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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:37 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002124

Secondary Accession Numbers

HMDB02124

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>
HMDB0002124

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Weight

270.2369

Monoisotopic Molecular Weight

270.05282343

IUPAC Name

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

Traditional Name

chamomile

CAS Registry Number

520-36-5

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 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	347.5 °C	Not Available
Boiling Point	555.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	182.5 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.02	PERRISSOUD,D & TESTA,B (1986)

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	162.15	30932474
DeepCCS	[M-H]-	159.792	30932474
DeepCCS	[M-2H]-	192.678	30932474
DeepCCS	[M+Na]+	168.244	30932474
AllCCS	[M+H]+	160.9	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	164.6	32859911
AllCCS	[M+Na]+	165.6	32859911
AllCCS	[M-H]-	160.7	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Apigenin	OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1	4774.2	Standard polar	33892256
Apigenin	OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1	3018.9	Standard non polar	33892256
Apigenin	OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1	3172.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Apigenin,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	3149.0	Semi standard non polar	33892256
Apigenin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O2	3039.7	Semi standard non polar	33892256
Apigenin,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1	3089.7	Semi standard non polar	33892256
Apigenin,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)C=C1	3065.7	Semi standard non polar	33892256
Apigenin,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1	3151.8	Semi standard non polar	33892256
Apigenin,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1	3066.8	Semi standard non polar	33892256
Apigenin,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1	3116.3	Semi standard non polar	33892256
Apigenin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1	3393.3	Semi standard non polar	33892256
Apigenin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O2	3295.2	Semi standard non polar	33892256
Apigenin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1	3346.7	Semi standard non polar	33892256
Apigenin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)C=C1	3614.1	Semi standard non polar	33892256
Apigenin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3669.4	Semi standard non polar	33892256
Apigenin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1	3609.0	Semi standard non polar	33892256
Apigenin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	3852.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Apigenin GC-MS (3 TMS)	splash10-00di-0000900000-b6d7fc88c039e719d164	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Apigenin GC-EI-TOF (Non-derivatized)	splash10-00di-0433900000-b411d851fccc9f228d84	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Apigenin GC-EI-TOF (Non-derivatized)	splash10-03xv-1913500000-be46740b1210f9e106ee	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Apigenin GC-MS (Non-derivatized)	splash10-00di-0000900000-b6d7fc88c039e719d164	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigenin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-0390000000-746c7fa7b11e53e27235	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigenin GC-MS (3 TMS) - 70eV, Positive	splash10-0229-4222900000-fe657c625506c272a036	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigenin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin ESI-TOF 30V, Negative-QTOF	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin ESI-TOF , Negative-QTOF	splash10-014i-0090000000-3fea3046af52ea21ae28	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin ESI-TOF 30V, Negative-QTOF	splash10-014i-0940000000-eb8b08c7beca627dc728	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin ESI-TOF , Negative-QTOF	splash10-014i-0090000000-3fea3046af52ea21ae28	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin DI-ESI-qTof , Negative-QTOF	splash10-014i-0890000000-c8366acac0c0d42ae2e8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin DI-ESI-qTof , Positive-QTOF	splash10-0udi-0920000000-812a3ee12823ec0b2025	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-qTof , Positive-QTOF	splash10-003r-0194000200-b2908d4b21e6769c5a08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-qTof , Positive-QTOF	splash10-00di-3970000000-5a23944b045cfe1763b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0090000000-0f608530bf761944dbf3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0090000000-0c659ac43b543480168b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0690000000-e19eed49b8311d9cd339	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0910000000-57a56bfe2cce55357a11	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-b8799a618cff0ac84ddb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0490000000-f9a416c79166c84ca773	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-1499c7f2bceeb3e13f52	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0490000000-413a7da79773bc92a112	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0090000000-8f4d30104539ae85cd50	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-014i-0290000000-32e8793c17b364eee127	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Apigenin LC-ESI-QTOF , negative-QTOF	splash10-0uea-0900000000-52147353f7af35162dab	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 10V, Positive-QTOF	splash10-00di-0090000000-7c7c531f383cbaad5b23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 20V, Positive-QTOF	splash10-00di-0090000000-bb93867833cf83cbdb01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 40V, Positive-QTOF	splash10-0udi-7890000000-ef384ab54a966e53fb23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 10V, Negative-QTOF	splash10-014i-0090000000-31e5cabfee91b72de296	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 20V, Negative-QTOF	splash10-014i-0090000000-12d2a0ddf52acf6dc93a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 40V, Negative-QTOF	splash10-0gdi-3960000000-847553cbcf5b653a9059	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0106 +/- 0.0123 uM	Adult (>18 years old)	Both	Normal	19747418	details
Blood	Detected and Quantified	0.0119 +/- 0.0126 uM	Adult (>18 years old)	Both	Normal	20851305	details
Blood	Detected and Quantified	0.127 +/- 0.081 uM	Adult (>18 years old)	Both	Normal	16407641	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Urine	Detected and Quantified	0.000222 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21272408	details
Urine	Detected and Quantified	0.00533 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.0110 +/- 0.0210 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

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

VMH ID

Not Available

MarkerDB ID

MDB00000379

Good Scents ID

rw1108801

References

Synthesis Reference

Chen, Xin; Li, Ping. Processes for the preparation of apigenin from naringin via rhoifolin or naringenin intermediate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 9 pp

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. Epub 2006 Sep 18. [PubMed:16982614 ]
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. Epub 2006 Jul 17. [PubMed:16844095 ]
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. [PubMed:16648565 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

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

Showing metabocard for Apigenin (HMDB0002124)

MOL for HMDB0002124 (Apigenin)

3D MOL for HMDB0002124 (Apigenin)

3D SDF for HMDB0002124 (Apigenin)

3D-SDF for HMDB0002124 (Apigenin)

PDB for HMDB0002124 (Apigenin)

3D PDB for HMDB0002124 (Apigenin)

SMILES for HMDB0002124 (Apigenin)

INCHI for HMDB0002124 (Apigenin)

Structure for HMDB0002124 (Apigenin)

3D Structure for HMDB0002124 (Apigenin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions