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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:38:18 UTC

Update Date

2022-03-07 02:52:38 UTC

HMDB ID

HMDB0030667

Secondary Accession Numbers

HMDB30667

Metabolite Identification

Common Name

Chrysoeriol

Description

Chrysoeriol, also known as 3'-O-methylluteolin, belongs to the class of organic compounds known as 3'-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Thus, chrysoeriol is considered to be a flavonoid lipid molecule. Chrysoeriol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysoeriol is a bitter-tasting compound. Outside of the human body, chrysoeriol has been detected, but not quantified in, several different foods, such as wild celeries, ryes, hard wheat, alfalfa, and triticales. This could make chrysoeriol a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030667
     RDKit          3D
Chrysoeriol
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.9054    0.1418    2.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3652    0.3397    0.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668    0.3690   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1254    0.2023   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    0.2286   -1.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    0.0497   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0975    0.0719   -1.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643   -0.1036   -1.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -0.0826   -2.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8087   -0.2930   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547   -0.4696    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1647   -0.4709   -0.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727   -0.6600    1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.6696    2.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.8632    3.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1850   -0.4938    2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -0.3050    0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752   -0.1337    0.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.4270   -2.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858    0.5960   -2.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9730    0.5682   -1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3318    0.7300   -1.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4406    1.0054    2.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -0.7253    2.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840   -0.1596    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7481    0.0464    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    0.2176   -2.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2068   -0.3659   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   -0.7969    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    0.0079    4.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -0.4987    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656    0.4581   -3.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858    0.7533   -3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7236    0.8784   -2.6119 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  6  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
M  END


  Mrv1652304152022042D          

 22 24  0  0  0  0            999 V2000
    3.5723    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  4  1  0  0  0  0
 14 10  2  0  0  0  0
 15  6  2  0  0  0  0
 16 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  2  0  0  0  0
 21  1  1  0  0  0  0
 21 14  1  0  0  0  0
 22 13  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030667

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3

> <INCHI_KEY>
SCZVLDHREVKTSH-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.735983789529687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.5490178679999995

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.141815517431905

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.576709247833678

> <JCHEM_PKA_STRONGEST_BASIC>
-4.774070434432587

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
79.37710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chrysoeriol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030667
     RDKit          3D
Chrysoeriol
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.9054    0.1418    2.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3652    0.3397    0.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668    0.3690   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1254    0.2023   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    0.2286   -1.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    0.0497   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0975    0.0719   -1.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643   -0.1036   -1.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -0.0826   -2.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8087   -0.2930   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547   -0.4696    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1647   -0.4709   -0.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727   -0.6600    1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.6696    2.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.8632    3.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1850   -0.4938    2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -0.3050    0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752   -0.1337    0.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.4270   -2.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858    0.5960   -2.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9730    0.5682   -1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3318    0.7300   -1.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4406    1.0054    2.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -0.7253    2.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840   -0.1596    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7481    0.0464    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    0.2176   -2.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2068   -0.3659   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   -0.7969    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    0.0079    4.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -0.4987    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656    0.4581   -3.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858    0.7533   -3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7236    0.8784   -2.6119 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  6  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 15-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-20         0                                  
HETATM    1  C   UNK     0       6.668   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   3.465   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -1.155   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.668   1.155   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   3.465   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001  -3.465   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -3.465   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   0.385   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   1.155   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   10                                                       
CONECT    4    8   14                                                       
CONECT    5    9   11                                                       
CONECT    6    9   15                                                       
CONECT    7   12   13                                                       
CONECT    8    2    4   13                                                  
CONECT    9    5    6   17                                                  
CONECT   10    3   14   18                                                  
CONECT   11    5   16   19                                                  
CONECT   12    7   16   20                                                  
CONECT   13    7    8   22                                                  
CONECT   14    4   10   21                                                  
CONECT   15    6   16   22                                                  
CONECT   16   11   12   15                                                  
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21    1   14                                                       
CONECT   22   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030667
HETATM    1  C1  UNL     1      -3.905   0.142   2.113  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.365   0.340   0.817  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.467   0.369  -0.252  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.125   0.202  -0.028  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.219   0.229  -1.078  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.188   0.050  -0.808  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.098   0.072  -1.826  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.464  -0.104  -1.548  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.289  -0.083  -2.479  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.809  -0.293  -0.222  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.155  -0.470   0.084  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.165  -0.471  -0.822  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.473  -0.660   1.443  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.507  -0.670   2.403  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.866  -0.863   3.752  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.185  -0.494   2.082  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.828  -0.305   0.772  1.00  0.00           C  
HETATM   18  O5  UNL     1       0.575  -0.134   0.427  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.716   0.427  -2.344  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.086   0.596  -2.564  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.973   0.568  -1.516  1.00  0.00           C  
HETATM   22  O6  UNL     1      -5.332   0.730  -1.683  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.441   1.005   2.592  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.195  -0.725   2.193  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.784  -0.160   2.739  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.748   0.046   0.979  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.861   0.218  -2.873  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.207  -0.366  -1.769  1.00  0.00           H  
HETATM   29  H7  UNL     1       5.500  -0.797   1.695  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.069   0.008   4.256  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.394  -0.499   2.842  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.066   0.458  -3.205  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.486   0.753  -3.562  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.724   0.878  -2.612  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6   19   19
CONECT    6    7    7   18
CONECT    7    8   27
CONECT    8    9    9   10
CONECT   10   11   11   17
CONECT   11   12   13
CONECT   12   28
CONECT   13   14   14   29
CONECT   14   15   16
CONECT   15   30
CONECT   16   17   17   31
CONECT   17   18
CONECT   19   20   32
CONECT   20   21   21   33
CONECT   21   22
CONECT   22   34
END

HMDB0030667
     RDKit          3D
Chrysoeriol
 34 36  0  0  0  0  0  0  0  0999 V2000
   -3.9054    0.1418    2.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3652    0.3397    0.8171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4668    0.3690   -0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1254    0.2023   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193    0.2286   -1.0782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875    0.0497   -0.8076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0975    0.0719   -1.8263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643   -0.1036   -1.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -0.0826   -2.4787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8087   -0.2930   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1547   -0.4696    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1647   -0.4709   -0.8220 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4727   -0.6600    1.4432 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5068   -0.6696    2.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8658   -0.8632    3.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1850   -0.4938    2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -0.3050    0.7718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5752   -0.1337    0.4274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.4270   -2.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0858    0.5960   -2.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9730    0.5682   -1.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3318    0.7300   -1.6825 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4406    1.0054    2.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950   -0.7253    2.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840   -0.1596    2.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7481    0.0464    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8612    0.2176   -2.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2068   -0.3659   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5001   -0.7969    1.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0686    0.0079    4.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -0.4987    2.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0656    0.4581   -3.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4858    0.7533   -3.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7236    0.8784   -2.6119 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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  6  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 19 32  1  0
 20 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3'-Methoxyapigenin	ChEBI
3'-O-Methylluteolin	ChEBI
5,7,4'-Trihydroxy-3'-methoxyflavone	ChEBI
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone	ChEBI
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Chryseriol	ChEBI
Luteolin 3'-methyl ether	ChEBI
8-Chrysoeriol	MeSH
Chrysoeriol	ChEBI
2-(5-Methoxy,4-hydroxyphenyl)5,7-dihydroxy-benzpyran-4-one	HMDB
3'-Methoxy-4',5,7-trihydroxyflavone	HMDB
3'-O-Methyluteolin	HMDB
4',5,7-Trihydroxy-3'-methoxy-flavone	HMDB
5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
Scoparol	HMDB
3’-Methoxy-4’,5,7-trihydroxyflavone	HMDB
3’-Methoxyapigenin	HMDB
3’-O-Methylluteolin	HMDB
5,7,4’-Trihydroxy-3’-methoxyflavone	HMDB
Chrysoriol	HMDB
Luteolin 3’-methyl ether	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

Traditional Name

chrysoeriol

CAS Registry Number

491-71-4

SMILES

COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3

InChI Key

SCZVLDHREVKTSH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:16514 )
trihydroxyflavone (CHEBI:16514 )
flavones (C04293 )
Flavones and Flavonols (LMPK12110799 )

Ontology

Not Available

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	330 - 331 °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	0.068 g/L	ALOGPS
logP	3.07	ALOGPS
logP	2.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.58	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.38 m³·mol⁻¹	ChemAxon
Polarizability	29.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.002	30932474
DeepCCS	[M-H]-	168.644	30932474
DeepCCS	[M-2H]-	202.104	30932474
DeepCCS	[M+Na]+	177.331	30932474
AllCCS	[M+H]+	168.1	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	171.6	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	167.8	32859911
AllCCS	[M+HCOO]-	167.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chrysoeriol	COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1	4950.9	Standard polar	33892256
Chrysoeriol	COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1	3122.1	Standard non polar	33892256
Chrysoeriol	COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1	3261.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chrysoeriol,1TMS,isomer #1	COC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C	3246.5	Semi standard non polar	33892256
Chrysoeriol,1TMS,isomer #2	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O	3247.2	Semi standard non polar	33892256
Chrysoeriol,1TMS,isomer #3	COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O	3302.7	Semi standard non polar	33892256
Chrysoeriol,2TMS,isomer #1	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C	3113.5	Semi standard non polar	33892256
Chrysoeriol,2TMS,isomer #2	COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C	3189.0	Semi standard non polar	33892256
Chrysoeriol,2TMS,isomer #3	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O	3233.8	Semi standard non polar	33892256
Chrysoeriol,3TMS,isomer #1	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C	3138.0	Semi standard non polar	33892256
Chrysoeriol,1TBDMS,isomer #1	COC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3510.6	Semi standard non polar	33892256
Chrysoeriol,1TBDMS,isomer #2	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O	3508.3	Semi standard non polar	33892256
Chrysoeriol,1TBDMS,isomer #3	COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O	3572.0	Semi standard non polar	33892256
Chrysoeriol,2TBDMS,isomer #1	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3643.6	Semi standard non polar	33892256
Chrysoeriol,2TBDMS,isomer #2	COC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3728.0	Semi standard non polar	33892256
Chrysoeriol,2TBDMS,isomer #3	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O	3747.8	Semi standard non polar	33892256
Chrysoeriol,3TBDMS,isomer #1	COC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC=C1O[Si](C)(C)C(C)(C)C	3894.2	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 - Chrysoeriol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zn9-0591000000-7220607989921b5eb2cf	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysoeriol GC-MS (3 TMS) - 70eV, Positive	splash10-0ukc-2190860000-4372f124a3dd76bf7eee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chrysoeriol 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 - Chrysoeriol ESI-TOF , Negative-QTOF	splash10-0udj-0159000000-3b5e183acbd84887fe16	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 20V, Negative-QTOF	splash10-0udj-0159000000-3b5e183acbd84887fe16	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 40V, Negative-QTOF	splash10-0a59-0190000000-e41a7a0b369e042fae34	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 50V, Negative-QTOF	splash10-057i-0590000000-9bcbe16e3cceb12dd431	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 10V, Negative-QTOF	splash10-057i-0590000000-9bcbe16e3cceb12dd431	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF , Negative-QTOF	splash10-0002-0091010000-c79a20e1046701a4b60a	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 20V, Negative-QTOF	splash10-001j-0090000000-10b8cb8801e211ef50f3	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 40V, Negative-QTOF	splash10-0a59-0190000000-e41a7a0b369e042fae34	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 50V, Negative-QTOF	splash10-057i-0590000000-9bcbe16e3cceb12dd431	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol ESI-TOF 10V, Negative-QTOF	splash10-0002-0091000000-bcccd2fe60d84477404f	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol DI-ESI-qTof , Negative-QTOF	splash10-001i-0090000000-949568b80cb16a148dbc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0390000000-05ee89ba1f8ae9db73cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , negative-QTOF	splash10-0002-0090000000-1784fb1bc26ba2970df0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , negative-QTOF	splash10-001i-0090000000-8a5f685e7c770df2fae8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , negative-QTOF	splash10-0a59-0690000000-f42c517370ac99fa2b5f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-TOF , negative-QTOF	splash10-001j-0090000000-10b8cb8801e211ef50f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-TOF , negative-QTOF	splash10-0a59-0190000000-e41a7a0b369e042fae34	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-TOF , negative-QTOF	splash10-057i-0590000000-9bcbe16e3cceb12dd431	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chrysoeriol LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-af2dad55a1de3a0bb83b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoeriol 10V, Positive-QTOF	splash10-0udi-0009000000-092a839c4ea4b680b7eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoeriol 20V, Positive-QTOF	splash10-0udi-0029000000-cbb434b2646e02f29d56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoeriol 40V, Positive-QTOF	splash10-0udi-2590000000-ff4ac1c0435d02e5a2a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoeriol 10V, Negative-QTOF	splash10-0002-0090000000-1080ec21704ad22b1e2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoeriol 20V, Negative-QTOF	splash10-0002-0090000000-7da56dabd16c2e5c217a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chrysoeriol 40V, Negative-QTOF	splash10-0v0u-1390000000-a28554e987b0184da54f	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

574-TRIHYDROXY-3-METHOXYFLAVONE

BiGG ID

Not Available

Wikipedia Link

Chrysoeriol

METLIN ID

Not Available

PubChem Compound

5280666

PDB ID

Not Available

ChEBI ID

16514

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

Cha BY, Shi WL, Yonezawa T, Teruya T, Nagai K, Woo JT: An inhibitory effect of chrysoeriol on platelet-derived growth factor (PDGF)-induced proliferation and PDGF receptor signaling in human aortic smooth muscle cells. J Pharmacol Sci. 2009 May;110(1):105-10. Epub 2009 May 8. [PubMed:19423953 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Chrysoeriol (HMDB0030667)

MOL for HMDB0030667 (Chrysoeriol)

3D MOL for HMDB0030667 (Chrysoeriol)

3D SDF for HMDB0030667 (Chrysoeriol)

3D-SDF for HMDB0030667 (Chrysoeriol)

PDB for HMDB0030667 (Chrysoeriol)

3D PDB for HMDB0030667 (Chrysoeriol)

SMILES for HMDB0030667 (Chrysoeriol)

INCHI for HMDB0030667 (Chrysoeriol)

Structure for HMDB0030667 (Chrysoeriol)

3D Structure for HMDB0030667 (Chrysoeriol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra