NP-MRD: Showing NP-Card for Isosilybin A (NP0012442)

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Record Information

Version

2.0

Created at

2021-01-05 21:49:19 UTC

Updated at

2021-07-15 17:11:46 UTC

NP-MRD ID

NP0012442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isosilybin A

Provided By

NPAtlas

Description

Isosilybin A is found in Anastatica hierochuntica and Aspergillus iizukae. Isosilybin A was first documented in 2014 (PMID: 24456525). Based on a literature review very few articles have been published on Isosilybin a (PMID: 34318464) (PMID: 33706132) (PMID: 33251548) (PMID: 32806559) (PMID: 32705114) (PMID: 32284261).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117083D          

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    6.4693    2.4164    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6248    3.1734    0.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8774   -1.1239   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2414   -1.1173   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5046   -1.5149    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961   -0.7345   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3235   -1.1094    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0007   -2.4196    0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5044   -1.1071   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4635   -1.9174   -0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2915   -2.7870   -1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1321    2.6410    0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956    4.0136    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5163    2.7481    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  2  0  0  0  0
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 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
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  5 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34  3  1  0  0  0  0
 29  6  1  0  0  0  0
 27  8  1  0  0  0  0
 24 12  1  0  0  0  0
 21 14  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  4 39  1  0  0  0  0
  6 40  1  1  0  0  0
  9 41  1  0  0  0  0
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 15 44  1  0  0  0  0
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 20 47  1  0  0  0  0
 24 48  1  6  0  0  0
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 26 50  1  0  0  0  0
 29 51  1  6  0  0  0
 30 52  1  0  0  0  0
 30 53  1  0  0  0  0
 31 54  1  0  0  0  0
 32 55  1  0  0  0  0
 33 56  1  0  0  0  0
 35 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0012442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C([H])=C4O[C@]([H])(C5=C([H])C([H])=C(O[H])C(OC([H])([H])[H])=C5[H])[C@]([H])(OC4=C3[H])C([H])([H])O[H])[C@@]([H])(O[H])C2=O)=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1

> <INCHI_KEY>
FDQAOULAVFHKBX-HKTJVKLFSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.441

> <EXACT_MASS>
482.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.92309649751088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.6293160946666667

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.27527432664632

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7549598356104035

> <JCHEM_PKA_STRONGEST_BASIC>
-2.990414182412958

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
120.29389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
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   -5.0137   -1.9275    0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -3.0307   -0.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0776   -2.7661    1.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423    0.0031    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228    0.1839    0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    0.5434   -0.7959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976    0.0741   -0.9872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0712   -1.2857   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -1.8417   -1.9004 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5046   -1.5149    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961   -0.7345   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3235   -1.1094    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6965   -0.4786    3.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7582   -0.7999    3.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3269    2.6377   -0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2690    3.3089   -0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4844    0.4367   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3504   -2.0650   -1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0007   -2.4196    0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7065   -2.2896    2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645    0.1465   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4635   -1.9174   -0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2915   -2.7870   -1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1321    2.6410    0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956    4.0136    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5163    2.7481    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  5 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34  3  1  0
 29  6  1  0
 27  8  1  0
 24 12  1  0
 21 14  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  6 40  1  1
  9 41  1  0
 10 42  1  0
 12 43  1  1
 15 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 24 48  1  6
 25 49  1  0
 26 50  1  0
 29 51  1  6
 30 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
 33 56  1  0
 35 57  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       7.824  -0.875  -0.544  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.763   0.496  -0.221  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.545   1.060   0.071  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.401   0.328   0.055  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.152   0.837   0.338  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.969  -0.049   0.291  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.193   0.216   1.439  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.825   0.011   1.499  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.148  -0.343   2.628  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.218  -0.519   2.563  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.946  -0.355   1.400  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.428  -0.555   1.368  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.972   0.515   0.645  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.170   0.484  -0.030  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.777   1.672  -0.361  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.981   1.668  -1.039  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.600   2.866  -1.376  0.00  0.00           O+0
HETATM   18  C   UNK     0      -7.534   0.449  -1.362  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.923  -0.741  -1.029  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.478  -1.969  -1.353  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.721  -0.725  -0.352  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.014  -1.928   0.035  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.440  -3.031  -0.377  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.825  -1.901   0.886  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.078  -2.766   1.977  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.242   0.003   0.268  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.123   0.184   0.314  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.874   0.543  -0.796  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.198   0.074  -0.987  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.071  -1.286  -1.664  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.323  -1.842  -1.900  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.077   2.178   0.656  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.236   2.960   0.682  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.469   2.416   0.393  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.625   3.173   0.414  0.00  0.00           O+0
HETATM   36  H   UNK     0       8.877  -1.124  -0.781  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.241  -1.117  -1.462  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.505  -1.515   0.314  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.496  -0.735  -0.203  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.324  -1.109   0.399  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.697  -0.479   3.555  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.758  -0.800   3.457  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.769  -0.446   2.421  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.327   2.638  -0.099  0.00  0.00           H+0
HETATM   45  H   UNK     0      -8.269   3.309  -0.728  0.00  0.00           H+0
HETATM   46  H   UNK     0      -8.484   0.437  -1.897  0.00  0.00           H+0
HETATM   47  H   UNK     0      -8.350  -2.065  -1.845  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.001  -2.420   0.314  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.707  -2.290   2.597  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.765   0.147  -0.677  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.716   0.727  -1.735  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.504  -1.107  -2.601  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.464  -1.917  -0.981  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.292  -2.787  -1.653  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.132   2.641   0.888  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.196   4.014   0.930  0.00  0.00           H+0
HETATM   57  H   UNK     0       8.516   2.748   0.197  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5   39                                                  
CONECT    5    4    6   32                                                  
CONECT    6    5    7   29   40                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10   41                                                  
CONECT   10    9   11   42                                                  
CONECT   11   10   12   26                                                  
CONECT   12   11   13   24   43                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   44                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   45                                                       
CONECT   18   16   19   46                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   47                                                       
CONECT   21   19   22   14                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   12   48                                             
CONECT   25   24   49                                                       
CONECT   26   11   27   50                                                  
CONECT   27   26   28    8                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30    6   51                                             
CONECT   30   29   31   52   53                                             
CONECT   31   30   54                                                       
CONECT   32    5   33   55                                                  
CONECT   33   32   34   56                                                  
CONECT   34   33   35    3                                                  
CONECT   35   34   57                                                       
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    4                                                            
CONECT   40    6                                                            
CONECT   41    9                                                            
CONECT   42   10                                                            
CONECT   43   12                                                            
CONECT   44   15                                                            
CONECT   45   17                                                            
CONECT   46   18                                                            
CONECT   47   20                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   30                                                            
CONECT   54   31                                                            
CONECT   55   32                                                            
CONECT   56   33                                                            
CONECT   57   35                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

RDKit          3D

57 61  0  0  0  0  0  0  0  0999 V2000
    7.8242   -0.8753   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633    0.4961   -0.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5449    1.0600    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4014    0.3282    0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1521    0.8374    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9693   -0.0486    0.2909 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1927    0.2161    1.4388 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8252    0.0108    1.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475   -0.3430    2.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2175   -0.5193    2.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -0.3549    1.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4283   -0.5552    1.3678 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9717    0.5154    0.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1695    0.4835   -0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7773    1.6716   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9809    1.6680   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6000    2.8660   -1.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5336    0.4493   -1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9228   -0.7406   -1.0289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4779   -1.9686   -1.3530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7214   -0.7250   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0137   -1.9275    0.0351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4397   -3.0307   -0.3774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8252   -1.9006    0.8864 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0776   -2.7661    1.9768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423    0.0031    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228    0.1839    0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737    0.5434   -0.7959 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1976    0.0741   -0.9872 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0712   -1.2857   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -1.8417   -1.9004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0772    2.1775    0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2355    2.9596    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4693    2.4164    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6248    3.1734    0.4136 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8774   -1.1239   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2414   -1.1173   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5046   -1.5149    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961   -0.7345   -0.2025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3235   -1.1094    0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6965   -0.4786    3.5555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7582   -0.7999    3.4570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7691   -0.4464    2.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3269    2.6377   -0.0985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2690    3.3089   -0.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4844    0.4367   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3504   -2.0650   -1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0007   -2.4196    0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7065   -2.2896    2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645    0.1465   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7159    0.7274   -1.7347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5044   -1.1071   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4635   -1.9174   -0.9813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2915   -2.7870   -1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1321    2.6410    0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956    4.0136    0.9295 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5163    2.7481    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 11 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
  5 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 34  3  1  0
 29  6  1  0
 27  8  1  0
 24 12  1  0
 21 14  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  6 40  1  1
  9 41  1  0
 10 42  1  0
 12 43  1  1
 15 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 24 48  1  6
 25 49  1  0
 26 50  1  0
 29 51  1  6
 30 52  1  0
 30 53  1  0
 31 54  1  0
 32 55  1  0
 33 56  1  0
 35 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
7-(4-Bromobenzoyl)isosilybin a	MeSH
Isosilybin b	MeSH

Chemical Formula

C₂₅H₂₂O₁₀

Average Mass

482.4410 Da

Monoisotopic Mass

482.12130 Da

IUPAC Name

(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)[C@H]1OC2=C(O[C@@H]1CO)C=C(C=C2)[C@H]1OC2=CC(O)=CC(O)=C2C(=O)[C@@H]1O

InChI Identifier

InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1

InChI Key

FDQAOULAVFHKBX-HKTJVKLFSA-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
Anastatica hierochuntica	LOTUS Database	35616633
Aspergillus iizukae	NPAtlas	24456525
Silybum marianum	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	2.35	ALOGPS
logP	2.63	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.29 m³·mol⁻¹	ChemAxon
Polarizability	48.92 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA008799

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039453

Chemspider ID

9235077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11059920

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El-Elimat T, Raja HA, Graf TN, Faeth SH, Cech NB, Oberlies NH: Flavonolignans from Aspergillus iizukae, a fungal endophyte of milk thistle (Silybum marianum). J Nat Prod. 2014 Feb 28;77(2):193-9. doi: 10.1021/np400955q. Epub 2014 Jan 23. [PubMed:24456525 ]
Islam A, Mishra A, Siddiqui MA, Siddiquie S: Recapitulation of Evidence of Phytochemical, Pharmacokinetic and Biomedical Application of Silybin. Drug Res (Stuttg). 2021 Jul 27. doi: 10.1055/a-1528-2721. [PubMed:34318464 ]
Faisal Z, Mohos V, Fliszar-Nyul E, Valentova K, Kanova K, Lemli B, Kunsagi-Mate S, Poor M: Interaction of silymarin components and their sulfate metabolites with human serum albumin and cytochrome P450 (2C9, 2C19, 2D6, and 3A4) enzymes. Biomed Pharmacother. 2021 Jun;138:111459. doi: 10.1016/j.biopha.2021.111459. Epub 2021 Mar 9. [PubMed:33706132 ]
Muchiri RN, van Breemen RB: Single Laboratory Validation of UHPLC-MS/MS Assays for Six Milk Thistle Flavonolignans in Human Serum. J AOAC Int. 2021 Mar 5;104(1):232-238. doi: 10.1093/jaoacint/qsaa110. [PubMed:33251548 ]
Vrba J, Papouskova B, Kosina P, Lnenickova K, Valentova K, Ulrichova J: Identification of Human Sulfotransferases Active towards Silymarin Flavonolignans and Taxifolin. Metabolites. 2020 Aug 12;10(8). pii: metabo10080329. doi: 10.3390/metabo10080329. [PubMed:32806559 ]
Hasany SM, Huma R, Akram S, Ashraf R, Mushtaq M: Maceration-Mediated Liquid-Liquid Extraction and Reverse-Phase High-Performance Liquid Chromatography-Based Pragmatic Analysis of Silybins. J Chromatogr Sci. 2020 Aug 21;58(8):779-787. doi: 10.1093/chromsci/bmaa035. [PubMed:32705114 ]
Nasab EM, Athari SM, Ghafarzade S, Nasab AM, Athari SS: Immunomodulatory effects of two silymarin isomers in a Balb/c mouse model of allergic asthma. Allergol Immunopathol (Madr). 2020 Nov - Dec;48(6):646-653. doi: 10.1016/j.aller.2020.01.003. Epub 2020 Apr 10. [PubMed:32284261 ]
Vrba J, Papouskova B, Lnenickova K, Kosina P, Kren V, Ulrichova J: Identification of UDP-glucuronosyltransferases involved in the metabolism of silymarin flavonolignans. J Pharm Biomed Anal. 2020 Jan 30;178:112972. doi: 10.1016/j.jpba.2019.112972. Epub 2019 Nov 4. [PubMed:31727359 ]
Kim JY, Kim JY, Jenis J, Li ZP, Ban YJ, Baiseitova A, Park KH: Tyrosinase inhibitory study of flavonolignans from the seeds of Silybum marianum (Milk thistle). Bioorg Med Chem. 2019 Jun 15;27(12):2499-2507. doi: 10.1016/j.bmc.2019.03.013. Epub 2019 Mar 7. [PubMed:30871862 ]

Showing NP-Card for Isosilybin A (NP0012442)

MOL for NP0012442 (Isosilybin A)

3D MOL for NP0012442 (Isosilybin A)

3D SDF for NP0012442 (Isosilybin A)

3D-SDF for NP0012442 (Isosilybin A)

PDB for NP0012442 (Isosilybin A)

3D PDB for NP0012442 (Isosilybin A)

SMILES for NP0012442 (Isosilybin A)

INCHI for NP0012442 (Isosilybin A)

Structure for NP0012442 (Isosilybin A)

3D Structure for NP0012442 (Isosilybin A)