NP-MRD: Showing NP-Card for 5,7,4'-Trihydroxy-6-prenylisoflavone (NP0051497)

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Record Information

Version

2.0

Created at

2022-04-27 22:50:29 UTC

Updated at

2022-04-27 22:50:29 UTC

NP-MRD ID

NP0051497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,4'-Trihydroxy-6-prenylisoflavone

Description

Wighteone, also known as erythrinin b, belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, wighteone is considered to be a flavonoid lipid molecule. 5,7,4'-Trihydroxy-6-prenylisoflavone is found in Anthyllis hermanniae, Argyrocytisus battandieri, Bolusanthus speciosus, Cudrania cochinchinensis var. gerontogea , Erythrina fusca, Erythrina latissima, Erythrina lysistemon , Erythrina mildbraedii, Erythrina orientalis, Erythrina poeppigiana , Erythrina suberosa, Erythrina suberosa var. glabrescences , Erythrina indica , Ficus glumosa, Ficus mucuso, Flemingia macrophylla, Flemingia philippinensis, Genista ephedroides, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza uralensis , Laburnum anagyroides , Lupinus albus , Lupinus angustifolius , Lupinus luteus, Lupinus polyphyllus, Maclura cochinchinensis, Maclura pomifera, Maclura tricuspidata, Neonotonia wightii, Sophora flavescens and Sophora tomentosa. 5,7,4'-Trihydroxy-6-prenylisoflavone was first documented in 2002 (PMID: 12150799). Wighteone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 16369693) (PMID: 22837700) (PMID: 23850732).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -4.7642   -0.6529   -1.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8426   -0.6025    0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7030   -1.6459    0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1988    0.3046    0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490    1.3415    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9520    1.2978    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6836    1.7708    1.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564    2.2842    2.6816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4375    1.7724    2.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6008    1.2642    1.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017    1.2580    2.2178 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172    0.7889    1.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6827    0.2805    0.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8183   -0.2438   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -1.0919    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8105   -1.5987   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0268   -1.2761   -1.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1042   -1.7634   -2.6462 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1247   -0.4302   -2.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385    0.0767   -1.8137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4240    0.2753   -0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261   -0.1933   -1.4505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589    0.7759    0.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130    0.7812   -0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083    0.3141   -1.3452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2009   -1.6199   -1.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7530   -0.5220   -1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4425    0.1250   -1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4511   -1.7325    1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5909   -2.6243    0.2548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7786   -1.3733    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3000    0.2862    1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    1.2816   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952    2.3237    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817    2.6404    3.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154    2.1510    3.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8139    0.7826    1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5580   -1.3459    1.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5139   -2.2621   -0.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7859   -2.3828   -2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016   -0.1781   -3.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3283    0.7456   -2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6453   -0.0688   -2.0137 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 24  6  1  0
 20 14  1  0
 23 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  8 35  1  0
  9 36  1  0
 12 37  1  0
 25 43  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv1533004251510022D          

 25 27  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    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
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  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
 13 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  2  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3

> <INCHI_KEY>
KIMDVVKVNNSHGZ-UHFFFAOYSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.359

> <EXACT_MASS>
338.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.19544667160608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
4.805439389

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.927685913290125

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.361273258379078

> <JCHEM_PKA_STRONGEST_BASIC>
-5.3459550164455365

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
95.9257

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
wighteone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9   16                                                  
CONECT   16   15    5   17                                                  
CONECT   17   16                                                            
CONECT   18   12   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
5,7,4'-Trihydroxy-6-prenylisoflavone	ChEBI
5,7-Dihydroxy-3-(4-hydroxyphenyl)-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one	ChEBI
Erythrinin b	ChEBI

Chemical Formula

C₂₀H₁₈O₅

Average Mass

338.3590 Da

Monoisotopic Mass

338.11542 Da

IUPAC Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

wighteone

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=C(O)C=C2OC=C(C(=O)C2=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3

InChI Key

KIMDVVKVNNSHGZ-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
Anthyllis hermanniae	LOTUS Database	35616633
Argyrocytisus battandieri	Plant	KNApSAcK
Bolusanthus speciosus	LOTUS Database	35616633
Cudrania cochinchinensis var. gerontogea	Plant	KNApSAcK
Erythrina fusca	LOTUS Database	35616633
Erythrina latissima	LOTUS Database	35616633
Erythrina lysistemon	Plant	KNApSAcK
Erythrina mildbraedii	LOTUS Database	35616633
Erythrina orientalis	Plant	KNApSAcK
Erythrina poeppigiana	Plant	KNApSAcK
Erythrina suberosa	LOTUS Database	35616633
Erythrina suberosa var. glabrescences	Plant	KNApSAcK
Erythrina variegata	Plant	KNApSAcK
Ficus glumosa	LOTUS Database	35616633
Ficus mucuso	LOTUS Database	35616633
Flemingia macrophylla	LOTUS Database	35616633
Flemingia philippinensis	Plant	KNApSAcK
Genista ephedroides	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Laburnum anagyroides	Plant	KNApSAcK
Lupinus albus	Plant	KNApSAcK
Lupinus angustifolius	Plant	KNApSAcK
Lupinus luteus	LOTUS Database	35616633
Lupinus polyphyllus	Plant	KNApSAcK
Maclura cochinchinensis	LOTUS Database	35616633
Maclura pomifera	Plant	KNApSAcK
Maclura tricuspidata	LOTUS Database	35616633
Neonotonia wightii	Plant	KNApSAcK
Sophora flavescens	Plant	KNApSAcK
Sophora tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Isoflavone
Hydroxyisoflavonoid
Chromone
1-benzopyran
Benzopyran
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Phenol
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:10038 )
isoflavones (C10542 )
Isoflavonoids (C10542 )
Isoflavonoids (LMPK12050188 )

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	3.86	ALOGPS
logP	4.81	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.36	ChemAxon
pKa (Strongest Basic)	-5.3	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	3	ChemAxon
Refractivity	95.93 m³·mol⁻¹	ChemAxon
Polarizability	36.2 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002586

Chemspider ID

Not Available

KEGG Compound ID

C10542

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Wighteone

METLIN ID

Not Available

PubChem Compound

5281814

PDB ID

Not Available

ChEBI ID

10038

Good Scents ID

Not Available

References

General References

el-Masry S, Amer ME, Abdel-Kader MS, Zaatout HH: Prenylated flavonoids of Erythrina lysistemon grown in Egypt. Phytochemistry. 2002 Aug;60(8):783-7. doi: 10.1016/s0031-9422(02)00202-9. [PubMed:12150799 ]
Yin H, Zhao Y, Zhang Y, Zhang H, Xu L, Zou Z, Yang W, Cheng J, Zhou Y: Genome-wide analysis of the expression profile of Saccharomyces cerevisiae in response to treatment with the plant isoflavone, wighteone, as a potential antifungal agent. Biotechnol Lett. 2006 Jan;28(2):99-105. doi: 10.1007/s10529-005-4954-0. [PubMed:16369693 ]
Wei S, Wu W, Ji Z: New antifungal pyranoisoflavone from Ficus tikoua Bur. Int J Mol Sci. 2012;13(6):7375-82. doi: 10.3390/ijms13067375. Epub 2012 Jun 14. [PubMed:22837700 ]
Kumar S, Pathania AS, Saxena AK, Vishwakarma RA, Ali A, Bhushan S: The anticancer potential of flavonoids isolated from the stem bark of Erythrina suberosa through induction of apoptosis and inhibition of STAT signaling pathway in human leukemia HL-60 cells. Chem Biol Interact. 2013 Sep 25;205(2):128-37. doi: 10.1016/j.cbi.2013.06.020. Epub 2013 Jul 9. [PubMed:23850732 ]

Showing NP-Card for 5,7,4'-Trihydroxy-6-prenylisoflavone (NP0051497)

MOL for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

3D MOL for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

3D SDF for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

3D-SDF for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

PDB for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

3D PDB for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

SMILES for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

INCHI for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

Structure for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)

3D Structure for NP0051497 (5,7,4'-Trihydroxy-6-prenylisoflavone)