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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:08 UTC

Update Date

2022-03-07 02:52:42 UTC

HMDB ID

HMDB0030802

Secondary Accession Numbers

HMDB30802

Metabolite Identification

Common Name

Patuletin

Description

Patuletin 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, patuletin is considered to be a flavonoid lipid molecule. A trimethoxyflavone that is quercetagetin methylated at position 6. Patuletin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Patuletin has been detected, but not quantified in, a few different foods, such as german camomiles, herbs and spices, and spinachs. This could make patuletin a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030802
     RDKit          3D
Patuletin
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.9820   -0.1276   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1262   -0.8357    0.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.8066    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.7337   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -2.7342   -1.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -1.6529   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0372   -0.6704   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.6014   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352    0.2882    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    0.1986    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -1.0645   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3130   -1.2342   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2033   -0.1760   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5486   -0.3176   -0.7311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436    1.0657   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5637    2.1758    0.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939    1.1992    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    1.2405    1.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010    2.2111    1.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    1.2341    1.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    2.1084    2.1046 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    0.2817    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    0.2046    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469    1.0870    1.5728 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8731   -0.7591   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4982    0.1856   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3803    0.7922   -0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3541   -3.4127   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -2.3959   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2966   -1.9033   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6907   -2.2135   -0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9383   -1.2112   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1838    3.0701    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652    2.1982    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    2.4865    2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823    1.8228    2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 22  7  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 24 36  1  0
M  END

  Mrv0541 05061305312D          

 24 26  0  0  0  0            999 V2000
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 14  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23  1  1  0  0  0  0
 23 16  1  0  0  0  0
 24 10  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030802

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3

> <INCHI_KEY>
JMIFIYIEXODVTO-UHFFFAOYSA-N

> <FORMULA>
C16H12O8

> <MOLECULAR_WEIGHT>
332.2617

> <EXACT_MASS>
332.05321736

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
31.493583390060778

> <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-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
1.998628198333333

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.387166522441012

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.947215548984535

> <JCHEM_PKA_STRONGEST_BASIC>
-4.013407143613592

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
83.3254

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
patuletin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030802
     RDKit          3D
Patuletin
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.9820   -0.1276   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1262   -0.8357    0.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.8066    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.7337   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -2.7342   -1.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -1.6529   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0372   -0.6704   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.6014   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352    0.2882    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    0.1986    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -1.0645   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3130   -1.2342   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2033   -0.1760   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5486   -0.3176   -0.7311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436    1.0657   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5637    2.1758    0.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939    1.1992    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    1.2405    1.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010    2.2111    1.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    1.2341    1.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    2.1084    2.1046 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    0.2817    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    0.2046    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469    1.0870    1.5728 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8731   -0.7591   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4982    0.1856   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3803    0.7922   -0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3541   -3.4127   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -2.3959   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2966   -1.9033   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6907   -2.2135   -0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9383   -1.2112   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1838    3.0701    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652    2.1982    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    2.4865    2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823    1.8228    2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 22  7  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 24 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    6    8                                                       
CONECT    5    9   10                                                       
CONECT    6    2    4   15                                                  
CONECT    7    3    8   17                                                  
CONECT    8    4    7   18                                                  
CONECT    9    5   16   19                                                  
CONECT   10    5   11   24                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   14   20                                                  
CONECT   13   11   16   21                                                  
CONECT   14   12   15   22                                                  
CONECT   15    6   14   24                                                  
CONECT   16    9   13   23                                                  
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   14                                                            
CONECT   23    1   16                                                       
CONECT   24   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0030802
HETATM    1  C1  UNL     1       5.982  -0.128  -0.620  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.126  -0.836   0.257  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.742  -0.807   0.126  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.120  -1.734  -0.652  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.837  -2.734  -1.336  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.753  -1.653  -0.741  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.037  -0.670  -0.070  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.252  -0.601  -0.161  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.035   0.288   0.433  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.476   0.199   0.206  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.992  -1.065  -0.170  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.313  -1.234  -0.475  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.203  -0.176  -0.429  1.00  0.00           C  
HETATM   14  O4  UNL     1      -6.549  -0.318  -0.731  1.00  0.00           O  
HETATM   15  C11 UNL     1      -4.744   1.066  -0.071  1.00  0.00           C  
HETATM   16  O5  UNL     1      -5.564   2.176   0.000  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.394   1.199   0.231  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.485   1.241   1.229  1.00  0.00           C  
HETATM   19  O6  UNL     1      -1.101   2.211   1.928  1.00  0.00           O  
HETATM   20  C14 UNL     1       0.933   1.234   1.378  1.00  0.00           C  
HETATM   21  O7  UNL     1       1.450   2.108   2.105  1.00  0.00           O  
HETATM   22  C15 UNL     1       1.655   0.282   0.726  1.00  0.00           C  
HETATM   23  C16 UNL     1       3.037   0.205   0.820  1.00  0.00           C  
HETATM   24  O8  UNL     1       3.747   1.087   1.573  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.873  -0.759  -0.827  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.498   0.186  -1.543  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.380   0.792  -0.101  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.354  -3.413  -1.908  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.251  -2.396  -1.364  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.297  -1.903  -0.208  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.691  -2.214  -0.761  1.00  0.00           H  
HETATM   32  H8  UNL     1      -6.938  -1.211  -1.001  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.184   3.070   0.268  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.065   2.198   0.449  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.975   2.486   2.116  1.00  0.00           H  
HETATM   36  H12 UNL     1       3.482   1.823   2.105  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5    6
CONECT    5   28
CONECT    6    7    7   29
CONECT    7    8   22
CONECT    8    9
CONECT    9   10   18   18
CONECT   10   11   11   17
CONECT   11   12   30
CONECT   12   13   13   31
CONECT   13   14   15
CONECT   14   32
CONECT   15   16   17   17
CONECT   16   33
CONECT   17   34
CONECT   18   19   20
CONECT   19   35
CONECT   20   21   21   22
CONECT   22   23   23
CONECT   23   24
CONECT   24   36
END

HMDB0030802
     RDKit          3D
Patuletin
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.9820   -0.1276   -0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1262   -0.8357    0.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.8066    0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1200   -1.7337   -0.6515 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373   -2.7342   -1.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -1.6529   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0372   -0.6704   -0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524   -0.6014   -0.1607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0352    0.2882    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4765    0.1986    0.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -1.0645   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3130   -1.2342   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2033   -0.1760   -0.4287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5486   -0.3176   -0.7311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7436    1.0657   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5637    2.1758    0.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3939    1.1992    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    1.2405    1.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010    2.2111    1.9283 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    1.2341    1.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4498    2.1084    2.1046 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    0.2817    0.7260 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0367    0.2046    0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7469    1.0870    1.5728 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8731   -0.7591   -0.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4982    0.1856   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3803    0.7922   -0.1014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3541   -3.4127   -1.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2508   -2.3959   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2966   -1.9033   -0.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6907   -2.2135   -0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9383   -1.2112   -1.0007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1838    3.0701    0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652    2.1982    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9753    2.4865    2.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823    1.8228    2.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
  9 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 22  7  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 24 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone	ChEBI
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-one	ChEBI
3',4',5,7-Tetrahydroxy-6-methoxyflavonol	ChEBI
3,5,7,3',4'-Pentahydroxy-6-methoxyflavone	ChEBI
6-Methoxyquercetin	ChEBI
6-O-Methylquercetagetin	ChEBI
Quercetagetin 6-methyl ether	ChEBI
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-chromen-4-one	MeSH

Chemical Formula

C₁₆H₁₂O₈

Average Molecular Weight

332.2617

Monoisotopic Molecular Weight

332.05321736

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-chromen-4-one

Traditional Name

patuletin

CAS Registry Number

519-96-0

SMILES

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

InChI Identifier

InChI=1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3

InChI Key

JMIFIYIEXODVTO-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:75164 )
pentahydroxyflavone (CHEBI:75164 )
flavonols (CHEBI:75164 )
flavonols (C10118 )
Flavones and Flavonols (C10118 )
Flavones and Flavonols (LMPK12112986 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030802)
Cytoplasm (HMDB: HMDB0030802)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030802)

Source

Endogenous

Endogenous (HMDB: HMDB0030802)

Plant

Plant (HMDB: HMDB0030802)

Exogenous

Food

Food (HMDB: HMDB0030802)

Vegetable

Leaf vegetable

Spinach (FooDB: FOOD00178)

Herb and spice

Herb

German camomile (FooDB: FOOD00107)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0030802)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	262 - 264 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	1.82	ALOGPS
logP	2	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.95	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	83.33 m³·mol⁻¹	ChemAxon
Polarizability	31.49 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]+	175.825	30932474
DeepCCS	[M-H]-	173.401	30932474
DeepCCS	[M-2H]-	207.762	30932474
DeepCCS	[M+Na]+	182.997	30932474
AllCCS	[M+H]+	175.4	32859911
AllCCS	[M+H-H2O]+	172.0	32859911
AllCCS	[M+NH4]+	178.6	32859911
AllCCS	[M+Na]+	179.5	32859911
AllCCS	[M-H]-	174.2	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	173.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Patuletin	COC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)C=C1O	5264.3	Standard polar	33892256
Patuletin	COC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)C=C1O	3290.2	Standard non polar	33892256
Patuletin	COC1=C(O)C2=C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)C=C1O	3172.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Patuletin,1TMS,isomer #1	COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3349.8	Semi standard non polar	33892256
Patuletin,1TMS,isomer #2	COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3332.2	Semi standard non polar	33892256
Patuletin,1TMS,isomer #3	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O	3422.8	Semi standard non polar	33892256
Patuletin,1TMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O	3443.2	Semi standard non polar	33892256
Patuletin,1TMS,isomer #5	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O)C(=O)C2=C1O	3376.3	Semi standard non polar	33892256
Patuletin,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3244.1	Semi standard non polar	33892256
Patuletin,2TMS,isomer #10	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O	3396.9	Semi standard non polar	33892256
Patuletin,2TMS,isomer #2	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3363.1	Semi standard non polar	33892256
Patuletin,2TMS,isomer #3	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3339.0	Semi standard non polar	33892256
Patuletin,2TMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3162.7	Semi standard non polar	33892256
Patuletin,2TMS,isomer #5	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3201.4	Semi standard non polar	33892256
Patuletin,2TMS,isomer #6	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3369.5	Semi standard non polar	33892256
Patuletin,2TMS,isomer #7	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3332.7	Semi standard non polar	33892256
Patuletin,2TMS,isomer #8	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O	3367.5	Semi standard non polar	33892256
Patuletin,2TMS,isomer #9	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O	3346.8	Semi standard non polar	33892256
Patuletin,3TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3245.5	Semi standard non polar	33892256
Patuletin,3TMS,isomer #10	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O	3221.3	Semi standard non polar	33892256
Patuletin,3TMS,isomer #2	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3225.0	Semi standard non polar	33892256
Patuletin,3TMS,isomer #3	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3141.0	Semi standard non polar	33892256
Patuletin,3TMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3177.5	Semi standard non polar	33892256
Patuletin,3TMS,isomer #5	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3203.4	Semi standard non polar	33892256
Patuletin,3TMS,isomer #6	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3187.0	Semi standard non polar	33892256
Patuletin,3TMS,isomer #7	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3230.0	Semi standard non polar	33892256
Patuletin,3TMS,isomer #8	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3209.0	Semi standard non polar	33892256
Patuletin,3TMS,isomer #9	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3226.8	Semi standard non polar	33892256
Patuletin,4TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C	3184.5	Semi standard non polar	33892256
Patuletin,4TMS,isomer #2	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3207.3	Semi standard non polar	33892256
Patuletin,4TMS,isomer #3	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3191.3	Semi standard non polar	33892256
Patuletin,4TMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3163.7	Semi standard non polar	33892256
Patuletin,4TMS,isomer #5	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O	3196.5	Semi standard non polar	33892256
Patuletin,5TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)=C(O[Si](C)(C)C)C(=O)C2=C1O[Si](C)(C)C	3197.1	Semi standard non polar	33892256
Patuletin,1TBDMS,isomer #1	COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3629.8	Semi standard non polar	33892256
Patuletin,1TBDMS,isomer #2	COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	3627.0	Semi standard non polar	33892256
Patuletin,1TBDMS,isomer #3	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O	3688.2	Semi standard non polar	33892256
Patuletin,1TBDMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O	3712.6	Semi standard non polar	33892256
Patuletin,1TBDMS,isomer #5	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O)C(=O)C2=C1O	3666.0	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3816.1	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #10	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O	3920.6	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #2	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3882.9	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #3	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3842.8	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3716.3	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #5	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	3765.8	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #6	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	3901.0	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #7	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	3855.6	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #8	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O	3882.1	Semi standard non polar	33892256
Patuletin,2TBDMS,isomer #9	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O	3864.6	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4053.0	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #10	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O	4023.1	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4002.0	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #3	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3885.7	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3964.8	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #5	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3981.3	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #6	COC1=C(O)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	3931.6	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #7	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	4046.3	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #8	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	3999.5	Semi standard non polar	33892256
Patuletin,3TBDMS,isomer #9	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	4005.9	Semi standard non polar	33892256
Patuletin,4TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4138.6	Semi standard non polar	33892256
Patuletin,4TBDMS,isomer #2	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4104.0	Semi standard non polar	33892256
Patuletin,4TBDMS,isomer #3	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4054.8	Semi standard non polar	33892256
Patuletin,4TBDMS,isomer #4	COC1=C(O)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O[Si](C)(C)C(C)(C)C	4029.9	Semi standard non polar	33892256
Patuletin,4TBDMS,isomer #5	COC1=C(O[Si](C)(C)C(C)(C)C)C=C2OC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)=C(O[Si](C)(C)C(C)(C)C)C(=O)C2=C1O	4134.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Patuletin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0529000000-80eb16e79922e773ce42	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Patuletin GC-MS (5 TMS) - 70eV, Positive	splash10-004i-0024029000-5b6566c1e3d3b3e22ad5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Patuletin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Patuletin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 10V, Positive-QTOF	splash10-001i-0009000000-0433b24ac8fa3594d2ef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 20V, Positive-QTOF	splash10-001i-0109000000-8ce46b5c40f4ed741ffd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 40V, Positive-QTOF	splash10-05n0-4921000000-98be6ac7065ad4f7fb0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 10V, Negative-QTOF	splash10-001i-0109000000-0074b1f85f21aec6fa6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 20V, Negative-QTOF	splash10-001i-0139000000-11cfd247fb3babf52f64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 40V, Negative-QTOF	splash10-05fr-6941000000-01e1b2cba8f4e48697a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 10V, Positive-QTOF	splash10-001i-0009000000-9a57877c53466fab202c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 20V, Positive-QTOF	splash10-001i-0009000000-58dc8929de3f58a5353d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 40V, Positive-QTOF	splash10-001i-1903000000-74531964f65f03d51054	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 10V, Negative-QTOF	splash10-001i-0009000000-60f511470aa84a372601	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 20V, Negative-QTOF	splash10-001i-0439000000-9d8b568c9fc819b97088	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patuletin 40V, Negative-QTOF	splash10-01c0-1921000000-7210a1e07ea954f6ac6a	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002744

KNApSAcK ID

C00004680

Chemspider ID

Not Available

KEGG Compound ID

C10118

BioCyc ID

CPD-14907

BiGG ID

Not Available

Wikipedia Link

Patuletin

METLIN ID

Not Available

PubChem Compound

5281678

PDB ID

Not Available

ChEBI ID

75164

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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

Patuletin → Spinacetin	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

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

Enzyme Details

3. 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

Patuletin → [2-hydroxy-5-(3,5,7-trihydroxy-6-methoxy-4-oxo-4H-chromen-2-yl)phenyl]oxidanesulfonic acid	details

Showing metabocard for Patuletin (HMDB0030802)

MOL for HMDB0030802 (Patuletin)

3D MOL for HMDB0030802 (Patuletin)

3D SDF for HMDB0030802 (Patuletin)

3D-SDF for HMDB0030802 (Patuletin)

PDB for HMDB0030802 (Patuletin)

3D PDB for HMDB0030802 (Patuletin)

SMILES for HMDB0030802 (Patuletin)

INCHI for HMDB0030802 (Patuletin)

Structure for HMDB0030802 (Patuletin)

3D Structure for HMDB0030802 (Patuletin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions