NP-MRD: Showing NP-Card for trans-Piceid (NP0333536)

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Record Information

Version

2.0

Created at

2024-06-27 21:45:11 UTC

Updated at

2026-02-06 22:06:30 UTC

NP-MRD ID

NP0333536

Natural Product DOI

https://doi.org/10.57994/2999

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-Piceid

Description

Trans-Piceid, also known as polydatin or piceid, 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, trans-piceid is considered to be an aromatic polyketide. Trans-Piceid 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. trans-Piceid was first documented in 2000 (PMID: 11140601). Based on a literature review a significant number of articles have been published on trans-Piceid (PMID: 34315603) (PMID: 34202535) (PMID: 33918825) (PMID: 33807609) (PMID: 33466330).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119422D          

 28 30  0  0  1  0            999 V2000
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   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 18 25  1  1  0  0  0
 17 26  1  6  0  0  0
 11 27  1  0  0  0  0
  3 28  1  0  0  0  0
M  END

NP0043955
     RDKit          3D

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   -4.4607   -1.5329    3.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2513   -0.4599    2.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8342   -0.2329    1.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306222119422D          

 28 30  0  0  1  0            999 V2000
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0333536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC(\C=C\C3=CC=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

> <INCHI_KEY>
HSTZMXCBWJGKHG-CUYWLFDKSA-N

> <FORMULA>
C20H22O8

> <MOLECULAR_WEIGHT>
390.388

> <EXACT_MASS>
390.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.19156614682632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
1.134322793

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.220864385265285

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.602215116349766

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092343730565

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
99.59989999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piceid

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043955
     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.4607   -1.5329    3.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2513   -0.4599    2.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8342   -0.2329    1.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
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    9.0237   -1.8323   -0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3885   -0.0620   -0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0609    0.3802   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    0.7222   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875   -0.3437   -1.0438 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8136    0.3674   -1.3928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0468   -1.7501   -0.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9255   -2.3988   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0534   -1.5498    0.5667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3649   -1.6954    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7655   -1.1839    3.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3261   -0.7188    2.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0910    0.4503    3.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4485    0.5931    0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    1.4695   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501    2.8659   -0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138    5.0358   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771    3.6057   -0.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572    1.9167   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -0.8274   -0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5151   -2.5168   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8808   -3.3017   -0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5283   -1.8329    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2028    0.6277   -0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8888    1.4186   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481   -0.3304   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901   -0.4588   -1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5983    0.9691   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4452   -2.3271   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -2.6422   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8635   -2.3573    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9102   -2.1177    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 12 22  2  0
  5 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27  3  1  0
 22  7  1  0
 21 15  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  6
  5 33  1  6
  8 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  6
 26 48  1  0
 27 49  1  1
 28 50  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.667 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13    9                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   26                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   19                                                            
CONECT   25   18                                                            
CONECT   26   17                                                            
CONECT   27   11                                                            
CONECT   28    3                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    NP0043955
HETATM    1  O1  UNL     1      -4.461  -1.533   3.187  1.00  0.00           O  
HETATM    2  C1  UNL     1      -5.251  -0.460   2.740  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.834  -0.233   1.280  1.00  0.00           C  
HETATM    4  O2  UNL     1      -3.482   0.066   1.318  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.956   0.405   0.069  1.00  0.00           C  
HETATM    6  O3  UNL     1      -1.592   0.216  -0.006  1.00  0.00           O  
HETATM    7  C4  UNL     1      -0.590   1.133  -0.228  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.855   2.465  -0.419  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.178   3.388  -0.644  1.00  0.00           C  
HETATM   10  O4  UNL     1      -0.140   4.732  -0.832  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.456   2.919  -0.667  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.788   1.590  -0.482  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.177   1.155  -0.520  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.614  -0.062  -0.360  1.00  0.00           C  
HETATM   15  C11 UNL     1       5.011  -0.485  -0.400  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.344  -1.822  -0.213  1.00  0.00           C  
HETATM   17  C13 UNL     1       6.652  -2.259  -0.244  1.00  0.00           C  
HETATM   18  C14 UNL     1       7.699  -1.390  -0.462  1.00  0.00           C  
HETATM   19  O5  UNL     1       9.024  -1.832  -0.493  1.00  0.00           O  
HETATM   20  C15 UNL     1       7.389  -0.062  -0.649  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.061   0.380  -0.618  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.753   0.722  -0.266  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.688  -0.344  -1.044  1.00  0.00           C  
HETATM   24  O6  UNL     1      -4.814   0.367  -1.393  1.00  0.00           O  
HETATM   25  C19 UNL     1      -4.047  -1.750  -0.555  1.00  0.00           C  
HETATM   26  O7  UNL     1      -2.925  -2.399  -0.056  1.00  0.00           O  
HETATM   27  C20 UNL     1      -5.053  -1.550   0.567  1.00  0.00           C  
HETATM   28  O8  UNL     1      -6.365  -1.695   0.123  1.00  0.00           O  
HETATM   29  H1  UNL     1      -3.765  -1.184   3.793  1.00  0.00           H  
HETATM   30  H2  UNL     1      -6.326  -0.719   2.806  1.00  0.00           H  
HETATM   31  H3  UNL     1      -5.091   0.450   3.350  1.00  0.00           H  
HETATM   32  H4  UNL     1      -5.449   0.593   0.841  1.00  0.00           H  
HETATM   33  H5  UNL     1      -3.206   1.469  -0.079  1.00  0.00           H  
HETATM   34  H6  UNL     1      -1.850   2.866  -0.406  1.00  0.00           H  
HETATM   35  H7  UNL     1      -0.314   5.036  -1.785  1.00  0.00           H  
HETATM   36  H8  UNL     1       2.277   3.606  -0.839  1.00  0.00           H  
HETATM   37  H9  UNL     1       3.957   1.917  -0.700  1.00  0.00           H  
HETATM   38  H10 UNL     1       2.873  -0.827  -0.181  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.515  -2.517  -0.039  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.881  -3.302  -0.095  1.00  0.00           H  
HETATM   41  H13 UNL     1       9.528  -1.833   0.406  1.00  0.00           H  
HETATM   42  H14 UNL     1       8.203   0.628  -0.821  1.00  0.00           H  
HETATM   43  H15 UNL     1       5.889   1.419  -0.769  1.00  0.00           H  
HETATM   44  H16 UNL     1       0.948  -0.330  -0.114  1.00  0.00           H  
HETATM   45  H17 UNL     1      -2.990  -0.459  -1.871  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.598   0.969  -2.148  1.00  0.00           H  
HETATM   47  H19 UNL     1      -4.445  -2.327  -1.392  1.00  0.00           H  
HETATM   48  H20 UNL     1      -2.353  -2.642  -0.847  1.00  0.00           H  
HETATM   49  H21 UNL     1      -4.864  -2.357   1.297  1.00  0.00           H  
HETATM   50  H22 UNL     1      -6.910  -2.118   0.860  1.00  0.00           H  
CONECT    1    2   29
CONECT    2    3   30   31
CONECT    3    4   27   32
CONECT    4    5
CONECT    5    6   23   33
CONECT    6    7
CONECT    7    8    8   22
CONECT    8    9   34
CONECT    9   10   11   11
CONECT   10   35
CONECT   11   12   36
CONECT   12   13   22   22
CONECT   13   14   14   37
CONECT   14   15   38
CONECT   15   16   16   21
CONECT   16   17   39
CONECT   17   18   18   40
CONECT   18   19   20
CONECT   19   41
CONECT   20   21   21   42
CONECT   21   43
CONECT   22   44
CONECT   23   24   25   45
CONECT   24   46
CONECT   25   26   27   47
CONECT   26   48
CONECT   27   28   49
CONECT   28   50
END

NP0043955
     RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
   -4.4607   -1.5329    3.1872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2513   -0.4599    2.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8342   -0.2329    1.2803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4818    0.0656    1.3179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9564    0.4047    0.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5916    0.2163   -0.0061 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5903    1.1326   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8550    2.4650   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    3.3885   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403    4.7318   -0.8324 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4563    2.9194   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877    1.5897   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1771    1.1553   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6137   -0.0618   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0108   -0.4853   -0.3996 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3438   -1.8222   -0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6519   -2.2589   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986   -1.3903   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0237   -1.8323   -0.4932 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3885   -0.0620   -0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0609    0.3802   -0.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7528    0.7222   -0.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875   -0.3437   -1.0438 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8136    0.3674   -1.3928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0468   -1.7501   -0.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9255   -2.3988   -0.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0534   -1.5498    0.5667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3649   -1.6954    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7655   -1.1839    3.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3261   -0.7188    2.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0910    0.4503    3.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4485    0.5931    0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    1.4695   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501    2.8659   -0.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138    5.0358   -1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2771    3.6057   -0.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572    1.9167   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8727   -0.8274   -0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5151   -2.5168   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8808   -3.3017   -0.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5283   -1.8329    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2028    0.6277   -0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8888    1.4186   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481   -0.3304   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9901   -0.4588   -1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5983    0.9691   -2.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4452   -2.3271   -1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -2.6422   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8635   -2.3573    1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9102   -2.1177    0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 12 22  2  0
  5 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27  3  1  0
 22  7  1  0
 21 15  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  6
  5 33  1  6
  8 34  1  0
 10 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 16 39  1  0
 17 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  6
 24 46  1  0
 25 47  1  6
 26 48  1  0
 27 49  1  1
 28 50  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
3,4',5-Trihydroxystilbene-3-beta-D-glucoside	ChEBI
3,4,5-Trihydroxystilbene-3-beta-monoglucoside	ChEBI
Piceid	ChEBI
Polydatin	ChEBI
trans-Resveratrol 3-beta-D-glucoside	ChEBI
trans-Resveratrol 3-beta-glucoside	ChEBI
trans-Resveratrol 3-O-beta-D-glucoside	ChEBI
3,4',5-Trihydroxystilbene-3-b-D-glucoside	Generator
3,4',5-Trihydroxystilbene-3-β-D-glucoside	Generator
3,4,5-Trihydroxystilbene-3-b-monoglucoside	Generator
3,4,5-Trihydroxystilbene-3-β-monoglucoside	Generator
trans-Resveratrol 3-b-D-glucoside	Generator
trans-Resveratrol 3-β-D-glucoside	Generator
trans-Resveratrol 3-b-glucoside	Generator
trans-Resveratrol 3-β-glucoside	Generator
trans-Resveratrol 3-O-b-D-glucoside	Generator
trans-Resveratrol 3-O-β-D-glucoside	Generator
3,4'-5-Trihydroxystilbene-3-beta-D-glucopyranoside	HMDB
3,5,4'-Trihydroxystilbene 3-glucoside	HMDB
Resveratrol 3-beta-D-glucoside	HMDB
Resveratrol 3-beta-mono-D-glucoside	HMDB
Resveratrol 3-glucoside	HMDB
Resveratrol 3-O-glucoside	HMDB
Resveratrol 5-O-glucoside	HMDB
trans-Resveratrol 3-glucoside	HMDB
trans-Resveratrol 3-O-glucoside	HMDB
3,4,5-TSG	HMDB
Polydatin, (e)-isomer	HMDB
Resveratrol 3-O-beta-D-glucoside	HMDB
3-Hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenyl-beta-D-glucoside	HMDB
5,4'-Dihydroxystilbene-3-O-beta-D-GLCP	HMDB
3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl beta-D-glucopyranoside	HMDB
3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl β-D-glucopyranoside	HMDB
(-)-trans-Resveratrol 13-O-beta-D-glucopyranoside	HMDB
(-)-trans-Resveratrol 13-O-β-D-glucopyranoside	HMDB
(e)-Piceid	HMDB
(e)-Polydatin	HMDB
(e)-Resveratrol 3-O-beta-D-glucopyranoside	HMDB
(e)-Resveratrol 3-O-β-D-glucopyranoside	HMDB
3-Hydroxy-5-(p-hydroxystyryl)phenyl beta-D-glucoside	HMDB
3-Hydroxy-5-(p-hydroxystyryl)phenyl β-D-glucoside	HMDB
3-O-Glucosyl-resveratrol	HMDB
Pieceid	HMDB
Polydotin peceid	HMDB
Resveratrol 3-O-β-D-glucoside	HMDB
Resveratrol 3-O-beta-glucopyranoside	HMDB
Resveratrol 3-O-β-glucopyranoside	HMDB
Resveratrol beta-D-glucoside	HMDB
Resveratrol β-D-glucoside	HMDB
Resveratrol beta-glucoside	HMDB
Resveratrol β-glucoside	HMDB
Resveratrol glucoside	HMDB
trans-Polydatin	HMDB
trans-3,5,4'-Trihydroxystilbene 3-O-beta-glucopyranoside	HMDB
trans-3,5,4'-Trihydroxystilbene 3-O-β-glucopyranoside	HMDB
trans-3,5,4’-trihydroxystilbene 3-O-β-glucopyranoside	HMDB
trans-3,5,4'-Trihydroxystilbene 3-O-beta-glucoside	HMDB
trans-3,5,4'-Trihydroxystilbene 3-O-β-glucoside	HMDB
trans-3,5,4’-trihydroxystilbene 3-O-β-glucoside	HMDB
trans-3,5,4'-Trihydroxystilbene 3-O-glucoside	HMDB
trans-3,5,4’-trihydroxystilbene 3-O-glucoside	HMDB
trans-3,5,4'-Trihydroxystilbene 3-glucoside	HMDB
trans-3,5,4’-trihydroxystilbene 3-glucoside	HMDB
3,5,4'-Trihydroxystilbene 3-O-beta-glucopyranoside	HMDB
3,5,4'-Trihydroxystilbene 3-O-β-glucopyranoside	HMDB
3,5,4’-trihydroxystilbene 3-O-β-glucopyranoside	HMDB
3,5,4'-Trihydroxystilbene 3-O-beta-glucoside	HMDB
3,5,4'-Trihydroxystilbene 3-O-β-glucoside	HMDB
3,5,4’-trihydroxystilbene 3-O-β-glucoside	HMDB
3,5,4'-Trihydroxystilbene 3-O-glucoside	HMDB
3,5,4’-trihydroxystilbene 3-O-glucoside	HMDB
3,5,4’-trihydroxystilbene 3-glucoside	HMDB
Resveratrol-3-O-glucoside	MeSH
trans-Piceid	PhytoBank

Chemical Formula

C₂₀H₂₂O₈

Average Mass

390.3880 Da

Monoisotopic Mass

390.13147 Da

IUPAC Name

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

Traditional Name

piceid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC(\C=C\C3=CC=C(O)C=C3)=CC(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1

InChI Key

HSTZMXCBWJGKHG-CUYWLFDKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	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	¹H 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, 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, 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, 125 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, 500 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, 600 MHz, Dimethylsulfoxide-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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 200.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75.0, Dimethylsulfoxide-d6, simulated)	epoynton@sfu.ca	Not Available	Not Available	2026-02-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-06-27	View Spectrum

Species

Species of Origin

Not Available

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

Substituents

Stilbene glycoside
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Phenoxy compound
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:8198 )
monosaccharide derivative (CHEBI:8198 )
polyphenol (CHEBI:8198 )
stilbenoid (CHEBI:8198 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10275 )
Stilbenes (C10275 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090012 )

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	0.65	ALOGPS
logP	1.13	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.6	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.6 m³·mol⁻¹	ChemAxon
Polarizability	40.19 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

HMDB0030564

DrugBank ID

DB11263

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281718

PDB ID

Not Available

ChEBI ID

8198

Good Scents ID

rw1589071

References

General References

Yan C, Yang N, Wang X, Wang Y: VqBGH40a isolated from Chinese wild Vitis quinquangularis degrades trans-piceid and enhances trans-resveratrol. Plant Sci. 2021 Sep;310:110989. doi: 10.1016/j.plantsci.2021.110989. Epub 2021 Jul 7. [PubMed:34315603 ]
Ogneva ZV, Volkonskaia VV, Dubrovina AS, Suprun AR, Aleynova OA, Kiselev KV: Exogenous Stilbenes Improved Tolerance of Arabidopsis thaliana to a Shock of Ultraviolet B Radiation. Plants (Basel). 2021 Jun 24;10(7):1282. doi: 10.3390/plants10071282. [PubMed:34202535 ]
Suprun AR, Dubrovina AS, Tyunin AP, Kiselev KV: Profile of Stilbenes and Other Phenolics in Fanagoria White and Red Russian Wines. Metabolites. 2021 Apr 9;11(4):231. doi: 10.3390/metabo11040231. [PubMed:33918825 ]
Sak M, Dokupilova I, Kanukova S, Mrkvova M, Mihalik D, Hauptvogel P, Kraic J: Biotic and Abiotic Elicitors of Stilbenes Production in Vitis vinifera L. Cell Culture. Plants (Basel). 2021 Mar 5;10(3):490. doi: 10.3390/plants10030490. [PubMed:33807609 ]
Diaz-Maroto MC, Lopez Vinas M, Marchante L, Alanon ME, Diaz-Maroto IJ, Perez-Coello MS: Evaluation of the Storage Conditions and Type of Cork Stopper on the Quality of Bottled White Wines. Molecules. 2021 Jan 5;26(1):232. doi: 10.3390/molecules26010232. [PubMed:33466330 ]
Aburjai TA: Anti-platelet stilbenes from aerial parts of Rheum palaestinum. Phytochemistry. 2000 Nov;55(5):407-10. doi: 10.1016/s0031-9422(00)00341-1. [PubMed:11140601 ]
DOI: 10.1016/s0031-9422(00)00341-1
PMID: 11140601

Showing NP-Card for trans-Piceid (NP0333536)

MOL for NP0333536 (trans-Piceid)

3D MOL for NP0333536 (trans-Piceid)

3D SDF for NP0333536 (trans-Piceid)

3D-SDF for NP0333536 (trans-Piceid)

PDB for NP0333536 (trans-Piceid)

3D PDB for NP0333536 (trans-Piceid)

SMILES for NP0333536 (trans-Piceid)

INCHI for NP0333536 (trans-Piceid)

Structure for NP0333536 (trans-Piceid)

3D Structure for NP0333536 (trans-Piceid)