Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:06:36 UTC

Update Date

2022-03-07 02:55:32 UTC

HMDB ID

HMDB0037851

Secondary Accession Numbers

HMDB37851

Metabolite Identification

Common Name

Apigenin 7-sulfate

Description

Apigenin 7-sulfate is isolated from Bixa orellana (annatto) Apigenin is a flavone that is the aglycone of several glycosides. It is a yellow crystalline solid that has been used to dye wool. 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, 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 and the increase in hINV promoter activity. 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 ); Apigenin is a potent inhibitor of CYP2C9, an enzyme responsible for the metabolism of many pharmaceutical drugs in the body.

Structure

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

HMDB0037851
     RDKit          3D
Apigenin 7-sulfate
 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.2008   -3.6942    0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0901   -2.4624    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -1.8083    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.4517    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    0.1968    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299   -0.4570    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419    0.1968    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    1.5666    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2075    2.2587    0.7256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8523    2.2541    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684    1.5677    0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    0.2059   -0.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712   -0.3531   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366    0.4623   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2715   -0.0798   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124    0.7745   -1.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    1.5339   -0.1615 S   0  0  0  0  0  6  0  0  0  0  0  0
   -6.6872    0.9700   -0.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7779    1.3457    1.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3807    3.1983   -0.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663   -1.4308   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4100   -2.2890   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6908   -3.5954   -0.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1881   -1.7204   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -2.4604    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7200   -1.5183    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8555   -0.3135    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0351    1.7485    0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8960    3.3246    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687    2.0990   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    1.5169   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5494    3.6586   -0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4464   -1.8357   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -4.4093   -0.0675 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
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24  2  1  0
 11  5  1  0
 24 13  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 20 32  1  0
 21 33  1  0
 23 34  1  0
M  END


  Mrv0541 05061310022D          

 24 26  0  0  0  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 22 13  1  0  0  0  0
 22 14  1  0  0  0  0
 23 10  1  0  0  0  0
 24 19  1  0  0  0  0
 24 20  2  0  0  0  0
 24 21  2  0  0  0  0
 24 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037851

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O8S/c16-9-3-1-8(2-4-9)13-7-12(18)15-11(17)5-10(6-14(15)22-13)23-24(19,20)21/h1-7,16-17H,(H,19,20,21)

> <INCHI_KEY>
UQUHXFINOFUDCC-UHFFFAOYSA-N

> <FORMULA>
C15H10O8S

> <MOLECULAR_WEIGHT>
350.3

> <EXACT_MASS>
350.009637986

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
32.09728927886712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxidanesulfonic acid

> <ALOGPS_LOGP>
0.82

> <JCHEM_LOGP>
2.2313757873333326

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.004662924895747

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.5082026713693546

> <JCHEM_PKA_STRONGEST_BASIC>
-5.384876647148162

> <JCHEM_POLAR_SURFACE_AREA>
130.36

> <JCHEM_REFRACTIVITY>
82.9057

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apigenin 7-sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037851
     RDKit          3D
Apigenin 7-sulfate
 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.2008   -3.6942    0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0901   -2.4624    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -1.8083    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.4517    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    0.1968    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299   -0.4570    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419    0.1968    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    1.5666    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2075    2.2587    0.7256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8523    2.2541    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684    1.5677    0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    0.2059   -0.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712   -0.3531   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366    0.4623   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2715   -0.0798   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124    0.7745   -1.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    1.5339   -0.1615 S   0  0  0  0  0  6  0  0  0  0  0  0
   -6.6872    0.9700   -0.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7779    1.3457    1.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3807    3.1983   -0.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663   -1.4308   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4100   -2.2890   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6908   -3.5954   -0.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1881   -1.7204   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -2.4604    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7200   -1.5183    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8555   -0.3135    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0351    1.7485    0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8960    3.3246    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687    2.0990   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    1.5169   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5494    3.6586   -0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4464   -1.8357   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -4.4093   -0.0675 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
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24  2  1  0
 11  5  1  0
 24 13  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 20 32  1  0
 21 33  1  0
 23 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.206  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.874  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   11                                                       
CONECT    6   10   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   13                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   23                                                  
CONECT   11    5   15   17                                                  
CONECT   12    7   15   18                                                  
CONECT   13    7    8   22                                                  
CONECT   14    6   15   22                                                  
CONECT   15   11   12   14                                                  
CONECT   16    9                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   24                                                            
CONECT   20   24                                                            
CONECT   21   24                                                            
CONECT   22   13   14                                                       
CONECT   23   10   24                                                       
CONECT   24   19   20   21   23                                             
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0037851
HETATM    1  O1  UNL     1      -0.201  -3.694   0.256  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.090  -2.462   0.092  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.130  -1.808   0.254  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.285  -0.452   0.082  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.575   0.197   0.260  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.730  -0.457   0.607  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.942   0.197   0.767  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.999   1.567   0.572  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.207   2.259   0.726  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.852   2.254   0.221  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.668   1.568   0.072  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.203   0.206  -0.250  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.971  -0.353  -0.417  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.037   0.462  -0.769  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.272  -0.080  -0.952  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.312   0.774  -1.305  1.00  0.00           O  
HETATM   17  S1  UNL     1      -5.278   1.534  -0.162  1.00  0.00           S  
HETATM   18  O5  UNL     1      -6.687   0.970  -0.195  1.00  0.00           O  
HETATM   19  O6  UNL     1      -4.778   1.346   1.249  1.00  0.00           O  
HETATM   20  O7  UNL     1      -5.381   3.198  -0.446  1.00  0.00           O  
HETATM   21  C13 UNL     1      -3.466  -1.431  -0.788  1.00  0.00           C  
HETATM   22  C14 UNL     1      -2.410  -2.289  -0.432  1.00  0.00           C  
HETATM   23  O8  UNL     1      -2.691  -3.595  -0.293  1.00  0.00           O  
HETATM   24  C15 UNL     1      -1.188  -1.720  -0.256  1.00  0.00           C  
HETATM   25  H1  UNL     1       1.956  -2.460   0.531  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.720  -1.518   0.766  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.855  -0.313   1.041  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.035   1.748   0.981  1.00  0.00           H  
HETATM   29  H5  UNL     1       3.896   3.325   0.068  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.769   2.099  -0.202  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.853   1.517  -0.890  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.549   3.659  -0.183  1.00  0.00           H  
HETATM   33  H9  UNL     1      -4.446  -1.836  -0.937  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.214  -4.409  -0.067  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4    4   25
CONECT    4    5   12
CONECT    5    6    6   11
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   10
CONECT    9   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13
CONECT   13   14   14   24
CONECT   14   15   31
CONECT   15   16   21   21
CONECT   16   17
CONECT   17   18   18   19   19
CONECT   17   20
CONECT   20   32
CONECT   21   22   33
CONECT   22   23   24   24
CONECT   23   34
END

HMDB0037851
     RDKit          3D
Apigenin 7-sulfate
 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.2008   -3.6942    0.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0901   -2.4624    0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1299   -1.8083    0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.4517    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5751    0.1968    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299   -0.4570    0.6068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9419    0.1968    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9994    1.5666    0.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2075    2.2587    0.7256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8523    2.2541    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6684    1.5677    0.0717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2032    0.2059   -0.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9712   -0.3531   -0.4170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366    0.4623   -0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2715   -0.0798   -0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124    0.7745   -1.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2779    1.5339   -0.1615 S   0  0  0  0  0  6  0  0  0  0  0  0
   -6.6872    0.9700   -0.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7779    1.3457    1.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3807    3.1983   -0.4461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4663   -1.4308   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4100   -2.2890   -0.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6908   -3.5954   -0.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1881   -1.7204   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -2.4604    0.5307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7200   -1.5183    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8555   -0.3135    1.0408 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0351    1.7485    0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8960    3.3246    0.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7687    2.0990   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    1.5169   -0.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5494    3.6586   -0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4464   -1.8357   -0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -4.4093   -0.0675 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
 16 17  1  0
 17 18  2  0
 17 19  2  0
 17 20  1  0
 15 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24  2  1  0
 11  5  1  0
 24 13  1  0
  3 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 20 32  1  0
 21 33  1  0
 23 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Apigenin 7-sulfuric acid	Generator
Apigenin 7-sulphate	Generator
Apigenin 7-sulphuric acid	Generator

Chemical Formula

C₁₅H₁₀O₈S

Average Molecular Weight

350.3

Monoisotopic Molecular Weight

350.009637986

IUPAC Name

[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxidanesulfonic acid

Traditional Name

apigenin 7-sulfate

CAS Registry Number

56857-56-8

SMILES

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

InChI Identifier

InChI=1S/C15H10O8S/c16-9-3-1-8(2-4-9)13-7-12(18)15-11(17)5-10(6-14(15)22-13)23-24(19,20)21/h1-7,16-17H,(H,19,20,21)

InChI Key

UQUHXFINOFUDCC-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
Flavone
Hydroxyflavonoid
Chromone
Arylsulfate
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Organic sulfuric acid or derivatives
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12110431 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037851)

Cellular substructure

Membrane (HMDB: HMDB0037851)

Source

Exogenous

Food

Food (HMDB: HMDB0037851)

Endogenous

Plant

Plant (HMDB: HMDB0037851)

Not Available

Nutrient (HMDB: HMDB0037851)

Industrial application

Dye (HMDB: HMDB0037851)

Environmental role

Environmental contaminant (HMDB: HMDB0037851)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	347.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.02	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	0.82	ALOGPS
logP	2.23	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	-2.5	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.91 m³·mol⁻¹	ChemAxon
Polarizability	32.1 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]+	173.534	30932474
DeepCCS	[M-H]-	171.176	30932474
DeepCCS	[M-2H]-	205.449	30932474
DeepCCS	[M+Na]+	180.879	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.2	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.6	32859911
AllCCS	[M-H]-	172.0	32859911
AllCCS	[M+Na-2H]-	171.4	32859911
AllCCS	[M+HCOO]-	170.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Apigenin 7-sulfate	OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1	5333.4	Standard polar	33892256
Apigenin 7-sulfate	OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1	2845.2	Standard non polar	33892256
Apigenin 7-sulfate	OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(OS(O)(=O)=O)C=C2O1	3428.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Apigenin 7-sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(OS(=O)(=O)O)C=C3O2)C=C1	3508.2	Semi standard non polar	33892256
Apigenin 7-sulfate,1TMS,isomer #2	C[Si](C)(C)OC1=CC(OS(=O)(=O)O)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O2	3428.7	Semi standard non polar	33892256
Apigenin 7-sulfate,1TMS,isomer #3	C[Si](C)(C)OS(=O)(=O)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1	3470.4	Semi standard non polar	33892256
Apigenin 7-sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(OS(=O)(=O)O)C=C3O2)C=C1	3488.5	Semi standard non polar	33892256
Apigenin 7-sulfate,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(OS(=O)(=O)O[Si](C)(C)C)C=C3O2)C=C1	3470.3	Semi standard non polar	33892256
Apigenin 7-sulfate,2TMS,isomer #3	C[Si](C)(C)OC1=CC(OS(=O)(=O)O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O2	3412.3	Semi standard non polar	33892256
Apigenin 7-sulfate,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(OS(=O)(=O)O[Si](C)(C)C)C=C3O2)C=C1	3462.9	Semi standard non polar	33892256
Apigenin 7-sulfate,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(OS(=O)(=O)O[Si](C)(C)C)C=C3O2)C=C1	3381.9	Standard non polar	33892256
Apigenin 7-sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(OS(=O)(=O)O)C=C3O2)C=C1	3793.9	Semi standard non polar	33892256
Apigenin 7-sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(OS(=O)(=O)O)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O2	3725.9	Semi standard non polar	33892256
Apigenin 7-sulfate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1	3746.2	Semi standard non polar	33892256
Apigenin 7-sulfate,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(OS(=O)(=O)O)C=C3O2)C=C1	4025.6	Semi standard non polar	33892256
Apigenin 7-sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	4000.9	Semi standard non polar	33892256
Apigenin 7-sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O2	3966.5	Semi standard non polar	33892256
Apigenin 7-sulfate,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(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	4190.0	Semi standard non polar	33892256
Apigenin 7-sulfate,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(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1	4131.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Apigenin 7-sulfate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fl0-1469000000-a1b28fc2dcdc9ecaaf1c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigenin 7-sulfate GC-MS (2 TMS) - 70eV, Positive	splash10-00di-4212900000-4c6b3938ac063372794e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Apigenin 7-sulfate 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 10V, Positive-QTOF	splash10-0udi-0009000000-3252e2cc0544038f2b08	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 20V, Positive-QTOF	splash10-0fk9-1095000000-9e77e41ea21b23bc6679	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 40V, Positive-QTOF	splash10-001i-8694000000-5217415118f0815d660d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 10V, Negative-QTOF	splash10-0002-0009000000-97094030a112081a348f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 20V, Negative-QTOF	splash10-014i-0093000000-85f96f5d8ec1a71122de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 40V, Negative-QTOF	splash10-014i-0290000000-e7461bc36e5496f2c350	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 10V, Negative-QTOF	splash10-0002-0009000000-1d04c6044305d5ee1e15	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 20V, Negative-QTOF	splash10-0002-0009000000-775b0740512cc8f93598	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 40V, Negative-QTOF	splash10-0a4i-0932000000-3cbd6ecfda8da3a321e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 10V, Positive-QTOF	splash10-0udi-0009000000-f5df4eaea294d10b85d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 20V, Positive-QTOF	splash10-0udi-0009000000-f5df4eaea294d10b85d5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Apigenin 7-sulfate 40V, Positive-QTOF	splash10-0f89-0696000000-46cb06a8ee3aba9e9481	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017004

KNApSAcK ID

C00004197

Chemspider ID

24843470

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14016776

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Apigenin 7-sulfate (HMDB0037851)

MOL for HMDB0037851 (Apigenin 7-sulfate)

3D MOL for HMDB0037851 (Apigenin 7-sulfate)

3D SDF for HMDB0037851 (Apigenin 7-sulfate)

3D-SDF for HMDB0037851 (Apigenin 7-sulfate)

PDB for HMDB0037851 (Apigenin 7-sulfate)

3D PDB for HMDB0037851 (Apigenin 7-sulfate)

SMILES for HMDB0037851 (Apigenin 7-sulfate)

INCHI for HMDB0037851 (Apigenin 7-sulfate)

Structure for HMDB0037851 (Apigenin 7-sulfate)

3D Structure for HMDB0037851 (Apigenin 7-sulfate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra