NP-MRD: Showing NP-Card for astringin (NP0029494)

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Record Information

Version

2.0

Created at

2021-06-19 21:06:18 UTC

Updated at

2021-06-29 23:56:52 UTC

NP-MRD ID

NP0029494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

astringin

Provided By

JEOL Database JEOL Logo

Description

Astringin, also known as (e)-astringin, belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. Thus, astringin is considered to be an aromatic polyketide. astringin is found in Abies nephrolepis, Eskemukerjea megacarpum HARA, Fagopyrum megacarpum, Picea jezoensis, Vitis vinifera and Vitis vinifera . astringin was first documented in 2017 (PMID: 29194377). Based on a literature review a significant number of articles have been published on Astringin (PMID: 33669268) (PMID: 33151680) (PMID: 31023874) (PMID: 33669598) (PMID: 31719245) (PMID: 30892883).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306192123063D          

 51 53  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306192123063D          

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   -1.4016   -3.9891    2.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -3.9026    5.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3831   -2.0711    4.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6927   -4.3637    4.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 28  3  1  0  0  0  0
  7 23  1  0  0  0  0
  3  4  1  0  0  0  0
 23 12  2  0  0  0  0
  4  5  1  0  0  0  0
 12 11  1  0  0  0  0
 11  9  2  0  0  0  0
 12 13  1  0  0  0  0
 28 29  1  0  0  0  0
 13 14  2  0  0  0  0
 26 27  1  0  0  0  0
 14 15  1  0  0  0  0
 24 25  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
  2  1  1  0  0  0  0
 18 20  1  0  0  0  0
  5 24  1  0  0  0  0
 20 22  2  0  0  0  0
 22 15  1  0  0  0  0
 24 26  1  0  0  0  0
 18 19  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
  7  6  1  0  0  0  0
 26 28  1  0  0  0  0
 20 21  1  0  0  0  0
  5  6  1  0  0  0  0
  3  2  1  0  0  0  0
  5 34  1  6  0  0  0
 28 50  1  1  0  0  0
 29 51  1  0  0  0  0
 26 48  1  6  0  0  0
 27 49  1  0  0  0  0
 24 46  1  1  0  0  0
 25 47  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3 33  1  6  0  0  0
  1 30  1  0  0  0  0
  8 35  1  0  0  0  0
 23 45  1  0  0  0  0
 11 37  1  0  0  0  0
 13 38  1  0  0  0  0
 14 39  1  0  0  0  0
 16 40  1  0  0  0  0
 17 41  1  0  0  0  0
 22 44  1  0  0  0  0
 19 42  1  0  0  0  0
 10 36  1  0  0  0  0
 21 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029494

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(\C([H])=C(/[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C([H])C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
PERPNFLGJXUDDW-CUYWLFDKSA-N

> <FORMULA>
C20H22O9

> <MOLECULAR_WEIGHT>
406.387

> <EXACT_MASS>
406.126382288

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
40.838151086985405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.8307574713333334

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.096600192142327

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.492505059442484

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343730565

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
101.58080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
astringin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -4.6627   -0.6799    0.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6115   -1.3951    1.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -1.9756    2.0808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2768   -0.8770    2.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172   -1.3131    2.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0135   -0.1982    2.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474    0.4611    0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309    0.1973   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609    0.9620   -1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604    0.6713   -2.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812    1.9868   -1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783    2.2548   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    3.3435   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    3.6239   -1.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2478    4.7099   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384    4.9672    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8908    5.9876    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570    6.7416   -0.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0874    7.7382   -0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4914    6.4891   -2.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076    7.2695   -3.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5423    5.4741   -2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918    1.4946    0.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -2.0204    3.4652 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6650   -2.5326    3.5705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -3.1866    3.6171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5243   -3.7721    4.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0920   -2.7244    3.4131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9556   -3.8609    3.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9014   -0.0679    0.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3734   -2.1792    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8614   -0.6853    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9949   -2.6414    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6732   -2.0041    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2836   -0.5791   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    1.3067   -3.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5839   -2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240    3.9206    0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031    3.0454   -1.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7509    4.3687    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4219    6.1866    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1033    8.1190   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611    6.9849   -3.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235    5.2762   -3.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    1.7001    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -1.3167    4.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2572   -1.7806    3.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4016   -3.9891    2.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -3.9026    5.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3831   -2.0711    4.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6927   -4.3637    4.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
 28  3  1  0
  7 23  1  0
  3  4  1  0
 23 12  2  0
  4  5  1  0
 12 11  1  0
 11  9  2  0
 12 13  1  0
 28 29  1  0
 13 14  2  0
 26 27  1  0
 14 15  1  0
 24 25  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  2  1  1  0
 18 20  1  0
  5 24  1  0
 20 22  2  0
 22 15  1  0
 24 26  1  0
 18 19  1  0
  9  8  1  0
  9 10  1  0
  7  6  1  0
 26 28  1  0
 20 21  1  0
  5  6  1  0
  3  2  1  0
  5 34  1  6
 28 50  1  1
 29 51  1  0
 26 48  1  6
 27 49  1  0
 24 46  1  1
 25 47  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  6
  1 30  1  0
  8 35  1  0
 23 45  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 22 44  1  0
 19 42  1  0
 10 36  1  0
 21 43  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -4.663  -0.680   0.647  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.612  -1.395   1.884  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.208  -1.976   2.081  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.277  -0.877   2.037  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.917  -1.313   2.117  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.014  -0.198   2.084  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.147   0.461   0.897  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.531   0.197  -0.290  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.261   0.962  -1.422  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.960   0.671  -2.558  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.681   1.987  -1.396  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.378   2.255  -0.213  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.360   3.344  -0.112  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.263   3.624  -1.067  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.248   4.710  -0.957  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.938   4.967   0.239  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.891   5.988   0.309  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.157   6.742  -0.823  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.087   7.738  -0.756  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.491   6.489  -2.019  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.808   7.269  -3.097  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.542   5.474  -2.097  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.092   1.495   0.930  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.674  -2.020   3.465  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.665  -2.533   3.571  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.648  -3.187   3.617  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.524  -3.772   4.923  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.092  -2.724   3.413  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.956  -3.861   3.445  0.00  0.00           O+0
HETATM   30  H   UNK     0      -3.901  -0.068   0.664  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.373  -2.179   1.856  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.861  -0.685   2.679  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.995  -2.641   1.234  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.673  -2.004   1.298  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.284  -0.579  -0.371  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.717   1.307  -3.251  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.865   2.584  -2.284  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.324   3.921   0.809  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.303   3.045  -1.986  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.751   4.369   1.128  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.422   6.187   1.234  0.00  0.00           H+0
HETATM   42  H   UNK     0       7.103   8.119  -1.657  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.261   6.985  -3.849  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.024   5.276  -3.030  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.613   1.700   1.863  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.803  -1.317   4.297  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.257  -1.781   3.371  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.402  -3.989   2.910  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.563  -3.903   5.055  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.383  -2.071   4.245  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.693  -4.364   4.243  0.00  0.00           H+0
CONECT    1    2   30                                                       
CONECT    2    1    3   31   32                                             
CONECT    3   28    4    2   33                                             
CONECT    4    3    5                                                       
CONECT    5    4   24    6   34                                             
CONECT    6    7    5                                                       
CONECT    7    8   23    6                                                  
CONECT    8    7    9   35                                                  
CONECT    9   11    8   10                                                  
CONECT   10    9   36                                                       
CONECT   11   12    9   37                                                  
CONECT   12   23   11   13                                                  
CONECT   13   12   14   38                                                  
CONECT   14   13   15   39                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   40                                                  
CONECT   17   16   18   41                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18   42                                                       
CONECT   20   18   22   21                                                  
CONECT   21   20   43                                                       
CONECT   22   20   15   44                                                  
CONECT   23    7   12   45                                                  
CONECT   24   25    5   26   46                                             
CONECT   25   24   47                                                       
CONECT   26   27   24   28   48                                             
CONECT   27   26   49                                                       
CONECT   28    3   29   26   50                                             
CONECT   29   28   51                                                       
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    5                                                            
CONECT   35    8                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   19                                                            
CONECT   43   21                                                            
CONECT   44   22                                                            
CONECT   45   23                                                            
CONECT   46   24                                                            
CONECT   47   25                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

RDKit          3D

51 53  0  0  0  0  0  0  0  0999 V2000
   -4.6627   -0.6799    0.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6115   -1.3951    1.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -1.9756    2.0808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2768   -0.8770    2.0365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172   -1.3131    2.1169 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0135   -0.1982    2.0844 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474    0.4611    0.8969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309    0.1973   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609    0.9620   -1.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9604    0.6713   -2.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6812    1.9868   -1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783    2.2548   -0.2133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603    3.3435   -0.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    3.6239   -1.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2478    4.7099   -0.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9384    4.9672    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8908    5.9876    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1570    6.7416   -0.8227 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0874    7.7382   -0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4914    6.4891   -2.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8076    7.2695   -3.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5423    5.4741   -2.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0918    1.4946    0.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -2.0204    3.4652 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6650   -2.5326    3.5705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6479   -3.1866    3.6171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5243   -3.7721    4.9231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0920   -2.7244    3.4131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9556   -3.8609    3.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9014   -0.0679    0.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3734   -2.1792    1.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8614   -0.6853    2.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9949   -2.6414    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6732   -2.0041    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2836   -0.5791   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7168    1.3067   -3.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5839   -2.2837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3240    3.9206    0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031    3.0454   -1.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7509    4.3687    1.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4219    6.1866    1.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1033    8.1190   -1.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611    6.9849   -3.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235    5.2762   -3.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131    1.7001    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8027   -1.3167    4.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2572   -1.7806    3.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4016   -3.9891    2.9103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -3.9026    5.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3831   -2.0711    4.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6927   -4.3637    4.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
 28  3  1  0
  7 23  1  0
  3  4  1  0
 23 12  2  0
  4  5  1  0
 12 11  1  0
 11  9  2  0
 12 13  1  0
 28 29  1  0
 13 14  2  0
 26 27  1  0
 14 15  1  0
 24 25  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  2  1  1  0
 18 20  1  0
  5 24  1  0
 20 22  2  0
 22 15  1  0
 24 26  1  0
 18 19  1  0
  9  8  1  0
  9 10  1  0
  7  6  1  0
 26 28  1  0
 20 21  1  0
  5  6  1  0
  3  2  1  0
  5 34  1  6
 28 50  1  1
 29 51  1  0
 26 48  1  6
 27 49  1  0
 24 46  1  1
 25 47  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  6
  1 30  1  0
  8 35  1  0
 23 45  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 16 40  1  0
 17 41  1  0
 22 44  1  0
 19 42  1  0
 10 36  1  0
 21 43  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(e)-Astringin	ChEBI
3,4,3',5'-Tetrahydroxystilbene 3'-glucoside	ChEBI
Piceatannol 3-beta-D-glucoside	ChEBI
Piceatannol 3-beta-glucoside	ChEBI
Piceatannol 3-O-beta-D-glucoside	ChEBI
Piceatannol 3-b-D-glucoside	Generator
Piceatannol 3-β-D-glucoside	Generator
Piceatannol 3-b-glucoside	Generator
Piceatannol 3-β-glucoside	Generator
Piceatannol 3-O-b-D-glucoside	Generator
Piceatannol 3-O-β-D-glucoside	Generator
trans-Astringin	MeSH
3-[(1E)-2-(3,4-Dihydroxyphenyl)ethenyl]-5-hydroxyphenyl beta-D-glucopyranoside	PhytoBank
3-[(1E)-2-(3,4-Dihydroxyphenyl)ethenyl]-5-hydroxyphenyl β-D-glucopyranoside	PhytoBank
3,4,3’,5’-Tetrahydroxystilbene 3’-glucoside	PhytoBank

Chemical Formula

C₂₀H₂₂O₉

Average Mass

406.3870 Da

Monoisotopic Mass

406.12638 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{3-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

astringin

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(\C([H])=C(/[H])C2=C([H])C([H])=C(O[H])C(O[H])=C2[H])=C([H])C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])=C1[H]

InChI Identifier

InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-13-6-11(5-12(22)8-13)2-1-10-3-4-14(23)15(24)7-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

InChI Key

PERPNFLGJXUDDW-CUYWLFDKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	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, 50 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, dmso, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, dmso, 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
Abies nephrolepis	LOTUS Database	35616633
Angophora cordifolia	KNApSAcK Database	22123792
Eskemukerjea megacarpum HARA	JEOL database	Miyaichi, Y., et al, Chem. Pharm. Bull. 54, 136 (2006)
Eucalyptus spp.	KNApSAcK Database	22123792
Fagopyrum megacarpum	LOTUS Database	35616633
Guibourtia coleosperma	KNApSAcK Database	22123792
Picea abies	KNApSAcK Database	22123792
Picea engelmannii	KNApSAcK Database	22123792
Picea glauca	KNApSAcK Database	22123792
Picea glehnii	KNApSAcK Database	22123792
Picea jezoensis	Plant	KNApSAcK
Picea koraiensis	KNApSAcK Database	22123792
Picea mariana	KNApSAcK Database	22123792
Picea obovata	KNApSAcK Database	22123792
Picea ojanensis	KNApSAcK Database	22123792
Picea rubens	KNApSAcK Database	22123792
Picea sitchensis	KNApSAcK Database	22123792
Rheum spp.	KNApSAcK Database	22123792
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.44	ALOGPS
logP	0.83	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.58 m³·mol⁻¹	ChemAxon
Polarizability	40.84 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Astringin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

2899

Good Scents ID

Not Available

References

General References

Latva-Maenpaa H, Wufu R, Mulat D, Sarjala T, Saranpaa P, Wahala K: Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots. Molecules. 2021 Feb 16;26(4). pii: molecules26041036. doi: 10.3390/molecules26041036. [PubMed:33669268 ]
Gabaston J, Valls Fonayet J, Franc C, Waffo-Teguo P, de Revel G, Hilbert G, Gomes E, Richard T, Merillon JM: Characterization of Stilbene Composition in Grape Berries from Wild Vitis Species in Year-To-Year Harvest. J Agric Food Chem. 2020 Nov 25;68(47):13408-13417. doi: 10.1021/acs.jafc.0c04907. Epub 2020 Nov 5. [PubMed:33151680 ]
Rencoret J, Neiva D, Marques G, Gutierrez A, Kim H, Gominho J, Pereira H, Ralph J, Del Rio JC: Hydroxystilbene Glucosides Are Incorporated into Norway Spruce Bark Lignin. Plant Physiol. 2019 Jul;180(3):1310-1321. doi: 10.1104/pp.19.00344. Epub 2019 Apr 25. [PubMed:31023874 ]
Chen B, Li X, Ouyang X, Liu J, Liu Y, Chen D: Comparison of Ferroptosis-Inhibitory Mechanisms between Ferrostatin-1 and Dietary Stilbenes (Piceatannol and Astringin). Molecules. 2021 Feb 19;26(4). pii: molecules26041092. doi: 10.3390/molecules26041092. [PubMed:33669598 ]
Freyssin A, Page G, Fauconneau B, Rioux Bilan A: Natural stilbenes effects in animal models of Alzheimer's disease. Neural Regen Res. 2020 May;15(5):843-849. doi: 10.4103/1673-5374.268970. [PubMed:31719245 ]
Fernandez-Cruz E, Cerezo AB, Cantos-Villar E, Richard T, Troncoso AM, Garcia-Parrilla MC: Inhibition of VEGFR-2 Phosphorylation and Effects on Downstream Signaling Pathways in Cultivated Human Endothelial Cells by Stilbenes from Vitis Spp. J Agric Food Chem. 2019 Apr 10;67(14):3909-3918. doi: 10.1021/acs.jafc.9b00282. Epub 2019 Mar 28. [PubMed:30892883 ]
Heo KT, Lee B, Son S, Ahn JS, Jang JH, Hong YS: Production of Bioactive 3'-Hydroxystilbene Compounds Using the Flavin-Dependent Monooxygenase Sam5. J Microbiol Biotechnol. 2018 Jul 28;28(7):1105-1111. doi: 10.4014/jmb.1804.04007. [PubMed:30021423 ]
Erasalo H, Hamalainen M, Leppanen T, Maki-Opas I, Laavola M, Haavikko R, Yli-Kauhaluoma J, Moilanen E: Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner. J Nat Prod. 2018 May 25;81(5):1131-1142. doi: 10.1021/acs.jnatprod.7b00384. Epub 2018 May 4. [PubMed:29726680 ]
Francezon N, Meda NR, Stevanovic T: Optimization of Bioactive Polyphenols Extraction from Picea Mariana Bark. Molecules. 2017 Dec 1;22(12). pii: molecules22122118. doi: 10.3390/molecules22122118. [PubMed:29194377 ]
Rojas-Garbanzo C, Zimmermann BF, Schulze-Kaysers N, Schieber A: Characterization of phenolic and other polar compounds in peel and flesh of pink guava (Psidium guajava L. cv. 'Criolla') by ultra-high performance liquid chromatography with diode array and mass spectrometric detection. Food Res Int. 2017 Oct;100(Pt 3):445-453. doi: 10.1016/j.foodres.2016.12.004. Epub 2016 Dec 12. [PubMed:28964367 ]
Rusjan D, Persic M, Likar M, Biniari K, Mikulic-Petkovsek M: Phenolic Responses to Esca-Associated Fungi in Differently Decayed Grapevine Woods from Different Trunk Parts of 'Cabernet Sauvignon'. J Agric Food Chem. 2017 Aug 9;65(31):6615-6624. doi: 10.1021/acs.jafc.7b02188. Epub 2017 Jul 26. [PubMed:28692264 ]
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Showing NP-Card for astringin (NP0029494)

MOL for NP0029494 (astringin)

3D MOL for NP0029494 (astringin)

3D SDF for NP0029494 (astringin)

3D-SDF for NP0029494 (astringin)

PDB for NP0029494 (astringin)

3D PDB for NP0029494 (astringin)

SMILES for NP0029494 (astringin)

INCHI for NP0029494 (astringin)

Structure for NP0029494 (astringin)

3D Structure for NP0029494 (astringin)