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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-10-08 19:18:21 UTC

Update Date

2022-03-07 03:18:17 UTC

HMDB ID

HMDB0240498

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydroresveratrol

Description

Dihydroresveratrol 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, dihydroresveratrol is considered to be an aromatic polyketide. Dihydroresveratrol has been detected, but not quantified in, red wine and white wine. This could make dihydroresveratrol a potential biomarker for the consumption of these foods. Dihydroresveratrol 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. Based on a literature review a significant number of articles have been published on Dihydroresveratrol.

Structure

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

HMDB0240498
     RDKit          3D
Dihydroresveratrol
 31 32  0  0  0  0  0  0  0  0999 V2000
   -6.0637   -0.0209    0.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7074   -0.0833    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866   -1.2006    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375   -1.2765    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9528   -0.2639   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005   -0.3645   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    0.2089    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7499    0.1316    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5109   -0.9554    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8729   -1.0064    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305   -2.1040    0.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    0.0551   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7456    1.1574   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    2.2406   -1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858    1.1815   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925    0.8626   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    0.9383   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4208    0.3655    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -2.0498    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0817   -2.1661    0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922    0.1656   -1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -1.4368   -0.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0192    1.2663    0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.3098    1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0598   -1.8039    1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6183   -2.1311    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5655    0.0253   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    3.0336   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392    2.0597   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1669    1.6742   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6145    1.8067   -0.7230 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  1  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
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv1652303202019002D          

 17 18  0  0  0  0            999 V2000
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.6000    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
   -0.7145   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240498

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2

> <INCHI_KEY>
HITJFUSPLYBJPE-UHFFFAOYSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.2592

> <EXACT_MASS>
230.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.867194788712546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.5989125430000004

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.220351203729487

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.30352527101386

> <JCHEM_PKA_STRONGEST_BASIC>
-5.442613297531204

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
66.3389

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroresveratrol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240498
     RDKit          3D
Dihydroresveratrol
 31 32  0  0  0  0  0  0  0  0999 V2000
   -6.0637   -0.0209    0.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7074   -0.0833    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866   -1.2006    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375   -1.2765    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9528   -0.2639   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005   -0.3645   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    0.2089    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7499    0.1316    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5109   -0.9554    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8729   -1.0064    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305   -2.1040    0.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    0.0551   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7456    1.1574   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    2.2406   -1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858    1.1815   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925    0.8626   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    0.9383   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4208    0.3655    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -2.0498    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0817   -2.1661    0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922    0.1656   -1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -1.4368   -0.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0192    1.2663    0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.3098    1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0598   -1.8039    1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6183   -2.1311    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5655    0.0253   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    3.0336   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392    2.0597   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1669    1.6742   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6145    1.8067   -0.7230 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  1  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
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1   11                                                       
CONECT    3    5   10                                                       
CONECT    4    6   10                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7   11   13                                                       
CONECT    8   11   14                                                       
CONECT    9   13   14                                                       
CONECT   10    1    3    4                                                  
CONECT   11    2    7    8                                                  
CONECT   12    5    6   15                                                  
CONECT   13    7    9   16                                                  
CONECT   14    8    9   17                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0240498
HETATM    1  O1  UNL     1      -6.064  -0.021   0.500  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.707  -0.083   0.208  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.987  -1.201   0.574  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.637  -1.276   0.291  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.953  -0.264  -0.358  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.500  -0.364  -0.655  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.291   0.209   0.509  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.750   0.132   0.261  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.511  -0.955   0.634  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.873  -1.006   0.392  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.631  -2.104   0.771  1.00  0.00           O  
HETATM   12  C10 UNL     1       4.483   0.055  -0.236  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.746   1.157  -0.621  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.330   2.241  -1.254  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.386   1.181  -0.367  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.692   0.863  -0.725  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.044   0.938  -0.441  1.00  0.00           C  
HETATM   18  H1  UNL     1      -6.421   0.365   1.367  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.428  -2.050   1.088  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.082  -2.166   0.587  1.00  0.00           H  
HETATM   21  H4  UNL     1      -0.292   0.166  -1.593  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.250  -1.437  -0.756  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.019   1.266   0.603  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.015  -0.310   1.435  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.060  -1.804   1.129  1.00  0.00           H  
HETATM   26  H9  UNL     1       5.618  -2.131   0.591  1.00  0.00           H  
HETATM   27  H10 UNL     1       5.565   0.025  -0.433  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.792   3.034  -1.529  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.839   2.060  -0.681  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.167   1.674  -1.240  1.00  0.00           H  
HETATM   31  H14 UNL     1      -4.614   1.807  -0.723  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   21   22
CONECT    7    8   23   24
CONECT    8    9    9   15
CONECT    9   10   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   13   27
CONECT   13   14   15   15
CONECT   14   28
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   31
END

HMDB0240498
     RDKit          3D
Dihydroresveratrol
 31 32  0  0  0  0  0  0  0  0999 V2000
   -6.0637   -0.0209    0.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7074   -0.0833    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9866   -1.2006    0.5744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6375   -1.2765    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9528   -0.2639   -0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5005   -0.3645   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2913    0.2089    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7499    0.1316    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5109   -0.9554    0.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8729   -1.0064    0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305   -2.1040    0.7710 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    0.0551   -0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7456    1.1574   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3303    2.2406   -1.2542 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858    1.1815   -0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6925    0.8626   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    0.9383   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4208    0.3655    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4284   -2.0498    1.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0817   -2.1661    0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922    0.1656   -1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -1.4368   -0.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0192    1.2663    0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0150   -0.3098    1.4346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0598   -1.8039    1.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6183   -2.1311    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5655    0.0253   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917    3.0336   -1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8392    2.0597   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1669    1.6742   -1.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6145    1.8067   -0.7230 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  1  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
  6 22  1  0
  7 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4',5-Trihydroxybibenzyl	ChEBI
Dihydro-resveratrol	HMDB

Chemical Formula

C₁₄H₁₄O₃

Average Molecular Weight

230.2592

Monoisotopic Molecular Weight

230.094294314

IUPAC Name

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

Traditional Name

dihydroresveratrol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1

InChI Identifier

InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2

InChI Key

HITJFUSPLYBJPE-UHFFFAOYSA-N

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

Substituents

Stilbene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenol (CHEBI:4582 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10255 )
Bibenzyls (C10255 )
Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090035 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0240498)

Food

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0240498)

Fermented beverage

Red wine (FooDB: FOOD00911)
White wine (FooDB: FOOD00917)

Fruit

Grapes (HMDB: HMDB0240498)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.45	ALOGPS
logP	3.6	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-5.4	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	3	ChemAxon
Refractivity	66.34 m³·mol⁻¹	ChemAxon
Polarizability	24.87 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	154.574	30932474
DeepCCS	[M-H]-	152.193	30932474
DeepCCS	[M-2H]-	185.369	30932474
DeepCCS	[M+Na]+	160.645	30932474
AllCCS	[M+H]+	153.0	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	156.9	32859911
AllCCS	[M+Na]+	158.0	32859911
AllCCS	[M-H]-	154.4	32859911
AllCCS	[M+Na-2H]-	154.3	32859911
AllCCS	[M+HCOO]-	154.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.8 minutes	32390414
Predicted by Siyang on May 30, 2022	12.1302 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1534.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	315.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	150.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	627.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	415.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	123.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1068.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	445.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1300.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	337.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	394.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	191.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	53.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydroresveratrol	OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1	4245.4	Standard polar	33892256
Dihydroresveratrol	OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1	2626.2	Standard non polar	33892256
Dihydroresveratrol	OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1	2513.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydroresveratrol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1	2461.3	Semi standard non polar	33892256
Dihydroresveratrol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC(CCC2=CC=C(O)C=C2)=C1	2463.4	Semi standard non polar	33892256
Dihydroresveratrol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCC2=CC(O)=CC(O[Si](C)(C)C)=C2)C=C1	2454.9	Semi standard non polar	33892256
Dihydroresveratrol,2TMS,isomer #2	C[Si](C)(C)OC1=CC(CCC2=CC=C(O)C=C2)=CC(O[Si](C)(C)C)=C1	2442.9	Semi standard non polar	33892256
Dihydroresveratrol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CCC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C2)C=C1	2373.9	Semi standard non polar	33892256
Dihydroresveratrol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1	2749.7	Semi standard non polar	33892256
Dihydroresveratrol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC(CCC2=CC=C(O)C=C2)=C1	2729.5	Semi standard non polar	33892256
Dihydroresveratrol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	2978.9	Semi standard non polar	33892256
Dihydroresveratrol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CCC2=CC=C(O)C=C2)=CC(O[Si](C)(C)C(C)(C)C)=C1	2949.2	Semi standard non polar	33892256
Dihydroresveratrol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3149.4	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08466

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydro-resveratrol

METLIN ID

Not Available

PubChem Compound

185914

PDB ID

Not Available

ChEBI ID

4582

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Dihydroresveratrol (HMDB0240498)

MOL for HMDB0240498 (Dihydroresveratrol)

3D MOL for HMDB0240498 (Dihydroresveratrol)

3D SDF for HMDB0240498 (Dihydroresveratrol)

3D-SDF for HMDB0240498 (Dihydroresveratrol)

PDB for HMDB0240498 (Dihydroresveratrol)

3D PDB for HMDB0240498 (Dihydroresveratrol)

SMILES for HMDB0240498 (Dihydroresveratrol)

INCHI for HMDB0240498 (Dihydroresveratrol)

Structure for HMDB0240498 (Dihydroresveratrol)

3D Structure for HMDB0240498 (Dihydroresveratrol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized