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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:33:27 UTC

Update Date

2022-03-07 02:55:16 UTC

HMDB ID

HMDB0037319

Secondary Accession Numbers

HMDB37319

Metabolite Identification

Common Name

2'-O-Methylisoliquiritigenin

Description

2'-O-Methylisoliquiritigenin (CAS: 51828-10-5), also known as 4,4'-dihydroxy-2'-methoxychalcone or 3-deoxysappanchalcone, belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. Thus, 2'-O-methylisoliquiritigenin is considered to be a flavonoid lipid molecule. 2'-O-Methylisoliquiritigenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2'-O-Methylisoliquiritigenin is a stress metabolite of Pisum sativum (pea).

Structure

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

HMDB0037319
     RDKit          3D
2'-O-Methylisoliquiritigenin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.7031   -2.3287    0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -1.8360    0.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1394   -0.4894    0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089    0.3582    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0283    1.7147    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093    2.5791    0.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7619    2.2164    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6622    1.3806    0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8361    0.0168    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -0.9317    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1946   -2.1800    0.3827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148   -0.8714    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.1186   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941    0.0197   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -1.1645   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9751   -1.1923   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078   -0.0533   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0841   -0.1318   -0.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0384    1.1491   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    1.1676   -0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2137   -1.8185    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3063   -2.1614   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7071   -3.4095    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2301    0.0181    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5938    2.8260   -0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    3.2745   -0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    1.8318   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055   -1.8626    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    1.1229   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -2.1013    0.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720   -2.1562   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6037    0.7196   -0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    2.0413   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    2.1337   -0.4013 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9  3  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1652304072023402D          

 20 21  0  0  0  0            999 V2000
 9999.308910000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0234 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.308910001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.738110000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880010001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4511 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5988 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880010000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.165610000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1656 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8800 9998.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5945 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594510000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.883310000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.168910000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.454310000.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4543 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1687 9998.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8833 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.165610001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  1 13  1  0  0  0  0
  8  5  1  0  0  0  0
 10  6  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
 19 14  1  0  0  0  0
  4 16  1  0  0  0  0
 19  7  1  0  0  0  0
  5 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037319

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+

> <INCHI_KEY>
PACBGANPVNHGNP-RUDMXATFSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.642672720828052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.1255233999999996

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.067578960400153

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.89416895889298

> <JCHEM_PKA_STRONGEST_BASIC>
-4.885442490286645

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
77.30199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-deoxysappanchalcone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037319
     RDKit          3D
2'-O-Methylisoliquiritigenin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.7031   -2.3287    0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -1.8360    0.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1394   -0.4894    0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089    0.3582    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0283    1.7147    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093    2.5791    0.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7619    2.2164    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6622    1.3806    0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8361    0.0168    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -0.9317    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1946   -2.1800    0.3827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148   -0.8714    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.1186   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941    0.0197   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -1.1645   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9751   -1.1923   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078   -0.0533   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0841   -0.1318   -0.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0384    1.1491   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    1.1676   -0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2137   -1.8185    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3063   -2.1614   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7071   -3.4095    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2301    0.0181    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5938    2.8260   -0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    3.2745   -0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    1.8318   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055   -1.8626    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    1.1229   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -2.1013    0.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720   -2.1562   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6037    0.7196   -0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    2.0413   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    2.1337   -0.4013 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9  3  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 07-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-APR-20         0                                  
HETATM    1  C   UNK     0    8665.3778667.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.7108666.666   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.3778668.977   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8668.0448667.437   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8662.7098668.977   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.0428664.356   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8673.3848664.356   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8662.7098667.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3768666.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.3768665.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.7098664.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0438665.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0438666.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8672.0498666.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.7158667.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.3818666.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.3818665.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.7158664.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.0498665.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.3768669.747   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2   16                                                       
CONECT    5    8   20                                                       
CONECT    6   10                                                            
CONECT    7   19                                                            
CONECT    8    9   13    5                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8    1                                                  
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    4                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14    7                                                  
CONECT   20    5                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0037319
HETATM    1  C1  UNL     1      -4.703  -2.329   0.671  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.393  -1.836   0.518  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.139  -0.489   0.360  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.209   0.358   0.356  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.028   1.715   0.202  1.00  0.00           C  
HETATM    6  O2  UNL     1      -5.109   2.579   0.197  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.762   2.216   0.052  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.662   1.381   0.052  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.836   0.017   0.206  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.782  -0.932   0.222  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.195  -2.180   0.383  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.615  -0.871   0.106  1.00  0.00           C  
HETATM   13  C10 UNL     1       1.414   0.119  -0.058  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.894   0.020  -0.164  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.576  -1.165  -0.095  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.975  -1.192  -0.201  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.708  -0.053  -0.376  1.00  0.00           C  
HETATM   18  O4  UNL     1       7.084  -0.132  -0.475  1.00  0.00           O  
HETATM   19  C15 UNL     1       5.038   1.149  -0.448  1.00  0.00           C  
HETATM   20  C16 UNL     1       3.666   1.168  -0.342  1.00  0.00           C  
HETATM   21  H1  UNL     1      -5.214  -1.819   1.534  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.306  -2.161  -0.261  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.707  -3.410   0.868  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.230   0.018   0.470  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.594   2.826  -0.655  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.591   3.275  -0.071  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.693   1.832  -0.070  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.205  -1.863   0.163  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.071   1.123  -0.135  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.058  -2.101   0.043  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.472  -2.156  -0.140  1.00  0.00           H  
HETATM   32  H12 UNL     1       7.604   0.720  -0.603  1.00  0.00           H  
HETATM   33  H13 UNL     1       5.632   2.041  -0.586  1.00  0.00           H  
HETATM   34  H14 UNL     1       3.141   2.134  -0.401  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   15   20
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   19
CONECT   18   32
CONECT   19   20   20   33
CONECT   20   34
END

HMDB0037319
     RDKit          3D
2'-O-Methylisoliquiritigenin
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.7031   -2.3287    0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3928   -1.8360    0.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1394   -0.4894    0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2089    0.3582    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0283    1.7147    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1093    2.5791    0.1971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7619    2.2164    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6622    1.3806    0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8361    0.0168    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -0.9317    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1946   -2.1800    0.3827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148   -0.8714    0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    0.1186   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8941    0.0197   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -1.1645   -0.0945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9751   -1.1923   -0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078   -0.0533   -0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0841   -0.1318   -0.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0384    1.1491   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6658    1.1676   -0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2137   -1.8185    1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3063   -2.1614   -0.2612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7071   -3.4095    0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2301    0.0181    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5938    2.8260   -0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5910    3.2745   -0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926    1.8318   -0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2055   -1.8626    0.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    1.1229   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0576   -2.1013    0.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4720   -2.1562   -0.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6037    0.7196   -0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6319    2.0413   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    2.1337   -0.4013 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
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9  3  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Dihydroxy-2'-methoxychalcone	ChEBI
Isoliquiritigenin 2'-methy ether	HMDB
3-Deoxysappanchalcone	MeSH, HMDB
(2E)-1-(4-Hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
1-(4-Hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
2'-Methoxyisoliquiritigenin	HMDB
2'-Methylisoliquiritigenin	HMDB
2'-O-Methylisoliquiritigenin	HMDB
2’-Methoxyisoliquiritigenin	HMDB
2’-Methylisoliquiritigenin	HMDB
2’-O-Methylisoliquiritigenin	HMDB
3-(4-Hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one	HMDB
4,4’-Dihydroxy-2’-methoxychalcone	HMDB
Isoliquiritigenin 2'-methyl ether	HMDB
Isoliquiritigenin 2’-methyl ether	HMDB

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

IUPAC Name

(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

3-deoxysappanchalcone

CAS Registry Number

112408-67-0

SMILES

COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+

InChI Key

PACBGANPVNHGNP-RUDMXATFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Cinnamylphenols

Direct Parent

Cinnamylphenols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:519567 )
monomethoxybenzene (CHEBI:519567 )
chalcones (CHEBI:519567 )
chalcones (C15531 )
Chalcones and dihydrochalcones (LMPK12120098 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037319)

Cellular substructure

Membrane (HMDB: HMDB0037319)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037319)

Source

Endogenous

Plant

Fabaceae (HMDB: HMDB0037319)
Plant (HMDB: HMDB0037319)

Exogenous

Food

Food (HMDB: HMDB0037319)

Pulse

Pea

Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Not Available

Nutrient (HMDB: HMDB0037319)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 - 212 °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	0.023 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.13	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.89	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	4	ChemAxon
Refractivity	77.3 m³·mol⁻¹	ChemAxon
Polarizability	28.64 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]+	168.707	30932474
DeepCCS	[M-H]-	166.349	30932474
DeepCCS	[M-2H]-	199.235	30932474
DeepCCS	[M+Na]+	174.8	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.3	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	163.4	32859911
AllCCS	[M+HCOO]-	163.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2'-O-Methylisoliquiritigenin	COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1	4342.5	Standard polar	33892256
2'-O-Methylisoliquiritigenin	COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1	2677.2	Standard non polar	33892256
2'-O-Methylisoliquiritigenin	COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1	2978.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2'-O-Methylisoliquiritigenin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O)C=C1	2799.6	Semi standard non polar	33892256
2'-O-Methylisoliquiritigenin,1TMS,isomer #2	COC1=CC(O)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2813.5	Semi standard non polar	33892256
2'-O-Methylisoliquiritigenin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2824.1	Semi standard non polar	33892256
2'-O-Methylisoliquiritigenin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O)C=C1	3063.3	Semi standard non polar	33892256
2'-O-Methylisoliquiritigenin,1TBDMS,isomer #2	COC1=CC(O)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3098.4	Semi standard non polar	33892256
2'-O-Methylisoliquiritigenin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3375.3	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'-O-Methylisoliquiritigenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zfr-0970000000-da53691eb80b42283f35	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-O-Methylisoliquiritigenin GC-MS (2 TMS) - 70eV, Positive	splash10-006y-1249200000-6f33947cad76377fa989	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2'-O-Methylisoliquiritigenin 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'-O-Methylisoliquiritigenin , positive-QTOF	splash10-00di-0920000000-08ee4123d744fbaeb767	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Positive-QTOF	splash10-00di-0290000000-d7f4f496b64c815f02c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Positive-QTOF	splash10-0uka-0960000000-a4e95566966f0337e292	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Positive-QTOF	splash10-01ba-4910000000-eeafd6d970e54ae279b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Negative-QTOF	splash10-014i-0290000000-c4e9856285707151c722	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Negative-QTOF	splash10-014i-0590000000-2242dd1e9b5a297c52a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Negative-QTOF	splash10-06dr-5920000000-82cb523aefcbbfa3c088	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Positive-QTOF	splash10-00di-0090000000-3a2225995fb790b444d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Positive-QTOF	splash10-0f6t-0910000000-cc4740823efa036a9fa5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Positive-QTOF	splash10-0ldi-2910000000-2eeebb03ff944c10ad39	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 10V, Negative-QTOF	splash10-014i-0290000000-aa85c230448d752d6795	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 20V, Negative-QTOF	splash10-014s-0920000000-3a2b8141d088f42fa276	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2'-O-Methylisoliquiritigenin 40V, Negative-QTOF	splash10-014i-2960000000-a78eb0f3f2dfc5c55be9	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319688

PDB ID

Not Available

ChEBI ID

519567

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'-O-Methylisoliquiritigenin (HMDB0037319)

MOL for HMDB0037319 (2'-O-Methylisoliquiritigenin)

3D MOL for HMDB0037319 (2'-O-Methylisoliquiritigenin)

3D SDF for HMDB0037319 (2'-O-Methylisoliquiritigenin)

3D-SDF for HMDB0037319 (2'-O-Methylisoliquiritigenin)

PDB for HMDB0037319 (2'-O-Methylisoliquiritigenin)

3D PDB for HMDB0037319 (2'-O-Methylisoliquiritigenin)

SMILES for HMDB0037319 (2'-O-Methylisoliquiritigenin)

INCHI for HMDB0037319 (2'-O-Methylisoliquiritigenin)

Structure for HMDB0037319 (2'-O-Methylisoliquiritigenin)

3D Structure for HMDB0037319 (2'-O-Methylisoliquiritigenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra