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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:28:26 UTC

Update Date

2022-03-07 02:56:46 UTC

HMDB ID

HMDB0040868

Secondary Accession Numbers

HMDB40868

Metabolite Identification

Common Name

4-O-Methylpinosylvic acid

Description

4-O-Methylpinosylvic acid, also known as 4-O-methylpinosylvate, 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. 4-O-Methylpinosylvic acid has been detected, but not quantified in, pigeon peas (Cajanus cajan). This could make 4-O-methylpinosylvic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-O-Methylpinosylvic acid.

Structure

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

HMDB0040868
     RDKit          3D
4-O-Methylpinosylvic acid
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.9798    2.5883    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    1.2285    0.8140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    0.2371    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7181   -1.0941    0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817   -2.0776    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519   -3.4042    0.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -1.7396    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878   -2.8203   -0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373   -4.0347   -0.2026 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -2.7373   -0.7015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382   -0.4375   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.1274   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -0.2926    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290    0.3597    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634   -0.2387    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218    0.2988    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474    1.4610   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621    2.0750   -0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089    1.5105   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    0.5608    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    2.7318    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7503    3.2778    1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    2.7624   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -1.3432    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680   -3.6567    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -2.4648   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    1.0637   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3134   -1.1648    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -1.1471    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9064   -0.1535    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1185    1.9193   -0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195    2.9795   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    2.0027   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    1.6223    0.0743 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  2  0
 20  3  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061312122D          

 20 21  0  0  0  0            999 V2000
   -0.7145    2.0625    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
    2.1434   -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
    2.1434   -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
    1.4289   -1.6500    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
    0.0000    0.0000    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
    1.4289   -2.4750    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 18 16  2  0  0  0  0
 19 16  1  0  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040868

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-20-13-9-12(15(16(18)19)14(17)10-13)8-7-11-5-3-2-4-6-11/h2-10,17H,1H3,(H,18,19)/b8-7+

> <INCHI_KEY>
PICDNGANOHNCPT-BQYQJAHWSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.52246360421526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-4-methoxy-6-[(E)-2-phenylethenyl]benzoic acid

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
4.159433172

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.5556557759767

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.811699365926566

> <JCHEM_PKA_STRONGEST_BASIC>
-4.858539377841778

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
77.2131

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-4-methoxy-6-[(E)-2-phenylethenyl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040868
     RDKit          3D
4-O-Methylpinosylvic acid
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.9798    2.5883    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    1.2285    0.8140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    0.2371    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7181   -1.0941    0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817   -2.0776    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519   -3.4042    0.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -1.7396    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878   -2.8203   -0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373   -4.0347   -0.2026 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -2.7373   -0.7015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382   -0.4375   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.1274   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -0.2926    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290    0.3597    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634   -0.2387    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218    0.2988    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474    1.4610   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621    2.0750   -0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089    1.5105   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    0.5608    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    2.7318    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7503    3.2778    1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    2.7624   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -1.3432    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680   -3.6567    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -2.4648   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    1.0637   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3134   -1.1648    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -1.1471    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9064   -0.1535    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1185    1.9193   -0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195    2.9795   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    2.0027   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    1.6223    0.0743 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  2  0
 20  3  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  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      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -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       4.001  -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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9   12   13                                                       
CONECT   10   13   14                                                       
CONECT   11    5    6    7                                                  
CONECT   12    8    9   15                                                  
CONECT   13    9   10   20                                                  
CONECT   14   10   15   17                                                  
CONECT   15   12   14   16                                                  
CONECT   16   15   18   19                                                  
CONECT   17   14                                                            
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20    1   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0040868
HETATM    1  C1  UNL     1      -3.980   2.588   0.652  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.354   1.229   0.814  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.387   0.237   0.573  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.718  -1.094   0.721  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.782  -2.078   0.485  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.152  -3.404   0.645  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.470  -1.740   0.087  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.588  -2.820  -0.272  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.037  -4.035  -0.203  1.00  0.00           O  
HETATM   10  O4  UNL     1       0.702  -2.737  -0.702  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.138  -0.437  -0.052  1.00  0.00           C  
HETATM   12  C8  UNL     1       0.191   0.127  -0.205  1.00  0.00           C  
HETATM   13  C9  UNL     1       1.332  -0.293   0.241  1.00  0.00           C  
HETATM   14  C10 UNL     1       2.629   0.360   0.013  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.763  -0.239   0.571  1.00  0.00           C  
HETATM   16  C12 UNL     1       5.022   0.299   0.412  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.147   1.461  -0.321  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.062   2.075  -0.882  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.809   1.511  -0.705  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.117   0.561   0.193  1.00  0.00           C  
HETATM   21  H1  UNL     1      -3.061   2.732   1.289  1.00  0.00           H  
HETATM   22  H2  UNL     1      -4.750   3.278   1.003  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.783   2.762  -0.415  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.723  -1.343   1.026  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.068  -3.657   0.923  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.939  -2.465  -1.664  1.00  0.00           H  
HETATM   27  H7  UNL     1       0.258   1.064  -0.812  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.313  -1.165   0.910  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.690  -1.147   1.148  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.906  -0.153   0.838  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.118   1.919  -0.472  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.120   2.979  -1.459  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.962   2.003  -1.151  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.856   1.622   0.074  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    7    7
CONECT    6   25
CONECT    7    8   11
CONECT    8    9    9   10
CONECT   10   26
CONECT   11   12   20   20
CONECT   12   13   13   27
CONECT   13   14   28
CONECT   14   15   15   19
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   18   31
CONECT   18   19   19   32
CONECT   19   33
CONECT   20   34
END

HMDB0040868
     RDKit          3D
4-O-Methylpinosylvic acid
 34 35  0  0  0  0  0  0  0  0999 V2000
   -3.9798    2.5883    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3537    1.2285    0.8140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3873    0.2371    0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7181   -1.0941    0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7817   -2.0776    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519   -3.4042    0.6446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4700   -1.7396    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5878   -2.8203   -0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0373   -4.0347   -0.2026 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7020   -2.7373   -0.7015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382   -0.4375   -0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914    0.1274   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324   -0.2926    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290    0.3597    0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634   -0.2387    0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0218    0.2988    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1474    1.4610   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621    2.0750   -0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089    1.5105   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174    0.5608    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    2.7318    1.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7503    3.2778    1.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    2.7624   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232   -1.3432    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0680   -3.6567    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387   -2.4648   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    1.0637   -0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3134   -1.1648    0.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -1.1471    1.1479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9064   -0.1535    0.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1185    1.9193   -0.4723 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195    2.9795   -1.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    2.0027   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556    1.6223    0.0743 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
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 11 20  2  0
 20  3  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-O-Methylpinosylvate	Generator
2-Hydroxy-4-methoxy-6-styrylbenzoic acid	HMDB
2-Hydroxy-4-methoxy-6-(2-phenylethenyl)benzoate	HMDB
3-Hydroxy-5-methoxystilbene-2-carboxylate	HMDB

Chemical Formula

C₁₆H₁₄O₄

Average Molecular Weight

270.28

Monoisotopic Molecular Weight

270.089208936

IUPAC Name

2-hydroxy-4-methoxy-6-[(E)-2-phenylethenyl]benzoic acid

Traditional Name

2-hydroxy-4-methoxy-6-[(E)-2-phenylethenyl]benzoic acid

CAS Registry Number

149697-30-3

SMILES

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

InChI Identifier

InChI=1S/C16H14O4/c1-20-13-9-12(15(16(18)19)14(17)10-13)8-7-11-5-3-2-4-6-11/h2-10,17H,1H3,(H,18,19)/b8-7+

InChI Key

PICDNGANOHNCPT-BQYQJAHWSA-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
P-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Salicylic acid or derivatives
Salicylic acid
Benzoic acid
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
Anisole
Methoxybenzene
Styrene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Membrane (FooDB: )
Cell membrane (FooDB: )

Route of exposure

Enteral

Ingestion (FooDB: )

Source

Exogenous

Food

Food (FooDB: )

Pulse

Pea

Pigeon pea (FooDB: FOOD00037)

Endogenous

Plant

Plant (FooDB: )
Fabaceae (FooDB: )

Not Available

Nutrient (FooDB: )

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
Water Solubility	0.069 g/L	ALOGPS
logP	3.44	ALOGPS
logP	4.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.21 m³·mol⁻¹	ChemAxon
Polarizability	28.52 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]+	167.12	30932474
DeepCCS	[M-H]-	164.762	30932474
DeepCCS	[M-2H]-	197.648	30932474
DeepCCS	[M+Na]+	173.213	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	165.7	32859911
AllCCS	[M+Na]+	166.7	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	162.4	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-O-Methylpinosylvic acid	COC1=CC(O)=C(C(O)=O)C(\C=C\C2=CC=CC=C2)=C1	4089.8	Standard polar	33892256
4-O-Methylpinosylvic acid	COC1=CC(O)=C(C(O)=O)C(\C=C\C2=CC=CC=C2)=C1	2492.6	Standard non polar	33892256
4-O-Methylpinosylvic acid	COC1=CC(O)=C(C(O)=O)C(\C=C\C2=CC=CC=C2)=C1	2659.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-O-Methylpinosylvic acid,1TMS,isomer #1	COC1=CC(/C=C/C2=CC=CC=C2)=C(C(=O)O)C(O[Si](C)(C)C)=C1	2501.5	Semi standard non polar	33892256
4-O-Methylpinosylvic acid,1TMS,isomer #2	COC1=CC(O)=C(C(=O)O[Si](C)(C)C)C(/C=C/C2=CC=CC=C2)=C1	2522.3	Semi standard non polar	33892256
4-O-Methylpinosylvic acid,2TMS,isomer #1	COC1=CC(/C=C/C2=CC=CC=C2)=C(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2533.4	Semi standard non polar	33892256
4-O-Methylpinosylvic acid,1TBDMS,isomer #1	COC1=CC(/C=C/C2=CC=CC=C2)=C(C(=O)O)C(O[Si](C)(C)C(C)(C)C)=C1	2771.5	Semi standard non polar	33892256
4-O-Methylpinosylvic acid,1TBDMS,isomer #2	COC1=CC(O)=C(C(=O)O[Si](C)(C)C(C)(C)C)C(/C=C/C2=CC=CC=C2)=C1	2785.2	Semi standard non polar	33892256
4-O-Methylpinosylvic acid,2TBDMS,isomer #1	COC1=CC(/C=C/C2=CC=CC=C2)=C(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3015.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O-Methylpinosylvic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-0190000000-19363047d088057d58fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O-Methylpinosylvic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00fs-7229100000-5ac2519299f753972bc1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-O-Methylpinosylvic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid , positive-QTOF	splash10-0uxr-0960000000-48255922bdb7620acf61	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 10V, Positive-QTOF	splash10-00di-0090000000-f19434555033b3f2ceb7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 20V, Positive-QTOF	splash10-0fi0-0190000000-a2f0efaa6d7bde51b5aa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 40V, Positive-QTOF	splash10-0ufu-0930000000-2a9dd452f33f3a0f69c1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 10V, Negative-QTOF	splash10-016r-0090000000-dfb53f1defc1bd849b29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 20V, Negative-QTOF	splash10-056r-0190000000-35f20474ffa72dc00ebe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 40V, Negative-QTOF	splash10-0a4i-1690000000-cef2c78cf1c14ccce051	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 10V, Positive-QTOF	splash10-0uk9-0090000000-9b8321101d252f3f2169	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 20V, Positive-QTOF	splash10-0ufr-0290000000-7e0c2405f0749746f8c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 40V, Positive-QTOF	splash10-0fb9-0970000000-136ea5705c76ae58aa66	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 10V, Negative-QTOF	splash10-1000-0090000000-ebdef20cab8283670c6c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 20V, Negative-QTOF	splash10-0aor-0090000000-a35f9b7ad13d7d2a4b76	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-Methylpinosylvic acid 40V, Negative-QTOF	splash10-0a4m-1930000000-068a7aee578d795ad6cd	2021-09-23	Wishart Lab	View Spectrum

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

FDB001744

KNApSAcK ID

C00015521

Chemspider ID

30777513

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67322417

PDB ID

Not Available

ChEBI ID

174558

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 4-O-Methylpinosylvic acid (HMDB0040868)

MOL for HMDB0040868 (4-O-Methylpinosylvic acid)

3D MOL for HMDB0040868 (4-O-Methylpinosylvic acid)

3D SDF for HMDB0040868 (4-O-Methylpinosylvic acid)

3D-SDF for HMDB0040868 (4-O-Methylpinosylvic acid)

PDB for HMDB0040868 (4-O-Methylpinosylvic acid)

3D PDB for HMDB0040868 (4-O-Methylpinosylvic acid)

SMILES for HMDB0040868 (4-O-Methylpinosylvic acid)

INCHI for HMDB0040868 (4-O-Methylpinosylvic acid)

Structure for HMDB0040868 (4-O-Methylpinosylvic acid)

3D Structure for HMDB0040868 (4-O-Methylpinosylvic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra