeSH
2',4'-Dihydroxy-3-(P-hydroxyphenyl)-acrylophenone	HMDB
2',4,4'-Trihydroxy-chalcone	HMDB
42'4'-Trihydroxychalcone	HMDB
6'-Deoxychalcone	HMDB, MeSH
GU 17	MeSH, HMDB
GU-17	MeSH, HMDB

Molecular Formula

C₁₅H₁₂O₄

Average Mass

256.2534

Monoisotopic Mass

256.073558872

IUPAC Name

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

Traditional Name

isoliquiritigenin

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=C(O)C=C1)C(=O)C1=C(O)C=C(O)C=C1

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

chalcones (CHEBI:310312 )
chalcones (C08650 )
Chalcones and dihydrochalcones (C08650 )
Chalcones and dihydrochalcones (LMPK12120096 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	3.04	ALOGPS
logP	3.63	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-6.4	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	26.66 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1970000000-6164f65f5d6241a006f8	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0a4i-1034900000-76ae3aa74bffdff7ee01	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0000009000-afd1640b539ec58a4616	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0000009000-afd1640b539ec58a4616	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014r-0900000000-e7c4095e90f57884e80c	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0090000000-788e4464b6a542aa7c22	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTOF , Positive	splash10-000i-0910000000-15db3efa5c81e3e8fc3e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014r-0900000000-e7c4095e90f57884e80c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-0910000000-15db3efa5c81e3e8fc3e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-1930000000-6d143294fc9a6a343052	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 17V, positive	splash10-000j-0490000000-5d95d877601bf1780cf7	2020-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 17V, positive	splash10-000j-0970000000-6f6553743b88b6c220e2	2020-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-6646b871effe2fc1dec4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0790000000-a0a66b537f815a68529a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-1900000000-f6d8867bba0f74e95f4c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-001c-7900000000-d9f65201f86e97a92305	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000x-9600000000-4607845a4f3c870a8b7d	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-1900000000-5b283194f8e6438d1cb4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0900000000-e7c4095e90f57884e80c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4r-0690000000-7996084c7a5f23179366	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-803b7c0679a83bac81f6	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-810f1a7ccbea17d944d3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052s-0960000000-9529b79414d923c90873	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ks-4910000000-f074bc6f0bf8212cf9cc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0290000000-a373dc716189e73d742c	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0690000000-12c68dfca23fb3e6405d	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066u-5910000000-ecfe8b4bdcef6eaa160e	2016-08-04	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Other Exposures

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0037316

DrugBank ID

DB03285

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isoliquiritigenin

METLIN ID

Not Available

PubChem Compound

638278

PDB ID

HCC

ChEBI ID

310312

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Tawata M, Aida K, Noguchi T, Ozaki Y, Kume S, Sasaki H, Chin M, Onaya T: Anti-platelet action of isoliquiritigenin, an aldose reductase inhibitor in licorice. Eur J Pharmacol. 1992 Feb 25;212(1):87-92. doi: 10.1016/0014-2999(92)90076-g. [PubMed:1555643 ]
Yu SM, Kuo SC: Vasorelaxant effect of isoliquiritigenin, a novel soluble guanylate cyclase activator, in rat aorta. Br J Pharmacol. 1995 Apr;114(8):1587-94. doi: 10.1111/j.1476-5381.1995.tb14943.x. [PubMed:7599926 ]
de Barros Machado T, Leal IC, Kuster RM, Amaral AC, Kokis V, de Silva MG, dos Santos KR: Brazilian phytopharmaceuticals--evaluation against hospital bacteria. Phytother Res. 2005 Jun;19(6):519-25. doi: 10.1002/ptr.1696. [PubMed:16114081 ]
Park I, Park KK, Park JH, Chung WY: Isoliquiritigenin induces G2 and M phase arrest by inducing DNA damage and by inhibiting the metaphase/anaphase transition. Cancer Lett. 2009 May 18;277(2):174-81. doi: 10.1016/j.canlet.2008.12.005. Epub 2009 Jan 23. [PubMed:19167809 ]
Gaur R, Kumar S, Trivedi P, Bhakuni RS, Bawankule DU, Pal A, Shanker K: Liquiritigenin derivatives and their hepatotoprotective activity. Nat Prod Commun. 2010 Aug;5(8):1243-6. [PubMed:20839627 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for Isoliquiritigenin (MMDBc0053372)

MOL for #<Metabolite:0x000055eeec1d4710>

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3D-SDF for #<Metabolite:0x000055eeec1d4710>

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3D PDB for #<Metabolite:0x000055eeec1d4710>

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INCHI for #<Metabolite:0x000055eeec1d4710>

Structure for #<Metabolite:0x000055eeec1d4710>

3D Structure for #<Metabolite:0x000055eeec1d4710>