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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:30:30 UTC

Update Date

2022-03-07 02:54:10 UTC

HMDB ID

HMDB0034621

Secondary Accession Numbers

HMDB34621

Metabolite Identification

Common Name

2-O-Acetyl-trans-coutaric acid

Description

2-O-Acetyl-trans-coutaric acid belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 2-O-Acetyl-trans-coutaric acid has been detected, but not quantified in, green vegetables. This could make 2-O-acetyl-trans-coutaric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-O-Acetyl-trans-coutaric acid.

Structure

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

HMDB0034621
     RDKit          3D
2-O-Acetyl-trans-coutaric acid
 38 38  0  0  0  0  0  0  0  0999 V2000
   -6.4050    1.7040    1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9462    1.6923    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2927    2.7535    1.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673    0.5882    0.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9118    0.5219    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.1437   -1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.0668   -1.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    0.0114   -1.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751   -0.5280    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260   -0.4598    0.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248   -0.1355    1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    0.1147    2.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -0.0645    1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -0.3034   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3720   -0.2300   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996   -0.5037   -1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985   -0.4499   -2.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0306   -0.1193   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3357   -0.0724   -2.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7379    0.1499   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4238    0.0918    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -1.8780    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -2.1135    1.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896   -2.8951    0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5650    2.3418    2.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7977    0.6886    1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9919    2.1482    0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591    1.4670    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -0.9430   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2857   -0.2867    2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605    0.2020    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -0.5676   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066   -0.7628   -2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352   -0.6666   -3.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7388    0.7641   -2.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5262    0.4107    0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441    0.3128    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770   -3.0599    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 24 38  1  0
M  END


  Mrv0541 05061307582D          

 24 24  0  0  0  0            999 V2000
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    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
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    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
   -3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  1  1  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  2  0  0  0  0
 17 10  1  0  0  0  0
 18 11  2  0  0  0  0
 19 14  2  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 15  1  0  0  0  0
 23  8  1  0  0  0  0
 23 12  1  0  0  0  0
 24 11  1  0  0  0  0
 24 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034621

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O9/c1-8(16)23-12(14(19)20)13(15(21)22)24-11(18)7-4-9-2-5-10(17)6-3-9/h2-7,12-13,17H,1H3,(H,19,20)(H,21,22)/b7-4+

> <INCHI_KEY>
AILCSCQIQZTQJR-QPJJXVBHSA-N

> <FORMULA>
C15H14O9

> <MOLECULAR_WEIGHT>
338.2663

> <EXACT_MASS>
338.063782046

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
31.066308719306907

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.3426509180000001

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.6246475338985835

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1533553806152494

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954733576925379

> <JCHEM_POLAR_SURFACE_AREA>
147.42999999999998

> <JCHEM_REFRACTIVITY>
76.91350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034621
     RDKit          3D
2-O-Acetyl-trans-coutaric acid
 38 38  0  0  0  0  0  0  0  0999 V2000
   -6.4050    1.7040    1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9462    1.6923    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2927    2.7535    1.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673    0.5882    0.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9118    0.5219    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.1437   -1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.0668   -1.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    0.0114   -1.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751   -0.5280    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260   -0.4598    0.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248   -0.1355    1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    0.1147    2.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -0.0645    1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -0.3034   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3720   -0.2300   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996   -0.5037   -1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985   -0.4499   -2.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0306   -0.1193   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3357   -0.0724   -2.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7379    0.1499   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4238    0.0918    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -1.8780    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -2.1135    1.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896   -2.8951    0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5650    2.3418    2.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7977    0.6886    1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9919    2.1482    0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591    1.4670    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -0.9430   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2857   -0.2867    2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605    0.2020    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -0.5676   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066   -0.7628   -2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352   -0.6666   -3.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7388    0.7641   -2.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5262    0.4107    0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441    0.3128    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770   -3.0599    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 24 38  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      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -6.668  11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002  12.320   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.335  12.320   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667  12.320   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334  10.010   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    5    9                                                       
CONECT    3    6    9                                                       
CONECT    4    7    9                                                       
CONECT    5    2   10                                                       
CONECT    6    3   10                                                       
CONECT    7    4   11                                                       
CONECT    8    1   16   23                                                  
CONECT    9    2    3    4                                                  
CONECT   10    5    6   17                                                  
CONECT   11    7   18   24                                                  
CONECT   12   13   14   23                                                  
CONECT   13   12   15   24                                                  
CONECT   14   12   19   20                                                  
CONECT   15   13   21   22                                                  
CONECT   16    8                                                            
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   14                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   15                                                            
CONECT   23    8   12                                                       
CONECT   24   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

COMPND    HMDB0034621
HETATM    1  C1  UNL     1      -6.405   1.704   1.293  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.946   1.692   0.994  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.293   2.753   1.164  1.00  0.00           O  
HETATM    4  O2  UNL     1      -4.267   0.588   0.542  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.912   0.522   0.248  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.739   0.144  -1.174  1.00  0.00           C  
HETATM    7  O3  UNL     1      -3.739  -0.067  -1.927  1.00  0.00           O  
HETATM    8  O4  UNL     1      -1.458   0.011  -1.713  1.00  0.00           O  
HETATM    9  C5  UNL     1      -2.175  -0.528   1.087  1.00  0.00           C  
HETATM   10  O5  UNL     1      -0.826  -0.460   0.662  1.00  0.00           O  
HETATM   11  C6  UNL     1       0.225  -0.135   1.484  1.00  0.00           C  
HETATM   12  O6  UNL     1      -0.033   0.115   2.683  1.00  0.00           O  
HETATM   13  C7  UNL     1       1.622  -0.064   1.046  1.00  0.00           C  
HETATM   14  C8  UNL     1       2.003  -0.303  -0.171  1.00  0.00           C  
HETATM   15  C9  UNL     1       3.372  -0.230  -0.583  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.700  -0.504  -1.919  1.00  0.00           C  
HETATM   17  C11 UNL     1       4.999  -0.450  -2.378  1.00  0.00           C  
HETATM   18  C12 UNL     1       6.031  -0.119  -1.521  1.00  0.00           C  
HETATM   19  O7  UNL     1       7.336  -0.072  -2.013  1.00  0.00           O  
HETATM   20  C13 UNL     1       5.738   0.150  -0.223  1.00  0.00           C  
HETATM   21  C14 UNL     1       4.424   0.092   0.226  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.751  -1.878   0.885  1.00  0.00           C  
HETATM   23  O8  UNL     1      -3.927  -2.114   1.204  1.00  0.00           O  
HETATM   24  O9  UNL     1      -1.990  -2.895   0.339  1.00  0.00           O  
HETATM   25  H1  UNL     1      -6.565   2.342   2.182  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.798   0.689   1.497  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.992   2.148   0.455  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.359   1.467   0.405  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.158  -0.943  -1.932  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.286  -0.287   2.171  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.361   0.202   1.787  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.236  -0.568  -0.887  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.907  -0.763  -2.599  1.00  0.00           H  
HETATM   34  H10 UNL     1       5.235  -0.667  -3.423  1.00  0.00           H  
HETATM   35  H11 UNL     1       7.739   0.764  -2.396  1.00  0.00           H  
HETATM   36  H12 UNL     1       6.526   0.411   0.466  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.244   0.313   1.259  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.077  -3.060   0.778  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    9   28
CONECT    6    7    7    8
CONECT    8   29
CONECT    9   10   22   30
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   14   31
CONECT   14   15   32
CONECT   15   16   16   21
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19   20
CONECT   19   35
CONECT   20   21   21   36
CONECT   21   37
CONECT   22   23   23   24
CONECT   24   38
END

HMDB0034621
     RDKit          3D
2-O-Acetyl-trans-coutaric acid
 38 38  0  0  0  0  0  0  0  0999 V2000
   -6.4050    1.7040    1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9462    1.6923    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2927    2.7535    1.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2673    0.5882    0.5419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9118    0.5219    0.2480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7385    0.1437   -1.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7389   -0.0668   -1.9271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575    0.0114   -1.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1751   -0.5280    1.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8260   -0.4598    0.6625 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248   -0.1355    1.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    0.1147    2.6831 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6215   -0.0645    1.0460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027   -0.3034   -0.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3720   -0.2300   -0.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996   -0.5037   -1.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9985   -0.4499   -2.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0306   -0.1193   -1.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3357   -0.0724   -2.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7379    0.1499   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4238    0.0918    0.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -1.8780    0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9274   -2.1135    1.2045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9896   -2.8951    0.3394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5650    2.3418    2.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7977    0.6886    1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9919    2.1482    0.4548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3591    1.4670    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1577   -0.9430   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2857   -0.2867    2.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3605    0.2020    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2359   -0.5676   -0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9066   -0.7628   -2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2352   -0.6666   -3.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7388    0.7641   -2.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5262    0.4107    0.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2441    0.3128    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0770   -3.0599    0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
  9 22  1  0
 22 23  2  0
 22 24  1  0
 21 15  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  8 29  1  0
  9 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 24 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-O-Acetyl-trans-coutarate	Generator
2-O-Acetyl-3-trans-O-P-coumaroyltartaric acid	HMDB
2-(Acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioate	Generator

Chemical Formula

C₁₅H₁₄O₉

Average Molecular Weight

338.2663

Monoisotopic Molecular Weight

338.063782046

IUPAC Name

2-(acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

Traditional Name

2-(acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

CAS Registry Number

106928-35-2

SMILES

CC(=O)OC(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C15H14O9/c1-8(16)23-12(14(19)20)13(15(21)22)24-11(18)7-4-9-2-5-10(17)6-3-9/h2-7,12-13,17H,1H3,(H,19,20)(H,21,22)/b7-4+

InChI Key

AILCSCQIQZTQJR-QPJJXVBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

Coumaric acid ester
Tetracarboxylic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Sugar acid
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034621)
Cytoplasm (HMDB: HMDB0034621)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034621)

Source

Exogenous

Food

Food (HMDB: HMDB0034621)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034621)

Not Available

Nutrient (HMDB: HMDB0034621)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 - 198 °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	0.27 g/L	ALOGPS
logP	1.94	ALOGPS
logP	1.34	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.15	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	147.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	76.91 m³·mol⁻¹	ChemAxon
Polarizability	31.07 Å³	ChemAxon
Number of Rings	1	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]+	169.7	30932474
DeepCCS	[M-H]-	167.342	30932474
DeepCCS	[M-2H]-	201.166	30932474
DeepCCS	[M+Na]+	176.728	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	177.4	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	173.8	32859911
AllCCS	[M+Na-2H]-	173.8	32859911
AllCCS	[M+HCOO]-	173.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-O-Acetyl-trans-coutaric acid	CC(=O)OC(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O	5043.5	Standard polar	33892256
2-O-Acetyl-trans-coutaric acid	CC(=O)OC(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O	2681.4	Standard non polar	33892256
2-O-Acetyl-trans-coutaric acid	CC(=O)OC(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O	2940.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-O-Acetyl-trans-coutaric acid,1TMS,isomer #1	CC(=O)OC(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2789.3	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,1TMS,isomer #2	CC(=O)OC(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2716.7	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,1TMS,isomer #3	CC(=O)OC(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	2717.7	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,2TMS,isomer #1	CC(=O)OC(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O	2759.4	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,2TMS,isomer #2	CC(=O)OC(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2760.9	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,2TMS,isomer #3	CC(=O)OC(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C	2696.3	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,3TMS,isomer #1	CC(=O)OC(C(=O)O[Si](C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C	2785.6	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,1TBDMS,isomer #1	CC(=O)OC(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3032.0	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,1TBDMS,isomer #2	CC(=O)OC(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	2956.4	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,1TBDMS,isomer #3	CC(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O	2954.6	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,2TBDMS,isomer #1	CC(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O	3261.2	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,2TBDMS,isomer #2	CC(=O)OC(C(=O)O)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3265.2	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,2TBDMS,isomer #3	CC(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3169.3	Semi standard non polar	33892256
2-O-Acetyl-trans-coutaric acid,3TBDMS,isomer #1	CC(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C	3477.8	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 - 2-O-Acetyl-trans-coutaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0005-4910000000-b49ffe2cf366fa81ae95	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Acetyl-trans-coutaric acid GC-MS (3 TMS) - 70eV, Positive	splash10-01bl-9360330000-de8dc951995157a09450	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Acetyl-trans-coutaric 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 10V, Positive-QTOF	splash10-009b-1946000000-a96cb96a8f5c391c5d58	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 20V, Positive-QTOF	splash10-002b-0921000000-61429a01d06f041f657e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 40V, Positive-QTOF	splash10-000t-2900000000-8a4e68251c193b7a6bd3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 10V, Negative-QTOF	splash10-06rg-4972000000-13326cd7eaa2968bb9bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 20V, Negative-QTOF	splash10-0bt9-4930000000-6c1d2cf284fa9bd05f7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 40V, Negative-QTOF	splash10-052b-8910000000-c25646efb0d6dc657b12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 10V, Positive-QTOF	splash10-0095-0986000000-000f9bd40fa96e6112ab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 20V, Positive-QTOF	splash10-00kb-2930000000-98d12d5e4d9f389fb730	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 40V, Positive-QTOF	splash10-014i-2910000000-7dc8d63e0290016d6703	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 10V, Negative-QTOF	splash10-003s-3790000000-e59591232d06d6c216ff	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 20V, Negative-QTOF	splash10-001i-2920000000-0a2195ebb7e2331916bd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Acetyl-trans-coutaric acid 40V, Negative-QTOF	splash10-0aor-9600000000-5ee80c0bad7797b9d952	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB013140

KNApSAcK ID

Not Available

Chemspider ID

8557914

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10382471

PDB ID

Not Available

ChEBI ID

140766

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 2-O-Acetyl-trans-coutaric acid (HMDB0034621)

MOL for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

3D MOL for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

3D SDF for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

3D-SDF for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

PDB for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

3D PDB for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

SMILES for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

INCHI for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

Structure for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

3D Structure for HMDB0034621 (2-O-Acetyl-trans-coutaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra