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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:33:30 UTC

Update Date

2022-03-07 02:55:16 UTC

HMDB ID

HMDB0037320

Secondary Accession Numbers

HMDB37320

Metabolite Identification

Common Name

Licochalcone B

Description

Licochalcone B 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. Thus, licochalcone b is considered to be a flavonoid. Licochalcone B has been detected, but not quantified in, several different foods, such as herbal tea, green tea, black tea, teas (Camellia sinensis), and red tea. This could make licochalcone b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Licochalcone B.

Structure

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

HMDB0037320
     RDKit          3D
Licochalcone B
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.3226   -2.4522    1.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941   -1.8895    0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1371   -0.5584   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    0.1039   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -0.6707   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -0.1751   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053   -0.9818    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -2.1988    0.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -0.4407    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -1.2606    0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4454   -0.8107    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    0.5100    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0374    0.9494    0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6646    1.3399   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663    0.8747   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851    1.4356   -0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    2.1228   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2467    1.4926   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128    2.1984   -1.1298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2938    0.1340   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5468   -0.4895   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786   -3.1658    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2509   -1.7019    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899   -3.0044    1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617   -1.7318    0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    0.8683   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.2961    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864   -1.4546    0.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6149    0.9247   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8692    2.3721   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447    1.5646   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    1.9482   -0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0389    3.1893   -1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542    3.1779   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3529    0.0762   -0.7186 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  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20  3  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061309422D          

 21 22  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
 10  2  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21  1  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037320

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-21-16-11(5-9-14(19)15(16)20)4-8-13(18)10-2-6-12(17)7-3-10/h2-9,17,19-20H,1H3/b8-4+

> <INCHI_KEY>
DRDRYGIIYOPBBZ-XBXARRHUSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.515283894531635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.821958078333333

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.271110716637406

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.855134456643042

> <JCHEM_PKA_STRONGEST_BASIC>
-4.917284412328462

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
79.2829

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
licochalcone B

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037320
     RDKit          3D
Licochalcone B
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.3226   -2.4522    1.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941   -1.8895    0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1371   -0.5584   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    0.1039   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -0.6707   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -0.1751   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053   -0.9818    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -2.1988    0.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -0.4407    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -1.2606    0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4454   -0.8107    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    0.5100    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0374    0.9494    0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6646    1.3399   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663    0.8747   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851    1.4356   -0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    2.1228   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2467    1.4926   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128    2.1984   -1.1298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2938    0.1340   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5468   -0.4895   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786   -3.1658    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2509   -1.7019    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899   -3.0044    1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617   -1.7318    0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    0.8683   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.2961    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864   -1.4546    0.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6149    0.9247   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8692    2.3721   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447    1.5646   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    1.9482   -0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0389    3.1893   -1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542    3.1779   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3529    0.0762   -0.7186 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  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20  3  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    6   10                                                       
CONECT    3    7   10                                                       
CONECT    4    8   11                                                       
CONECT    5    9   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   12                                                       
CONECT    8    4   13                                                       
CONECT    9    5   14                                                       
CONECT   10    2    3   13                                                  
CONECT   11    4    5   16                                                  
CONECT   12    6    7   17                                                  
CONECT   13    8   10   18                                                  
CONECT   14    9   15   19                                                  
CONECT   15   14   16   20                                                  
CONECT   16   11   15   21                                                  
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21    1   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0037320
HETATM    1  C1  UNL     1      -3.323  -2.452   1.279  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.194  -1.889   0.011  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.137  -0.558  -0.293  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.914   0.104  -0.341  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.688  -0.671  -0.055  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.525  -0.175  -0.065  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.705  -0.982   0.225  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.549  -2.199   0.494  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.055  -0.441   0.216  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.144  -1.261   0.500  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.445  -0.811   0.509  1.00  0.00           C  
HETATM   12  C10 UNL     1       5.722   0.510   0.226  1.00  0.00           C  
HETATM   13  O3  UNL     1       7.037   0.949   0.238  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.665   1.340  -0.058  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.366   0.875  -0.063  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.885   1.436  -0.647  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.034   2.123  -0.906  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.247   1.493  -0.865  1.00  0.00           C  
HETATM   19  O4  UNL     1      -5.413   2.198  -1.130  1.00  0.00           O  
HETATM   20  C16 UNL     1      -4.294   0.134  -0.554  1.00  0.00           C  
HETATM   21  O5  UNL     1      -5.547  -0.489  -0.518  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.479  -3.166   1.420  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.251  -1.702   2.079  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.290  -3.004   1.306  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.762  -1.732   0.185  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.659   0.868  -0.295  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.952  -2.296   0.724  1.00  0.00           H  
HETATM   28  H7  UNL     1       6.286  -1.455   0.731  1.00  0.00           H  
HETATM   29  H8  UNL     1       7.615   0.925  -0.591  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.869   2.372  -0.280  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.545   1.565  -0.294  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.938   1.948  -0.684  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.039   3.189  -1.154  1.00  0.00           H  
HETATM   34  H13 UNL     1      -5.354   3.178  -1.352  1.00  0.00           H  
HETATM   35  H14 UNL     1      -6.353   0.076  -0.719  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   16
CONECT    5    6    6   25
CONECT    6    7   26
CONECT    7    8    8    9
CONECT    9   10   10   15
CONECT   10   11   27
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29
CONECT   14   15   15   30
CONECT   15   31
CONECT   16   17   17   32
CONECT   17   18   33
CONECT   18   19   20   20
CONECT   19   34
CONECT   20   21
CONECT   21   35
END

HMDB0037320
     RDKit          3D
Licochalcone B
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.3226   -2.4522    1.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941   -1.8895    0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1371   -0.5584   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    0.1039   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6882   -0.6707   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -0.1751   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7053   -0.9818    0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -2.1988    0.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545   -0.4407    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -1.2606    0.5004 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4454   -0.8107    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    0.5100    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0374    0.9494    0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6646    1.3399   -0.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3663    0.8747   -0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8851    1.4356   -0.6473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    2.1228   -0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2467    1.4926   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4128    2.1984   -1.1298 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2938    0.1340   -0.5538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5468   -0.4895   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786   -3.1658    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2509   -1.7019    2.0785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899   -3.0044    1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617   -1.7318    0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6594    0.8683   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9517   -2.2961    0.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2864   -1.4546    0.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6149    0.9247   -0.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8692    2.3721   -0.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5447    1.5646   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379    1.9482   -0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0389    3.1893   -1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3542    3.1779   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3529    0.0762   -0.7186 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  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 20  3  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 19 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4,4'-Trihydroxy-2-methoxychalcone	HMDB
3-(3,4-Dihydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

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

Traditional Name

licochalcone B

CAS Registry Number

58749-23-8

SMILES

COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O

InChI Identifier

InChI=1S/C16H14O5/c1-21-16-11(5-9-14(19)15(16)20)4-8-13(18)10-2-6-12(17)7-3-10/h2-9,17,19-20H,1H3/b8-4+

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120434 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037320)

Cellular substructure

Membrane (HMDB: HMDB0037320)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037320)

Source

Exogenous

Food

Food (HMDB: HMDB0037320)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037320)

Not Available

Nutrient (HMDB: HMDB0037320)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 - 197 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1011 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	0.037 g/L	ALOGPS
logP	3.17	ALOGPS
logP	2.82	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.28 m³·mol⁻¹	ChemAxon
Polarizability	29.52 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]+	167.486	30932474
DeepCCS	[M-H]-	165.128	30932474
DeepCCS	[M-2H]-	198.873	30932474
DeepCCS	[M+Na]+	174.1	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.2	32859911
AllCCS	[M+NH4]+	170.5	32859911
AllCCS	[M+Na]+	171.5	32859911
AllCCS	[M-H]-	166.2	32859911
AllCCS	[M+Na-2H]-	165.9	32859911
AllCCS	[M+HCOO]-	165.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Licochalcone B	COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O	4715.0	Standard polar	33892256
Licochalcone B	COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O	2856.4	Standard non polar	33892256
Licochalcone B	COC1=C(\C=C\C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O	3203.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Licochalcone B,1TMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O)=C1O	2979.3	Semi standard non polar	33892256
Licochalcone B,1TMS,isomer #2	COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C)=C1O	2967.9	Semi standard non polar	33892256
Licochalcone B,1TMS,isomer #3	COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O[Si](C)(C)C	2929.4	Semi standard non polar	33892256
Licochalcone B,2TMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O[Si](C)(C)C)=C1O	2954.6	Semi standard non polar	33892256
Licochalcone B,2TMS,isomer #2	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O)=C1O[Si](C)(C)C	2940.0	Semi standard non polar	33892256
Licochalcone B,2TMS,isomer #3	COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	2896.6	Semi standard non polar	33892256
Licochalcone B,3TMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C)C=C2)C=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	2939.1	Semi standard non polar	33892256
Licochalcone B,1TBDMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O)=C1O	3275.5	Semi standard non polar	33892256
Licochalcone B,1TBDMS,isomer #2	COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O	3260.7	Semi standard non polar	33892256
Licochalcone B,1TBDMS,isomer #3	COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O)=C1O[Si](C)(C)C(C)(C)C	3225.6	Semi standard non polar	33892256
Licochalcone B,2TBDMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O	3534.7	Semi standard non polar	33892256
Licochalcone B,2TBDMS,isomer #2	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O)=C1O[Si](C)(C)C(C)(C)C	3496.1	Semi standard non polar	33892256
Licochalcone B,2TBDMS,isomer #3	COC1=C(/C=C/C(=O)C2=CC=C(O)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3481.8	Semi standard non polar	33892256
Licochalcone B,3TBDMS,isomer #1	COC1=C(/C=C/C(=O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	3699.0	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 - Licochalcone B GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-2690000000-358dcbfa3ef3c89c6b8d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licochalcone B GC-MS (3 TMS) - 70eV, Positive	splash10-000i-0001900000-dcef9c9a4d3d7beda21a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Licochalcone B 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 - Licochalcone B , positive-QTOF	splash10-00di-0930000000-e66ffb2c5d7bf56f571b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Licochalcone B 20V, Negative-QTOF	splash10-0udi-0930000000-db3da56b339271a7bace	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Licochalcone B 40V, Negative-QTOF	splash10-0uka-0900000000-ecea7b5e35d6a0033c7a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Licochalcone B 40V, Positive-QTOF	splash10-00di-0900000000-f64407be17876dad151f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Licochalcone B 10V, Negative-QTOF	splash10-000i-0190000000-1717e8fef49c860a66fc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Licochalcone B 20V, Positive-QTOF	splash10-00di-0910000000-38b594f6092ab3d6cade	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Licochalcone B 10V, Positive-QTOF	splash10-000i-0490000000-cd3ab1dc17d4a17a97df	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 10V, Positive-QTOF	splash10-000i-0190000000-5af3dba7415fbbef4e66	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 20V, Positive-QTOF	splash10-00ri-0970000000-1c965c89876c67e3c3cc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 40V, Positive-QTOF	splash10-00dl-4900000000-1b3b1aeda1e725cdd1d9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 10V, Negative-QTOF	splash10-000i-0290000000-c2652c467cc82725fd20	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 20V, Negative-QTOF	splash10-00kr-0490000000-f6e00598644f89e80774	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 40V, Negative-QTOF	splash10-01bc-5950000000-be797e2f0744297850f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 10V, Negative-QTOF	splash10-000i-0090000000-47410b095ae44693234e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 20V, Negative-QTOF	splash10-0udr-1390000000-62e6742a1fbf9f08a234	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 40V, Negative-QTOF	splash10-006x-4920000000-cb245567146abdcd29a3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 10V, Positive-QTOF	splash10-000i-0190000000-d30f02e34f4320b2aa52	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 20V, Positive-QTOF	splash10-0076-2930000000-de7b822b51d0d1e215ba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Licochalcone B 40V, Positive-QTOF	splash10-05fu-5910000000-3943a7ba7c64e061b6d7	2021-09-24	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

FDB016340

KNApSAcK ID

C00006938

Chemspider ID

4477423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318999

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859811

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 Licochalcone B (HMDB0037320)

MOL for HMDB0037320 (Licochalcone B)

3D MOL for HMDB0037320 (Licochalcone B)

3D SDF for HMDB0037320 (Licochalcone B)

3D-SDF for HMDB0037320 (Licochalcone B)

PDB for HMDB0037320 (Licochalcone B)

3D PDB for HMDB0037320 (Licochalcone B)

SMILES for HMDB0037320 (Licochalcone B)

INCHI for HMDB0037320 (Licochalcone B)

Structure for HMDB0037320 (Licochalcone B)

3D Structure for HMDB0037320 (Licochalcone B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra