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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:36:56 UTC

Update Date

2022-11-23 22:29:21 UTC

HMDB ID

HMDB0259761

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vanillyl mandelic acid

Description

2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropanoic acid 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. Based on a literature review very few articles have been published on 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vanillyl mandelic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vanillyl mandelic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259761
     RDKit          3D
vanillyl mandelic acid
 37 38  0  0  0  0  0  0  0  0999 V2000
   -4.2067    1.8046   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3638    0.9348   -0.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    0.1090    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343    0.1417   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -0.6718    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175   -0.7439   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    0.2034    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -0.1129    1.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    1.6100   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469    2.0979   -1.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    2.4595    1.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401   -0.1593   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487   -0.9148    0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826   -1.2560   -0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.8277   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.0760   -2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9182    0.2524   -1.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -1.4967    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -1.5375    1.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -0.7165    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8872   -0.7159    1.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4453    1.2675   -2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2314    2.3018   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    2.6276   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837    0.7744   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532   -0.5506   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6101   -1.7642   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517    0.3286    1.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    3.4143    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.2618    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3997   -1.8503    0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9949   -1.0943   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406    0.2688   -3.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3057    0.8433   -2.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -2.1636    1.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -2.2032    2.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683   -1.3226    2.6798 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
M  END


  Mrv1652309122100372D          

 21 22  0  0  0  0            999 V2000
   -1.4289   -0.8250    0.0000 C   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
   -0.7145   -2.0625    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
   -1.4289   -3.3000    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
    0.0000   -3.3000    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
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    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
    2.1434   -2.0625    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
    3.5724   -2.0625    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
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -4.0145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.5855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 10 20  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259761

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O5/c1-21-14-9-11(7-8-13(14)17)10-16(20,15(18)19)12-5-3-2-4-6-12/h2-9,17,20H,10H2,1H3,(H,18,19)

> <INCHI_KEY>
TVZUXSRMYHHBOO-UHFFFAOYSA-N

> <FORMULA>
C16H16O5

> <MOLECULAR_WEIGHT>
288.299

> <EXACT_MASS>
288.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.451923788749014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropanoic acid

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.5236913110000003

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.943445826095171

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.445658886558475

> <JCHEM_PKA_STRONGEST_BASIC>
-4.279962556127626

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
76.4802

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259761
     RDKit          3D
vanillyl mandelic acid
 37 38  0  0  0  0  0  0  0  0999 V2000
   -4.2067    1.8046   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3638    0.9348   -0.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    0.1090    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343    0.1417   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -0.6718    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175   -0.7439   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    0.2034    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -0.1129    1.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    1.6100   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469    2.0979   -1.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    2.4595    1.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401   -0.1593   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487   -0.9148    0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826   -1.2560   -0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.8277   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.0760   -2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9182    0.2524   -1.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -1.4967    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -1.5375    1.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -0.7165    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8872   -0.7159    1.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4453    1.2675   -2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2314    2.3018   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    2.6276   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837    0.7744   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532   -0.5506   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6101   -1.7642   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517    0.3286    1.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    3.4143    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.2618    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3997   -1.8503    0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9949   -1.0943   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406    0.2688   -3.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3057    0.8433   -2.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -2.1636    1.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -2.2032    2.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683   -1.3226    2.6798 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.437  -7.494   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.977  -7.494   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -8.827   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.897  -4.826   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   17   20                                             
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   10   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   10                                                            
CONECT   21    4                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0259761
HETATM    1  C1  UNL     1      -4.207   1.805  -1.332  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.364   0.935  -0.255  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.359   0.109   0.233  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.134   0.142  -0.374  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.130  -0.672   0.100  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.218  -0.744  -0.441  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.207   0.203   0.170  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.270  -0.113   1.554  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.890   1.610  -0.030  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.747   2.098  -1.168  1.00  0.00           O  
HETATM   11  O4  UNL     1       0.735   2.460   1.053  1.00  0.00           O  
HETATM   12  C8  UNL     1       2.540  -0.159  -0.361  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.449  -0.915   0.349  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.683  -1.256  -0.147  1.00  0.00           C  
HETATM   15  C11 UNL     1       5.019  -0.828  -1.395  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.168  -0.076  -2.154  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.918   0.252  -1.615  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.416  -1.497   1.186  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.636  -1.537   1.799  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.635  -0.716   1.314  1.00  0.00           C  
HETATM   21  O5  UNL     1      -4.887  -0.716   1.895  1.00  0.00           O  
HETATM   22  H1  UNL     1      -4.445   1.267  -2.273  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.231   2.302  -1.339  1.00  0.00           H  
HETATM   24  H3  UNL     1      -4.969   2.628  -1.204  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.884   0.774  -1.221  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.153  -0.551  -1.552  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.610  -1.764  -0.329  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.452   0.329   1.933  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.446   3.414   0.975  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.182  -1.262   1.354  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.400  -1.850   0.410  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.995  -1.094  -1.794  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.441   0.269  -3.160  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.306   0.843  -2.278  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.642  -2.164   1.597  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.820  -2.203   2.653  1.00  0.00           H  
HETATM   37  H16 UNL     1      -5.068  -1.323   2.680  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   25
CONECT    5    6   18   18
CONECT    6    7   26   27
CONECT    7    8    9   12
CONECT    8   28
CONECT    9   10   10   11
CONECT   11   29
CONECT   12   13   13   17
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   17   33
CONECT   17   34
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   20   21
CONECT   21   37
END

HMDB0259761
     RDKit          3D
vanillyl mandelic acid
 37 38  0  0  0  0  0  0  0  0999 V2000
   -4.2067    1.8046   -1.3324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3638    0.9348   -0.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    0.1090    0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1343    0.1417   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1297   -0.6718    0.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175   -0.7439   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    0.2034    0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2696   -0.1129    1.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8897    1.6100   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7469    2.0979   -1.1676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    2.4595    1.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401   -0.1593   -0.3609 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4487   -0.9148    0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6826   -1.2560   -0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.8277   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.0760   -2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9182    0.2524   -1.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4156   -1.4967    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -1.5375    1.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6348   -0.7165    1.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8872   -0.7159    1.8950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4453    1.2675   -2.2732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2314    2.3018   -1.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9688    2.6276   -1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8837    0.7744   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1532   -0.5506   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6101   -1.7642   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517    0.3286    1.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    3.4143    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824   -1.2618    1.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3997   -1.8503    0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9949   -1.0943   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4406    0.2688   -3.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3057    0.8433   -2.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -2.1636    1.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196   -2.2032    2.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683   -1.3226    2.6798 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  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20  3  1  0
 17 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropanoate	Generator
Vanillyl mandelate	Generator

Chemical Formula

C₁₆H₁₆O₅

Average Molecular Weight

288.299

Monoisotopic Molecular Weight

288.099773615

IUPAC Name

2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropanoic acid

Traditional Name

2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-2-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H16O5/c1-21-14-9-11(7-8-13(14)17)10-16(20,15(18)19)12-5-3-2-4-6-12/h2-9,17,20H,10H2,1H3,(H,18,19)

InChI Key

TVZUXSRMYHHBOO-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
3-phenylpropanoic-acid
Methoxyphenol
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Alcohol
Organooxygen compound
Carbonyl group
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	2.41	ALOGPS
logP	2.52	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	76.48 m³·mol⁻¹	ChemAxon
Polarizability	28.45 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
AllCCS	[M+H]+	166.892	32859911
AllCCS	[M+H-H2O]+	163.204	32859911
AllCCS	[M+Na]+	171.301	32859911
AllCCS	[M+NH4]+	170.316	32859911
AllCCS	[M-H]-	167.943	32859911
AllCCS	[M+Na-2H]-	167.694	32859911
AllCCS	[M+HCOO]-	167.55	32859911
DeepCCS	[M+H]+	170.619	30932474
DeepCCS	[M-H]-	168.261	30932474
DeepCCS	[M-2H]-	201.147	30932474
DeepCCS	[M+Na]+	176.712	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
vanillyl mandelic acid	COC1=C(O)C=CC(CC(O)(C(O)=O)C2=CC=CC=C2)=C1	3777.3	Standard polar	33892256
vanillyl mandelic acid	COC1=C(O)C=CC(CC(O)(C(O)=O)C2=CC=CC=C2)=C1	2513.9	Standard non polar	33892256
vanillyl mandelic acid	COC1=C(O)C=CC(CC(O)(C(O)=O)C2=CC=CC=C2)=C1	2384.2	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 - Vanillyl mandelic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-4940000000-078596c99bdfbd9fc274	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillyl mandelic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10719991

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21962642

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Vanillyl mandelic acid (HMDB0259761)

MOL for HMDB0259761 (Vanillyl mandelic acid)

3D MOL for HMDB0259761 (Vanillyl mandelic acid)

3D SDF for HMDB0259761 (Vanillyl mandelic acid)

3D-SDF for HMDB0259761 (Vanillyl mandelic acid)

PDB for HMDB0259761 (Vanillyl mandelic acid)

3D PDB for HMDB0259761 (Vanillyl mandelic acid)

SMILES for HMDB0259761 (Vanillyl mandelic acid)

INCHI for HMDB0259761 (Vanillyl mandelic acid)

Structure for HMDB0259761 (Vanillyl mandelic acid)

3D Structure for HMDB0259761 (Vanillyl mandelic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra