NP-MRD: Showing NP-Card for Silibinin (NP0331835)

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Record Information

Version

2.0

Created at

2023-09-20 16:01:16 UTC

Updated at

2024-09-03 04:17:10 UTC

NP-MRD ID

NP0331835

Natural Product DOI

https://doi.org/10.57994/0940

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Silibinin

Description

Silibinin is also known as silybin or legalon. Silibinin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Silibinin was first documented in 2021 (PMID: 34353693). Based on a literature review a significant number of articles have been published on Silibinin (PMID: 34399200) (PMID: 34360650) (PMID: 34348081) (PMID: 34344191) (PMID: 34285784) (PMID: 34258250).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117083D          

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    5.2883    2.8528   -0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4670    2.1508   -0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6626    2.8000   -0.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3161    3.9316   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4992    2.2378   -0.8555 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  1  0  0  0  0
 11 12  1  0  0  0  0
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 13 14  2  0  0  0  0
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 18 20  2  0  0  0  0
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 23 24  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
 23 11  1  0  0  0  0
 20 13  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
 11 42  1  6  0  0  0
 14 43  1  0  0  0  0
 16 44  1  0  0  0  0
 17 45  1  0  0  0  0
 19 46  1  0  0  0  0
 23 47  1  1  0  0  0
 24 48  1  0  0  0  0
 25 49  1  0  0  0  0
 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>
NP0331835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C([H])=C4O[C@]([H])(C([H])([H])O[H])[C@]([H])(OC4=C3[H])C3=C([H])C([H])=C(O[H])C(OC([H])([H])[H])=C3[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)33-16-5-3-12(7-18(16)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>
SEBFKMXJBCUCAI-HKTJVKLFSA-N

> <FORMULA>
C25H22O10

> <MOLECULAR_WEIGHT>
482.441

> <EXACT_MASS>
482.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.6374535953362

> <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)-3-(4-hydroxy-3-methoxyphenyl)-2-(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>
9.275274448635567

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7549598399992865

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904140611148753

> <JCHEM_POLAR_SURFACE_AREA>
155.14

> <JCHEM_REFRACTIVITY>
120.29390000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
silibinin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 13 14  2  0
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 23 24  1  0
 10 25  2  0
 25 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
 23 11  1  0
 20 13  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
 11 42  1  6
 14 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 23 47  1  1
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 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       7.732  -1.301  -0.171  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.604   0.077  -0.353  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.428   0.793  -0.229  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.228   0.145   0.105  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.046   0.826   0.236  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.735   0.230   0.579  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.700   0.799  -0.255  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.438   0.284  -0.270  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.725   1.017  -0.424  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.976   0.435  -0.430  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.230   1.206  -0.595  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.038   0.533  -1.507  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.234  -0.090  -1.270  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.009  -0.613  -2.305  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.210  -1.237  -2.047  0.00  0.00           C+0
HETATM   16  O   UNK     0      -7.950  -1.744  -3.111  0.00  0.00           O+0
HETATM   17  C   UNK     0      -7.622  -1.330  -0.745  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.876  -0.820   0.320  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.369  -0.957   1.599  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.689  -0.207   0.019  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.854   0.348   1.073  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.912  -0.098   2.247  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.922   1.472   0.706  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.738   2.596   0.532  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.063  -0.933  -0.276  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.908  -1.700  -0.118  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.331  -1.097  -0.115  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.498  -1.787   0.035  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.681  -1.244   0.603  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.842  -1.764   2.038  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.974  -1.253   2.626  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.117   2.212   0.013  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.288   2.853  -0.315  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.467   2.151  -0.442  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.663   2.800  -0.775  0.00  0.00           O+0
HETATM   36  H   UNK     0       8.618  -1.669  -0.751  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.880  -1.620   0.862  0.00  0.00           H+0
HETATM   38  H   UNK     0       6.859  -1.860  -0.602  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.267  -0.915   0.260  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.428   0.581   1.613  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.643   2.077  -0.543  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.988   2.210  -1.050  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.648  -0.518  -3.312  0.00  0.00           H+0
HETATM   44  H   UNK     0      -8.825  -2.205  -2.993  0.00  0.00           H+0
HETATM   45  H   UNK     0      -8.558  -1.815  -0.532  0.00  0.00           H+0
HETATM   46  H   UNK     0      -7.034  -0.681   2.462  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.229   1.706   1.523  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.692   2.369   0.452  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.002  -1.450  -0.271  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.951  -2.769   0.005  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.506  -1.684   0.021  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.944  -1.409   2.586  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.896  -2.865   1.980  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.727  -1.897   2.540  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.182   2.769   0.113  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.316   3.932  -0.483  0.00  0.00           H+0
HETATM   57  H   UNK     0       8.499   2.238  -0.856  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   25                                                  
CONECT   11   10   12   23   42                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   43                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   44                                                       
CONECT   17   15   18   45                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   46                                                       
CONECT   20   18   21   13                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   11   47                                             
CONECT   24   23   48                                                       
CONECT   25   10   26   49                                                  
CONECT   26   25   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   11                                                            
CONECT   43   14                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   19                                                            
CONECT   47   23                                                            
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
    7.7318   -1.3014   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6043    0.0774   -0.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4279    0.7927   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2281    0.1449    0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0458    0.8256    0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7351    0.2295    0.5787 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7000    0.7985   -0.2550 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379    0.2836   -0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7246    1.0172   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757    0.4351   -0.4304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304    1.2058   -0.5949 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0383    0.5325   -1.5067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2339   -0.0902   -1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0093   -0.6130   -2.3052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2104   -1.2372   -2.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9503   -1.7439   -3.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6217   -1.3296   -0.7448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8757   -0.8195    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3689   -0.9573    1.5985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6885   -0.2074    0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8537    0.3482    1.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9121   -0.0981    2.2468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9219    1.4719    0.7064 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7381    2.5962    0.5315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0625   -0.9326   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076   -1.6995   -0.1176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3311   -1.0973   -0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4984   -1.7867    0.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -1.2435    0.6028 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8418   -1.7643    2.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9735   -1.2527    2.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1175    2.2121    0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    2.8528   -0.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4670    2.1508   -0.4416 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6626    2.8000   -0.7752 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6184   -1.6689   -0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8805   -1.6202    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8586   -1.8604   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2671   -0.9149    0.2598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4275    0.5814    1.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6432    2.0774   -0.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9878    2.2098   -1.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6477   -0.5178   -3.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8247   -2.2052   -2.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5581   -1.8151   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0340   -0.6806    2.4625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2293    1.7057    1.5228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6924    2.3686    0.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0025   -1.4498   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9514   -2.7691    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5060   -1.6839    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9445   -1.4086    2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -2.8650    1.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7266   -1.8972    2.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1817    2.7693    0.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3161    3.9316   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4992    2.2378   -0.8555 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  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 10 25  2  0
 25 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
 23 11  1  0
 20 13  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
 11 42  1  6
 14 43  1  0
 16 44  1  0
 17 45  1  0
 19 46  1  0
 23 47  1  1
 24 48  1  0
 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

Synonyms

Value	Source
Flavobin	ChEBI
Karsil	ChEBI
Silibinina	ChEBI
Silibinine	ChEBI
Silibininum	ChEBI
Silybin	ChEBI
Silymarin	ChEBI
Silymarin I	Kegg
Legalon	Kegg
2,3 Dehydrosilybin	MeSH
2,3-Dehydrosilybin	MeSH
Alepa forte	MeSH
Alepa-forte	MeSH
Ardeyhepan	MeSH
Cefasilymarin	MeSH
Hepa merz sil	MeSH
Hepa loges	MeSH
Hepa-merz sil	MeSH
HepaBesch	MeSH
Hepar pasc	MeSH
Hepar-pasc	MeSH
Heparsyx	MeSH
Heplant	MeSH
Lagosa	MeSH
Silibinin a	MeSH
Silibinin b	MeSH
Durasilymarin	MeSH
Hepa-loges	MeSH
Legalon forte	MeSH
Silibin	MeSH
Silybin a	MeSH
Silybin b	MeSH
Silybinin	MeSH
Silibinin	MeSH
Hepatos	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)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

silibinin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C([H])=C4O[C@]([H])(C([H])([H])O[H])[C@]([H])(OC4=C3[H])C3=C([H])C([H])=C(O[H])C(OC([H])([H])[H])=C3[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)33-16-5-3-12(7-18(16)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

SEBFKMXJBCUCAI-HKTJVKLFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-20	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-20	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-20	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

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Flavonolignans

Sub Class

Not Available

Direct Parent

Flavonolignans

Alternative Parents

Substituents

Flavonolignan
Hydroxyflavonoid
3-hydroxyflavonoid
Flavanonol
Flavanone
7-hydroxyflavonoid
5-hydroxyflavonoid
Flavan
Phenylbenzodioxane
2-phenylbenzo-1,4-dioxane
Chromone
1-benzopyran
Methoxyphenol
Benzopyran
Chromane
Benzodioxane
Benzo-1,4-dioxane
Phenoxy compound
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Para-dioxin
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:9144 )
polyphenol (CHEBI:9144 )
benzodioxine (CHEBI:9144 )
flavonolignan (CHEBI:9144 )

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	48.64 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

HMDB ID

Not Available

DrugBank ID

DB09298

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001003

Chemspider ID

29263

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Silibinin

METLIN ID

Not Available

PubChem Compound

31553

PDB ID

Not Available

ChEBI ID

9144

Good Scents ID

rw1108841

References

General References

Dhami-Shah H, Vaidya R, Talwadekar M, Shaw E, Udipi S, Kolthur-Seetharam U, Vaidya ADB: Intervention by picroside II on FFAs induced lipid accumulation and lipotoxicity in HepG2 cells. J Ayurveda Integr Med. 2021 Jul-Sep;12(3):465-473. doi: 10.1016/j.jaim.2021.04.007. Epub 2021 Aug 2. [PubMed:34353693 ]
Fallah M, Davoodvandi A, Nikmanzar S, Aghili S, Mirazimi SMA, Aschner M, Rashidian A, Hamblin MR, Chamanara M, Naghsh N, Mirzaei H: Silymarin (milk thistle extract) as a therapeutic agent in gastrointestinal cancer. Biomed Pharmacother. 2021 Oct;142:112024. doi: 10.1016/j.biopha.2021.112024. Epub 2021 Aug 13. [PubMed:34399200 ]
Kren V: Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners. Int J Mol Sci. 2021 Jul 23;22(15):7885. doi: 10.3390/ijms22157885. [PubMed:34360650 ]
Mukherjee S, Sharma D, Sharma AK, Jaiswal S, Sharma N, Borah S, Kaur G: Flavan-based phytoconstituents inhibit Mpro, a SARS-COV-2 molecular target, in silico. J Biomol Struct Dyn. 2022;40(22):11545-11559. doi: 10.1080/07391102.2021.1960196. Epub 2021 Aug 4. [PubMed:34348081 ]
Schenk-Jager K, Gessler M, Weiler S: [CME: Mushroom Poisoning in the Family Practice]. Praxis (Bern 1994). 2021 Aug;110(10):543-553. doi: 10.1024/1661-8157/a003715. [PubMed:34344191 ]
Yan B, Zhang C: Liver Protection Mechanism and Absorption Promotion Technology of Silybin Based on Intelligent Medical Analysis. J Healthc Eng. 2021 Jul 3;2021:9968016. doi: 10.1155/2021/9968016. eCollection 2021. [PubMed:34285784 ]
Cho K, Lee HG, Piao JY, Kim SJ, Na HK, Surh YJ: Protective Effects of Silibinin on Helicobacter pylori-induced Gastritis: NF-kappaB and STAT3 as Potential Targets. J Cancer Prev. 2021 Jun 30;26(2):118-127. doi: 10.15430/JCP.2021.26.2.118. [PubMed:34258250 ]
Ali SA, Saifi MA, Godugu C, Talla V: Silibinin alleviates silica-induced pulmonary fibrosis: Potential role in modulating inflammation and epithelial-mesenchymal transition. Phytother Res. 2021 Sep;35(9):5290-5304. doi: 10.1002/ptr.7210. Epub 2021 Jul 12. [PubMed:34250649 ]
Vidimce J, Pennell EN, Foo M, Shiels RG, Shibeeb S, Watson M, Bulmer AC: Effect of Silymarin Treatment on Circulating Bilirubin and Cardiovascular Disease Risk Factors in Healthy Men: A Single-Blind, Randomized Crossover Trial. Clin Pharmacol Drug Dev. 2021 Oct;10(10):1156-1165. doi: 10.1002/cpdd.962. Epub 2021 Jul 9. [PubMed:34242497 ]
Prabu SM, Muthumani M: Retraction Note to: Silibinin ameliorates arsenic induced nephrotoxicity by abrogation of oxidative stress, inflammation and apoptosis in rats. Mol Biol Rep. 2021 Jun;48(6):5377. doi: 10.1007/s11033-021-06475-x. [PubMed:34235619 ]
Mohammadi H, Manouchehri H, Changizi R, Bootorabi F, Khorramizadeh MR: Correction to: Concurrent metformin and silibinin therapy in diabetes: assessments in zebrafish (Danio rerio) animal model. J Diabetes Metab Disord. 2020 Dec 7;20(1):1099. doi: 10.1007/s40200-020-00698-8. eCollection 2021 Jun. [PubMed:34222101 ]
Zarpou S, Mosavi H, Bagheri A, Malekzadeh Shafaroudi M, Khonakdar-Tarsi A: NF-kappaB and NLRP3 gene expression changes during warm hepatic ischemia-reperfusion in rats with and without silibinin. Gastroenterol Hepatol Bed Bench. 2021 Summer;14(3):267-275. [PubMed:34221267 ]
Rugamba A, Kang DY, Sp N, Jo ES, Lee JM, Bae SW, Jang KJ: Silibinin Regulates Tumor Progression and Tumorsphere Formation by Suppressing PD-L1 Expression in Non-Small Cell Lung Cancer (NSCLC) Cells. Cells. 2021 Jun 29;10(7):1632. doi: 10.3390/cells10071632. [PubMed:34209829 ]
Verdura S, Cuyas E, Ruiz-Torres V, Micol V, Joven J, Bosch-Barrera J, Menendez JA: Lung Cancer Management with Silibinin: A Historical and Translational Perspective. Pharmaceuticals (Basel). 2021 Jun 11;14(6):559. doi: 10.3390/ph14060559. [PubMed:34208282 ]
Liu X, Liu W, Wang C, Chen Y, Liu P, Hayashi T, Mizuno K, Hattori S, Fujisaki H, Ikejima T: Silibinin attenuates motor dysfunction in a mouse model of Parkinson's disease by suppression of oxidative stress and neuroinflammation along with promotion of mitophagy. Physiol Behav. 2021 Oct 1;239:113510. doi: 10.1016/j.physbeh.2021.113510. Epub 2021 Jun 25. [PubMed:34181930 ]

Showing NP-Card for Silibinin (NP0331835)

MOL for NP0331835 (Silibinin)

3D MOL for NP0331835 (Silibinin)

3D SDF for NP0331835 (Silibinin)

3D-SDF for NP0331835 (Silibinin)

PDB for NP0331835 (Silibinin)

3D PDB for NP0331835 (Silibinin)

SMILES for NP0331835 (Silibinin)

INCHI for NP0331835 (Silibinin)

Structure for NP0331835 (Silibinin)

3D Structure for NP0331835 (Silibinin)