NP-MRD: Showing NP-Card for Apigenin 7-sulfate (NP0052543)

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Record Information

Version

2.0

Created at

2022-04-27 23:32:56 UTC

Updated at

2022-04-27 23:32:56 UTC

NP-MRD ID

NP0052543

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apigenin 7-sulfate

Description

Apigenin 7-sulfate 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). Apigenin 7-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Apigenin 7-sulfate is isolated from Bixa orellana (annatto) Apigenin is a flavone that is the aglycone of several glycosides. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. 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. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. 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. 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. 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. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. 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. Apigenin 7-sulfate is found in Bixa orellana and Fuchsia procumbens. It is a yellow crystalline solid that has been used to dye wool.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -0.3641   -2.1524    2.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328   -1.3638    1.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0504   -1.2365    1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -0.4012    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6595   -0.2583   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542    0.6174   -1.3340 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    0.7862   -1.8944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2121    0.1106   -1.4298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4523    0.3090   -2.0224 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0286   -0.7504   -0.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7627   -0.9283    0.2036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    0.2654   -0.1799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9211    0.2035    0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454    0.9360   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2448    0.8826    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    1.6364   -0.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1224    0.9334   -1.7439 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.3056    0.9042   -3.0030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4973   -0.5009   -1.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5310    1.8028   -2.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224    0.0522    1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5376   -0.7327    1.8106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8684   -1.5374    2.8450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -0.6324    1.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -1.8411    1.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9763    1.1502   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2258    1.4671   -2.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1090    1.0246   -1.7149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8716   -1.3015    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6458   -1.6157    1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050    1.5973   -1.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2304    2.7544   -2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5179   -0.0548    1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3410   -2.1263    3.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5 11  1  0
 11 10  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 24  1  0
 24 22  2  0
 22 23  1  0
 22 21  1  0
 21 15  2  0
 15 16  1  0
 16 17  1  0
 17 20  1  0
 17 18  2  0
 17 19  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 10  8  1  0
 12  4  1  0
 13 24  1  0
  9 28  1  0
  7 27  1  0
  6 26  1  0
 11 30  1  0
 10 29  1  0
  3 25  1  0
 23 34  1  0
 21 33  1  0
 20 32  1  0
 14 31  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>
NP0052543

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

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

Chemical Formula

C₁₅H₁₀O₈S

Average Mass

350.3000 Da

Monoisotopic Mass

350.00964 Da

IUPAC Name

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

Traditional Name

apigenin 7-sulfate

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bixa orellana	Plant	KNApSAcK
Fuchsia procumbens	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0037851

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Showing NP-Card for Apigenin 7-sulfate (NP0052543)

MOL for NP0052543 (Apigenin 7-sulfate)

3D MOL for NP0052543 (Apigenin 7-sulfate)

3D SDF for NP0052543 (Apigenin 7-sulfate)

3D-SDF for NP0052543 (Apigenin 7-sulfate)

PDB for NP0052543 (Apigenin 7-sulfate)

3D PDB for NP0052543 (Apigenin 7-sulfate)

SMILES for NP0052543 (Apigenin 7-sulfate)

INCHI for NP0052543 (Apigenin 7-sulfate)

Structure for NP0052543 (Apigenin 7-sulfate)

3D Structure for NP0052543 (Apigenin 7-sulfate)