MiMeDB: Showing metabocard for Apigenin (MMDBc0000583)

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

Functional Ontology

Physical Properties

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

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Apigenin (MMDBc0000583)

MOL for #<Metabolite:0x00007fb7a4f19560>

3D MOL for #<Metabolite:0x00007fb7a4f19560>

3D SDF for #<Metabolite:0x00007fb7a4f19560>

3D-SDF for #<Metabolite:0x00007fb7a4f19560>

PDB for #<Metabolite:0x00007fb7a4f19560>

3D PDB for #<Metabolite:0x00007fb7a4f19560>

SMILES for #<Metabolite:0x00007fb7a4f19560>

INCHI for #<Metabolite:0x00007fb7a4f19560>

Structure for #<Metabolite:0x00007fb7a4f19560>

3D Structure for #<Metabolite:0x00007fb7a4f19560>