NP-MRD: Showing NP-Card for Kaempferide (NP0043913)

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Record Information

Version

2.0

Created at

2021-06-22 17:28:51 UTC

Updated at

2021-08-20 00:00:48 UTC

NP-MRD ID

NP0043913

Secondary Accession Numbers

None

Natural Product 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 is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Kaempferide is found in Agnorhiza bolanderi, Agrimonia eupatoria, Alnus glutinosa, Alnus japonica, Alpinia conchigera, Alpinia galanga, Arnica parryi, Baccharis darwinii, Baccharis dracunculifolia, Balsamorhiza deltoidea, Butea monosperma, Catharanthus roseus, Centaurea deflexa, Chromolaena odorata, Cistus creticus, Cistus laurifolius, Cistus parviflorus, Cota altissima, Currania robertiana, Deinandra kelloggii, Dianthus caryophyllus, Ericameria laricifolia, Ageratina altissima, Grindelia tarapacana, Gymnocarpium robertianum, Hazardia squarrosa, Monticalia vaccinioides, Notholaena standleyi, Pentagramma triangularis, Phyllanthus virgatus, Populus alba, Populus tremula, Populus tremuloides and Tamarix nilotica. Kaempferide was first documented in 2009 (PMID: 19571393). Based on a literature review a small amount of articles have been published on Kaempferide (PMID: 22993853) (PMID: 23123452) (PMID: 23208771).

Structure

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

NP0043913
     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    6.0315    1.0585    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762   -0.2389    0.3752 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.3596    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4557   -1.5800    0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514   -1.6957    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583   -0.5882    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922   -0.6175    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    0.5397   -0.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156    0.6804   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033    1.9231   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599    2.1027   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237    3.3840   -0.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8422    0.9828   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375   -0.3108   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1704   -1.3841   -0.0330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -0.4289   -0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.6312    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9806   -2.7114    0.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646   -1.7202    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -2.9727    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980    0.6601    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    0.7251    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002    1.4343   -0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324    1.7165    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1244    1.0033    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337   -2.4799    0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341   -2.6763    0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    2.8185   -0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540    4.1988   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9147    1.0595   -0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0882   -2.3351    0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460   -3.8073    0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    1.5293   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    1.7215    0.0857 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

  Mrv1652306222119282D          

 22 24  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -0.7145   -1.2375    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   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
    2.8579    0.0000    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 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 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 16 20  1  0  0  0  0
 14 21  1  0  0  0  0
 10 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043913

> <DATABASE_NAME>
NP-MRD

> <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_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.730806674735064

> <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>
7.9543821995856625

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.383164711761815

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8875590348819307

> <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

$$$$

NP0043913
     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    6.0315    1.0585    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762   -0.2389    0.3752 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.3596    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4557   -1.5800    0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514   -1.6957    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583   -0.5882    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922   -0.6175    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    0.5397   -0.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156    0.6804   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033    1.9231   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599    2.1027   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237    3.3840   -0.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8422    0.9828   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375   -0.3108   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1704   -1.3841   -0.0330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -0.4289   -0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.6312    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9806   -2.7114    0.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646   -1.7202    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -2.9727    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980    0.6601    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    0.7251    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002    1.4343   -0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324    1.7165    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1244    1.0033    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337   -2.4799    0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341   -2.6763    0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    2.8185   -0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540    4.1988   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9147    1.0595   -0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0882   -2.3351    0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460   -3.8073    0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    1.5293   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    1.7215    0.0857 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                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   19                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    9                                                       
CONECT   20   16                                                            
CONECT   21   14                                                            
CONECT   22   10                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    NP0043913
HETATM    1  C1  UNL     1       6.031   1.058   0.269  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.476  -0.239   0.375  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.080  -0.360   0.319  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.456  -1.580   0.414  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.051  -1.696   0.356  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.258  -0.588   0.203  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.192  -0.618   0.134  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.832   0.540  -0.017  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.116   0.680  -0.095  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.703   1.923  -0.253  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.060   2.103  -0.338  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.624   3.384  -0.498  1.00  0.00           O  
HETATM   13  C10 UNL     1      -4.842   0.983  -0.261  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.338  -0.311  -0.103  1.00  0.00           C  
HETATM   15  O4  UNL     1      -5.170  -1.384  -0.033  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.971  -0.429  -0.023  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.361  -1.631   0.131  1.00  0.00           C  
HETATM   18  O5  UNL     1      -2.981  -2.711   0.212  1.00  0.00           O  
HETATM   19  C14 UNL     1      -0.965  -1.720   0.210  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.394  -2.973   0.367  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.898   0.660   0.105  1.00  0.00           C  
HETATM   22  C16 UNL     1       3.263   0.725   0.166  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.800   1.434  -0.739  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.532   1.716   1.012  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.124   1.003   0.471  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.034  -2.480   0.535  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.634  -2.676   0.437  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.070   2.818  -0.314  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.054   4.199  -0.554  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.915   1.060  -0.322  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.088  -2.335   0.069  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.946  -3.807   0.426  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.269   1.529  -0.015  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.715   1.721   0.086  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

NP0043913
     RDKit          3D

34 36  0  0  0  0  0  0  0  0999 V2000
    6.0315    1.0585    0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4762   -0.2389    0.3752 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.3596    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4557   -1.5800    0.4138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0514   -1.6957    0.3562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583   -0.5882    0.2027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1922   -0.6175    0.1340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    0.5397   -0.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1156    0.6804   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7033    1.9231   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599    2.1027   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6237    3.3840   -0.4985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8422    0.9828   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3375   -0.3108   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1704   -1.3841   -0.0330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -0.4289   -0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3614   -1.6312    0.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9806   -2.7114    0.2124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646   -1.7202    0.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -2.9727    0.3673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980    0.6601    0.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    0.7251    0.1662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8002    1.4343   -0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5324    1.7165    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1244    1.0033    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0337   -2.4799    0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6341   -2.6763    0.4369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701    2.8185   -0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0540    4.1988   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9147    1.0595   -0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0882   -2.3351    0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9460   -3.8073    0.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2686    1.5293   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7147    1.7215    0.0857 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

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	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2629 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

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

Traditional Name

kaempferide

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agnorhiza bolanderi	LOTUS Database	35616633
Agrimonia eupatoria	LOTUS Database	35616633
Alnus glutinosa	LOTUS Database	35616633
Alnus japonica	LOTUS Database	35616633
Alpinia conchigera	LOTUS Database	35616633
Alpinia galanga	LOTUS Database	35616633
Alpinia officinarum	KNApSAcK Database	22123792
Arnica parryi	LOTUS Database	35616633
Astragalus complanatus	KNApSAcK Database	22123792
Baccharis darwinii	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Baccharis pilularis	KNApSAcK Database	22123792
Baccharis viminea	KNApSAcK Database	22123792
Balsamorhiza deltoidea	LOTUS Database	35616633
Butea monosperma	LOTUS Database	35616633
Calceolaria irazeunsis	KNApSAcK Database	22123792
Capsella bursa-pastoris	KNApSAcK Database	22123792
Catharanthus roseus	LOTUS Database	35616633
Centaurea deflexa	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Chrysothamnus nauseosus	KNApSAcK Database	22123792
Cistus creticus	LOTUS Database	35616633
Cistus laurifolius	LOTUS Database	35616633
Cistus parviflorus	LOTUS Database	35616633
Citrus paradisi	FooDB	PHENOL EXPLORER
Costus spicatus	KNApSAcK Database	22123792
Cota altissima	LOTUS Database	35616633
Crocus sativus	KNApSAcK Database	22123792
Currania robertiana	-	KNApSAcK
Deinandra kelloggii	LOTUS Database	35616633
Dianthus caryophyllus	LOTUS Database	35616633
Ericameria laricifolia	LOTUS Database	35616633
Eriodictyon sessilifolium	KNApSAcK Database	22123792
Eucryphia jinksii	KNApSAcK Database	22123792
Eupatorium rugosum	LOTUS Database	35616633
Genista aetnensis	KNApSAcK Database	22123792
Grindelia tarapacana	LOTUS Database	35616633
Gymnocarpium robertianum	LOTUS Database	35616633
Hazardia squarrosa	LOTUS Database	35616633
Kaempferia galanga	KNApSAcK Database	22123792
Linaria dalmatica	KNApSAcK Database	22123792
Mirabilis viscosa	KNApSAcK Database	22123792
Monticalia vaccinioides	LOTUS Database	35616633
Nothofagus menziesii	KNApSAcK Database	22123792
Nothofagus nervosa	KNApSAcK Database	22123792
Notholaena standleyi	LOTUS Database	35616633
Ozothamnus scutellifolius	KNApSAcK Database	22123792
Pentagramma triangularis	LOTUS Database	35616633
Phyllanthus virgatus	LOTUS Database	35616633
Populus alba	LOTUS Database	35616633
Populus tremula	LOTUS Database	35616633
Populus tremuloides	LOTUS Database	35616633
Prunus cerasus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus domestica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sedum sarmentosum	KNApSAcK Database	22123792
Semecarpus vitiensis	KNApSAcK Database	22123792
Syzygium aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tamarix chinensis	KNApSAcK Database	22123792
Tamarix nilotica	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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

Predicted Properties

Property	Value	Source
logP	2.48	ALOGPS
logP	2.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.38	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

External Links

HMDB ID

HMDB0037441

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

rw1504521

References

General References

Maruyama H, Sumitou Y, Sakamoto T, Araki Y, Hara H: Antihypertensive effects of flavonoids isolated from brazilian green propolis in spontaneously hypertensive rats. Biol Pharm Bull. 2009 Jul;32(7):1244-50. doi: 10.1248/bpb.32.1244. [PubMed:19571393 ]
Song P, Yao J, Ma HP, Ge BF, Chen KM, Guo XY, Lu X: [Comparison of effects of kaempferide and anhydroicaritin on biomineralization of cultured osteoblasts]. Yao Xue Xue Bao. 2012 Jul;47(7):890-6. [PubMed:22993853 ]
Nawwar MA, Swilam NF, Hashim AN, Al-Abd AM, Abdel-Naim AB, Lindequist U: Cytotoxic isoferulic acidamide from Myricaria germanica (Tamaricaceae). Plant Signal Behav. 2013 Jan;8(1):e22642. doi: 10.4161/psb.22642. Epub 2012 Nov 3. [PubMed:23123452 ]
Horibe I, Satoh Y, Shiota Y, Kumagai A, Horike N, Takemori H, Uesato S, Sugie S, Obata K, Kawahara H, Nagaoka Y: Induction of melanogenesis by 4'-O-methylated flavonoids in B16F10 melanoma cells. J Nat Med. 2013 Oct;67(4):705-10. doi: 10.1007/s11418-012-0727-y. Epub 2012 Dec 4. [PubMed:23208771 ]

Showing NP-Card for Kaempferide (NP0043913)

MOL for NP0043913 (Kaempferide)

3D MOL for NP0043913 (Kaempferide)

3D SDF for NP0043913 (Kaempferide)

3D-SDF for NP0043913 (Kaempferide)

PDB for NP0043913 (Kaempferide)

3D PDB for NP0043913 (Kaempferide)

SMILES for NP0043913 (Kaempferide)

INCHI for NP0043913 (Kaempferide)

Structure for NP0043913 (Kaempferide)

3D Structure for NP0043913 (Kaempferide)