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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-17 19:01:04 UTC

Update Date

2020-04-07 19:17:34 UTC

HMDB ID

HMDB0132893

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Helichysetin

Description

Helichrysetin, also known as 2',4',4-trihydroxy-6'-methoxychalcone, belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing a chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, helichrysetin is considered to be a flavonoid lipid molecule. Helichrysetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. BioTransformer predicts that helichysetin is a product of 2'-O-methylisoliquiritigenin metabolism via a hydroxylation-of-benzene-ortho-to-edg reaction catalyzed by CYP2C9 and CYP2C19 enzymes (PMID: 30612223 ).

Structure

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

HMDB0132893
     RDKit          3D
Helichysetin
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.3455   -2.3783   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -1.7245   -0.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -0.3786   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    0.3484   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    1.6812    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4604    2.3962    0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    2.2484    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590    1.5339    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    2.2019    0.7298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8843    0.2157    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103   -0.5944   -0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486   -1.8235   -0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -0.1661    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418   -1.0489    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.6498    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535    0.6104    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6992    0.9309    0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874   -0.0083    0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0211    0.2784    0.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3139   -1.2767    0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0132   -1.6092    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649   -2.0474   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2528   -3.4663   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0779   -2.1418   -0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180   -0.1250   -0.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464    2.9095   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973    3.2773    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089    3.1532    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    0.8321    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055   -2.0565   -0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723    1.4068    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9642    1.9296    1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4585    0.1600    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0985   -2.0087    0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143   -2.6100   -0.2075 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10  3  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

  Mrv1652304072021162D          

 21 22  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
 9999.3089 9998.7624    0.0000 O   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
10000.0234 9999.1760    0.0000 C   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
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  5  7  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 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 10  1  0  0  0  0
  1 15  1  0  0  0  0
 14  5  1  0  0  0  0
 10  6  1  0  0  0  0
 12  8  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 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 16  1  0  0  0  0
  4 18  1  0  0  0  0
 21  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0132893

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

> <INCHI_KEY>
OWGUBYRKZATRIT-QPJJXVBHSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.460257768072342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.4719580783333335

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.60957329894507

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.191991341437985

> <JCHEM_PKA_STRONGEST_BASIC>
-4.895833429103171

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
79.2829

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
helichrysetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0132893
     RDKit          3D
Helichysetin
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.3455   -2.3783   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -1.7245   -0.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -0.3786   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    0.3484   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    1.6812    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4604    2.3962    0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    2.2484    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590    1.5339    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    2.2019    0.7298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8843    0.2157    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103   -0.5944   -0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486   -1.8235   -0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -0.1661    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418   -1.0489    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.6498    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535    0.6104    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6992    0.9309    0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874   -0.0083    0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0211    0.2784    0.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3139   -1.2767    0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0132   -1.6092    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649   -2.0474   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2528   -3.4663   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0779   -2.1418   -0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180   -0.1250   -0.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464    2.9095   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973    3.2773    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089    3.1532    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    0.8321    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055   -2.0565   -0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723    1.4068    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9642    1.9296    1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4585    0.1600    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0985   -2.0087    0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143   -2.6100   -0.2075 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10  3  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  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    8665.3778664.356   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.7098668.977   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8666.7108665.129   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8660.0428664.356   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8673.3848664.356   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8662.7098667.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.3768666.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.3768665.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.7098664.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0438665.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.0438666.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8672.0498666.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8670.7158667.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.3818666.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.3818665.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8670.7158664.357   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.0498665.127   0.000  0.00  0.00           C+0
CONECT    1    2    3   15                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2   18                                                       
CONECT    5    7   14                                                       
CONECT    6   10                                                            
CONECT    7    5                                                            
CONECT    8   12                                                            
CONECT    9   21                                                            
CONECT   10   11   15    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13    8                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15    5                                                  
CONECT   15   14   10    1                                                  
CONECT   16   17   21                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19    4                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0132893
HETATM    1  C1  UNL     1       4.346  -2.378  -0.889  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.125  -1.725  -0.593  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.125  -0.379  -0.217  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.263   0.348  -0.119  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.285   1.681   0.251  1.00  0.00           C  
HETATM    6  O2  UNL     1       5.460   2.396   0.342  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.065   2.248   0.523  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.859   1.534   0.435  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.687   2.202   0.730  1.00  0.00           O  
HETATM   10  C7  UNL     1       1.884   0.216   0.064  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.710  -0.594  -0.054  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.849  -1.823  -0.410  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.636  -0.166   0.191  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.642  -1.049   0.037  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.000  -0.650   0.274  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.353   0.610   0.659  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.699   0.931   0.873  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.687  -0.008   0.702  1.00  0.00           C  
HETATM   19  O5  UNL     1      -7.021   0.278   0.906  1.00  0.00           O  
HETATM   20  C15 UNL     1      -5.314  -1.277   0.313  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.013  -1.609   0.100  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.765  -2.047  -1.852  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.253  -3.466  -0.912  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.078  -2.142  -0.077  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.218  -0.125  -0.340  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.846   2.909  -0.451  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.997   3.277   0.817  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.709   3.153   0.994  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.845   0.832   0.489  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.406  -2.057  -0.267  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.672   1.407   0.819  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.964   1.930   1.177  1.00  0.00           H  
HETATM   33  H12 UNL     1      -7.459   0.160   1.803  1.00  0.00           H  
HETATM   34  H13 UNL     1      -6.099  -2.009   0.181  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.714  -2.610  -0.207  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8   27
CONECT    8    9   10   10
CONECT    9   28
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   29
CONECT   14   15   30
CONECT   15   16   16   21
CONECT   16   17   31
CONECT   17   18   18   32
CONECT   18   19   20
CONECT   19   33
CONECT   20   21   21   34
CONECT   21   35
END

HMDB0132893
     RDKit          3D
Helichysetin
 35 36  0  0  0  0  0  0  0  0999 V2000
    4.3455   -2.3783   -0.8887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255   -1.7245   -0.5932 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1249   -0.3786   -0.2170 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    0.3484   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    1.6812    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4604    2.3962    0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0646    2.2484    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590    1.5339    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    2.2019    0.7298 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8843    0.2157    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7103   -0.5944   -0.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486   -1.8235   -0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -0.1661    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418   -1.0489    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9999   -0.6498    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3535    0.6104    0.6592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6992    0.9309    0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874   -0.0083    0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0211    0.2784    0.9060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3139   -1.2767    0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0132   -1.6092    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649   -2.0474   -1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2528   -3.4663   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0779   -2.1418   -0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180   -0.1250   -0.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8464    2.9095   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9973    3.2773    0.8165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7089    3.1532    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    0.8321    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4055   -2.0565   -0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6723    1.4068    0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9642    1.9296    1.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4585    0.1600    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0985   -2.0087    0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143   -2.6100   -0.2075 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  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 10  3  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
(2E)-1-(2,4-Dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
2',4',4-Trihydroxy-6'-methoxychalcone	HMDB
2’,4’,4-trihydroxy-6’-methoxychalcone	HMDB
4,2',4'-Trihydroxy-6'-methoxychalcone	HMDB
4,2’,4’-trihydroxy-6’-methoxychalcone	HMDB
Helichrysetin	HMDB
Helichysetin	ChEMBL, HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.283

Monoisotopic Molecular Weight

286.084123551

IUPAC Name

(2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

helichrysetin

CAS Registry Number

62014-87-3

SMILES

COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=CC(O)=C1

InChI Identifier

InChI=1S/C16H14O5/c1-21-15-9-12(18)8-14(20)16(15)13(19)7-4-10-2-5-11(17)6-3-10/h2-9,17-18,20H,1H3/b7-4+

InChI Key

OWGUBYRKZATRIT-QPJJXVBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Phenol ether
Resorcinol
Styrene
Aryl ketone
Benzoyl
Anisole
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Vinylogous acid
Enone
Alpha,beta-unsaturated ketone
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120300 )

Ontology

Not Available

Endogenous (HMDB: HMDB0132893)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.16	ALOGPS
logP	3.47	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.19	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	29.46 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]+	172.601	30932474
DeepCCS	[M-H]-	170.243	30932474
DeepCCS	[M-2H]-	203.887	30932474
DeepCCS	[M+Na]+	179.113	30932474
AllCCS	[M+H]+	166.7	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.2	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
Helichysetin	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=CC(O)=C1	4629.0	Standard polar	33892256
Helichysetin	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=CC(O)=C1	2860.4	Standard non polar	33892256
Helichysetin	COC1=C(C(=O)\C=C\C2=CC=C(O)C=C2)C(O)=CC(O)=C1	3155.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Helichysetin,1TMS,isomer #1	COC1=CC(O)=CC(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2884.4	Semi standard non polar	33892256
Helichysetin,1TMS,isomer #2	COC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	2903.4	Semi standard non polar	33892256
Helichysetin,1TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)/C=C/C1=CC=C(O)C=C1	2910.0	Semi standard non polar	33892256
Helichysetin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2843.9	Semi standard non polar	33892256
Helichysetin,2TMS,isomer #2	COC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2837.3	Semi standard non polar	33892256
Helichysetin,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	2839.6	Semi standard non polar	33892256
Helichysetin,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2867.4	Semi standard non polar	33892256
Helichysetin,1TBDMS,isomer #1	COC1=CC(O)=CC(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3195.5	Semi standard non polar	33892256
Helichysetin,1TBDMS,isomer #2	COC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3200.5	Semi standard non polar	33892256
Helichysetin,1TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3183.7	Semi standard non polar	33892256
Helichysetin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3447.2	Semi standard non polar	33892256
Helichysetin,2TBDMS,isomer #2	COC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3437.6	Semi standard non polar	33892256
Helichysetin,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O)C=C1	3419.9	Semi standard non polar	33892256
Helichysetin,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3703.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Helichysetin GC-MS (3 TMS) - 70eV, Positive	splash10-000i-1122900000-478d469d537cc9e85bdc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Helichysetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1970000000-599f1e5e3ace3e387ffe	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Helichysetin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 10V, Positive-QTOF	splash10-000i-0390000000-3afb99003f089ac2a708	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 20V, Positive-QTOF	splash10-0ap0-0940000000-78520a163728b2d8100e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 40V, Positive-QTOF	splash10-05pa-6910000000-8821d33bfae1015a8efd	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 10V, Negative-QTOF	splash10-000i-0390000000-3a6efb88a1a4573df24a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 20V, Negative-QTOF	splash10-000i-0950000000-002ed99305d709b4e81b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 40V, Negative-QTOF	splash10-0pb9-4920000000-0df9df5e553d457f5bdc	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 10V, Positive-QTOF	splash10-000i-0490000000-5eb5bc53a5aecb20fa7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 20V, Positive-QTOF	splash10-014i-0900000000-38e3cf94d1c9e348ee6c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 40V, Positive-QTOF	splash10-0gb9-3900000000-5cf07aa3e1827f51a83d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 10V, Negative-QTOF	splash10-000i-0290000000-5fff757e2e18668b90e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 20V, Negative-QTOF	splash10-00kr-0980000000-f118b64ac4fb2abd4dd7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helichysetin 40V, Negative-QTOF	splash10-014i-4910000000-e6f48f8e1fd32b9907a7	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB089950

KNApSAcK ID

C00006954

Chemspider ID

4863252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6253344

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1462731

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Showing metabocard for Helichysetin (HMDB0132893)

MOL for HMDB0132893 (Helichysetin)

3D MOL for HMDB0132893 (Helichysetin)

3D SDF for HMDB0132893 (Helichysetin)

3D-SDF for HMDB0132893 (Helichysetin)

PDB for HMDB0132893 (Helichysetin)

3D PDB for HMDB0132893 (Helichysetin)

SMILES for HMDB0132893 (Helichysetin)

INCHI for HMDB0132893 (Helichysetin)

Structure for HMDB0132893 (Helichysetin)

3D Structure for HMDB0132893 (Helichysetin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra