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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:41:29 UTC

Update Date

2022-03-07 02:55:20 UTC

HMDB ID

HMDB0037441

Secondary Accession Numbers

HMDB37441

Metabolite Identification

Common Name

Kaempferide

Description

Kaempferide 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, kaempferide is considered to be a flavonoid. Kaempferide has been detected, but not quantified in, several different foods, such as cloves (Syzygium aromaticum), european plums (Prunus domestica), grapefruits (Citrus X paradisi), herbs and spices, and sour cherries (Prunus cerasus). This could make kaempferide a potential biomarker for the consumption of these foods. Kaempferide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Kaempferide.

Structure

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

HMDB0037441
     RDKit          3D
Kaempferide
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.0297    1.1358   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4177   -0.1058    0.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -0.2339    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775   -1.4649    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -1.6545    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583   -0.5683    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1942   -0.6424    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627    0.5049    0.1001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519    0.6366    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7402    1.8922    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1087    2.0079    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7404    3.2658   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8986    0.8988    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2997   -0.3753    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1272   -1.4439    0.3336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9264   -0.5214    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999   -1.7333    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354   -2.7916    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930   -1.8024    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836   -3.0250    0.3513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    0.7095    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2018    0.8425   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0818    1.0876   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0460    1.7263    0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4847    1.7514   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -2.3880    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014   -2.6596    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    2.7581   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515    4.0934   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9753    0.9759    0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243   -2.3978    0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791   -3.8933    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    1.5597   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.8551   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 19  7  2  0
 16  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  END


  Mrv0541 02241220282D          

 22 24  0  0  0  0            999 V2000
    1.0711   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0725    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2148   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2148   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4 21  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 18  1  0  0  0  0
  9 10  2  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 20  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037441

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
SQFSKOYWJBQGKQ-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.730806674739984

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.6057588416666664

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.056619728018882

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.444929813531017

> <JCHEM_PKA_STRONGEST_BASIC>
-3.887559034881929

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
79.36359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kaempferide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037441
     RDKit          3D
Kaempferide
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.0297    1.1358   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4177   -0.1058    0.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -0.2339    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775   -1.4649    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -1.6545    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583   -0.5683    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1942   -0.6424    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627    0.5049    0.1001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519    0.6366    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7402    1.8922    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1087    2.0079    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7404    3.2658   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8986    0.8988    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2997   -0.3753    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1272   -1.4439    0.3336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9264   -0.5214    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999   -1.7333    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354   -2.7916    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930   -1.8024    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836   -3.0250    0.3513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    0.7095    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2018    0.8425   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0818    1.0876   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0460    1.7263    0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4847    1.7514   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -2.3880    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014   -2.6596    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    2.7581   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515    4.0934   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9753    0.9759    0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243   -2.3978    0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791   -3.8933    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    1.5597   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.8551   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 19  7  2  0
 16  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.999  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.334   0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.669  -0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.669  -1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.334  -2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.999  -1.925   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.668   4.235   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.668   2.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.002   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.334   2.695   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.334   4.235   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.669   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.669   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.334  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.002   0.385   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.668  -0.385   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.667   1.925   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.999   2.695   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.001  -0.385   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.001  -2.695   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.001  -4.235   0.000  0.00  0.00           C+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    8                                                            
CONECT    8    7    9   18                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15    9   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17    1   16   18                                                  
CONECT   18    8   17   19                                                  
CONECT   19   18                                                            
CONECT   20   13                                                            
CONECT   21    4   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0037441
HETATM    1  C1  UNL     1       6.030   1.136  -0.089  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.418  -0.106   0.016  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.052  -0.234   0.054  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.478  -1.465   0.157  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.083  -1.654   0.200  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.258  -0.568   0.136  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.194  -0.642   0.172  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.863   0.505   0.100  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.152   0.637   0.117  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.740   1.892   0.036  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.109   2.008   0.055  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.740   3.266  -0.026  1.00  0.00           O  
HETATM   13  C10 UNL     1      -4.899   0.899   0.154  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.300  -0.375   0.237  1.00  0.00           C  
HETATM   15  O4  UNL     1      -5.127  -1.444   0.334  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.926  -0.521   0.219  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.300  -1.733   0.297  1.00  0.00           C  
HETATM   18  O5  UNL     1      -2.935  -2.792   0.389  1.00  0.00           O  
HETATM   19  C14 UNL     1      -0.893  -1.802   0.273  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.284  -3.025   0.351  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.837   0.710   0.029  1.00  0.00           C  
HETATM   22  C16 UNL     1       3.202   0.842  -0.009  1.00  0.00           C  
HETATM   23  H1  UNL     1       7.082   1.088  -0.450  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.046   1.726   0.852  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.485   1.751  -0.838  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.054  -2.388   0.214  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.701  -2.660   0.283  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.101   2.758  -0.042  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.152   4.093  -0.099  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.975   0.976   0.171  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.024  -2.398   0.403  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.779  -3.893   0.426  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.180   1.560  -0.021  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.589   1.855  -0.092  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   21
CONECT    7    8   19   19
CONECT    8    9
CONECT    9   10   10   16
CONECT   10   11   28
CONECT   11   12   13   13
CONECT   12   29
CONECT   13   14   30
CONECT   14   15   16   16
CONECT   15   31
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   32
CONECT   21   22   22   33
CONECT   22   34
END

HMDB0037441
     RDKit          3D
Kaempferide
 34 36  0  0  0  0  0  0  0  0999 V2000
    6.0297    1.1358   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4177   -0.1058    0.0159 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0518   -0.2339    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775   -1.4649    0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0828   -1.6545    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583   -0.5683    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1942   -0.6424    0.1718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8627    0.5049    0.1001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519    0.6366    0.1170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7402    1.8922    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1087    2.0079    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7404    3.2658   -0.0255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8986    0.8988    0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2997   -0.3753    0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1272   -1.4439    0.3336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9264   -0.5214    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2999   -1.7333    0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354   -2.7916    0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8930   -1.8024    0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836   -3.0250    0.3513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    0.7095    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2018    0.8425   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0818    1.0876   -0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0460    1.7263    0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4847    1.7514   -0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0543   -2.3880    0.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014   -2.6596    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    2.7581   -0.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515    4.0934   -0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9753    0.9759    0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0243   -2.3978    0.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7791   -3.8933    0.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    1.5597   -0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.8551   -0.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
  6 21  1  0
 21 22  2  0
 22  3  1  0
 19  7  2  0
 16  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1.3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyrone	ChEBI
4'-O-Methylkaempferol	ChEBI
Campheride	ChEBI
Kaempferol 4'-methyl ether	ChEBI
Kempferide	Kegg
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4-benzopyrone	HMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
3,5,7-Trihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one	HMDB
3,5,7-Trihydroxy-4'-methoxy-flavone	HMDB
4'-Methoxy-3,5,7-trihydroxy-flavanone	HMDB
4'-Methoxy-3,5,7-trihydroxyflavone	HMDB
4'-Methylkaempferol	HMDB
5,7-Dihydroxy-4'-methoxyflavonol	HMDB
Kaemferide	HMDB
Kaempferid	HMDB
Kampferide	HMDB
Kampheride	HMDB
3 5 7-Trihydroxy-4'-methoxyflavone	MeSH

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

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

Traditional Name

kaempferide

CAS Registry Number

491-54-3

SMILES

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

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavone (CHEBI:6099 )
trihydroxyflavone (CHEBI:6099 )
7-hydroxyflavonol (CHEBI:6099 )
flavonols (C10098 )
Flavones and Flavonols (C10098 )
Flavones and Flavonols (LMPK12110563 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037441)
Cytoplasm (HMDB: HMDB0037441)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037441)

Source

Exogenous

Food

Food (HMDB: HMDB0037441)

Fruit

Citrus

Grapefruit (FooDB: FOOD00256)

Drupe

European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)

Herb and spice

Spice

Cloves (FooDB: FOOD00179)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037441)

Process

Not Available

Role

Biological role

anti inflammatory (HMDB: HMDB0037441)
anti mutagenic (HMDB: HMDB0037441)
quinone-reductase inducer (HMDB: HMDB0037441)

Modulator

Inhibitor

Enzyme inhibitor

EC 1.14.14.14 (aromatase) inhibitor (HMDB: HMDB0037441)
EC 5.99.1.2 (DNA topoisomerase) inhibitor (HMDB: HMDB0037441)

Nutrient

Nutrient (HMDB: HMDB0037441)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	227 - 229 °C	Not Available
Boiling Point	543.80 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	327.6 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.740 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.44	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.36 m³·mol⁻¹	ChemAxon
Polarizability	29.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	171.751	30932474
DeepCCS	[M-H]-	169.393	30932474
DeepCCS	[M-2H]-	202.826	30932474
DeepCCS	[M+Na]+	178.053	30932474
AllCCS	[M+H]+	168.6	32859911
AllCCS	[M+H-H2O]+	164.9	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	173.0	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.1	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kaempferide	COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1	4627.7	Standard polar	33892256
Kaempferide	COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1	3033.5	Standard non polar	33892256
Kaempferide	COC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1	3066.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kaempferide,1TMS,isomer #1	COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1	3103.2	Semi standard non polar	33892256
Kaempferide,1TMS,isomer #2	COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1	3144.0	Semi standard non polar	33892256
Kaempferide,1TMS,isomer #3	COC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	3193.9	Semi standard non polar	33892256
Kaempferide,2TMS,isomer #1	COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	3052.7	Semi standard non polar	33892256
Kaempferide,2TMS,isomer #2	COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1	3023.7	Semi standard non polar	33892256
Kaempferide,2TMS,isomer #3	COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1	3140.3	Semi standard non polar	33892256
Kaempferide,3TMS,isomer #1	COC1=CC=C(C2=C(O[Si](C)(C)C)C(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1	3045.4	Semi standard non polar	33892256
Kaempferide,1TBDMS,isomer #1	COC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1	3401.5	Semi standard non polar	33892256
Kaempferide,1TBDMS,isomer #2	COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1	3409.5	Semi standard non polar	33892256
Kaempferide,1TBDMS,isomer #3	COC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3458.8	Semi standard non polar	33892256
Kaempferide,2TBDMS,isomer #1	COC1=CC=C(C2=C(O[Si](C)(C)C(C)(C)C)C(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3574.9	Semi standard non polar	33892256
Kaempferide,2TBDMS,isomer #2	COC1=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=C1	3545.5	Semi standard non polar	33892256
Kaempferide,2TBDMS,isomer #3	COC1=CC=C(C2=C(O)C(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3642.3	Semi standard non polar	33892256
Kaempferide,3TBDMS,isomer #1	COC1=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[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3767.7	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 - Kaempferide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0791000000-3624bd10f2d622665fc6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kaempferide GC-MS (3 TMS) - 70eV, Positive	splash10-0fkc-2271950000-26095b3d4aa33777ac68	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kaempferide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 20V, Negative-QTOF	splash10-014i-0940000000-563e589b151a0bfb9b74	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 40V, Negative-QTOF	splash10-0lz9-0960000000-0dce6ae0f50391aaacb9	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 30V, Negative-QTOF	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 10V, Negative-QTOF	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 50V, Negative-QTOF	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 20V, Negative-QTOF	splash10-001j-0090000000-847e2fc8fc2afde2e8a4	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 40V, Negative-QTOF	splash10-0lz9-0960000000-0dce6ae0f50391aaacb9	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 30V, Negative-QTOF	splash10-001i-0190000000-172ba30afca1dd6391fe	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 10V, Negative-QTOF	splash10-0002-0091000000-57350f569441ea5d880f	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 50V, Negative-QTOF	splash10-03fr-0960000000-979796d59b40dcf37939	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide ESI-TOF 10V, Negative-QTOF	splash10-0002-0092000000-04e7a3c959e15791ba36	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOF	splash10-000t-0290000000-fa97943058aecfae6424	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOF	splash10-0lz9-1930000000-02a76c9065a4d7efea34	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOF	splash10-000t-1390000000-6bcab21096c8f7188eac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOF	splash10-0002-0090000000-e9170e82b1995679aeb3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOF	splash10-001j-0190000000-a2ea43e49a14ecee430e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-QTOF , negative-QTOF	splash10-0pc0-0930000000-7f0eb2e35a23d80bbe81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-TOF , negative-QTOF	splash10-001j-0090000000-847e2fc8fc2afde2e8a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Kaempferide LC-ESI-TOF , negative-QTOF	splash10-0lz9-0960000000-0dce6ae0f50391aaacb9	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kaempferide 10V, Positive-QTOF	splash10-0udi-0009000000-074f2d87992a7d211bc5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kaempferide 20V, Positive-QTOF	splash10-0udi-0019000000-b776fbc53676f3fbdefc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kaempferide 40V, Positive-QTOF	splash10-0udr-6890000000-8ec28b3eec5b952d0820	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kaempferide 10V, Negative-QTOF	splash10-0002-0090000000-47a5eafa7deb386a7c0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kaempferide 20V, Negative-QTOF	splash10-0002-0090000000-2ea66ca52cf34d166887	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kaempferide 40V, Negative-QTOF	splash10-0f89-3690000000-d8131b75040f06793f22	2016-08-03	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Kaempferide

METLIN ID

Not Available

PubChem Compound

5281666

PDB ID

Not Available

ChEBI ID

6099

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1504521

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. 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

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

Showing metabocard for Kaempferide (HMDB0037441)

MOL for HMDB0037441 (Kaempferide)

3D MOL for HMDB0037441 (Kaempferide)

3D SDF for HMDB0037441 (Kaempferide)

3D-SDF for HMDB0037441 (Kaempferide)

PDB for HMDB0037441 (Kaempferide)

3D PDB for HMDB0037441 (Kaempferide)

SMILES for HMDB0037441 (Kaempferide)

INCHI for HMDB0037441 (Kaempferide)

Structure for HMDB0037441 (Kaempferide)

3D Structure for HMDB0037441 (Kaempferide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions