NP-MRD: Showing NP-Card for Fisetin (NP0045391)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:19:09 UTC

Updated at

2025-02-11 15:48:09 UTC

NP-MRD ID

NP0045391

Natural Product DOI

https://doi.org/10.57994/2767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Fisetin

Description

Fisetin, also known as 5-desoxyquercetin or fisetinidin, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, fisetin is considered to be a flavonoid lipid molecule. Fisetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Fisetin is a bitter tasting compound. Outside of the human body, Fisetin has been detected, but not quantified in, soy beans. This could make fisetin a potential biomarker for the consumption of these foods. Fisetin is found in Acacia adunca, Acacia baileyana, Acacia berlandieri, Acacia buxifolia, Acacia calamifolia, Acacia cardiophylla, Acacia carnei, Acacia carneorum, Acacia catechu , Acacia chrysotricha, Acacia clunies-rossiae, Acacia constablei, Acacia crombei, Acacia dealbata, Acacia deanei, Acacia decora, Acacia elata, Acacia falciformis, Acacia fasciculifera, Acacia filicifolia, Acacia greggii, Acacia irrorata, Acacia kettlewelliae, Acacia lanigera, Acacia leucoclada, Acacia mabellae, Acacia mearnsii , Acacia mollifolia, Acacia montana, Acacia oshanesii, Acacia parramattensis, Acacia peuce, Acacia pycnantha, Acacia rubida, Acacia silvestris, Acacia trachyphloia, Acer glabrum, Albizia pedicellata, Albizia splendens, Amburana cearensis, Anthyllis vulneraria , Archidendron clypearia , Baptisia lecontei, Bischofia javanica, Brucea javanica, Butea frondosa , Cytisus austriacus, Chrysanthemum morifolium, Colophospermum mopane, Colophospermum mopane Kirk ex.J.Leonard , Cotinus coggygria, Cytisus albus, Cytisus cantabricus, Cytisus commutatus, Cytisus eriocarpus, Cytisus procumbens, Cytisus proliferus, Cytisus striatus, Dalbergia odorifera , Endosamara racemosa, Erythroxylum coca , Erythroxylum novogranatense, Fumaria capreolata , Fumaria officinalis , Fumaria schleicheri, Fumaria vaillantii , Garcinia kola , Genista canariensis, Genista cinerea, Genista florida, Genista microphylla, Genista obtusiramea, Genista pulchella, Genista ramosissima, Genista sericea, Genista sessilifolia, Genista stenopetala, Genista subcapitata, Genista valentina, Genista versicolor, Gleditsia japonica, Gleditsia spp., Gleditsia triacanthos , Glycyrrhiza uralensis, Hesperolaburnum platycarpum, Lembotropis nigricans, Lotus corniculatus , Mangifera indica , Millettia racemosa , Myroxylon peruiferum , Peltophorum africanum, Petteria ramentacea, Picrasma quassioides, Pistacia chinensis , Quebracho colorado, Rhus chinensis, Rhus cotinus, Rhus glabra, Rhus spp., Rhus sylvestris, Robinia pseudoacacia , Schinopsis spp., Schinus molle, Senna lindheimeriana, Sophora secundiflora , Sphaerostephanos penniger, Tilia tomentosa, Toxicodendron succedaneum, Toxicodendron vernicifluum, Trifolium subterraneum , Umtiza listerana, Virgilia oroboides and Xanthocercis zambesiaca. Fisetin was first documented in 2005 (PMID: 15781213). A 7-hydroxyflavonol with additional hydroxy groups at positions 3, 3' and 4' (PMID: 22842629) (PMID: 23054013) (PMID: 23121441) (PMID: 23277230).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
   -2.0558   -2.9390   -0.9870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424   -1.7941   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590   -1.5813   -0.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -2.6442   -0.9489 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2102   -0.3560   -0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228   -0.0152   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9561    1.2705    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2498    1.7047    0.3450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2867    0.8164    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6102    1.2056    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9677   -0.4557   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9754   -1.3452   -0.6347 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6331   -0.8708   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6788    0.5771    0.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659    0.4096    0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8410    1.4373    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2034    1.2607    0.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0253    2.3154    0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7668    0.0353   -0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8973   -0.9785   -0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5319   -0.8028   -0.3155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127   -3.5222   -1.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    2.0138    0.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4919    2.7083    0.6511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8806    2.1365    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7376   -2.2799   -0.9196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4810   -1.8980   -0.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    2.4155    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442    3.2121    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8391   -0.1048   -0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3004   -1.9310   -0.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 15  1  0
 15 14  1  0
 14  5  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
  2  1  2  0
  5  6  1  0
  6 13  2  0
 13 11  1  0
 11 12  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
 15 16  2  0
 16 17  1  0
  2 21  1  0
  7  6  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
  4 22  1  0
 13 27  1  0
 12 26  1  0
 10 25  1  0
  8 24  1  0
  7 23  1  0
 16 28  1  0
M  END


  Mrv1652309272007352D          

 21 23  0  0  0  0            999 V2000
   -4.6477    1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898    1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898   -0.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -0.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825    2.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0680    1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042    1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2186    1.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9332    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9332    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2187   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5042    0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    3.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  9  2  0  0  0  0
  3  4  2  0  0  0  0
  9  5  1  0  0  0  0
  7  5  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  8 14  2  0  0  0  0
 14 12  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
  2 15  1  0  0  0  0
 20  3  1  0  0  0  0
 17  1  1  0  0  0  0
  6 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045391

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H

> <INCHI_KEY>
XHEFDIBZLJXQHF-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.63536387895102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.03

> <JCHEM_LOGP>
1.8098647856666665

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.481610772232772

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.3180160019747795

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8562477265818123

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
74.88130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
viset

> <JCHEM_VEBER_RULE>
0

$$$$

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      -8.676   2.940   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -3.341   2.940   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.341  -0.140   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.341  -1.680   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.673   2.940   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.660   5.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.673   4.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.660   2.170   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.007   2.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.007   0.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.673  -0.140   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.994   4.480   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.327   5.250   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.994   2.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.675   2.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.008   2.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.342   2.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.342   0.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.008  -0.140   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.675   0.630   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.660   6.790   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    9   15                                                       
CONECT    3   10    4   20                                                  
CONECT    4    3                                                            
CONECT    5    9    7    8                                                  
CONECT    6    7   12   21                                                  
CONECT    7    5    6                                                       
CONECT    8    5   14                                                       
CONECT    9    2   10    5                                                  
CONECT   10    3    9   11                                                  
CONECT   11   10                                                            
CONECT   12    6   14   13                                                  
CONECT   13   12                                                            
CONECT   14    8   12                                                       
CONECT   15   16   20    2                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18    1                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15    3                                                  
CONECT   21    6                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
3,3',4',7-Tetrahydroxyflavone	ChEBI
3,7,3',4'-TETRAHYDROXYFLAVONE	ChEBI
5-Desoxyquercetin	ChEBI
7,3',4'-Trihydroxyflavonol	ChEBI
3,3',4',7-Tetrahydroxy-flavone	MeSH
5-Desoxy-quercetin	MeSH
Fisetinidin	MeSH
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-benzopyran-4-one	PhytoBank
3,3’,4’,7-Tetrahydroxyflavone	PhytoBank
Fiestin	PhytoBank
Fietin	PhytoBank
Fisetholz	PhytoBank
Fisitin	PhytoBank
Superfustel	PhytoBank
Superfustel K	PhytoBank

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2363 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one

Traditional Name

viset

CAS Registry Number

528-48-3

SMILES

OC1=CC=C2C(OC(=C(O)C2=O)C2=CC(O)=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H

InChI Key

XHEFDIBZLJXQHF-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-06	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Acacia adunca	Plant	KNApSAcK
Acacia baileyana	Plant	KNApSAcK
Acacia berlandieri	Plant	KNApSAcK
Acacia buxifolia	Plant	KNApSAcK
Acacia calamifolia	Plant	KNApSAcK
Acacia cardiophylla	Plant	KNApSAcK
Acacia carnei	Plant	KNApSAcK
Acacia carneorum	LOTUS Database	35616633
Acacia catechu	Plant	KNApSAcK
Acacia chrysotricha	Plant	KNApSAcK
Acacia clunies-rossiae	Plant	KNApSAcK
Acacia constablei	Plant	KNApSAcK
Acacia crombei	Plant	KNApSAcK
Acacia dealbata	Plant	KNApSAcK
Acacia deanei	Plant	KNApSAcK
Acacia decora	Plant	KNApSAcK
Acacia elata	Plant	KNApSAcK
Acacia falciformis	Plant	KNApSAcK
Acacia fasciculifera	Plant	KNApSAcK
Acacia filicifolia	Plant	KNApSAcK
Acacia greggii	Plant	KNApSAcK
Acacia irrorata	Plant	KNApSAcK
Acacia kettlewelliae	Plant	KNApSAcK
Acacia lanigera	Plant	KNApSAcK
Acacia leucoclada	Plant	KNApSAcK
Acacia mabellae	Plant	KNApSAcK
Acacia mearnsii	Plant	KNApSAcK
Acacia mollifolia	Plant	KNApSAcK
Acacia montana	Plant	KNApSAcK
Acacia oshanesii	Plant	KNApSAcK
Acacia parramattensis	Plant	KNApSAcK
Acacia peuce	Plant	KNApSAcK
Acacia pycnantha	Plant	KNApSAcK
Acacia rubida	Plant	KNApSAcK
Acacia silvestris	Plant	KNApSAcK
Acacia trachyphloia	Plant	KNApSAcK
Acer glabrum	LOTUS Database	35616633
Albizia pedicellata	Plant	KNApSAcK
Albizia splendens	Plant	KNApSAcK
Amburana cearensis	LOTUS Database	35616633
Anthyllis vulneraria	Plant	KNApSAcK
Archidendron clypearia	Plant	KNApSAcK
Baptisia lecontei	Plant	KNApSAcK
Bischofia javanica	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Butea monosperma	Plant	KNApSAcK
Chamaecytisus austriacus	Plant	KNApSAcK
Chrysanthemum morifolium	LOTUS Database	35616633
Colophospermum mopane	LOTUS Database	35616633
Colophospermum mopane Kirk ex.J.Leonard	Plant	KNApSAcK
Cotinus coggygria	LOTUS Database	35616633
Cytisus albus	Plant	KNApSAcK
Cytisus cantabricus	Plant	KNApSAcK
Cytisus commutatus	Plant	KNApSAcK
Cytisus eriocarpus	Plant	KNApSAcK
Cytisus procumbens	Plant	KNApSAcK
Cytisus proliferus	Plant	KNApSAcK
Cytisus striatus	Plant	KNApSAcK
Dalbergia odorifera	Plant	KNApSAcK
Endosamara racemosa	LOTUS Database	35616633
Erythroxylum coca	Plant	KNApSAcK
Erythroxylum novogranatense	Plant	KNApSAcK
Fumaria capreolata	Plant	KNApSAcK
Fumaria officinalis	Plant	KNApSAcK
Fumaria schleicheri	Plant	KNApSAcK
Fumaria vaillantii	Plant	KNApSAcK
Garcinia kola	Plant	KNApSAcK
Genista canariensis	Plant	KNApSAcK
Genista cinerea	Plant	KNApSAcK
Genista florida	Plant	KNApSAcK
Genista microphylla	Plant	KNApSAcK
Genista obtusiramea	Plant	KNApSAcK
Genista pulchella	Plant	KNApSAcK
Genista ramosissima	Plant	KNApSAcK
Genista sericea	Plant	KNApSAcK
Genista sessilifolia	Plant	KNApSAcK
Genista stenopetala	Plant	KNApSAcK
Genista subcapitata	Plant	KNApSAcK
Genista valentina	Plant	KNApSAcK
Genista versicolor	Plant	KNApSAcK
Gleditsia japonica	LOTUS Database	35616633
Gleditsia spp.	Plant	KNApSAcK
Gleditsia triacanthos	Plant	KNApSAcK
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Glycyrrhiza uralensis	LOTUS Database	35616633
Hesperolaburnum platycarpum	Plant	KNApSAcK
Lembotropis nigricans	Plant	KNApSAcK
Lotus corniculatus	Plant	KNApSAcK
Mangifera indica	Plant	KNApSAcK
Millettia racemosa	Plant	KNApSAcK
Myroxylon peruiferum	Plant	KNApSAcK
Peltophorum africanum	LOTUS Database	35616633
Petteria ramentacea	Plant	KNApSAcK
Picrasma quassioides	LOTUS Database	35616633
Pistacia chinensis	Plant	KNApSAcK
Quebracho colorado	-	KNApSAcK
Rhus chinensis	LOTUS Database	35616633
Rhus cotinus	Plant	KNApSAcK
Rhus glabra	LOTUS Database	35616633
Rhus spp.	Plant	KNApSAcK
Rhus sylvestris	Plant	KNApSAcK
Robinia pseudoacacia	Plant	KNApSAcK
Schinopsis spp.	Plant	KNApSAcK
Schinus molle	LOTUS Database	35616633
Senna lindheimeriana	LOTUS Database	35616633
Sophora secundiflora	Plant	KNApSAcK
Sphaerostephanos penniger	LOTUS Database	35616633
Tilia tomentosa	LOTUS Database	35616633
Toxicodendron succedaneum	Plant	KNApSAcK
Toxicodendron vernicifluum	LOTUS Database	35616633
Trifolium subterraneum	Plant	KNApSAcK
Umtiza listerana	Plant	KNApSAcK
Virgilia oroboides	Plant	KNApSAcK
Xanthocercis zambesiaca	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tetrahydroxyflavone (CHEBI:42567 )
3'-hydroxyflavonoid (CHEBI:42567 )
7-hydroxyflavonol (CHEBI:42567 )
flavonols (C10041 )
Flavones and Flavonols (LMPK12111566 )

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	2.03	ALOGPS
logP	1.81	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.32	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.88 m³·mol⁻¹	ChemAxon
Polarizability	27.64 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

HMDB0147719

DrugBank ID

DB07795

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000624

KNApSAcK ID

C00004579

Chemspider ID

Not Available

KEGG Compound ID

C10041

BioCyc ID

CPD-13503

BiGG ID

Not Available

Wikipedia Link

Fisetin

METLIN ID

Not Available

PubChem Compound

5281614

PDB ID

Not Available

ChEBI ID

42567

Good Scents ID

Not Available

References

General References

Olaharski AJ, Mondrala ST, Eastmond DA: Chromosomal malsegregation and micronucleus induction in vitro by the DNA topoisomerase II inhibitor fisetin. Mutat Res. 2005 Apr 4;582(1-2):79-86. doi: 10.1016/j.mrgentox.2005.01.002. [PubMed:15781213 ]
Adhami VM, Syed DN, Khan N, Mukhtar H: Dietary flavonoid fisetin: a novel dual inhibitor of PI3K/Akt and mTOR for prostate cancer management. Biochem Pharmacol. 2012 Nov 15;84(10):1277-81. doi: 10.1016/j.bcp.2012.07.012. Epub 2012 Jul 25. [PubMed:22842629 ]
Gutierrez-Venegas G, Contreras-Sanchez A: Luteolin and fisetin inhibit the effects of lipopolysaccharide obtained from Porphyromonas gingivalis in human gingival fibroblasts. Mol Biol Rep. 2013 Jan;40(1):477-85. doi: 10.1007/s11033-012-2083-0. Epub 2012 Oct 11. [PubMed:23054013 ]
Khan N, Syed DN, Ahmad N, Mukhtar H: Fisetin: a dietary antioxidant for health promotion. Antioxid Redox Signal. 2013 Jul 10;19(2):151-62. doi: 10.1089/ars.2012.4901. Epub 2012 Dec 18. [PubMed:23121441 ]
Prasath GS, Sundaram CS, Subramanian SP: Fisetin averts oxidative stress in pancreatic tissues of streptozotocin-induced diabetic rats. Endocrine. 2013 Oct;44(2):359-68. doi: 10.1007/s12020-012-9866-x. Epub 2013 Jan 1. [PubMed:23277230 ]

Showing NP-Card for Fisetin (NP0045391)

MOL for NP0045391 (Fisetin)

3D MOL for NP0045391 (Fisetin)

3D SDF for NP0045391 (Fisetin)

3D-SDF for NP0045391 (Fisetin)

PDB for NP0045391 (Fisetin)

3D PDB for NP0045391 (Fisetin)

SMILES for NP0045391 (Fisetin)

INCHI for NP0045391 (Fisetin)

Structure for NP0045391 (Fisetin)

3D Structure for NP0045391 (Fisetin)