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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:08 UTC

Update Date

2022-03-07 02:49:16 UTC

HMDB ID

HMDB0002755

Secondary Accession Numbers

HMDB02755

Metabolite Identification

Common Name

Myricetin

Description

Myricetin, also known as cannabiscetin or myricetol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, myricetin is considered to be a flavonoid lipid molecule. A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3', 4', 5, 5' and 7. Myricetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Myricetin is found, on average, in the highest concentration within a few different foods, such as common walnuts, carobs, and fennels and in a lower concentration in welsh onions, yellow bell peppers, and jutes. Myricetin has also been detected, but not quantified in several different foods, such as napa cabbages, sesames, mixed nuts, lichee, and garden cress.

Structure

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

HMDB0002755
     RDKit          3D
Myricetin
 33 35  0  0  0  0  0  0  0  0999 V2000
    2.2196   -2.9621    0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -1.8127    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226   -1.6503    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373   -2.8257    0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059   -0.4109    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -0.0715    0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5566   -0.8373    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288   -0.5213    0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -1.3257    1.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3280    0.5959    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6808    0.8987    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726    1.3929   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735    2.5099   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    1.0815   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    0.6318    0.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    0.5034   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.6322   -0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0768    1.5219   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8971    2.6542   -0.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    0.2909   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.8904   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744   -2.0818    0.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.7221    0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2548   -3.0620    0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3071   -1.6964    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6262   -2.1486    1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0433    1.7192   -0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138    3.1694   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.7021   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2341    2.6160   -0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030    2.9317   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7410    0.1817   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526   -3.0144    0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 14  6  1  0
 23 16  1  0
  4 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 22 33  1  0
M  END


  Mrv1652309272007442D          

 23 25  0  0  0  0            999 V2000
 9999.6270 9997.7169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0536 9998.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.769310002.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1966 9999.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.196610001.4380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2022 9997.7169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.773310000.2026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.202310000.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4877 9999.7855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4877 9998.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2022 9998.5480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.483110001.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.768710001.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.054110001.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.054110000.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7686 9999.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.483110000.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.627910000.1981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9134 9999.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9134 9998.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6279 9998.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3424 9998.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3424 9999.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  9  7  1  0  0  0  0
 11  6  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 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 13  3  1  0  0  0  0
 12  5  1  0  0  0  0
 17  4  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
  1 21  2  0  0  0  0
 23 15  1  0  0  0  0
 22  2  1  0  0  0  0
 19  8  2  0  0  0  0
 11 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002755

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H

> <INCHI_KEY>
IKMDFBPHZNJCSN-UHFFFAOYSA-N

> <FORMULA>
C15H10O8

> <MOLECULAR_WEIGHT>
318.2351

> <EXACT_MASS>
318.037567296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
29.468621048343266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.8527341423333332

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.717616180605627

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.37283944754045

> <JCHEM_PKA_STRONGEST_BASIC>
-4.050760199655586

> <JCHEM_POLAR_SURFACE_AREA>
147.68

> <JCHEM_REFRACTIVITY>
78.8431

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
myricetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002755
     RDKit          3D
Myricetin
 33 35  0  0  0  0  0  0  0  0999 V2000
    2.2196   -2.9621    0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -1.8127    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226   -1.6503    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373   -2.8257    0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059   -0.4109    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -0.0715    0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5566   -0.8373    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288   -0.5213    0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -1.3257    1.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3280    0.5959    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6808    0.8987    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726    1.3929   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735    2.5099   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    1.0815   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    0.6318    0.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    0.5034   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.6322   -0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0768    1.5219   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8971    2.6542   -0.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    0.2909   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.8904   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744   -2.0818    0.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.7221    0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2548   -3.0620    0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3071   -1.6964    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6262   -2.1486    1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0433    1.7192   -0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138    3.1694   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.7021   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2341    2.6160   -0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030    2.9317   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7410    0.1817   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526   -3.0144    0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 14  6  1  0
 23 16  1  0
  4 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 22 33  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8665.9708662.405   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8668.6338663.953   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8669.9698670.891   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8672.6348666.272   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.6348669.351   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.3118662.405   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8660.6438667.045   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8663.3118667.036   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.9778666.266   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.9778664.726   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3118663.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8671.3028668.584   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.9688669.354   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.6348668.584   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.6348667.044   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.9688666.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.3028667.044   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8665.9728667.036   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8664.6388666.266   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8664.6388664.726   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8665.9728663.956   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3068664.726   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8667.3068666.266   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   13                                                            
CONECT    4   17                                                            
CONECT    5   12                                                            
CONECT    6   11                                                            
CONECT    7    9                                                            
CONECT    8    9   19                                                       
CONECT    9    8   10    7                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   20                                                  
CONECT   12   13   17    5                                                  
CONECT   13   12   14    3                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12    4                                                  
CONECT   18   19   23                                                       
CONECT   19   20   18    8                                                  
CONECT   20   19   21   11                                                  
CONECT   21   20   22    1                                                  
CONECT   22   21   23    2                                                  
CONECT   23   22   18   15                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0002755
HETATM    1  O1  UNL     1       2.220  -2.962   0.231  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.738  -1.813   0.160  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.323  -1.650   0.225  1.00  0.00           C  
HETATM    4  O2  UNL     1      -0.337  -2.826   0.349  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.206  -0.411   0.153  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.606  -0.071   0.204  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.557  -0.837   0.820  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.929  -0.521   0.776  1.00  0.00           C  
HETATM    9  O3  UNL     1      -4.825  -1.326   1.407  1.00  0.00           O  
HETATM   10  C7  UNL     1      -4.328   0.596   0.093  1.00  0.00           C  
HETATM   11  O4  UNL     1      -5.681   0.899   0.055  1.00  0.00           O  
HETATM   12  C8  UNL     1      -3.373   1.393  -0.541  1.00  0.00           C  
HETATM   13  O5  UNL     1      -3.873   2.510  -1.210  1.00  0.00           O  
HETATM   14  C9  UNL     1      -2.047   1.082  -0.496  1.00  0.00           C  
HETATM   15  O6  UNL     1       0.613   0.632   0.016  1.00  0.00           O  
HETATM   16  C10 UNL     1       1.913   0.503  -0.048  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.708   1.632  -0.191  1.00  0.00           C  
HETATM   18  C12 UNL     1       4.077   1.522  -0.260  1.00  0.00           C  
HETATM   19  O7  UNL     1       4.897   2.654  -0.405  1.00  0.00           O  
HETATM   20  C13 UNL     1       4.671   0.291  -0.188  1.00  0.00           C  
HETATM   21  C14 UNL     1       3.919  -0.890  -0.043  1.00  0.00           C  
HETATM   22  O8  UNL     1       4.574  -2.082   0.023  1.00  0.00           O  
HETATM   23  C15 UNL     1       2.538  -0.722   0.022  1.00  0.00           C  
HETATM   24  H1  UNL     1      -1.255  -3.062   0.363  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.307  -1.696   1.424  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.626  -2.149   1.921  1.00  0.00           H  
HETATM   27  H4  UNL     1      -6.043   1.719  -0.438  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.314   3.169  -1.707  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.315   1.702  -0.988  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.234   2.616  -0.249  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.103   2.932  -1.355  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.741   0.182  -0.239  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.353  -3.014   0.116  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   23
CONECT    3    4    5    5
CONECT    4   24
CONECT    5    6   15
CONECT    6    7    7   14
CONECT    7    8   25
CONECT    8    9   10   10
CONECT    9   26
CONECT   10   11   12
CONECT   11   27
CONECT   12   13   14   14
CONECT   13   28
CONECT   14   29
CONECT   15   16
CONECT   16   17   17   23
CONECT   17   18   30
CONECT   18   19   20   20
CONECT   19   31
CONECT   20   21   32
CONECT   21   22   23   23
CONECT   22   33
END

HMDB0002755
     RDKit          3D
Myricetin
 33 35  0  0  0  0  0  0  0  0999 V2000
    2.2196   -2.9621    0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -1.8127    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226   -1.6503    0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373   -2.8257    0.3486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2059   -0.4109    0.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055   -0.0715    0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5566   -0.8373    0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9288   -0.5213    0.7756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8254   -1.3257    1.4072 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3280    0.5959    0.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6808    0.8987    0.0549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726    1.3929   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735    2.5099   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0466    1.0815   -0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    0.6318    0.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9128    0.5034   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    1.6322   -0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0768    1.5219   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8971    2.6542   -0.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6713    0.2909   -0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -0.8904   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744   -2.0818    0.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -0.7221    0.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2548   -3.0620    0.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3071   -1.6964    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6262   -2.1486    1.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0433    1.7192   -0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138    3.1694   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3151    1.7021   -0.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2341    2.6160   -0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030    2.9317   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7410    0.1817   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526   -3.0144    0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23  2  1  0
 14  6  1  0
 23 16  1  0
  4 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
 19 31  1  0
 20 32  1  0
 22 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,3',4',5,5',7-Hexahydroxyflavone	ChEBI
3,5,7,3',4',5'-Hexahydroxyflavone	ChEBI
Cannabiscetin	ChEBI
Myricetol	ChEBI
3,3',4',5,5',7-Hexahydroxy-(8ci)- flavone	HMDB
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one	MeSH, HMDB
3,3’,4’,5,5’,7-Hexahydroxyflavone	PhytoBank
3,5,7,3’,4’,5’-Hexahydroxyflavone	PhytoBank

Chemical Formula

C₁₅H₁₀O₈

Average Molecular Weight

318.2351

Monoisotopic Molecular Weight

318.037567296

IUPAC Name

3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

Traditional Name

myricetin

CAS Registry Number

529-44-2

SMILES

OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1

InChI Identifier

InChI=1S/C15H10O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,16-20,22H

InChI Key

IKMDFBPHZNJCSN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyflavonol (CHEBI:18152 )
hexahydroxyflavone (CHEBI:18152 )
flavonols (C10107 )
Flavones and Flavonols (C10107 )
Flavones and Flavonols (LMPK12110001 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9892086)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002755)

Source

Exogenous

Exogenous (HMDB: HMDB0002755)

Food

Food (HMDB: HMDB0002755)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Evergreen blackberry (FooDB: FOOD00901)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Beverage

Fermented beverage

Fortified wines

Sherry (FooDB: FOOD00632)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Confectionery

Other confectionery

Honey (FooDB: FOOD00626)

Cocoa and cocoa product

Cocoa product

Hot chocolate (FooDB: FOOD00688)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0002755)

Process

Not Available

Role

Industrial applicationBiological role

Modulator

Inhibitor

EC 2.1.1.6 (catechol O-methyltransferase) inhibitor (HMDB: HMDB0002755)
Cyclooxygenase 1 inhibitor (HMDB: HMDB0002755)
EC 5.99.1.2 (DNA topoisomerase) inhibitor (HMDB: HMDB0002755)
Topoisomerase-II inhibitor (HMDB: HMDB0002755)

Enzyme inhibitor

Lipoxygenase inhibitor (HMDB: HMDB0002755)
Tyrosine-kinase inhibitor (HMDB: HMDB0002755)
Oxidase inhibitor (HMDB: HMDB0002755)

Apoptotic (HMDB: HMDB0002755)

Allelochemic (HMDB: HMDB0002755)
Anti allergenic (HMDB: HMDB0002755)
Anti bacterial (HMDB: HMDB0002755)
Anti feedant (HMDB: HMDB0002755)
Anti gastric (HMDB: HMDB0002755)
Anti gingivitic (HMDB: HMDB0002755)
Anti gonadotrophic (HMDB: HMDB0002755)
Anti histaminic (HMDB: HMDB0002755)
Anti HIV (HMDB: HMDB0002755)
Anti-inflammatory (HMDB: HMDB0002755)
Anti mutagenic (HMDB: HMDB0002755)
Anti periodontic (HMDB: HMDB0002755)
Anti plaque (HMDB: HMDB0002755)
Anti septic (HMDB: HMDB0002755)
Candidicide (HMDB: HMDB0002755)
Larvistat (HMDB: HMDB0002755)
Mutagenic (HMDB: HMDB0002755)
Quinone-reductase inducer (HMDB: HMDB0002755)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	357 °C	Not Available
Boiling Point	747.63 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2234 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.206 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Baker	174.399	30932474
[M+H]+	Not Available	170.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001490

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.66	ALOGPS
logP	1.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.84 m³·mol⁻¹	ChemAxon
Polarizability	29.47 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	177.237	30932474
DeepCCS	[M-H]-	174.879	30932474
DeepCCS	[M-2H]-	209.011	30932474
DeepCCS	[M+Na]+	184.739	30932474
AllCCS	[M+H]+	171.3	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	174.6	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	168.6	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.17 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9867 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1848.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	91.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	148.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	605.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	477.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	416.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	767.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	348.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1494.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	627.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	269.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	353.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Myricetin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1	5428.6	Standard polar	33892256
Myricetin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1	3314.4	Standard non polar	33892256
Myricetin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C(O)=C2)=C1	3334.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Myricetin,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	3444.6	Semi standard non polar	33892256
Myricetin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC(O)=C(O)C(O)=C1)O2	3399.0	Semi standard non polar	33892256
Myricetin,1TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC(O)=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2C1=O	3382.7	Semi standard non polar	33892256
Myricetin,1TMS,isomer #4	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O	3404.3	Semi standard non polar	33892256
Myricetin,1TMS,isomer #5	C[Si](C)(C)OC1=C(O)C=C(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3421.9	Semi standard non polar	33892256
Myricetin,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	3385.9	Semi standard non polar	33892256
Myricetin,2TMS,isomer #10	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O	3355.6	Semi standard non polar	33892256
Myricetin,2TMS,isomer #11	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C	3317.8	Semi standard non polar	33892256
Myricetin,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	3375.5	Semi standard non polar	33892256
Myricetin,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3389.1	Semi standard non polar	33892256
Myricetin,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3424.1	Semi standard non polar	33892256
Myricetin,2TMS,isomer #5	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O	3318.8	Semi standard non polar	33892256
Myricetin,2TMS,isomer #6	C[Si](C)(C)OC1=C(O)C=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O	3363.1	Semi standard non polar	33892256
Myricetin,2TMS,isomer #7	C[Si](C)(C)OC1=C(C2=CC(O)=C(O)C(O)=C2)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O	3333.3	Semi standard non polar	33892256
Myricetin,2TMS,isomer #8	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O	3305.2	Semi standard non polar	33892256
Myricetin,2TMS,isomer #9	C[Si](C)(C)OC1=C(O)C=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3300.1	Semi standard non polar	33892256
Myricetin,3TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	3262.1	Semi standard non polar	33892256
Myricetin,3TMS,isomer #10	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C	3209.9	Semi standard non polar	33892256
Myricetin,3TMS,isomer #11	C[Si](C)(C)OC1=C(O)C=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O	3217.4	Semi standard non polar	33892256
Myricetin,3TMS,isomer #12	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O	3211.9	Semi standard non polar	33892256
Myricetin,3TMS,isomer #13	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C	3196.4	Semi standard non polar	33892256
Myricetin,3TMS,isomer #14	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3225.2	Semi standard non polar	33892256
Myricetin,3TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3241.8	Semi standard non polar	33892256
Myricetin,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3315.8	Semi standard non polar	33892256
Myricetin,3TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3230.2	Semi standard non polar	33892256
Myricetin,3TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3237.6	Semi standard non polar	33892256
Myricetin,3TMS,isomer #6	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3262.6	Semi standard non polar	33892256
Myricetin,3TMS,isomer #7	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3248.6	Semi standard non polar	33892256
Myricetin,3TMS,isomer #8	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O	3208.5	Semi standard non polar	33892256
Myricetin,3TMS,isomer #9	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O	3236.8	Semi standard non polar	33892256
Myricetin,4TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3162.3	Semi standard non polar	33892256
Myricetin,4TMS,isomer #10	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3172.8	Semi standard non polar	33892256
Myricetin,4TMS,isomer #11	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3191.9	Semi standard non polar	33892256
Myricetin,4TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3267.9	Semi standard non polar	33892256
Myricetin,4TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3246.9	Semi standard non polar	33892256
Myricetin,4TMS,isomer #4	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3229.9	Semi standard non polar	33892256
Myricetin,4TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3159.4	Semi standard non polar	33892256
Myricetin,4TMS,isomer #6	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3150.5	Semi standard non polar	33892256
Myricetin,4TMS,isomer #7	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3210.1	Semi standard non polar	33892256
Myricetin,4TMS,isomer #8	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O	3144.6	Semi standard non polar	33892256
Myricetin,4TMS,isomer #9	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C	3135.8	Semi standard non polar	33892256
Myricetin,5TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3270.3	Semi standard non polar	33892256
Myricetin,5TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3242.5	Semi standard non polar	33892256
Myricetin,5TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3252.6	Semi standard non polar	33892256
Myricetin,5TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3179.5	Semi standard non polar	33892256
Myricetin,5TMS,isomer #5	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3155.9	Semi standard non polar	33892256
Myricetin,6TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3251.6	Semi standard non polar	33892256
Myricetin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	3722.2	Semi standard non polar	33892256
Myricetin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC(O)=C(O)C(O)=C1)O2	3677.6	Semi standard non polar	33892256
Myricetin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC(O)=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2C1=O	3682.4	Semi standard non polar	33892256
Myricetin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O	3701.9	Semi standard non polar	33892256
Myricetin,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=C(O)C=C(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3698.9	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	3953.5	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O	3934.3	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3887.0	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	3909.7	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3960.0	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3972.9	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O	3910.2	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=C(O)C=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O	3922.7	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=C(C2=CC(O)=C(O)C(O)=C2)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3869.1	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O	3882.8	Semi standard non polar	33892256
Myricetin,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=C(O)C=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3886.7	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O)C(O)=C3)OC2=C1	4016.0	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C(C)(C)C	4016.4	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=C(O)C=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O	4029.7	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4015.4	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C(C)(C)C	3976.8	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4025.5	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4071.5	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	4158.3	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4009.6	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	4055.1	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4103.1	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4075.4	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O	3980.7	Semi standard non polar	33892256
Myricetin,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4044.2	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4107.6	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4152.4	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4081.1	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	4218.3	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4246.7	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4223.1	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4114.8	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4098.6	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4198.8	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O	4089.6	Semi standard non polar	33892256
Myricetin,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O)=C1O[Si](C)(C)C(C)(C)C	4071.9	Semi standard non polar	33892256
Myricetin,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4318.3	Semi standard non polar	33892256
Myricetin,5TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4296.6	Semi standard non polar	33892256
Myricetin,5TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(O)=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4339.9	Semi standard non polar	33892256
Myricetin,5TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C(C)(C)C)=C(C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4201.4	Semi standard non polar	33892256
Myricetin,5TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4183.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Myricetin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000t-0943100000-fa00c6f71be0c6675599	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Myricetin GC-MS (6 TMS)	splash10-005c-2954350000-46c24c9458aadfd2a711	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Myricetin GC-EI-TOF (Non-derivatized)	splash10-000t-0943100000-fa00c6f71be0c6675599	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Myricetin GC-MS (Non-derivatized)	splash10-005c-2954350000-46c24c9458aadfd2a711	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myricetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kr-0962000000-771167ae1d9403c88d56	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myricetin GC-MS (5 TMS) - 70eV, Positive	splash10-0bt9-1021109000-c6b0cd1ae27d5b8c74c1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myricetin 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 - Myricetin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOF	splash10-014i-0009000000-99c784d42ece911ecc13	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-014i-0907000000-0b4ff7a72a459baa829c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0pbi-0900000000-b492f594bdca4c8132a0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0uxr-0950000000-55c90a0d932630c6d644	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-014i-0329000000-43069a5bf007fae18a27	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-ITTOF (LCMS-IT-TOF) , Positive-QTOF	splash10-014i-0009000000-2b98dfcc4f869be90285	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-ITTOF (LCMS-IT-TOF) , Negative-QTOF	splash10-014i-0009104000-6dada42248181a0149f3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin ESI-TOF 10V, Negative-QTOF	splash10-014i-0009000000-bdbe61e1aba659fd27d2	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin ESI-TOF 20V, Negative-QTOF	splash10-014i-0009000000-bdbe61e1aba659fd27d2	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin ESI-TOF , Negative-QTOF	splash10-014i-0009000000-2499e01afe3b3651b392	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin ESI-TOF 10V, Negative-QTOF	splash10-014i-0009000000-bdbe61e1aba659fd27d2	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin ESI-TOF 10V, Negative-QTOF	splash10-014i-0009000000-35024ff951cd0ca242e4	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin ESI-TOF 20V, Negative-QTOF	splash10-014r-0079000000-b798a1be942ffa6396d2	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin ESI-TOF , Negative-QTOF	splash10-014i-0009000000-2499e01afe3b3651b392	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-qTof , Positive-QTOF	splash10-0gb9-2951000000-55186f59f5d6ec659c2d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF , negative-QTOF	splash10-014i-0009000000-7494718b3a96d5664b53	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF , negative-QTOF	splash10-014i-0209000000-2b4763ddb9eb888c9bfd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF , negative-QTOF	splash10-0v09-0901000000-6861fe274e8b0b6b663e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myricetin LC-ESI-QTOF , negative-QTOF	splash10-0udr-0900000000-e982d07ed9f6838c4ee0	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myricetin 10V, Positive-QTOF	splash10-014i-0009000000-9a84f52c6a2f1aaec1a7	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myricetin 20V, Positive-QTOF	splash10-014i-0219000000-36b340f32ee87232a4d1	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myricetin 40V, Positive-QTOF	splash10-0v0a-5931000000-56b06c0109d323a15bc9	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myricetin 10V, Negative-QTOF	splash10-014i-0009000000-7c52125f5ee8fbc51ba0	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myricetin 20V, Negative-QTOF	splash10-014i-0229000000-413e7e87d4aaf205ca23	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myricetin 40V, Negative-QTOF	splash10-066u-5930000000-ebd17a876ef4c64d13c0	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	45.0 (0.62-94.2) uM	Adult (>18 years old)	Both	Normal	9892086	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02375

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Myricetin

METLIN ID

3448

PubChem Compound

5281672

PDB ID

Not Available

ChEBI ID

18152

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1261881

References

Synthesis Reference

De Israilev, Lidia R. A.; Del Pero de Martinez, Maria A.; Seeligmann, Peter. Myricetin in Tagetes: chemosystematic significance. Phytochemistry (1991), 30(12), 4037-8.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Noroozi M, Burns J, Crozier A, Kelly IE, Lean ME: Prediction of dietary flavonol consumption from fasting plasma concentration or urinary excretion. Eur J Clin Nutr. 2000 Feb;54(2):143-9. [PubMed:10694785 ]
Noguchi Y, Fukuda K, Matsushima A, Haishi D, Hiroto M, Kodera Y, Nishimura H, Inada Y: Inhibition of Df-protease associated with allergic diseases by polyphenol. J Agric Food Chem. 1999 Aug;47(8):2969-72. [PubMed:10552595 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Myricetin → 6-[2,3-dihydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Myricetin → 6-[2,6-dihydroxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Myricetin → 6-{[5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Myricetin → 6-{[3,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Myricetin → 6-{[3,5-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Myricetin (HMDB0002755)

MOL for HMDB0002755 (Myricetin)

3D MOL for HMDB0002755 (Myricetin)

3D SDF for HMDB0002755 (Myricetin)

3D-SDF for HMDB0002755 (Myricetin)

PDB for HMDB0002755 (Myricetin)

3D PDB for HMDB0002755 (Myricetin)

SMILES for HMDB0002755 (Myricetin)

INCHI for HMDB0002755 (Myricetin)

Structure for HMDB0002755 (Myricetin)

3D Structure for HMDB0002755 (Myricetin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions