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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-01-22 21:47:08 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0005794

Secondary Accession Numbers

HMDB05794

Metabolite Identification

Common Name

Quercetin

Description

Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250 ).

Structure

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

HMDB0005794
     RDKit          3D
Quercetin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.1438   -2.7699    0.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6502   -1.6281    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -1.4898    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600   -2.6475    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183   -0.2701    0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -0.0580   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    1.2477   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5920    1.5188   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    0.4855   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.7308   -0.2000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -0.7933   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9700   -1.8514   -0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001   -1.0388   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    0.8110    0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.7265    0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    1.9159    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    1.8995    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6433    3.0762    0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193    0.6761    0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7965   -0.5355    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588   -1.7191    0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191   -0.4987    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256   -3.5468    0.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447    2.0490   -0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894    2.5404   -0.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2577    1.6902   -0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -2.8016   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205   -2.0736   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210    2.8540    0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8970    3.5417    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6131    0.6100    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2878   -2.6512    0.2124 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  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 13  6  1  0
 22 15  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 21 32  1  0
M  END


  Mrv1652309272007442D          

 22 24  0  0  0  0            999 V2000
 9999.6614 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0876 9998.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.805210002.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.232110001.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2367 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.807810000.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.236710000.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5222 9999.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5221 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2366 9998.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710001.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.803210001.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088610000.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8031 9999.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710000.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662310000.1884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6623 9998.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  8  6  1  0  0  0  0
 10  5  1  0  0  0  0
 12  3  1  0  0  0  0
 11  4  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 18  1  0  0  0  0
 17 22  1  0  0  0  0
  1 20  2  0  0  0  0
 22 14  1  0  0  0  0
 21  2  1  0  0  0  0
 18  7  2  0  0  0  0
 10 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005794

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H

> <INCHI_KEY>
REFJWTPEDVJJIY-UHFFFAOYSA-N

> <FORMULA>
C15H10O7

> <MOLECULAR_WEIGHT>
302.2357

> <EXACT_MASS>
302.042652674

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.535207697849263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
2.156299464

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.848394398897066

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.379031589669055

> <JCHEM_PKA_STRONGEST_BASIC>
-3.98964468301513

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
76.8622

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quercetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005794
     RDKit          3D
Quercetin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.1438   -2.7699    0.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6502   -1.6281    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -1.4898    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600   -2.6475    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183   -0.2701    0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -0.0580   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    1.2477   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5920    1.5188   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    0.4855   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.7308   -0.2000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -0.7933   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9700   -1.8514   -0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001   -1.0388   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    0.8110    0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.7265    0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    1.9159    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    1.8995    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6433    3.0762    0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193    0.6761    0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7965   -0.5355    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588   -1.7191    0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191   -0.4987    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256   -3.5468    0.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447    2.0490   -0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894    2.5404   -0.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2577    1.6902   -0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -2.8016   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205   -2.0736   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210    2.8540    0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8970    3.5417    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6131    0.6100    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2878   -2.6512    0.2124 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  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 13  6  1  0
 22 15  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 21 32  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    8666.0358662.387   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8668.6978663.934   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.0368670.872   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8672.7008669.332   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.3758662.387   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.7088667.026   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8663.3758667.018   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.0418666.248   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.0418664.708   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3758663.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8671.3668668.565   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.0338669.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.6998668.565   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.6998667.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.0328666.255   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8671.3668667.025   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8666.0368667.018   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8664.7038666.248   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8664.7038664.708   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8666.0368663.938   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8667.3708664.708   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8667.3708666.248   0.000  0.00  0.00           C+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3   12                                                            
CONECT    4   11                                                            
CONECT    5   10                                                            
CONECT    6    8                                                            
CONECT    7    8   18                                                       
CONECT    8    7    9    6                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   19                                                  
CONECT   11   12   16    4                                                  
CONECT   12   11   13    3                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   18   22                                                       
CONECT   18   19   17    7                                                  
CONECT   19   18   20   10                                                  
CONECT   20   19   21    1                                                  
CONECT   21   20   22    2                                                  
CONECT   22   21   17   14                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0005794
HETATM    1  O1  UNL     1      -2.144  -2.770   0.133  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.650  -1.628   0.104  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.263  -1.490   0.051  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.460  -2.648   0.034  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.318  -0.270   0.018  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.755  -0.058  -0.038  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.252   1.248  -0.068  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.592   1.519  -0.121  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.518   0.485  -0.146  1.00  0.00           C  
HETATM   10  O3  UNL     1       5.888   0.731  -0.200  1.00  0.00           O  
HETATM   11  C8  UNL     1       4.071  -0.793  -0.118  1.00  0.00           C  
HETATM   12  O4  UNL     1       4.970  -1.851  -0.142  1.00  0.00           O  
HETATM   13  C9  UNL     1       2.700  -1.039  -0.064  1.00  0.00           C  
HETATM   14  O5  UNL     1      -0.480   0.811   0.038  1.00  0.00           O  
HETATM   15  C10 UNL     1      -1.786   0.727   0.088  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.538   1.916   0.105  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.908   1.900   0.157  1.00  0.00           C  
HETATM   18  O6  UNL     1      -4.643   3.076   0.173  1.00  0.00           O  
HETATM   19  C13 UNL     1      -4.519   0.676   0.191  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.796  -0.535   0.175  1.00  0.00           C  
HETATM   21  O7  UNL     1      -4.459  -1.719   0.210  1.00  0.00           O  
HETATM   22  C15 UNL     1      -2.419  -0.499   0.123  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.026  -3.547   0.059  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.545   2.049  -0.049  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.989   2.540  -0.145  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.258   1.690  -0.223  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.662  -2.802  -0.122  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.420  -2.074  -0.045  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.021   2.854   0.077  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.897   3.542   1.035  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.613   0.610   0.232  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.288  -2.651   0.212  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4    5    5
CONECT    4   23
CONECT    5    6   14
CONECT    6    7    7   13
CONECT    7    8   24
CONECT    8    9    9   25
CONECT    9   10   11
CONECT   10   26
CONECT   11   12   13   13
CONECT   12   27
CONECT   13   28
CONECT   14   15
CONECT   15   16   16   22
CONECT   16   17   29
CONECT   17   18   19   19
CONECT   18   30
CONECT   19   20   31
CONECT   20   21   22   22
CONECT   21   32
END

HMDB0005794
     RDKit          3D
Quercetin
 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.1438   -2.7699    0.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6502   -1.6281    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2632   -1.4898    0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4600   -2.6475    0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3183   -0.2701    0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7554   -0.0580   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    1.2477   -0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5920    1.5188   -0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    0.4855   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.7308   -0.2000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0712   -0.7933   -0.1180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9700   -1.8514   -0.1422 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001   -1.0388   -0.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4799    0.8110    0.0380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.7265    0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5382    1.9159    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9084    1.8995    0.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6433    3.0762    0.1734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193    0.6761    0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7965   -0.5355    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4588   -1.7191    0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191   -0.4987    0.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256   -3.5468    0.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5447    2.0490   -0.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9894    2.5404   -0.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2577    1.6902   -0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616   -2.8016   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205   -2.0736   -0.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210    2.8540    0.0771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8970    3.5417    1.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6131    0.6100    0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2878   -2.6512    0.2124 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  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22  2  1  0
 13  6  1  0
 22 15  1  0
  4 23  1  0
  7 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
 21 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one	ChEBI
3,3',4',5,7-Pentahydroxyflavone	ChEBI
3,5,7,3',4'-Pentahydroxyflavone	ChEBI
Sophoretin	ChEBI
Xanthaurine	ChEBI
3,3',4,5,7-Pentahydroxyflavone	Kegg
Dikvertin	MeSH
2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-one	HMDB
3',4',5,7-Tetrahydroxyflavan-3-ol	HMDB
3',4',5,7-Tetrahydroxyflavon-3-ol	HMDB
3,4',5,5',7-Pentahydroxy-flavone	HMDB
3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-ON	HMDB
Flavin meletin	HMDB
Meletin	HMDB
Quercetin dihydrate	HMDB
Quercetol	HMDB
Quertin	HMDB
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-benzopyran-4-one	PhytoBank
3,3’,4’,5,7-Pentahydroxyflavone	PhytoBank
3,5,7,3’,4’-Pentahydroxyflavone	PhytoBank
3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one	PhytoBank
3'-Hydroxykaempferol	PhytoBank
3’-Hydroxykaempferol	PhytoBank
Quercetine	PhytoBank
Quertine	PhytoBank

Chemical Formula

C₁₅H₁₀O₇

Average Molecular Weight

302.2357

Monoisotopic Molecular Weight

302.042652674

IUPAC Name

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

Traditional Name

quercetin

CAS Registry Number

117-39-5

SMILES

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

InChI Identifier

InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H

InChI Key

REFJWTPEDVJJIY-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
Catechol
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

pentahydroxyflavone (CHEBI:16243 )
7-hydroxyflavonol (CHEBI:16243 )
flavonols (C00389 )
Flavones and Flavonols (C00389 )
Flavones and Flavonols (LMPK12110004 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	316 - 318 °C	Not Available
Boiling Point	642.00 to 643.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.06 mg/mL at 16 °C	Not Available
LogP	1.989 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	158.977	30932474
[M+H]+	MetCCS_train_pos	166.741	30932474
[M-H]-	Not Available	158.977	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000438
[M+H]+	Not Available	165.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000438

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	1.81	ALOGPS
logP	2.16	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.38	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.86 m³·mol⁻¹	ChemAxon
Polarizability	28.54 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]+	173.704	30932474
DeepCCS	[M-H]-	171.346	30932474
DeepCCS	[M-2H]-	205.449	30932474
DeepCCS	[M+Na]+	180.822	30932474
AllCCS	[M+H]+	168.0	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	171.4	32859911
AllCCS	[M+Na]+	172.4	32859911
AllCCS	[M-H]-	166.0	32859911
AllCCS	[M+Na-2H]-	165.3	32859911
AllCCS	[M+HCOO]-	164.7	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.	5.58 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6273 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2029.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	268.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	104.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	588.1 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	480.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	188.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	787.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	386.1 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	1469.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	554.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	215.9 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	277.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quercetin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1	5048.5	Standard polar	33892256
Quercetin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1	3148.5	Standard non polar	33892256
Quercetin	OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1	3194.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quercetin,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O)C(O)=C3)OC2=C1	3305.1	Semi standard non polar	33892256
Quercetin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC=C(O)C(O)=C1)O2	3246.2	Semi standard non polar	33892256
Quercetin,1TMS,isomer #3	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2C1=O	3235.5	Semi standard non polar	33892256
Quercetin,1TMS,isomer #4	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O	3297.0	Semi standard non polar	33892256
Quercetin,1TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3298.2	Semi standard non polar	33892256
Quercetin,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC=C(O)C(O)=C3)OC2=C1	3220.5	Semi standard non polar	33892256
Quercetin,2TMS,isomer #10	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3167.7	Semi standard non polar	33892256
Quercetin,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=C(O)C(O)=C3)OC2=C1	3212.8	Semi standard non polar	33892256
Quercetin,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3292.7	Semi standard non polar	33892256
Quercetin,2TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3262.8	Semi standard non polar	33892256
Quercetin,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O	3222.2	Semi standard non polar	33892256
Quercetin,2TMS,isomer #6	C[Si](C)(C)OC1=CC(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC=C1O	3203.2	Semi standard non polar	33892256
Quercetin,2TMS,isomer #7	C[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O[Si](C)(C)C)=C2C1=O	3160.7	Semi standard non polar	33892256
Quercetin,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3180.6	Semi standard non polar	33892256
Quercetin,2TMS,isomer #9	C[Si](C)(C)OC1=CC(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)=CC=C1O	3155.2	Semi standard non polar	33892256
Quercetin,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=C(O)C(O)=C3)OC2=C1	3101.7	Semi standard non polar	33892256
Quercetin,3TMS,isomer #10	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3076.2	Semi standard non polar	33892256
Quercetin,3TMS,isomer #2	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3191.4	Semi standard non polar	33892256
Quercetin,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3172.3	Semi standard non polar	33892256
Quercetin,3TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3103.8	Semi standard non polar	33892256
Quercetin,3TMS,isomer #5	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3086.2	Semi standard non polar	33892256
Quercetin,3TMS,isomer #6	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3118.0	Semi standard non polar	33892256
Quercetin,3TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O	3080.1	Semi standard non polar	33892256
Quercetin,3TMS,isomer #8	C[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3079.4	Semi standard non polar	33892256
Quercetin,3TMS,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=C1O	3067.0	Semi standard non polar	33892256
Quercetin,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=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3161.7	Semi standard non polar	33892256
Quercetin,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=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3147.6	Semi standard non polar	33892256
Quercetin,4TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3124.3	Semi standard non polar	33892256
Quercetin,4TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2C(=O)C(O[Si](C)(C)C)=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3056.2	Semi standard non polar	33892256
Quercetin,4TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	3035.3	Semi standard non polar	33892256
Quercetin,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=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3154.9	Semi standard non polar	33892256
Quercetin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O)C(O)=C3)OC2=C1	3572.0	Semi standard non polar	33892256
Quercetin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C(O)=C(C1=CC=C(O)C(O)=C1)O2	3518.6	Semi standard non polar	33892256
Quercetin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O)=C2C1=O	3533.6	Semi standard non polar	33892256
Quercetin,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=C1O	3571.1	Semi standard non polar	33892256
Quercetin,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3576.9	Semi standard non polar	33892256
Quercetin,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=C(O)C(O)=C3)OC2=C1	3786.7	Semi standard non polar	33892256
Quercetin,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3748.0	Semi standard non polar	33892256
Quercetin,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=C(O)C(O)=C3)OC2=C1	3771.3	Semi standard non polar	33892256
Quercetin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3841.1	Semi standard non polar	33892256
Quercetin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3800.3	Semi standard non polar	33892256
Quercetin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O	3787.6	Semi standard non polar	33892256
Quercetin,2TBDMS,isomer #6	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=C1O	3753.2	Semi standard non polar	33892256
Quercetin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=C(C2=CC=C(O)C(O)=C2)OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2C1=O	3726.5	Semi standard non polar	33892256
Quercetin,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O	3774.0	Semi standard non polar	33892256
Quercetin,2TBDMS,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)C=C(O)C=C3O2)=CC=C1O	3731.1	Semi standard non polar	33892256
Quercetin,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=C(O)C(O)=C3)OC2=C1	3867.2	Semi standard non polar	33892256
Quercetin,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3856.3	Semi standard non polar	33892256
Quercetin,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=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	4037.9	Semi standard non polar	33892256
Quercetin,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=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3995.8	Semi standard non polar	33892256
Quercetin,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=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3937.7	Semi standard non polar	33892256
Quercetin,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=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3898.0	Semi standard non polar	33892256
Quercetin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C(O)=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3939.8	Semi standard non polar	33892256
Quercetin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=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	3903.7	Semi standard non polar	33892256
Quercetin,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3889.3	Semi standard non polar	33892256
Quercetin,3TBDMS,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=C1O	3864.2	Semi standard non polar	33892256
Quercetin,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=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	4108.1	Semi standard non polar	33892256
Quercetin,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=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4060.5	Semi standard non polar	33892256
Quercetin,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=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4107.2	Semi standard non polar	33892256
Quercetin,4TBDMS,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=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3980.3	Semi standard non polar	33892256
Quercetin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=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[Si](C)(C)C(C)(C)C	3948.5	Semi standard non polar	33892256
Quercetin,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=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	4175.0	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

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	0.06 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	17135030	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0-0.255 uM	Adult (>18 years old)	Both	Normal	19747418	details
Blood	Detected and Quantified	0.0802 +/- 0.0817 uM	Adult (>18 years old)	Both	Normal	19747418	details
Blood	Detected and Quantified	0.0723 +/- 0.0810 uM	Adult (>18 years old)	Both	Normal	20851305	details
Blood	Detected and Quantified	0.0229 +/- 0.0166 uM	Adult (>18 years old)	Female	Normal	12395214	details
Blood	Detected and Quantified	0.03 +/- 0.015 uM	Adult (>18 years old)	Both	Normal	17135030	details
Urine	Detected and Quantified	0.0110-0.248 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0065 +/- 0.013 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	14969553	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	16197573	details
Urine	Detected and Quantified	0.0467 +/- 0.0333 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.0400 +/- 0.0400 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.0133 +/- 0.00730 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17538531	details
Urine	Detected and Quantified	0.0135 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21272408	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	10637051	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	19812218	details
Urine	Detected and Quantified	0.034 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.02666 +/- 0.01333 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	16869998	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	15595664	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	18424596	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	10938233	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	10080647	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	19671472	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	12592675	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 291	21970858	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0037 +/- 0.0016 umol/mmol creatinine	Adult (>18 years old)	Both	Non-insulin dependent diabetes	10694785	details
Urine	Detected and Quantified	0.057 +/- 0.017 umol/mmol creatinine	Adult (>18 years old)	Both	Diabetes mellitus type 2	10694785	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
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 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)

External Links

DrugBank ID

DB04216

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Quercetin

METLIN ID

Not Available

PubChem Compound

5280343

PDB ID

QUE

ChEBI ID

16243

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000472

Good Scents ID

rw1343701

References

Synthesis Reference

Krewson, Charles F. Colloidal flavonols. (1953), US 2637725 19530505 CAN 47:42700 AN 1953:42700

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Perez-Vizcaino F, Duarte J, Andriantsitohaina R: Endothelial function and cardiovascular disease: effects of quercetin and wine polyphenols. Free Radic Res. 2006 Oct;40(10):1054-65. [PubMed:17015250 ]

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

Quercetin → Isorhamnetin	details

Enzyme Details

2. 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

Quercetin → 3,4,5-trihydroxy-6-[2-hydroxy-5-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic acid	details
Quercetin → Quercetin-4'-glucuronide	details
Quercetin → 6-{[2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Quercetin → 6-{[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Quercetin → Quercetin 3-O-glucuronide	details

Enzyme Details

3. NAD-dependent protein deacetylase sirtuin-1

General function:: Involved in zinc ion binding
Specific function:: NAD-dependent protein deacetylase that links transcriptional regulation directly to intracellular energetics and participates in the coordination of several separated cellular functions such as cell cycle, response to DNA damage, metobolism, apoptosis and autophagy. Can modulate chromatin function through deacetylation of histones and can promote alterations in the methylation of histones and DNA, leading to transcriptional repression. Deacetylates a broad range of transcription factors and coregulators, thereby regulating target gene expression positively and negatively. Serves as a sensor of the cytosolic ratio of NAD(+)/NADH which is altered by glucose deprivation and metabolic changes associated with caloric restriction. Is essential in skeletal muscle cell differentiation and in response to low nutrients mediates the inhibitory effect on skeletal myoblast differentiation which also involves 5'-AMP-activated protein kinase (AMPK) and nicotinamide phosphoribosyltransferase (NAMPT). Component of the eNoSC (energy-dependent nucleolar silencing) complex, a complex that mediates silencing of rDNA in response to intracellular energy status and acts by recruiting histone-modifying enzymes. The eNoSC complex is able to sense the energy status of cell: upon glucose starvation, elevation of NAD(+)/NADP(+) ratio activates SIRT1, leading to histone H3 deacetylation followed by dimethylation of H3 at 'Lys-9' (H3K9me2) by SUV39H1 and the formation of silent chromatin in the rDNA locus. Deacetylates 'Lys-266' of SUV39H1, leading to its activation. Inhibits skeletal muscle differentiation by deacetylating PCAF and MYOD1. Deacetylates H2A and 'Lys-26' of HIST1H1E. Deacetylates 'Lys-16' of histone H4 (in vitro). Involved in NR0B2/SHP corepression function through chromatin remodeling: Recruited to LRH1 target gene promoters by NR0B2/SHP thereby stimulating histone H3 and H4 deacetylation leading to transcriptional repression. Proposed to contribute to genomic integrity via positive regulation of telomere length; however, reports on localization to pericentromeric heterochromatin are conflicting. Proposed to play a role in constitutive heterochromatin (CH) formation and/or maintenance through regulation of the available pool of nuclear SUV39H1. Upon oxidative/metabolic stress decreases SUV39H1 degradation by inhibiting SUV39H1 polyubiquitination by MDM2. This increase in SUV39H1 levels enhances SUV39H1 turnover in CH, which in turn seems to accelerate renewal of the heterochromatin which correlates with greater genomic integrity during stress response. Deacetylates 'Lys-382' of p53/TP53 and impairs its ability to induce transcription-dependent proapoptotic program and modulate cell senescence. Deacetylates TAF1B and thereby represses rDNA transcription by the RNA polymerase I. Deacetylates MYC, promotes the association of MYC with MAX and decreases MYC stability leading to compromised transformational capability. Deacetylates FOXO3 in response to oxidative stress thereby increasing its ability to induce cell cycle arrest and resistance to oxidative stress but inhibiting FOXO3-mediated induction of apoptosis transcriptional activity; also leading to FOXO3 ubiquitination and protesomal degradation. Appears to have a similar effect on MLLT7/FOXO4 in regulation of transcriptional activity and apoptosis. Deacetylates DNMT1; thereby impairs DNMT1 methyltransferase-independent transcription repressor activity, modulates DNMT1 cell cycle regulatory function and DNMT1-mediated gene silencing. Deacetylates RELA/NF-kappa-B p65 thereby inhibiting its transactivating potential and augments apoptosis in response to TNF-alpha. Deacetylates HIF1A, KAT5/TIP60, RB1 and HIC1. Deacetylates FOXO1 resulting in its nuclear retention and enhancement of its transcriptional activity leading to increased gluconeogenesis in liver. Inhibits E2F1 transcriptional activity and apoptotic function, possibly by deacetylation. Involved in HES1- and HEY2-mediated transcriptional repression. In cooperation with MYCN seems to be involved in transcriptional repression of DUSP6/MAPK3 leading to MYCN stabilization by phosphorylation at 'Ser-62'. Deacetylates MEF2D. Required for antagonist-mediated transcription suppression of AR-dependent genes which may be linked to local deacetylation of histone H3. Represses HNF1A-mediated transcription. Required for the repression of ESRRG by CREBZF. Modulates AP-1 transcription factor activity. Deacetylates NR1H3 AND NR1H2 and deacetylation of NR1H3 at 'Lys-434' positively regulates transcription of NR1H3:RXR target genes, promotes NR1H3 proteosomal degradation and results in cholesterol efflux; a promoter clearing mechanism after reach round of transcription is proposed. Involved in lipid metabolism. Implicated in regulation of adipogenesis and fat mobilization in white adipocytes by repression of PPARG which probably involves association with NCOR1 and SMRT/NCOR2. Deacetylates ACSS2 leading to its activation, and HMGCS1. Involved in liver and muscle metabolism. Through deacteylation and activation of PPARGC1A is required to activate fatty acid oxidation in skeletel muscle under low-glucose conditions and is involved in glucose homeostasis. Involved in regulation of PPARA and fatty acid beta-oxidation in liver. Involved in positive regulation of insulin secretion in pancreatic beta cells in response to glucose; the function seems to imply transcriptional repression of UCP2. Proposed to deacetylate IRS2 thereby facilitating its insuline-induced tyrosine phosphorylation. Deacetylates SREBF1 isoform SREBP-1C thereby decreasing its stability and transactivation in lipogenic gene expression. Involved in DNA damage response by repressing genes which are involved in DNA repair, such as XPC and TP73, deacetylating XRCC6/Ku70, and faciliting recruitment of additional factors to sites of damaged DNA, such as SIRT1-deacetylated NBN can recruit ATM to initiate DNA repair and SIRT1-deacetylated XPA interacts with RPA2. Also involved in DNA repair of DNA double-strand breaks by homologous recombination and specifically single-strand annealing independently of XRCC6/Ku70 and NBN. Transcriptional suppression of XPC probably involves an E2F4:RBL2 suppressor complex and protein kinase B (AKT) signaling. Transcriptional suppression of TP73 probably involves E2F4 and PCAF. Deacetylates WRN thereby regulating its helicase and exonuclease activities and regulates WRN nuclear translocation in response to DNA damage. Deacetylates APEX1 at 'Lys-6' and 'Lys-7' and stimulates cellular AP endonuclease activity by promoting the association of APEX1 to XRCC1. Increases p53/TP53-mediated transcription-independent apoptosis by blocking nuclear translocation of cytoplasmic p53/TP53 and probably redirecting it to mitochondria. Deacetylates XRCC6/Ku70 at 'Lys-539' and 'Lys-542' causing it to sequester BAX away from mitochondria thereby inhibiting stress-induced apoptosis. Is involved in autophagy, presumably by deacetylating ATG5, ATG7 and MAP1LC3B/ATG8. Deacetylates AKT1 which leads to enhanced binding of AKT1 and PDK1 to PIP3 and promotes their activation. Proposed to play role in regulation of STK11/LBK1-dependent AMPK signaling pathways implicated in cellular senescence which seems to involve the regulation of the acetylation status of STK11/LBK1. Can deacetylate STK11/LBK1 and thereby increase its activity, cytoplasmic localization and association with STRAD; however, the relevance of such activity in normal cells is unclear. In endothelial cells is shown to inhibit STK11/LBK1 activity and to promote its degradation. Deacetylates SMAD7 at 'Lys-64' and 'Lys-70' thereby promoting its degradation. Deacetylates CIITA and augments its MHC class II transacivation and contributes to its stability. Deacteylates MECOM/EVI1. Isoform 2 is shown to deacetylate 'Lys-382' of p53/TP53, however with lower activity than isoform 1. In combination, the two isoforms exert an additive effect. Isoform 2 regulates p53/TP53 expression and cellular stress response and is in turn repressed by p53/TP53 presenting a SIRT1 isoform-dependent auto-regulatory loop. In case of HIV-1 infection, interacts with and deacetylates the viral Tat protein. The viral Tat protein inhibits SIRT1 deacetylation activity toward RELA/NF-kappa-B p65, thereby potentiates its transcriptional activity and SIRT1 is proposed to contribute to T-cell hyperactivation during infection. SirtT1 75 kDa fragment: catalytically inactive 75SirT1 may be involved in regulation of apoptosis. May be involved in protecting chondrocytes from apoptotic death by associating with cytochrome C and interfering with apoptosome assembly.
Gene Name:: SIRT1
Uniprot ID:: Q96EB6
Molecular weight:: 50496.105

Enzyme Details

4. Pirin

General function:: Not Available
Specific function:: Possible transcriptional coregulator. May contribute to the regulation of cellular processes via its interaction with BCL3. May be required for efficient terminal myeloid maturation of hematopoietic cells. May play a role in the regulation of cell migration. May promote apoptosis when overexpressed. Has quercetin 2,3-dioxygenase activity (in vitro).
Gene Name:: PIR
Uniprot ID:: O00625
Molecular weight:: 32113.195

Reactions

Quercetin + Oxygen → 2-(3,4-Dihydroxybenzoyloxy)-4,6-dihydroxybenzoate + CO + Hydrogen Ion	details

Enzyme Details

5. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Quercetin → Quercetin 3'-sulfate	details

Showing metabocard for Quercetin (HMDB0005794)

MOL for HMDB0005794 (Quercetin)

3D MOL for HMDB0005794 (Quercetin)

3D SDF for HMDB0005794 (Quercetin)

3D-SDF for HMDB0005794 (Quercetin)

PDB for HMDB0005794 (Quercetin)

3D PDB for HMDB0005794 (Quercetin)

SMILES for HMDB0005794 (Quercetin)

INCHI for HMDB0005794 (Quercetin)

Structure for HMDB0005794 (Quercetin)

3D Structure for HMDB0005794 (Quercetin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

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