NP-MRD: Showing NP-Card for Trans-resveratrol (NP0331440)

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Record Information

Version

1.0

Created at

2023-01-14 16:03:17 UTC

Updated at

2024-05-11 13:24:27 UTC

NP-MRD ID

NP0331440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trans-resveratrol

Description

Resveratrol, also known as trans-resveratrol, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Thus, resveratrol is considered to be an aromatic polyketide. Resveratrol exists in all living species, ranging from bacteria to plants to humans. Resveratrol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2021 (PMID: 34606154). Based on a literature review a significant number of articles have been published on Resveratrol (PMID: 34598655) (PMID: 34597721) (PMID: 34597611) (PMID: 34594318).

Structure

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

NP0001738
     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -6.1172   -0.3742   -0.4969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -0.2778   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -0.1002    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -0.0073    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.0845    0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    0.0203    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516   -0.0391   -0.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807    0.0661   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3156    0.2433    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931    0.3444    1.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472    0.5250    2.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.2617    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463    0.0842   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9116   -0.0001   -2.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922   -0.0135   -1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889   -0.2602   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -0.3600   -1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7577   -0.3146    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9805   -0.0386    1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239    0.1320    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    0.1627    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558   -0.1786   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478    0.3100    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2812    1.4312    3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6081    0.3343    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -0.8843   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -0.1516   -2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -0.3326   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2699   -0.4981   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  8  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv1652309272007372D          

 17 18  0  0  0  0            999 V2000
 9998.233410000.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.092110000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.805710000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.664410002.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6623 9998.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662110000.8252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.947710000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9477 9999.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6621 9999.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3766 9999.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.376610000.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.949510001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.235110002.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.520610001.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.520510000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.235010000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.949610000.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
  3 15  1  0  0  0  0
 12  4  1  0  0  0  0
  1  7  1  0  0  0  0
 11  2  1  0  0  0  0
  9  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331440

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+

> <INCHI_KEY>
LUKBXSAWLPMMSZ-OWOJBTEDSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.247

> <EXACT_MASS>
228.078644246

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
24.551069139354443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
3.4023908863333325

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.12809455952825

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.493489164415605

> <JCHEM_PKA_STRONGEST_BASIC>
-6.178025720766969

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
67.4555

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
resveratrol

> <JCHEM_VEBER_RULE>
0

$$$$

NP0001738
     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -6.1172   -0.3742   -0.4969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -0.2778   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -0.1002    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -0.0073    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.0845    0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    0.0203    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516   -0.0391   -0.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807    0.0661   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3156    0.2433    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931    0.3444    1.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472    0.5250    2.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.2617    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463    0.0842   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9116   -0.0001   -2.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922   -0.0135   -1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889   -0.2602   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -0.3600   -1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7577   -0.3146    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9805   -0.0386    1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239    0.1320    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    0.1627    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558   -0.1786   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478    0.3100    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2812    1.4312    3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6081    0.3343    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -0.8843   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -0.1516   -2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -0.3326   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2699   -0.4981   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  8  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8663.3698668.207   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8668.7058668.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8670.0378667.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8675.3748670.517   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8666.0368663.588   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8666.0368668.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.7028667.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.7028665.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.0368665.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.3708665.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.3708667.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8674.0398669.747   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8672.7068670.517   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8671.3728669.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8671.3728668.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8672.7058667.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8674.0398668.207   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    3   11                                                       
CONECT    3    2   15                                                       
CONECT    4   12                                                            
CONECT    5    9                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8    1                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6    2                                                  
CONECT   12   13   17    4                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    3                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    NP0001738
HETATM    1  O1  UNL     1      -6.117  -0.374  -0.497  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.734  -0.278  -0.287  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.270  -0.100   0.999  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.922  -0.007   1.195  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.027  -0.085   0.162  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.593   0.020   0.421  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.352  -0.039  -0.484  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.781   0.066  -0.221  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.316   0.243   1.031  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.693   0.344   1.283  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.147   0.525   2.598  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.554   0.262   0.220  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.046   0.084  -1.047  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.912  -0.000  -2.126  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.692  -0.013  -1.280  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.489  -0.260  -1.109  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.862  -0.360  -1.352  1.00  0.00           C  
HETATM   18  H1  UNL     1      -6.758  -0.315   0.279  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.981  -0.039   1.821  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.524   0.132   2.189  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.241   0.163   1.460  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.056  -0.179  -1.525  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.648   0.310   1.877  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.281   1.431   3.011  1.00  0.00           H  
HETATM   25  H8  UNL     1       5.608   0.334   0.372  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.264  -0.884  -2.408  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.298  -0.152  -2.266  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.860  -0.333  -1.986  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.270  -0.498  -2.331  1.00  0.00           H  
CONECT    1    2   18
CONECT    2    3    3   17
CONECT    3    4   19
CONECT    4    5    5   20
CONECT    5    6   16
CONECT    6    7    7   21
CONECT    7    8   22
CONECT    8    9    9   15
CONECT    9   10   23
CONECT   10   11   12   12
CONECT   11   24
CONECT   12   13   25
CONECT   13   14   15   15
CONECT   14   26
CONECT   15   27
CONECT   16   17   17   28
CONECT   17   29
END

NP0001738
     RDKit          3D

29 30  0  0  0  0  0  0  0  0999 V2000
   -6.1172   -0.3742   -0.4969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7336   -0.2778   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -0.1002    0.9989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219   -0.0073    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0269   -0.0845    0.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5929    0.0203    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516   -0.0391   -0.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7807    0.0661   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3156    0.2433    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931    0.3444    1.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1472    0.5250    2.5982 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5540    0.2617    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0463    0.0842   -1.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9116   -0.0001   -2.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6922   -0.0135   -1.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4889   -0.2602   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -0.3600   -1.3515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7577   -0.3146    0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9805   -0.0386    1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239    0.1320    2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2411    0.1627    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558   -0.1786   -1.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6478    0.3100    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2812    1.4312    3.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6081    0.3343    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638   -0.8843   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2980   -0.1516   -2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8602   -0.3326   -1.9861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2699   -0.4981   -2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  5 16  1  0
 16 17  2  0
 17  2  1  0
 15  8  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  9 23  1  0
 11 24  1  0
 12 25  1  0
 14 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol

Synonyms

Value	Source
(e)-5-(2-(4-Hydroxyphenyl)ethenyl)-1,3-benzenediol	ChEBI
(e)-Resveratrol	ChEBI
3,4',5-Stilbenetriol	ChEBI
3,4',5-Trihydroxy-trans-stilbene	ChEBI
3,4',5-Trihydroxystilbene	ChEBI
3,5,4'-Trihydroxystilbene	ChEBI
5-[(e)-2-(4-Hydroxyphenyl)vinyl]benzene-1,3-diol	ChEBI
trans-Resveratrol	Kegg
trans-3,4',5 - Trihydroxystilbene	HMDB
SRT 501	MeSH, HMDB
SRT-501	MeSH, HMDB
trans Resveratrol	MeSH, HMDB
(E)-2-(3,5-Dihydroxyphenyl)-1-(4-hydroxyphenyl)ethene	HMDB
(E)-3,4',5-Trihydroxystilbene	HMDB
(E)-3,4’,5-Trihydroxystilbene	HMDB
(E)-5-(p-Hydroxystyryl)resorcinol	HMDB
3,4’,5-Stilbenetriol	HMDB
3,4’,5-Trihydroxy-trans-stilbene	HMDB
3,4’,5-Trihydroxystilbene	HMDB
5-[(1E)-2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol	HMDB
Resveratrol	HMDB
trans-3,5,4'-Trihydroxystilbene	HMDB
trans-3,5,4’-Trihydroxystilbene	HMDB
(E)-5-[2-(4-Hydroxyphenyl)ethenyl]-1,3-benzenediol	PhytoBank

Chemical Formula

C₁₄H₁₂O₃

Average Mass

228.2470 Da

Monoisotopic Mass

228.07864 Da

IUPAC Name

5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol

Traditional Name

resveratrol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C\C2=CC(O)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1+

InChI Key

LUKBXSAWLPMMSZ-OWOJBTEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CD3OD, experimental)	lpecio@iung.pulawy.pl	Not Available	Not Available	2023-01-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400Mz MHz, DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.2, CD₃OD, simulated)	lpecio@iung.pulawy.pl	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
schidigera		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic 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	2.57	ALOGPS
logP	3.4	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.46 m³·mol⁻¹	ChemAxon
Polarizability	24.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003747

DrugBank ID

DB02709

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Resveratrol

METLIN ID

Not Available

PubChem Compound

445154

PDB ID

Not Available

ChEBI ID

45713

Good Scents ID

rw1588831

References

General References

Tarallo A, Damiano C, Strollo S, Minopoli N, Indrieri A, Polishchuk E, Zappa F, Nusco E, Fecarotta S, Porto C, Coletta M, Iacono R, Moracci M, Polishchuk R, Medina DL, Imbimbo P, Monti DM, De Matteis MA, Parenti G: Correction of oxidative stress enhances enzyme replacement therapy in Pompe disease. EMBO Mol Med. 2021 Nov 8;13(11):e14434. doi: 10.15252/emmm.202114434. Epub 2021 Oct 4. [PubMed:34606154 ]
Wang Z, Li L, Gu W, Mao Y, Wang T: Resveratrol Reverses Osteogenic Decline of Bone Marrow Mesenchymal Stem Cells Via Upregulation of YAP Expression in Inflammatory Environment. Stem Cells Dev. 2021 Dec 15;30(24):1202-1214. doi: 10.1089/scd.2021.0195. Epub 2021 Oct 27. [PubMed:34598655 ]
Huang Y, Zhang J, Tao Y, Ji C, Aniagu S, Jiang Y, Chen T: AHR/ROS-mediated mitochondria apoptosis contributes to benzo[a]pyrene-induced heart defects and the protective effects of resveratrol. Toxicology. 2021 Oct;462:152965. doi: 10.1016/j.tox.2021.152965. Epub 2021 Sep 28. [PubMed:34597721 ]
Chhabra G, Singh CK, Guzman-Perez G, Ndiaye MA, Iczkowski KA, Ahmad N: Antimelanoma Effects of Concomitant Inhibition of SIRT1 and SIRT3 in Braf(V600E)/Pten(NULL) Mice. J Invest Dermatol. 2022 Apr;142(4):1145-1157.e7. doi: 10.1016/j.jid.2021.08.434. Epub 2021 Sep 29. [PubMed:34597611 ]
Santos CA, Lima EMF, Franco BDGM, Pinto UM: Exploring Phenolic Compounds as Quorum Sensing Inhibitors in Foodborne Bacteria. Front Microbiol. 2021 Sep 14;12:735931. doi: 10.3389/fmicb.2021.735931. eCollection 2021. [PubMed:34594318 ]

Pecio L, Alilou M, Kozachok S, Orhan IE, Eren G, Senol Deniz FS, Stuppner H, Oleszek W: Absolute configuration of spiro-flavostilbenoids from Yucca schidigera Roezl ex Ortgies: First indication of (2R)-naringenin as the key building block. Phytochemistry. 2023 Mar;207:113584. doi: 10.1016/j.phytochem.2022.113584. Epub 2023 Jan 2. [PubMed:36603655 ]

Showing NP-Card for Trans-resveratrol (NP0331440)

MOL for NP0331440 (Trans-resveratrol)

3D MOL for NP0331440 (Trans-resveratrol)

3D SDF for NP0331440 (Trans-resveratrol)

3D-SDF for NP0331440 (Trans-resveratrol)

PDB for NP0331440 (Trans-resveratrol)

3D PDB for NP0331440 (Trans-resveratrol)

SMILES for NP0331440 (Trans-resveratrol)

INCHI for NP0331440 (Trans-resveratrol)

Structure for NP0331440 (Trans-resveratrol)

3D Structure for NP0331440 (Trans-resveratrol)