Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:15 UTC

Update Date

2022-03-07 02:53:29 UTC

HMDB ID

HMDB0032847

Secondary Accession Numbers

HMDB32847

Metabolite Identification

Common Name

1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene

Description

1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene, also known as 4,4'-(Z)-ethene-1,2-diylbis(2-methoxyphenol), 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. 1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene has been detected, but not quantified in, fats and oils. This could make 1,2-bis(4-hydroxy-3-methoxyphenyl)ethylene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene.

Structure

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

HMDB0032847
     RDKit          3D
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.5546    0.5268   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259   -0.7608   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6640   -0.8397    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.2527    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894    0.2170    0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8140    1.4704    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    1.7350    0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3622    0.8584   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -0.1674   -1.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806   -0.9884   -1.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807   -0.8048   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206   -1.6143   -1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7280    0.2309   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496    0.4474    0.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2868    1.5101    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    1.0290    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -1.0424    0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -2.1788    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -2.0843    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9388   -3.2022    0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.1651    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378    1.0162   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    0.5052   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    1.2144   -0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515    2.3036    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688    2.7917    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -0.3060   -1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -1.7798   -2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4598   -1.4428   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3500    1.7139    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8517    2.4728    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8322    1.3256    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191    1.8532    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460   -1.1520    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469   -3.1663    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9174   -3.1095    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 16  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END


  Mrv0541 05061306452D          

 20 21  0  0  0  0            999 V2000
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  4  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  2  0  0  0  0
 16 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19  1  1  0  0  0  0
 19 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032847

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C/C2=CC(OC)=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-19-15-9-11(5-7-13(15)17)3-4-12-6-8-14(18)16(10-12)20-2/h3-10,17-18H,1-2H3/b4-3-

> <INCHI_KEY>
KQPXJFAYGYIGRU-ARJAWSKDSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.2958

> <EXACT_MASS>
272.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.64316996123303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-methoxyphenol

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.3906136766666664

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.264828530090647

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.662550924349265

> <JCHEM_PKA_STRONGEST_BASIC>
-4.592831996772672

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
78.40100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-methoxyphenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032847
     RDKit          3D
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.5546    0.5268   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259   -0.7608   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6640   -0.8397    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.2527    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894    0.2170    0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8140    1.4704    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    1.7350    0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3622    0.8584   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -0.1674   -1.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806   -0.9884   -1.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807   -0.8048   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206   -1.6143   -1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7280    0.2309   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496    0.4474    0.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2868    1.5101    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    1.0290    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -1.0424    0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -2.1788    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -2.0843    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9388   -3.2022    0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.1651    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378    1.0162   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    0.5052   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    1.2144   -0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515    2.3036    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688    2.7917    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -0.3060   -1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -1.7798   -2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4598   -1.4428   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3500    1.7139    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8517    2.4728    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8322    1.3256    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191    1.8532    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460   -1.1520    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469   -3.1663    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9174   -3.1095    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 16  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -5.390   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      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4   11                                                       
CONECT    4    3   12                                                       
CONECT    5    7   11                                                       
CONECT    6    8   12                                                       
CONECT    7    5   13                                                       
CONECT    8    6   14                                                       
CONECT    9   11   15                                                       
CONECT   10   12   16                                                       
CONECT   11    3    5    9                                                  
CONECT   12    4    6   10                                                  
CONECT   13    7   15   17                                                  
CONECT   14    8   16   18                                                  
CONECT   15    9   13   19                                                  
CONECT   16   10   14   20                                                  
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19    1   15                                                       
CONECT   20    2   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0032847
HETATM    1  C1  UNL     1       5.555   0.527  -0.490  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.026  -0.761  -0.233  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.664  -0.840   0.085  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.860   0.253   0.152  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.489   0.217   0.467  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.814   1.470   0.650  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.403   1.735   0.351  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.362   0.858  -0.260  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.156  -0.167  -1.122  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.181  -0.988  -1.568  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.481  -0.805  -1.158  1.00  0.00           C  
HETATM   12  O2  UNL     1      -4.521  -1.614  -1.592  1.00  0.00           O  
HETATM   13  C11 UNL     1      -3.728   0.231  -0.283  1.00  0.00           C  
HETATM   14  O3  UNL     1      -5.050   0.447   0.156  1.00  0.00           O  
HETATM   15  C12 UNL     1      -5.287   1.510   1.050  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.705   1.029   0.147  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.981  -1.042   0.720  1.00  0.00           C  
HETATM   18  C15 UNL     1       1.779  -2.179   0.658  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.113  -2.084   0.343  1.00  0.00           C  
HETATM   20  O4  UNL     1       3.939  -3.202   0.273  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.383   1.165   0.419  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.938   1.016  -1.293  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.608   0.505  -0.779  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.309   1.214  -0.052  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.451   2.304   1.115  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.769   2.792   0.592  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.138  -0.306  -1.515  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.932  -1.780  -2.249  1.00  0.00           H  
HETATM   29  H9  UNL     1      -5.460  -1.443  -1.265  1.00  0.00           H  
HETATM   30  H10 UNL     1      -6.350   1.714   1.209  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.852   2.473   0.650  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.832   1.326   2.056  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.919   1.853   0.847  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.046  -1.152   1.020  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.347  -3.166   0.861  1.00  0.00           H  
HETATM   36  H16 UNL     1       4.917  -3.109   0.039  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   24
CONECT    5    6   17   17
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   16
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   13
CONECT   12   29
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   30   31   32
CONECT   16   33
CONECT   17   18   34
CONECT   18   19   19   35
CONECT   19   20
CONECT   20   36
END

HMDB0032847
     RDKit          3D
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene
 36 37  0  0  0  0  0  0  0  0999 V2000
    5.5546    0.5268   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0259   -0.7608   -0.2330 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6640   -0.8397    0.0854 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.2527    0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4894    0.2170    0.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8140    1.4704    0.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4033    1.7350    0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3622    0.8584   -0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -0.1674   -1.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1806   -0.9884   -1.5684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807   -0.8048   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5206   -1.6143   -1.5921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7280    0.2309   -0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0496    0.4474    0.1556 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2868    1.5101    1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7054    1.0290    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -1.0424    0.7196 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -2.1788    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -2.0843    0.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9388   -3.2022    0.2728 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.1651    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9378    1.0162   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6079    0.5052   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091    1.2144   -0.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515    2.3036    1.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688    2.7917    0.5923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383   -0.3060   -1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -1.7798   -2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4598   -1.4428   -1.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3500    1.7139    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8517    2.4728    0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8322    1.3256    2.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9191    1.8532    0.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460   -1.1520    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3469   -3.1663    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9174   -3.1095    0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
  5 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 16  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-(Z)-Ethene-1,2-diylbis(2-methoxyphenol)	ChEBI
4,4'-Dihydroxy-3,3'-dimethoxystilbene	HMDB

Chemical Formula

C₁₆H₁₆O₄

Average Molecular Weight

272.2958

Monoisotopic Molecular Weight

272.104859

IUPAC Name

4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-methoxyphenol

Traditional Name

4-[(Z)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-2-methoxyphenol

CAS Registry Number

7329-69-3

SMILES

COC1=C(O)C=CC(\C=C/C2=CC(OC)=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C16H16O4/c1-19-15-9-11(5-7-13(15)17)3-4-12-6-8-14(18)16(10-12)20-2/h3-10,17-18H,1-2H3/b4-3-

InChI Key

KQPXJFAYGYIGRU-ARJAWSKDSA-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
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

3,3'-dimethoxystilbene-4,4'-diol (CHEBI:36391 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032847)
Cell membrane (HMDB: HMDB0032847)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032847)

Source

Exogenous

Exogenous (HMDB: HMDB0032847)

Food

Food (HMDB: HMDB0032847)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032847)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	212 - 215 °C	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
Water Solubility	0.023 g/L	ALOGPS
logP	3.01	ALOGPS
logP	3.39	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.66	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.4 m³·mol⁻¹	ChemAxon
Polarizability	28.64 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
DarkChem	[M+H]+	165.741	31661259
DarkChem	[M-H]-	166.938	31661259
DeepCCS	[M+H]+	173.362	30932474
DeepCCS	[M-H]-	171.004	30932474
DeepCCS	[M-2H]-	203.89	30932474
DeepCCS	[M+Na]+	179.455	30932474
AllCCS	[M+H]+	163.1	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.8	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	164.3	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.	6.95 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4132 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2066.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	301.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	655.4 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	491.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	111.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1280.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	448.0 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	1195.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	429.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	348.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	225.5 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	16.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene	COC1=C(O)C=CC(\C=C/C2=CC(OC)=C(O)C=C2)=C1	4539.1	Standard polar	33892256
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene	COC1=C(O)C=CC(\C=C/C2=CC(OC)=C(O)C=C2)=C1	2556.8	Standard non polar	33892256
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene	COC1=C(O)C=CC(\C=C/C2=CC(OC)=C(O)C=C2)=C1	2675.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene,1TMS,isomer #1	COC1=CC(/C=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O	2725.3	Semi standard non polar	33892256
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene,2TMS,isomer #1	COC1=CC(/C=C\C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C	2751.7	Semi standard non polar	33892256
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene,1TBDMS,isomer #1	COC1=CC(/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O	2992.8	Semi standard non polar	33892256
1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene,2TBDMS,isomer #1	COC1=CC(/C=C\C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3279.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

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

Not Available

METLIN ID

Not Available

PubChem Compound

9548762

PDB ID

Not Available

ChEBI ID

36391

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene (HMDB0032847)

MOL for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

3D MOL for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

3D SDF for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

3D-SDF for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

PDB for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

3D PDB for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

SMILES for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

INCHI for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

Structure for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

3D Structure for HMDB0032847 (1,2-Bis(4-hydroxy-3-methoxyphenyl)ethylene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized