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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:54 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029519

Secondary Accession Numbers

HMDB29519

Metabolite Identification

Common Name

Liquiritigenin

Description

Liquiritigenin belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, liquiritigenin is considered to be a flavonoid. Liquiritigenin is a bitter tasting compound. Liquiritigenin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), kai-lans (Brassica oleracea var. alboglabra), blackberries (Rubus), walnuts (Juglans), and tortilla. This could make liquiritigenin a potential biomarker for the consumption of these foods. Liquiritigenin 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 small amount of articles have been published on Liquiritigenin.

Structure

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

HMDB0029519
     RDKit          3D
Liquiritigenin
 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.0132   -3.0820    0.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -1.9439   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539   -1.7840   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.6672    0.6344 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7946   -0.2656    0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190    0.9105    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    1.3051    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4026    0.5000   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113    0.8056   -0.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8930   -0.6881   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861   -1.0623   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118    0.4661    0.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7630    0.4456    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615    1.5812    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966    1.5474   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479    2.7130   -0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.3215   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162   -0.8432   -0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578   -0.7628   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -2.7144    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -1.4951   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517   -0.9699    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938    1.5407    1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    2.2131    0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.3538   -1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5044   -1.3214   -1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.9947   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0688    2.5121    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805    2.9685    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5109    0.2261   -0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195   -1.8159   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 11  5  1  0
 19 13  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  1
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv1652309042000362D          

 20 22  0  0  1  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  6  5  2  0  0  0  0
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  1  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
 14 20  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0029519

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1

> <INCHI_KEY>
FURUXTVZLHCCNA-AWEZNQCLSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.413284948640513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.4886733719999996

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.480776938340991

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.788865277012675

> <JCHEM_PKA_STRONGEST_BASIC>
-4.939949525645975

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.30890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-deoxyflavanone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029519
     RDKit          3D
Liquiritigenin
 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.0132   -3.0820    0.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -1.9439   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539   -1.7840   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.6672    0.6344 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7946   -0.2656    0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190    0.9105    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    1.3051    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4026    0.5000   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113    0.8056   -0.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8930   -0.6881   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861   -1.0623   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118    0.4661    0.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7630    0.4456    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615    1.5812    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966    1.5474   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479    2.7130   -0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.3215   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162   -0.8432   -0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578   -0.7628   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -2.7144    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -1.4951   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517   -0.9699    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938    1.5407    1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    2.2131    0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.3538   -1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5044   -1.3214   -1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.9947   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0688    2.5121    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805    2.9685    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5109    0.2261   -0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195   -1.8159   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 11  5  1  0
 19 13  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  1
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3    9                                                       
CONECT    2    4    9                                                       
CONECT    3    1   10                                                       
CONECT    4    2   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   12                                                       
CONECT    7   11   15                                                       
CONECT    8   13   14                                                       
CONECT    9    1    2   14                                                  
CONECT   10    3    4   16                                                  
CONECT   11    5    7   17                                                  
CONECT   12    6   13   15                                                  
CONECT   13    8   12   18                                                  
CONECT   14    8    9   19   20                                             
CONECT   15    7   12   19                                                  
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   13                                                            
CONECT   19   14   15                                                       
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0029519
HETATM    1  O1  UNL     1      -2.013  -3.082   0.033  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.511  -1.944  -0.102  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.054  -1.784  -0.253  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.395  -0.667   0.634  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.795  -0.266   0.322  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.319   0.911   0.828  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.621   1.305   0.549  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.403   0.500  -0.251  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.711   0.806  -0.586  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.893  -0.688  -0.770  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.586  -1.062  -0.477  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.412   0.466   0.477  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.763   0.446   0.188  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.562   1.581   0.182  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.897   1.547  -0.106  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.648   2.713  -0.097  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.451   0.322  -0.399  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.716  -0.843  -0.411  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.358  -0.763  -0.112  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.498  -2.714   0.023  1.00  0.00           H  
HETATM   21  H2  UNL     1       0.162  -1.495  -1.303  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.352  -0.970   1.719  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.694   1.541   1.459  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.059   2.213   0.927  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.942   1.354  -1.422  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.504  -1.321  -1.398  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.230  -1.995  -0.902  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.069   2.512   0.420  1.00  0.00           H  
HETATM   29  H10 UNL     1      -5.080   2.969   0.786  1.00  0.00           H  
HETATM   30  H11 UNL     1      -5.511   0.226  -0.637  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.119  -1.816  -0.635  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   19
CONECT    3    4   20   21
CONECT    4    5   12   22
CONECT    5    6    6   11
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25
CONECT   10   11   11   26
CONECT   11   27
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   28
CONECT   15   16   17   17
CONECT   16   29
CONECT   17   18   30
CONECT   18   19   19   31
END

HMDB0029519
     RDKit          3D
Liquiritigenin
 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.0132   -3.0820    0.0328 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5112   -1.9439   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0539   -1.7840   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -0.6672    0.6344 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7946   -0.2656    0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190    0.9105    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    1.3051    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4026    0.5000   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113    0.8056   -0.5856 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8930   -0.6881   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861   -1.0623   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118    0.4661    0.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7630    0.4456    0.1877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615    1.5812    0.1818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966    1.5474   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6479    2.7130   -0.0972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4513    0.3215   -0.3989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7162   -0.8432   -0.4105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3578   -0.7628   -0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4981   -2.7144    0.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1623   -1.4951   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3517   -0.9699    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938    1.5407    1.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592    2.2131    0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.3538   -1.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5044   -1.3214   -1.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2295   -1.9947   -0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0688    2.5121    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0805    2.9685    0.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5109    0.2261   -0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1195   -1.8159   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  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
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 11  5  1  0
 19 13  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  1
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Liquiritigenin	ChEBI
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one	ChEBI
(2S)-Liquiritigenin	ChEBI
4',7-Dihydroxyflavanone	ChEBI
7,4'-Dihydroxyflavanone	ChEBI
(-)-(2S)-7,4'-Dihydroxyflavanone	HMDB
(-)-(2S)-7,4’-Dihydroxyflavanone	HMDB
(-)-(S)-4',7-Dihydroxyflavanone	HMDB
(-)-(S)-4’,7-Dihydroxyflavanone	HMDB
(2S)-2,3-Dihydro-7-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	HMDB
(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one	HMDB
4’,7-Dihydroxyflavanone	HMDB
7,4’-Dihydroxyflavanone	HMDB
Liquiritigenin	HMDB
5-Deoxyflavanone	HMDB
DFV	HMDB

Chemical Formula

C₁₅H₁₂O₄

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

IUPAC Name

(2S)-7-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5-deoxyflavanone

CAS Registry Number

578-86-9

SMILES

OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2

InChI Identifier

InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1

InChI Key

FURUXTVZLHCCNA-AWEZNQCLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavanone
Chromone
Chromane
1-benzopyran
Benzopyran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavanone (CHEBI:28777 )
flavanones (C09762 )
Flavanones (LMPK12140061 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203 - 205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	873.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.49	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.79	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.31 m³·mol⁻¹	ChemAxon
Polarizability	26.41 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	163.19	30932474
DeepCCS	[M-H]-	160.832	30932474
DeepCCS	[M-2H]-	194.003	30932474
DeepCCS	[M+Na]+	169.283	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	155.6	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	160.5	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	159.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Liquiritigenin	OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2	3729.6	Standard polar	33892256
Liquiritigenin	OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2	2760.0	Standard non polar	33892256
Liquiritigenin	OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2	2767.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Liquiritigenin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=CC=C(O)C=C3O2)C=C1	2677.6	Semi standard non polar	33892256
Liquiritigenin,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C1	2649.9	Semi standard non polar	33892256
Liquiritigenin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=CC=C(O[Si](C)(C)C)C=C3O2)C=C1	2753.1	Semi standard non polar	33892256
Liquiritigenin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=CC=C(O)C=C3O2)C=C1	2952.7	Semi standard non polar	33892256
Liquiritigenin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C1	2920.5	Semi standard non polar	33892256
Liquiritigenin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3239.1	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 - Liquiritigenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vr-1290000000-473372a9cbd8aa299c8c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liquiritigenin 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 - Liquiritigenin ESI-TOF 20V, Negative-QTOF	splash10-014r-0900000000-8829ca13726fa5ef2894	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin ESI-TOF , Negative-QTOF	splash10-0a4i-0090010000-4f0e0e7c69cd0563f154	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin LC-ESI-TOF , negative-QTOF	splash10-014r-0900000000-8829ca13726fa5ef2894	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin QIT 4V, positive-QTOF	splash10-0a4i-0090000000-e0ef2b922828538142d6	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin QIT 15V, positive-QTOF	splash10-01pa-0990000000-b55ccc74a2ff9f8ee58a	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin LC-ESI-QFT , positive-QTOF	splash10-0a4r-0690000000-e4eb8456793483d7e47b	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin LC-ESI-QTOF 35V, positive-QTOF	splash10-000i-0910000000-1b26412c239d13150a16	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin LC-ESI-QQQ , positive-QTOF	splash10-0a4i-0090000000-5a6df4ef73b17801c15b	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin LC-ESI-QFT 17V, positive-QTOF	splash10-0a4r-0390000000-030c074282d57f882ea6	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin LC-ESI-IT 17V, positive-QTOF	splash10-000j-0970000000-cc482ab502fe16da0b2c	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin 20V, Positive-QTOF	splash10-014r-0900000000-8829ca13726fa5ef2894	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin 20V, Negative-QTOF	splash10-014i-0900000000-7e114a20c600b4c23218	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin 40V, Negative-QTOF	splash10-014i-2900000000-00ac566b03c0d20a16bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin 35V, Negative-QTOF	splash10-014r-0900000000-37f3374e06351b592624	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin 35V, Positive-QTOF	splash10-000i-0910000000-afbe3e4c5fceeb057aac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin 30V, Negative-QTOF	splash10-014i-1900000000-541af142929c530ffba1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Liquiritigenin 10V, Negative-QTOF	splash10-0ap0-0970000000-5d4e47f2631f47124cc4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 10V, Positive-QTOF	splash10-0a4i-0290000000-93474b44c5d1cb8cb155	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 20V, Positive-QTOF	splash10-052r-0790000000-572e47bb5dd6e39a5083	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 40V, Positive-QTOF	splash10-00rj-5910000000-47c758a4f16f999867aa	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 10V, Negative-QTOF	splash10-0a4i-0090000000-b48d7117a74eb8dea54d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 20V, Negative-QTOF	splash10-0a4i-0290000000-24d9ef16fb94c78f6cd9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 40V, Negative-QTOF	splash10-014u-6930000000-82d8508c6ca9b5e8be2a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 10V, Negative-QTOF	splash10-0a4i-0090000000-74e7833e04a924835b1e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liquiritigenin 20V, Negative-QTOF	splash10-0a4r-0790000000-f21efeafedd047dfaebd	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

DB03601

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Liquiritigenin

METLIN ID

Not Available

PubChem Compound

114829

PDB ID

Not Available

ChEBI ID

28777

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1749581

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 Liquiritigenin (HMDB0029519)

MOL for HMDB0029519 (Liquiritigenin)

3D MOL for HMDB0029519 (Liquiritigenin)

3D SDF for HMDB0029519 (Liquiritigenin)

3D-SDF for HMDB0029519 (Liquiritigenin)

PDB for HMDB0029519 (Liquiritigenin)

3D PDB for HMDB0029519 (Liquiritigenin)

SMILES for HMDB0029519 (Liquiritigenin)

INCHI for HMDB0029519 (Liquiritigenin)

Structure for HMDB0029519 (Liquiritigenin)

3D Structure for HMDB0029519 (Liquiritigenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra