MiMeDB: Showing metabocard for Apigenin (MMDBc0000583)

Not Available

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:28 UTC

Update Date

2024-09-27 20:01:32 UTC

Metabolite ID

MMDBc0000583

Metabolite Identification

Common Name

Apigenin

Description

Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614 ). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095 ). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565 ).

Structure

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

HMDB0002124
     RDKit          3D
Apigenin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.8976   -2.9243    1.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -1.8462    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -1.6295    0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623   -0.4508    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062   -0.1415    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    1.0988   -0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6472    1.4561   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6237    0.5733   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788    0.9182   -0.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161   -0.6629    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744   -1.0259    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    0.4666   -0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    0.3210   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4227    1.3600   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7940    1.3173   -0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5483    2.4101   -1.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925    0.1642   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6342   -0.9329    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739   -2.0604    0.5678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.8521    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140   -2.4082    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    1.7985   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    2.4227   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574    1.3563    0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -1.3630    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -2.0121    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9467    2.2706   -1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0310    3.2263   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4863    0.0573   -0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9884   -2.9075    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END


  Mrv1652309272007452D          

 20 22  0  0  0  0            999 V2000
 9999.6614 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.232010001.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2367 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.807810000.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.236710000.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5222 9999.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5221 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2366 9998.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.803210001.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088510000.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8030 9999.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710000.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662310000.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6623 9998.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  6  4  1  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
  1 18  2  0  0  0  0
 20 12  1  0  0  0  0
 16  5  2  0  0  0  0
  8 17  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000583

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

> <INCHI_KEY>
KZNIFHPLKGYRTM-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.78231868537869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.706689133666666

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.074380554834784

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5746917607523745

> <JCHEM_PKA_STRONGEST_BASIC>
-5.381179969028214

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
72.91390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chamomile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002124
     RDKit          3D
Apigenin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.8976   -2.9243    1.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -1.8462    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -1.6295    0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623   -0.4508    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062   -0.1415    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    1.0988   -0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6472    1.4561   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6237    0.5733   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788    0.9182   -0.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161   -0.6629    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744   -1.0259    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    0.4666   -0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    0.3210   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4227    1.3600   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7940    1.3173   -0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5483    2.4101   -1.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925    0.1642   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6342   -0.9329    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739   -2.0604    0.5678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.8521    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140   -2.4082    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    1.7985   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    2.4227   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574    1.3563    0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -1.3630    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -2.0121    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9467    2.2706   -1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0310    3.2263   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4863    0.0573   -0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9884   -2.9075    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0358662.387   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8672.7008669.332   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8663.3758662.387   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8660.7088667.026   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8663.3758667.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0418666.248   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8662.0418664.708   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.3758663.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8671.3668668.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8670.0338669.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.6998668.565   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.6998667.025   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.0328666.255   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.3668667.025   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8666.0368667.018   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8664.7038666.248   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.7038664.708   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.0368663.938   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8667.3708664.708   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8667.3708666.248   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2    9                                                            
CONECT    3    8                                                            
CONECT    4    6                                                            
CONECT    5    6   16                                                       
CONECT    6    5    7    4                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3   17                                                  
CONECT    9   10   14    2                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   16   20                                                       
CONECT   16   17   15    5                                                  
CONECT   17   16   18    8                                                  
CONECT   18   17   19    1                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   12                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0002124
HETATM    1  O1  UNL     1      -1.898  -2.924   1.018  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.419  -1.846   0.622  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.042  -1.630   0.605  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.462  -0.451   0.171  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.906  -0.142   0.120  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.325   1.099  -0.341  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.647   1.456  -0.416  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.624   0.573  -0.026  1.00  0.00           C  
HETATM    9  O2  UNL     1       5.979   0.918  -0.095  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.216  -0.663   0.435  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.874  -1.026   0.511  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.378   0.467  -0.226  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.662   0.321  -0.232  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.423   1.360  -0.672  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.794   1.317  -0.722  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.548   2.410  -1.183  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.392   0.164  -0.303  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.634  -0.933   0.160  1.00  0.00           C  
HETATM   19  O5  UNL     1      -4.274  -2.060   0.568  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.254  -0.852   0.196  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.614  -2.408   0.939  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.552   1.798  -0.651  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.942   2.423  -0.778  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.457   1.356   0.668  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.981  -1.363   0.744  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.591  -2.012   0.881  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.947   2.271  -1.003  1.00  0.00           H  
HETATM   28  H8  UNL     1      -4.031   3.226  -1.475  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.486   0.057  -0.314  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.988  -2.908   0.911  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4    4   21
CONECT    4    5   12
CONECT    5    6    6   11
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   10
CONECT    9   24
CONECT   10   11   11   25
CONECT   11   26
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   27
CONECT   15   16   17   17
CONECT   16   28
CONECT   17   18   29
CONECT   18   19   20   20
CONECT   19   30
END

HMDB0002124
     RDKit          3D
Apigenin
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.8976   -2.9243    1.0183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4194   -1.8462    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -1.6295    0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623   -0.4508    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9062   -0.1415    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    1.0988   -0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6472    1.4561   -0.4165 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6237    0.5733   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9788    0.9182   -0.0948 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161   -0.6629    0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8744   -1.0259    0.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    0.4666   -0.2262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    0.3210   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4227    1.3600   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7940    1.3173   -0.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5483    2.4101   -1.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925    0.1642   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6342   -0.9329    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739   -2.0604    0.5678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.8521    0.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140   -2.4082    0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    1.7985   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424    2.4227   -0.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4574    1.3563    0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -1.3630    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -2.0121    0.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9467    2.2706   -1.0031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0310    3.2263   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4863    0.0573   -0.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9884   -2.9075    0.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END

Synonyms

Value	Source
2-(p-Hydroxyphenyl)-5,7-dihydroxychromone	ChEBI
4',5,7-Trihydroxyflavone	ChEBI
5,7,4'-Trihydroxyflavone	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
C.I. natural yellow 1	ChEBI
Chamomile	ChEBI
Spigenin	ChEBI
Versulin	ChEBI
4',5,7-Trihydroxy-flavone	HMDB
4,5, 7-Trihydroxyflavone	HMDB
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one	HMDB
Apigenol	HMDB
4’,5,7-Trihydroxyflavone	PhytoBank
5,7,4’-Trihydroxyflavone	PhytoBank
5,7-Dihydroxy-2-(4-Hydroxyphenyl)chromen-4-one	PhytoBank
5,7-Dihydroxy-2-p-hydroxyphenyl-4-chromenone	PhytoBank
Apegenin	PhytoBank
Apigenin	PhytoBank
Apigenine	PhytoBank

Molecular Formula

C₁₅H₁₀O₅

Average Mass

270.2369

Monoisotopic Mass

270.05282343

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

chamomile

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H

InChI Key

KZNIFHPLKGYRTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:18388 )
flavones (C01477 )
Flavones and Flavonols (C01477 )
Flavones and Flavonols (LMPK12110005 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.07	ALOGPS
logP	2.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.91 m³·mol⁻¹	ChemAxon
Polarizability	26.78 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-0000900000-b6d7fc88c039e719d164	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0433900000-b411d851fccc9f228d84	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03xv-1913500000-be46740b1210f9e106ee	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-0000900000-b6d7fc88c039e719d164	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-0390000000-746c7fa7b11e53e27235	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0229-4222900000-fe657c625506c272a036	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-3fea3046af52ea21ae28	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-3fea3046af52ea21ae28	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0890000000-c8366acac0c0d42ae2e8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-0f608530bf761944dbf3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-0c659ac43b543480168b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0690000000-e19eed49b8311d9cd339	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0910000000-57a56bfe2cce55357a11	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-b8799a618cff0ac84ddb	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0490000000-f9a416c79166c84ca773	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-1499c7f2bceeb3e13f52	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0490000000-413a7da79773bc92a112	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-8f4d30104539ae85cd50	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0290000000-32e8793c17b364eee127	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uea-0900000000-52147353f7af35162dab	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0090000000-7a9b77ceb393c9239412	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00vi-0290000000-c9cb9331a28763da83a8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-014i-0900000000-072fb056044b71de2967	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-014i-0900000000-35e54babc71b9d557d7b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-d0d7979a02697bd4d8fd	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0290000000-832bf870255aa3b01617	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0uea-0900000000-52147353f7af35162dab	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00am-0960000000-155c48a2761e351e02e3	2021-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Multistep Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0012763	Apigenin	4-Hydroxycinnamic acid	Not Available			Manually annotated by MiMeDB team
MMDBr0012805	4-Vinylphenol	4-Ethylphenol	Not Available	vinyl phenol reductase

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	3	Human feces; Human ; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Proteobacteria	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal		Haliotis	FooDB	Manually Annotated
Animal		Strombidae	FooDB	Manually Annotated
Animal		Clupea harengus harengus	FooDB	Manually Annotated
Animal		Undaria pinnatifida	FooDB	Manually Annotated
Animal		Peprilus triacanthus	FooDB	Manually Annotated
Animal		Rhodophyta	FooDB	Manually Annotated
Animal		Myoxocephalus	FooDB	Manually Annotated
Animal		Eucheuma	FooDB	Manually Annotated
Animal		Saccharina japonica	FooDB	Manually Annotated
Animal		Spirulina	FooDB	Manually Annotated
Animal		Lota lota	FooDB	Manually Annotated
Animal		Porphyra umbilicalis	FooDB	Manually Annotated
Animal		Chondrus crispus	FooDB	Manually Annotated
Animal		Laminaria	FooDB	Manually Annotated
Food		Coffea arabica	FooDB	Phenol Explorer
Food		Coffea canephora	FooDB	Phenol Explorer
Food	Cocoa products	Theobroma cacao	FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Food	Beer	Barley	FooDB	Not Available
Food			FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Food			FooDB	Phenol Explorer
Food	Cocoa products	Theobroma cacao	FooDB	34893796
Plant		Thelesperma	FooDB	Manually Annotated
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Cydonia oblonga	FooDB	34893796
Plant		Pisum sativum	FooDB	Phenol Explorer
Plant	Plant	Thymus vulgaris	FooDB	DUKE
Plant		Rorippa nasturtium-aquaticum	FooDB	Phenol Explorer
Plant		Asparagus officinalis	FooDB	Manually Annotated
Plant		Chamerion angustifolium	FooDB	Manually Annotated
Plant	Fruit	Actinidia chinensis	FooDB	Phenol Explorer
Plant		Vaccinium	FooDB	34893796
Plant		Cichorium endivia	FooDB	34893796
Plant		Vaccinium elliottii	FooDB	Manually Annotated
Plant		Tilia tomentosa	FooDB	Phenol Explorer
Plant		Ziziphus zizyphus	FooDB	Manually Annotated
Plant	Fruit	Psidium guajava	FooDB	34893796
Plant		Dimocarpus longan	FooDB	Manually Annotated
Plant	Oil	Olea europaea	FooDB	Phenol Explorer
Plant	Fruit	Pyrus communis	FooDB	Phenol Explorer
Plant	Fruit	Psidium guajava	FooDB	34893796
Plant	Juice	Citrus x paradisi	FooDB	Phenol Explorer
Plant		Salvia hispanica	FooDB	Manually Annotated
Plant		Cynara cardunculus	FooDB	Manually Annotated
Plant		Vitellaria paradoxa	FooDB	Manually Annotated
Plant		Pangium edule	FooDB	Manually Annotated
Plant		Apium graveolens	FooDB	34893796
Plant		Allium	FooDB	Manually Annotated
Plant		Brassica oleracea var. viridis	FooDB	Manually Annotated
Plant	Juice	Citrus x paradisi	FooDB	Phenol Explorer
Plant		Agave	FooDB	Manually Annotated
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Fruit	Ribes nigrum	FooDB	34893796
Plant		Hedysarum alpinum	FooDB	Manually Annotated
Plant		Diospyros	FooDB	Manually Annotated
Plant	Plant	Rosmarinus officinalis	FooDB	DUKE
Plant		Vigna aconitifolia	FooDB	Manually Annotated
Plant		Apium graveolens	FooDB	34893796
Plant		Cuminum cyminum	FooDB	Phenol Explorer
Plant		Amaranthus	FooDB	Manually Annotated
Plant	Stem	Phoenix dactylifera	FooDB	DUKE
Plant		Mammea americana	FooDB	Manually Annotated
Plant		Angelica keiskei	FooDB	Phenol Explorer
Plant		Gossypium	FooDB	Manually Annotated
Plant		Brassica alboglabra	FooDB	Manually Annotated
Plant		Beta vulgaris	FooDB	Manually Annotated
Plant		Annona squamosa	FooDB	Manually Annotated
Plant	Fruit	Rubus idaeus	FooDB	Phenol Explorer
Plant	Fruit	Coriandrum sativum	FooDB	DUKE
Plant		Vitis	FooDB	Manually Annotated
Plant		Xanthosoma sagittifolium	FooDB	Manually Annotated
Plant		Basella alba	FooDB	Manually Annotated
Plant		Brassica oleracea l. var. capitata l. f. alba dc.	FooDB	Phenol Explorer
Plant		Hyssopus officinalis	FooDB	Phenol Explorer
Plant		Capsicum baccatum var. baccatum	FooDB	Manually Annotated
Plant		Citrus latifolia	FooDB	Manually Annotated
Plant	Fruit	Citrus limon	FooDB	Phenol Explorer
Plant	Leaves	Mentha spicata	FooDB	DUKE
Plant		Byrsonima crassifolia	FooDB	Manually Annotated
Plant		Petroselinum crispum	FooDB	Phenol Explorer
Plant		Capsicum pubescens	FooDB	Manually Annotated
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Crateva religiosa	FooDB	Manually Annotated
Plant		Pinus	FooDB	Phenol Explorer
Plant		Vitis aestivalis	FooDB	Manually Annotated
Plant		Eugenia javanica	FooDB	Manually Annotated
Plant			FooDB	Manually Annotated
Plant		Mentha arvensis	FooDB	Manually Annotated
Plant		Spinacia oleracea	FooDB	Phenol Explorer
Plant	Stalk	Apium graveolens var. dulce	FooDB	Phenol Explorer
Plant		Spinacia oleracea	FooDB	34893796
Plant	Stalk	Apium graveolens var. dulce	FooDB	Phenol Explorer
Plant		Cinnamomum aromaticum	FooDB	Manually Annotated
Plant		Vaccinium stamineum	FooDB	Manually Annotated
Plant		Ipomoea batatas	FooDB	Manually Annotated
Plant		Chenopodium album	FooDB	Manually Annotated
Plant		Cucurbita maxima	FooDB	Manually Annotated
Plant		Psophocarpus tetragonolobus	FooDB	Manually Annotated
Plant	Plant	Linum usitatissimum	FooDB	DUKE
Plant		Thymus vulgaris	FooDB	Phenol Explorer
Plant		Allium ampeloprasum	FooDB	Manually Annotated
Plant		Sechium edule	FooDB	Manually Annotated
Plant		Grataegosorbus mitschurinii	FooDB	Manually Annotated
Plant		Fragaria x ananassa	FooDB	34893796
Plant		Vigna unguiculata ssp. sesquipedalis	FooDB	34893796
Plant		Lactuca sativa l. var. longifolia	FooDB	Manually Annotated
Plant		Fragaria x ananassa	FooDB	34893796
Plant	Fruit	Prunus cerasus	FooDB	34893796
Plant	Leaves	Punica granatum	FooDB	DUKE
Plant		Thymus vulgaris	FooDB	Phenol Explorer
Plant		Diospyros virginiana	FooDB	Manually Annotated
Plant		Armoracia rusticana	FooDB	Phenol Explorer
Plant		Thymus vulgaris	FooDB	Phenol Explorer
Plant		Rubus x loganobaccus	FooDB	Manually Annotated
Plant		Tragopogon porrifolius	FooDB	Manually Annotated
Plant		Solanum tuberosum	FooDB	34893796
Plant		Taraxacum officinale	FooDB	Manually Annotated
Plant		Rumex	FooDB	Manually Annotated
Plant		Allium ascalonicum	FooDB	Manually Annotated
Plant		Raphanus sativus	FooDB	34893796
Plant		Prunus dulcis	FooDB	34893796
Plant	Fruit	Ficus carica	FooDB	Phenol Explorer
Plant		Ipomoea aquatica	FooDB	34893796
Plant		Curcuma longa	FooDB	Manually Annotated
Plant		Rubus chamaemorus	FooDB	Manually Annotated
Plant		Citrullus lanatus var. fistulosus	FooDB	Manually Annotated
Plant		Elettaria cardamomum	FooDB	Manually Annotated
Plant		Amelanchier alnifolia	FooDB	Manually Annotated
Plant		Eugenia uniflora	FooDB	Manually Annotated
Plant		Apium graveolens	FooDB	34893796
Plant		Annona reticulata	FooDB	Manually Annotated
Plant		Sesbania bispinosa	FooDB	Manually Annotated
Plant		Melissa officinalis	FooDB	Phenol Explorer
Plant	Leaves	Daucus carota	FooDB	34893796
Plant		Solanum lycopersicum	FooDB	34893796
Plant	Fruit	Morus nigra	FooDB	34893796
Plant	Fruit	Vaccinium macrocarpon	FooDB	34893796
Plant		Brassica ruvo	FooDB	34893796
Plant		Ribes x nidigrolaria	FooDB	Manually Annotated
Plant		Pinus edulis	FooDB	34893796
Plant	Plant	Chamaemelum nobile	FooDB	DUKE
Plant		Garcinia mangostana	FooDB	Manually Annotated
Plant		Lathyrus sativus	FooDB	Manually Annotated
Plant		Melissa officinalis	FooDB	Phenol Explorer
Plant		Dioscorea pentaphylla	FooDB	Manually Annotated
Plant		Allium tuberosum	FooDB	Manually Annotated
Plant		Corchorus olitorius	FooDB	Manually Annotated
Plant		Juglans nigra	FooDB	Manually Annotated
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant		Foeniculum vulgare	FooDB	Phenol Explorer
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant	Fruit	Punica granatum	FooDB	Phenol Explorer
Plant	Seed	Medicago sativa	FooDB	34893796
Plant		Pyrus communis	FooDB	34893796
Plant		Mentha spicata	FooDB	Phenol Explorer
Plant		Gaylussacia baccata	FooDB	Manually Annotated
Plant	Fruit	Citrus aurantiifolia	FooDB	Phenol Explorer
Plant		Petasites japonicus	FooDB	Manually Annotated
Plant		Cinnamomum verum	FooDB	Manually Annotated
Plant		Melissa officinalis	FooDB	34893796
Plant	Leaves	Foeniculum vulgare	FooDB	Phenol Explorer
Plant		Allium	FooDB	34893796
Plant	Leaves	Laurus nobilis	FooDB	34893796
Plant	Leaves	Apium graveolens var. secalinum	FooDB	Phenol Explorer
Plant		Prunus tomentosa	FooDB	Manually Annotated
Plant		Arachis hypogaea	FooDB	34893796
Plant		Mentha x piperita	FooDB	Manually Annotated
Plant		Maranta arundinacea	FooDB	Manually Annotated
Plant		Matteuccia struthiopteris	FooDB	Manually Annotated
Plant		Cucurbita moschata	FooDB	Manually Annotated
Plant		Armoracia rusticana	FooDB	34893796
Plant	Fruit	Phoenix dactylifera	FooDB	Phenol Explorer
Plant		Macadamia	FooDB	Manually Annotated
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Tilia	FooDB	Manually Annotated
Plant		Vaccinium myrtilloides	FooDB	Manually Annotated
Plant	Nut	Arachis hypogaea	FooDB	Phenol Explorer
Plant	Leaves	Foeniculum vulgare	FooDB	34893796
Plant		Origanum majorana	FooDB	Phenol Explorer
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant	Plant	Trigonella foenum-graecum	FooDB	DUKE
Plant		Capsicum annuum var. annuum	FooDB	Manually Annotated
Plant		Origanum majorana	FooDB	Phenol Explorer
Plant		Papaver	FooDB	Manually Annotated
Plant		Rosa	FooDB	Manually Annotated
Plant		Nelumbo	FooDB	Manually Annotated
Plant	Root	Daucus carota ssp. sativus	FooDB	Phenol Explorer
Plant		Corylus	FooDB	34893796
Plant	Flower	Matricaria recutita	FooDB	DUKE
Plant	Fruit	Prunus domestica	FooDB	Phenol Explorer
Plant		Sesamum orientale	FooDB	Manually Annotated
Plant		Annona cherimola	FooDB	Manually Annotated
Plant		Lippia graveolens	FooDB	Manually Annotated
Plant	Bulb	Allium sativum l. var. sativum	FooDB	DUKE
Plant		Brassica rapa	FooDB	Manually Annotated
Plant		Pastinaca sativa	FooDB	Phenol Explorer
Plant		Allium cepa var. cepa	FooDB	Phenol Explorer
Plant		Prunus	FooDB	Manually Annotated
Plant		Rosmarinus officinalis	FooDB	Phenol Explorer
Plant		Brassica oleracea	FooDB	Phenol Explorer
Plant		Capparis spinosa	FooDB	Manually Annotated
Plant	Nut	Corylus avellana	FooDB	Phenol Explorer
Plant		Eruca vesicaria ssp. sativa	FooDB	34893796
Plant	Leaves	Ipomoea batatas	FooDB	34893796
Plant		Brassica oleracea	FooDB	Phenol Explorer
Plant		Mangifera indica	FooDB	34893796
Plant	Tea		FooDB	34893796
Plant		Lens culinaris	FooDB	Manually Annotated
Plant		Petroselinum crispum	FooDB	34893796
Plant		Vaccinium deliciosum	FooDB	Manually Annotated
Plant		Rorippa nasturtium-aquaticum	FooDB	34893796
Plant		Ipomoea batatas	FooDB	34893796
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Brassica napus	FooDB	34893796
Plant		Phaseolus lunatus	FooDB	Manually Annotated
Plant		Thymus vulgaris	FooDB	34893796
Plant	Fruit	Citrus sinensis	FooDB	Phenol Explorer
Plant		Artocarpus heterophyllus	FooDB	Manually Annotated
Plant		Brassica oleracea	FooDB	Phenol Explorer
Plant	Fruit	Prunus domestica	FooDB	Phenol Explorer
Plant		Prunus virginiana	FooDB	Manually Annotated
Plant		Pistacia vera	FooDB	Phenol Explorer
Plant	Fruit	Malus pumila	FooDB	Phenol Explorer
Plant		Allium cepa var. cepa	FooDB	34893796
Plant		Allium cepa var. cepa	FooDB	34893796
Plant		Actinidia chinensis	FooDB	34893796
Plant		Vigna unguiculata ssp. unguiculata	FooDB	Manually Annotated
Plant	Fruit	Phoenix dactylifera	FooDB	34893796
Plant		Petroselinum crispum	FooDB	34893796
Plant	Root	Beta vulgaris var. rubra	FooDB	Phenol Explorer
Plant		Pisum sativum	FooDB	34893796
Plant		Brassica oleracea var. gongylodes	FooDB	Phenol Explorer
Plant		Pisum sativum	FooDB	34893796
Plant		Lagenaria siceraria	FooDB	Manually Annotated
Plant		Brassica oleracea	FooDB	Phenol Explorer
Plant		Brassica oleracea var. gongylodes	FooDB	34893796
Plant		Carum carvi	FooDB	Manually Annotated
Plant		Carissa macrocarpa	FooDB	Manually Annotated
Plant		Phyllostachys edulis	FooDB	Manually Annotated
Plant		Satureja hortensis	FooDB	Manually Annotated
Plant		Origanum majorana	FooDB	34893796
Plant		Averrhoa carambola	FooDB	Manually Annotated
Plant		Vitis	FooDB	34893796
Plant		Sorbus aucuparia	FooDB	Manually Annotated
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Vitis	FooDB	34893796
Plant	Tea		FooDB	34893796
Plant	Fruit	Prunus armeniaca	FooDB	Phenol Explorer
Plant	Fruit	Ribes rubrum	FooDB	34893796
Plant		Cynara scolymus	FooDB	34893796
Plant		Citrus x paradisi	FooDB	34893796
Plant	Juice	Citrus sinensis	FooDB	Phenol Explorer
Plant		Nelumbo nucifera	FooDB	Manually Annotated
Plant		Cynara scolymus	FooDB	34893796
Plant		Brassica oleracea var. costata	FooDB	Manually Annotated
Plant		Prunus persica	FooDB	34893796
Plant		Pastinaca sativa	FooDB	34893796
Plant		Panax	FooDB	Manually Annotated
Plant	Fruit	Solanum lycopersicum var. cerasiforme	FooDB	Phenol Explorer
Plant		Cynara scolymus	FooDB	PhytoHub
Plant	Seed	Pimpinella anisum	FooDB	DUKE
Plant	Fruit	Ananas comosus	FooDB	Phenol Explorer
Plant		Agaricus bisporus	FooDB	34893796
Plant		Carica papaya	FooDB	34893796
Plant		Ceratonia siliqua	FooDB	Manually Annotated
Plant	Nut	Carya illinoinensis	FooDB	Phenol Explorer
Plant		Cymbopogon citratus	FooDB	Manually Annotated
Plant		Rosmarinus officinalis	FooDB	Phenol Explorer
Plant	Plant	Apium graveolens	FooDB	DUKE
Plant		Matricaria recutita	FooDB	Phenol Explorer
Plant		Rosmarinus officinalis	FooDB	Phenol Explorer
Plant		Luffa aegyptiaca	FooDB	Manually Annotated
Plant	Plant	Prunus cerasus	FooDB	DUKE
Plant	Plant	Phaseolus vulgaris	FooDB	DUKE
Plant		Rosmarinus officinalis	FooDB	34893796
Plant		Rubus occidentalis	FooDB	Manually Annotated
Plant		Vigna umbellata	FooDB	Manually Annotated
Plant		Brassica rapa var. rapa	FooDB	34893796
Plant		Carthamus tinctorius	FooDB	Manually Annotated
Plant		Cicer arietinum	FooDB	Manually Annotated
Plant		Allium fistulosum	FooDB	Manually Annotated
Plant		Capsicum	FooDB	Manually Annotated
Plant		Allium	FooDB	34893796
Plant		Lupinus	FooDB	Manually Annotated
Plant		Tilia cordata	FooDB	Manually Annotated
Plant		Raphanus sativus var. longipinnatus	FooDB	Manually Annotated
Plant		Levisticum officinale	FooDB	Phenol Explorer
Plant		Vaccinium alaskaense	FooDB	Manually Annotated
Plant		Brassica oleracea var. botrytis	FooDB	Phenol Explorer
Plant		Juglans regia	FooDB	Phenol Explorer
Plant		Tetragonia tetragonioides	FooDB	34893796
Plant		Prunus persica var. nucipersica	FooDB	Manually Annotated
Plant	Fruit	Daucus carota ssp. sativus	FooDB	DUKE
Plant		Brassica oleracea var. gemmifera	FooDB	34893796
Plant		Durio zibethinus	FooDB	Manually Annotated
Plant	Shoot	Cichorium intybus	FooDB	DUKE
Plant		Eriobotrya japonica	FooDB	Manually Annotated
Plant		Anethum graveolens	FooDB	34893796
Plant	Juice	Citrus limon	FooDB	Phenol Explorer
Plant		Origanum x majoricum	FooDB	Phenol Explorer
Plant		Brassica napus var. pabularia	FooDB	Manually Annotated
Plant		Lepidium sativum	FooDB	Phenol Explorer
Plant		Ribes glandulosum	FooDB	Manually Annotated
Plant		Levisticum officinale	FooDB	34893796
Plant		Origanum x majoricum	FooDB	34893796
Plant		Diospyros kaki	FooDB	Manually Annotated
Plant		Oenothera biennis	FooDB	Manually Annotated
Plant	Fruit	Ficus carica	FooDB	34893796
Plant		Verbena officinalis	FooDB	Manually Annotated
Plant	Fruit	Malpighia emarginata	FooDB	34893796
Plant	Plant	Ocimum basilicum	FooDB	DUKE
Plant		Virola surinamensis	FooDB	Manually Annotated
Plant		Vaccinium oxycoccos	FooDB	Manually Annotated
Plant		Theobroma cacao	FooDB	Manually Annotated
Plant		Pimpinella anisum	FooDB	Phenol Explorer
Plant		Brassica oleracea var. sabauda	FooDB	34893796
Plant		Rumex acetosa	FooDB	Manually Annotated
Plant	Plant	Artemisia dracunculus	FooDB	DUKE
Plant		Allium	FooDB	34893796
Plant		Lepidium sativum	FooDB	34893796
Plant		Vaccinium parvifolium	FooDB	Manually Annotated
Plant		Allium	FooDB	34893796
Plant		Aloysia triphylla	FooDB	Manually Annotated
Plant		Pyrus pyrifolia	FooDB	Manually Annotated
Plant	Fruit	Prunus cerasus	FooDB	Phenol Explorer
Plant	Fruit	Capsicum annuum	FooDB	Phenol Explorer
Plant		Capsicum chinense	FooDB	Manually Annotated
Plant		Brassica oleracea var. capitata	FooDB	Manually Annotated
Plant		Brassica napus	FooDB	Phenol Explorer
Plant		Vaccinium myrtillus	FooDB	Manually Annotated
Plant		Syzygium aromaticum	FooDB	Manually Annotated
Plant	Leaves		FooDB	DUKE
Plant	Tea		FooDB	34893796
Plant		Vaccinium reticulatum	FooDB	Manually Annotated
Plant		Solanum quitoense	FooDB	Manually Annotated
Plant	Nut	Bertholletia excelsa	FooDB	Phenol Explorer
Plant		Theobroma grandiflorum	FooDB	Manually Annotated
Plant	Leaves		FooDB	DUKE
Plant		Vigna unguiculata ssp. cylindrica	FooDB	Manually Annotated
Plant		Flammulina velutipes	FooDB	Manually Annotated
Plant		Anethum graveolens	FooDB	Phenol Explorer
Plant		Lactuca sativa	FooDB	34893796
Plant	Fruit	Persea americana	FooDB	Phenol Explorer
Plant			FooDB	Manually Annotated
Plant		Juglans regia	FooDB	34893796
Plant		Lactuca sativa	FooDB	34893796
Plant		Citrus japonica	FooDB	Manually Annotated
Plant		Pastinaca sativa	FooDB	Manually Annotated
Plant		Perideridia oregana	FooDB	Manually Annotated
Plant		Brassica oleracea var. sabauda	FooDB	Phenol Explorer
Plant		Brassica oleracea var. alboglabra	FooDB	Phenol Explorer
Plant		Anethum graveolens	FooDB	Phenol Explorer
Plant		Pastinaca sativa	FooDB	Manually Annotated
Plant		Vaccinium arboreum	FooDB	Manually Annotated
Plant		Pouteria sapota	FooDB	Manually Annotated
Plant		Wasabia japonica	FooDB	Manually Annotated
Plant		Origanum onites	FooDB	Manually Annotated
Plant	Fruit	Cucumis melo	FooDB	Phenol Explorer
Plant		Brassica oleracea	FooDB	Phenol Explorer
Plant		Piper nigrum	FooDB	Manually Annotated
Plant		Brassica oleracea	FooDB	34893796
Plant		Eragrostis tef	FooDB	Manually Annotated
Plant		Artemisia dracunculus	FooDB	Phenol Explorer
Plant	Nut	Pistacia vera	FooDB	Phenol Explorer
Plant		Artemisia dracunculus	FooDB	34893796
Plant	Fruit	Citrus reticulata	FooDB	Phenol Explorer
Plant		Coriandrum sativum	FooDB	Phenol Explorer
Plant		Viburnum edule	FooDB	Manually Annotated
Plant		Dioscorea	FooDB	Manually Annotated
Plant	Fruit	Ribes nigrum	FooDB	Phenol Explorer
Plant	Fruit	Prunus domestica	FooDB	34893796
Plant		Vaccinium uliginosum	FooDB	Manually Annotated
Plant		Momordica charantia	FooDB	Manually Annotated
Plant		Punica granatum	FooDB	34893796
Plant		Coriandrum sativum	FooDB	Phenol Explorer
Plant	Fruit	Capsicum annuum	FooDB	34893796
Plant	Oil	Olea europaea	FooDB	34893796
Plant	Fruit	Citrullus lanatus	FooDB	Phenol Explorer
Plant		Pistacia vera	FooDB	34893796
Plant		Rubus ursinus x idaeus	FooDB	Manually Annotated
Plant		Castanea	FooDB	Manually Annotated
Plant		Brassica oleracea var. viridis	FooDB	34893796
Plant	Seed	Vicia faba	FooDB	Phenol Explorer
Plant		Portulaca oleracea	FooDB	Phenol Explorer
Plant		Pleurotus ostreatus	FooDB	Manually Annotated
Plant		Cirsium	FooDB	Manually Annotated
Plant		Brassica oleracea var. gemmifera	FooDB	Phenol Explorer
Plant		Basella alba	FooDB	34893796
Plant		Opuntia	FooDB	Manually Annotated
Plant	Fruit	Capsicum annuum	FooDB	Phenol Explorer
Plant		Solanum melongena	FooDB	Manually Annotated
Plant		Colocasia esculenta	FooDB	Manually Annotated
Plant		Anthriscus cerefolium	FooDB	Manually Annotated
Plant		Nuphar lutea	FooDB	Manually Annotated
Plant		Beta vulgaris	FooDB	34893796
Plant	Fruit	Ribes rubrum	FooDB	Phenol Explorer
Plant	Nut	Juglans nigra	FooDB	34893796
Plant		Brassica oleracea	FooDB	34893796
Plant		Pachyrhizus erosus	FooDB	Manually Annotated
Plant		Lupinus albus	FooDB	Manually Annotated
Plant		Citrus paradisi x citrus maxima	FooDB	Manually Annotated
Plant		Myristica fragrans	FooDB	Manually Annotated
Plant	Fruit	Fragaria x ananassa	FooDB	Phenol Explorer
Plant		Cichorium endivia	FooDB	Manually Annotated
Plant		Musa acuminata	FooDB	Phenol Explorer
Plant	Leaves	Allium schoenoprasum	FooDB	Phenol Explorer
Plant		Carya illinoinensis	FooDB	34893796
Plant		Elaeis	FooDB	Manually Annotated
Plant		Juniperus communis	FooDB	34893796
Plant		Feijoa sellowiana	FooDB	Manually Annotated
Plant		Dysphania ambrosioides	FooDB	Manually Annotated
Plant		Cinnamomum	FooDB	Manually Annotated
Plant		Photinia melanocarpa	FooDB	Manually Annotated
Plant		Eugenia uniflora	FooDB	34893796
Plant		Capsicum annuum	FooDB	34893796
Plant		Citrus latifolia	FooDB	34893796
Plant		Juniperus communis	FooDB	34893796
Plant	Leaves	Papaver	FooDB	34893796
Plant	Fruit	Vaccinium	FooDB	34893796
Plant		Rheum rhabarbarum	FooDB	Manually Annotated
Plant		Vaccinium	FooDB	Manually Annotated
Plant		Lablab purpureus	FooDB	Manually Annotated
Plant		Crocus sativus	FooDB	Manually Annotated
Plant		Rumex	FooDB	34893796
Plant		Syzygium jambos	FooDB	Manually Annotated
Plant		Salix pulchra	FooDB	Manually Annotated
Plant		Castanea sativa	FooDB	Manually Annotated
Plant		Annona muricata	FooDB	Manually Annotated
Plant	Nut	Macadamia tetraphylla	FooDB	Phenol Explorer
Plant		Fagus	FooDB	Manually Annotated
Plant		Portulaca oleracea	FooDB	34893796
Plant		Malus pumila	FooDB	34893796
Plant		Opuntia cochenillifera	FooDB	Manually Annotated
Plant		Vaccinium ovatum	FooDB	Manually Annotated
Plant		Brassica rapa var. chinensis	FooDB	Phenol Explorer
Plant		Cucumis sativus	FooDB	34893796
Plant	Fruit	Cucurbita	FooDB	Phenol Explorer
Plant		Cocos nucifera	FooDB	Manually Annotated
Plant		Thymus pulegioides	FooDB	Manually Annotated
Plant			FooDB	PhytoHub
Plant		Phaseolus coccineus	FooDB	Manually Annotated
Plant	Fruit	Cucurbita	FooDB	34893796
Plant		Mespilus germanica	FooDB	Manually Annotated
Plant		Tamarindus indica	FooDB	Manually Annotated
Plant	Fruit	Vaccinium	FooDB	34893796
Plant		Brassica rapa var. perviridis	FooDB	Manually Annotated
Plant		Brassica oleracea var. conica	FooDB	Phenol Explorer
Plant	Fruit	Persea americana	FooDB	34893796
Plant	Leaves		FooDB	DUKE
Plant	Leaves	Olea europaea	FooDB	DUKE
Plant		Cucurbita pepo var. cylindrica	FooDB	Manually Annotated
Plant		Brassica oleracea var. italica	FooDB	Phenol Explorer
Plant		Salvia elegans	FooDB	Manually Annotated
Plant		Mentha	FooDB	Manually Annotated
Plant		Brassica rapa	FooDB	34893796
Plant	Leaves	Origanum vulgare	FooDB	DUKE
Plant		Chenopodium quinoa	FooDB	Manually Annotated
Plant		Sagittaria latifolia	FooDB	Manually Annotated
Plant		Glycine max	FooDB	Manually Annotated
Plant		Ocimum basilicum	FooDB	34893796
Plant		Sambucus	FooDB	Manually Annotated
Plant	Top part	Brassica rapa var. rapa	FooDB	Phenol Explorer
Plant		Syzygium cumini	FooDB	Manually Annotated
Plant		Brassica oleracea var. botrytis	FooDB	34893796
Plant		Psidium guajava	FooDB	Manually Annotated
Plant		Typha angustifolia	FooDB	Manually Annotated
Plant		Capsicum annuum	FooDB	Manually Annotated
Plant		Empetrum nigrum	FooDB	Manually Annotated
Plant		Myrica rubra	FooDB	Manually Annotated
Plant		Capsicum annuum	FooDB	Manually Annotated
Plant		Olive	FooDB	Not Available
Plant		Valerianella locusta	FooDB	Manually Annotated
Plant		Ananas comosus	FooDB	34893796
Plant		Allium ampeloprasum	FooDB	34893796
Plant		Cucumis melo	FooDB	34893796
Plant		Vaccinium angustifolium x vaccinium corymbosum	FooDB	Manually Annotated
Plant		Brassica rapa	FooDB	34893796
Plant		Celery	FooDB	Not Available
Plant		Sisymbrium	FooDB	Manually Annotated
Plant		Brassica napus var. pabularia	FooDB	34893796
Plant		Vanilla	FooDB	Manually Annotated
Plant		Cichorium intybus	FooDB	34893796
Plant		Mentha x piperita	FooDB	34893796
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	Phenol Explorer
Plant		Carya	FooDB	Manually Annotated
Plant		Physalis philadelphica var. immaculata	FooDB	Manually Annotated
Plant	Fruit	Solanum lycopersicum var. lycopersicum	FooDB	Phenol Explorer
Plant		Borago officinalis	FooDB	Manually Annotated
Plant		Raphanus sativus	FooDB	Manually Annotated
Plant		Manihot esculenta	FooDB	Manually Annotated
Plant		Prunus	FooDB	34893796
Plant		Scorzonera hispanica	FooDB	Manually Annotated
Plant		Vigna radiata	FooDB	Manually Annotated
Plant		Macadamia	FooDB	34893796
Plant		Apium graveolens var. rapaceum	FooDB	Phenol Explorer
Plant		Brassica rapa	FooDB	34893796
Plant		Beta vulgaris ssp. cicla	FooDB	Manually Annotated
Plant		Prunus	FooDB	34893796
Plant		Vigna unguiculata ssp. sesquipedalis	FooDB	Manually Annotated
Plant	Plant	Petroselinum crispum	FooDB	DUKE
Plant	Fruit	Capsicum annuum	FooDB	Phenol Explorer
Plant		Brassica rapa	FooDB	34893796
Plant	Fruit	Daucus carota	FooDB	DUKE
Plant		Lactuca sativa	FooDB	Phenol Explorer
Plant		Musa acuminata	FooDB	34893796
Plant		Ocimum basilicum	FooDB	Phenol Explorer
Plant		Lactuca sativa	FooDB	Phenol Explorer
Plant		Citrus limon	FooDB	34893796
Plant		Ipomoea aquatica	FooDB	Manually Annotated
Plant		Musa x paradisiaca	FooDB	Manually Annotated
Plant	Fruit	Ribes uva-crispa	FooDB	34893796
Plant		Rubus spectabilis	FooDB	Manually Annotated
Plant		Cichorium intybus var. foliosum	FooDB	Manually Annotated
Plant		Ocimum basilicum	FooDB	Phenol Explorer
Plant		Allium sativum	FooDB	Manually Annotated
Plant		Citrus sinensis	FooDB	34893796
Plant	Fruit	Luffa aegyptiaca	FooDB	34893796
Plant		Cantharellus cibarius	FooDB	Manually Annotated
Plant		Sinapis alba	FooDB	Manually Annotated
Plant		Brassica rapa var. pekinensis	FooDB	Phenol Explorer
Plant	Leaves	Ginkgo biloba	FooDB	DUKE
Plant	Fruit	Vitis vinifera	FooDB	Phenol Explorer
Plant	Bean	Phaseolus vulgaris	FooDB	Phenol Explorer
Plant	Fruit	Prunus avium	FooDB	34893796
Plant		Brassica ruvo	FooDB	Manually Annotated
Plant		Allium fistulosum	FooDB	Phenol Explorer
Plant		Lactuca sativa	FooDB	Phenol Explorer
Plant	Tea	Camellia sinensis	FooDB	34893796
Plant		Morus nigra	FooDB	Manually Annotated
Plant		Abelmoschus esculentus	FooDB	Manually Annotated
Plant		Moringa oleifera	FooDB	Manually Annotated
Plant		Solanum lycopersicum	FooDB	Manually Annotated
Plant		Pinus edulis	FooDB	Manually Annotated
Plant		Prunus domestica	FooDB	34893796
Plant		Salvia officinalis	FooDB	Phenol Explorer
Plant		Passiflora edulis	FooDB	Manually Annotated
Plant		Opuntia macrorhiza	FooDB	Manually Annotated
Plant		Vigna angularis	FooDB	Manually Annotated
Plant	Heart	Apium graveolens	FooDB	34893796
Plant	Plant	Satureja montana	FooDB	DUKE
Plant	Heart	Apium graveolens	FooDB	34893796
Plant		Manilkara zapota	FooDB	Manually Annotated
Plant	Fruit	Prunus armeniaca	FooDB	34893796
Plant		Apium graveolens	FooDB	34893796
Plant		Cucurbita pepo var. clypeata	FooDB	Manually Annotated
Plant		Allium cepa	FooDB	Manually Annotated
Plant		Corylus	FooDB	Manually Annotated
Plant		Malus	FooDB	Manually Annotated
Plant	Fruit	Vitis vinifera	FooDB	Phenol Explorer
Plant	Fruit	Cydonia oblonga	FooDB	Phenol Explorer
Plant		Salvia officinalis	FooDB	Phenol Explorer
Plant		Sambucus nigra	FooDB	Manually Annotated
Plant		Helianthus annuus	FooDB	Manually Annotated
Plant		Juglans	FooDB	Manually Annotated
Plant		Salvia officinalis	FooDB	Phenol Explorer
Plant	Fruit	Prunus persica var. persica	FooDB	Phenol Explorer
Plant	Fruit	Anacardium occidentale	FooDB	34893796
Plant		Citrullus lanatus	FooDB	34893796
Plant		Brassica oleracea	FooDB	34893796
Plant		Mangifera indica	FooDB	Manually Annotated
Plant		Zingiber officinale	FooDB	Manually Annotated
Plant		Illicium verum	FooDB	Manually Annotated
Plant		Citrus reticulata	FooDB	34893796
Plant			FooDB	Manually Annotated
Plant		Bertholletia excelsa	FooDB	34893796
Plant		Laurus nobilis	FooDB	Manually Annotated
Plant		Auricularia auricula-judae	FooDB	Manually Annotated
Plant	Seed oil	Brassica napus var. napus	FooDB	Phenol Explorer
Plant	Nut	Anacardium occidentale	FooDB	Phenol Explorer
Plant		Attalea speciosa	FooDB	Manually Annotated
Plant	Fruit	Prunus persica var. persica	FooDB	Phenol Explorer
Plant		Allium schoenoprasum	FooDB	34893796
Plant		Juglans ailanthifolia	FooDB	Manually Annotated
Plant		Hippophae rhamnoides	FooDB	Manually Annotated
Plant		Polygonum alpinum	FooDB	Manually Annotated
Plant		Brassica juncea	FooDB	Manually Annotated
Plant		Prunus dulcis	FooDB	Phenol Explorer
Plant		Prunus persica var. nucipersica	FooDB	34893796
Plant		Pediomelum esculentum	FooDB	Manually Annotated
Plant		Origanum vulgare	FooDB	Phenol Explorer
Plant		Coriandrum sativum	FooDB	34893796
Plant		Auricularia polytricha	FooDB	Manually Annotated
Plant		Camellia oleifera	FooDB	Manually Annotated
Plant	Fruit	Ribes uva-crispa	FooDB	Phenol Explorer
Plant		Vaccinium corymbosum	FooDB	Manually Annotated
Plant		Chrysanthemum coronarium	FooDB	Manually Annotated
Plant		Eleocharis dulcis	FooDB	Manually Annotated
Plant		Carica papaya	FooDB	Manually Annotated
Plant		Phaseolus vulgaris	FooDB	34893796
Plant		Anacardium occidentale	FooDB	34893796
Plant		Solanum tuberosum	FooDB	Phenol Explorer
Plant	Fruit	Malus pumila	FooDB	34893796
Plant	Fruit	Vitis vinifera	FooDB	Phenol Explorer
Plant		Origanum vulgare	FooDB	34893796
Plant	Leaves	Colocasia esculenta	FooDB	34893796
Plant		Rubus arcticus	FooDB	Manually Annotated
Plant		Pimenta dioica	FooDB	Manually Annotated
Plant		Medicago sativa	FooDB	Manually Annotated
Plant	Leaves	Camellia sinensis	FooDB	DUKE
Plant		Origanum vulgare	FooDB	34893796
Plant	Fruit	Solanum lycopersicum	FooDB	34893796
Plant		Agaricus bisporus	FooDB	Manually Annotated
Plant		Cajanus cajan	FooDB	Manually Annotated
Plant		Vigna mungo	FooDB	Manually Annotated
Plant		Rumex articus	FooDB	Manually Annotated
Plant	Fruit	Prunus avium	FooDB	Phenol Explorer
Plant		Spinacia oleracea	FooDB	34893796
Plant	Juice	Citrus maxima	FooDB	Phenol Explorer
Plant		Hibiscus sabdariffa	FooDB	Manually Annotated
Plant		Benincasa hispida	FooDB	Manually Annotated
Plant		Prunus persica	FooDB	Manually Annotated
Plant		Canarium ovatum	FooDB	Manually Annotated
Plant	Root	Raphanus sativus var. sativus	FooDB	Phenol Explorer
Plant		Ribes aureum var. villosum	FooDB	Manually Annotated
Plant		Cucurbita pepo var. cylindrica	FooDB	Manually Annotated
Plant	Fruit	Vaccinium vitis-idaea	FooDB	Phenol Explorer
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Arctium lappa	FooDB	Manually Annotated
Plant		Citrus japonica	FooDB	34893796
Plant		Vaccinium macrocarpon	FooDB	Manually Annotated
Plant		Juglans cinerea	FooDB	Manually Annotated
Plant		Eruca vesicaria ssp. sativa	FooDB	Manually Annotated
Plant		Phaseolus vulgaris	FooDB	Manually Annotated
Plant		Raphanus sativus var. niger	FooDB	Phenol Explorer
Plant		Artocarpus altilis	FooDB	Manually Annotated
Plant		Daucus carota ssp. sativus	FooDB	34893796
Plant		Metroxylon sagu	FooDB	Manually Annotated
Plant		Vigna unguiculata	FooDB	Manually Annotated
Plant		Cynara scolymus	FooDB	Manually Annotated
Plant		Cyathea	FooDB	Manually Annotated
Plant		Vitis rotundifolia	FooDB	Manually Annotated
Plant		Vicia faba	FooDB	34893796
Plant		Brosimum alicastrum	FooDB	Manually Annotated
Plant	Heart wood	Malus pumila	FooDB	DUKE
Plant		Lentinus edodes	FooDB	Manually Annotated
Plant		Psidium cattleianum	FooDB	Manually Annotated
Plant	Plant	Mentha aquatica	FooDB	DUKE
Plant		Castanea mollissima	FooDB	Manually Annotated
Plant	Fruit	Cucumis sativus	FooDB	Phenol Explorer
Plant		Capsicum annuum	FooDB	Manually Annotated
Plant		Morus	FooDB	Manually Annotated
Plant		Vitis labrusca	FooDB	Manually Annotated
Plant	Plant	Salvia officinalis	FooDB	DUKE
Plant	Fruit	Malus pumila	FooDB	34893796
Plant		Phytolacca americana	FooDB	Manually Annotated
Plant		Grifola frondosa	FooDB	Manually Annotated
Plant		Helianthus tuberosus	FooDB	Manually Annotated
Plant	Leaves	Anethum graveolens	FooDB	DUKE
Plant		Tetragonia tetragonioides	FooDB	Manually Annotated
Plant		Artemisia vulgaris	FooDB	Manually Annotated
Plant		Cucumis metuliferus	FooDB	Manually Annotated
Plant		Myrica	FooDB	Manually Annotated
Plant		Nephelium lappaceum	FooDB	Manually Annotated
Plant		Petroselinum crispum	FooDB	Phenol Explorer
Plant		Citrus maxima	FooDB	34893796
Plant	Oil	Olea europaea	FooDB	Phenol Explorer
Plant		Castanea crenata	FooDB	Manually Annotated
Plant		Vitis vinifera	FooDB	34893796
Plant		Brassica oleracea var. italica	FooDB	34893796
Plant		Litchi chinensis	FooDB	Manually Annotated
Plant		Vaccinium angustifolium	FooDB	Manually Annotated
Plant		Quercus	FooDB	Manually Annotated
Plant	Fruit	Citrus x paradisi	FooDB	Phenol Explorer
Plant		Malpighia emarginata	FooDB	Manually Annotated
Plant		Solanum melongena	FooDB	34893796
Plant	Oil	Olea europaea	FooDB	Phenol Explorer
Plant		Physalis	FooDB	Manually Annotated

Source Type	Activity	Data Source	Reference
Not Available	Antioxidant	U.S. Environmental Protection Agency	CompTox
Not Available	Androgen receptors binding	U.S. Environmental Protection Agency	CompTox
General Exposome	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.000222		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21272408
Human Urine	Detected and Quantified	0.00533		umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Blood	Detected and Quantified	0.0106	0.0123	uM	Adult (>18 years old)	Both	Normal	HMDB	19747418
Human Urine	Detected and Quantified	0.0110	0.0210	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Blood	Detected and Quantified	0.0119	0.0126	uM	Adult (>18 years old)	Both	Normal	HMDB	20851305
Human Blood	Detected and Quantified	0.127	0.081	uM	Adult (>18 years old)	Both	Normal	HMDB	16407641
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002124

DrugBank ID

DB07352

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Apigenin

METLIN ID

3397

PubChem Compound

5280443

PDB ID

Not Available

ChEBI ID

18388

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Sakai T: The dietary flavonoid apigenin sensitizes malignant tumor cells to tumor necrosis factor-related apoptosis-inducing ligand. Mol Cancer Ther. 2006 Apr;5(4):945-51. doi: 10.1158/1535-7163.MCT-05-0431. [PubMed:16648565 ]
Vargo MA, Voss OH, Poustka F, Cardounel AJ, Grotewold E, Doseff AI: Apigenin-induced-apoptosis is mediated by the activation of PKCdelta and caspases in leukemia cells. Biochem Pharmacol. 2006 Sep 14;72(6):681-92. doi: 10.1016/j.bcp.2006.06.010. Epub 2006 Jul 17. [PubMed:16844095 ]
Balasubramanian S, Zhu L, Eckert RL: Apigenin inhibition of involucrin gene expression is associated with a specific reduction in phosphorylation of protein kinase Cdelta Tyr311. J Biol Chem. 2006 Nov 24;281(47):36162-72. doi: 10.1074/jbc.M605368200. Epub 2006 Sep 18. [PubMed:16982614 ]

Showing metabocard for Apigenin (MMDBc0000583)

MOL for #<Metabolite:0x00007fdb3a52cd40>

3D MOL for #<Metabolite:0x00007fdb3a52cd40>

3D SDF for #<Metabolite:0x00007fdb3a52cd40>

3D-SDF for #<Metabolite:0x00007fdb3a52cd40>

PDB for #<Metabolite:0x00007fdb3a52cd40>

3D PDB for #<Metabolite:0x00007fdb3a52cd40>

SMILES for #<Metabolite:0x00007fdb3a52cd40>

INCHI for #<Metabolite:0x00007fdb3a52cd40>

Structure for #<Metabolite:0x00007fdb3a52cd40>

3D Structure for #<Metabolite:0x00007fdb3a52cd40>