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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 09:50:43 UTC

Update Date

2021-09-24 09:50:43 UTC

HMDB ID

HMDB0304447

Secondary Accession Numbers

None

Metabolite Identification

Common Name

p-coumaroyltriacetic acid lactone

Description

P-coumaroyltriacetic acid lactone belongs to hydroxycinnamic acids and derivatives class of compounds. Those are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. P-coumaroyltriacetic acid lactone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). P-coumaroyltriacetic acid lactone can be found in a number of food items such as yellow zucchini, lowbush blueberry, fruits, and napa cabbage, which makes P-coumaroyltriacetic acid lactone a potential biomarker for the consumption of these food products.

Structure

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

HMDB0304447
     RDKit          3D
p-coumaroyltriacetic acid lactone
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.3959   -0.7415    1.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889    0.0739    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4400    0.2069   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667   -0.5592    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6970   -0.5003    0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    0.3628   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6328    0.4336   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4160   -0.3966    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8169   -0.3765    0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8558   -1.2630    1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922   -1.3308    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283    0.9318   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383    0.6573   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1193   -0.2934   -0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435   -0.5159   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2286   -1.4770   -1.1034 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.9665    0.2448    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1129    1.1727    1.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    1.8763    2.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8817    1.3478    0.7320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643    0.9199   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -1.2686    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    1.0497   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0525    1.1112   -1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2788    0.2374   -0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4919   -1.9178    1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514   -2.0231    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077    2.0217   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7411    0.7861   -1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024   -0.8763   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873    0.1060    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 17 31  1  0
M  CHG  1  16  -1
M  END


  Mrv1533005141521462D          

 20 21  0  0  0  0            999 V2000
    1.4289   -4.1250    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
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   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
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   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
   -0.7145    1.2375    0.0000 O   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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  5  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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  2  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 13 20  2  0  0  0  0
M  CHG  1  19  -1
M  END
> <DATABASE_ID>
HMDB0304447

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=CC(=O)CC2=CC([O-])=CC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-11-4-1-10(2-5-11)3-6-12(17)7-14-8-13(18)9-15(19)20-14/h1-6,8-9,16,18H,7H2/p-1

> <INCHI_KEY>
ZUILKEWVWUKSAO-UHFFFAOYSA-M

> <FORMULA>
C15H11O5

> <MOLECULAR_WEIGHT>
271.249

> <EXACT_MASS>
271.061197034

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
26.332166358623034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl]-2-oxo-2H-pyran-4-olate

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
2.2927619149999994

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.052488770521204

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.419886145181068

> <JCHEM_PKA_STRONGEST_BASIC>
-4.917889763182406

> <JCHEM_POLAR_SURFACE_AREA>
86.66

> <JCHEM_REFRACTIVITY>
86.34080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl]-6-oxopyran-4-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304447
     RDKit          3D
p-coumaroyltriacetic acid lactone
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.3959   -0.7415    1.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889    0.0739    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4400    0.2069   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667   -0.5592    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6970   -0.5003    0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    0.3628   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6328    0.4336   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4160   -0.3966    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8169   -0.3765    0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8558   -1.2630    1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922   -1.3308    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283    0.9318   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383    0.6573   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1193   -0.2934   -0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435   -0.5159   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2286   -1.4770   -1.1034 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.9665    0.2448    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1129    1.1727    1.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    1.8763    2.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8817    1.3478    0.7320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643    0.9199   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -1.2686    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    1.0497   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0525    1.1112   -1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2788    0.2374   -0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4919   -1.9178    1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514   -2.0231    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077    2.0217   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7411    0.7861   -1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024   -0.8763   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873    0.1060    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 17 31  1  0
M  CHG  1  16  -1
M  END

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O-1
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0304447
HETATM    1  O1  UNL     1       1.396  -0.741   1.001  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.989   0.074   0.160  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.440   0.207  -0.080  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.267  -0.559   0.620  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.697  -0.500   0.454  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.259   0.363  -0.447  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.633   0.434  -0.620  1.00  0.00           C  
HETATM    8  C7  UNL     1      -5.416  -0.397   0.146  1.00  0.00           C  
HETATM    9  O2  UNL     1      -6.817  -0.376   0.021  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.856  -1.263   1.050  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.492  -1.331   1.219  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.928   0.932  -0.622  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.338   0.657  -0.243  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.119  -0.293  -0.865  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.443  -0.516  -0.473  1.00  0.00           C  
HETATM   16  O3  UNL     1       6.229  -1.477  -1.103  1.00  0.00           O1-
HETATM   17  C14 UNL     1       5.967   0.245   0.566  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.113   1.173   1.130  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.543   1.876   2.066  1.00  0.00           O  
HETATM   20  O5  UNL     1       3.882   1.348   0.732  1.00  0.00           O  
HETATM   21  H1  UNL     1      -0.764   0.920  -0.813  1.00  0.00           H  
HETATM   22  H2  UNL     1      -0.876  -1.269   1.354  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.694   1.050  -1.087  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.053   1.111  -1.325  1.00  0.00           H  
HETATM   25  H5  UNL     1      -7.279   0.237  -0.624  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.492  -1.918   1.653  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.051  -2.023   1.941  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.708   2.022  -0.434  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.741   0.786  -1.705  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.702  -0.876  -1.669  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.987   0.106   0.903  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6    6   11
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   10
CONECT    9   25
CONECT   10   11   11   26
CONECT   11   27
CONECT   12   13   28   29
CONECT   13   14   14   20
CONECT   14   15   30
CONECT   15   16   17   17
CONECT   17   18   31
CONECT   18   19   19   20
END

HMDB0304447
     RDKit          3D
p-coumaroyltriacetic acid lactone
 31 32  0  0  0  0  0  0  0  0999 V2000
    1.3959   -0.7415    1.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9889    0.0739    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4400    0.2069   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667   -0.5592    0.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6970   -0.5003    0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2587    0.3628   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6328    0.4336   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4160   -0.3966    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8169   -0.3765    0.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8558   -1.2630    1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4922   -1.3308    1.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9283    0.9318   -0.6223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3383    0.6573   -0.2434 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1193   -0.2934   -0.8653 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4435   -0.5159   -0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2286   -1.4770   -1.1034 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.9665    0.2448    0.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1129    1.1727    1.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5428    1.8763    2.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8817    1.3478    0.7320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643    0.9199   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -1.2686    1.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937    1.0497   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0525    1.1112   -1.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2788    0.2374   -0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4919   -1.9178    1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514   -2.0231    1.9407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7077    2.0217   -0.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7411    0.7861   -1.7051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7024   -0.8763   -1.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873    0.1060    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11  5  1  0
 20 13  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 17 31  1  0
M  CHG  1  16  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-[4-(4-Hydroxy-2-oxo-2H-pyran-6-yl)-3-oxobut-1-en-1-yl]benzen-1-olic acid	Generator
p-Coumaroyltriacetate lactone	Generator

Chemical Formula

C₁₅H₁₁O₅

Average Molecular Weight

271.249

Monoisotopic Molecular Weight

271.061197034

IUPAC Name

6-[4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl]-2-oxo-2H-pyran-4-olate

Traditional Name

2-[4-(4-hydroxyphenyl)-2-oxobut-3-en-1-yl]-6-oxopyran-4-olate

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=CC(=O)CC2=CC([O-])=CC(=O)O2)C=C1

InChI Identifier

InChI=1S/C15H12O5/c16-11-4-1-10(2-5-11)3-6-12(17)7-14-8-13(18)9-15(19)20-14/h1-6,8-9,16,18H,7H2/p-1

InChI Key

ZUILKEWVWUKSAO-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids and derivatives

Alternative Parents

Substituents

Hydroxycinnamic acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Acryloyl-group
Enone
Heteroaromatic compound
Vinylogous acid
Alpha,beta-unsaturated ketone
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic anion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-6955 )

Ontology

Not Available

Exogenous (HMDB: HMDB0304447)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

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	2.01	ALOGPS
logP	2.29	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.42	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.34 m³·mol⁻¹	ChemAxon
Polarizability	26.33 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]+	162.708	32859911
AllCCS	[M+H-H2O]+	158.675	32859911
AllCCS	[M+Na]+	167.539	32859911
AllCCS	[M+NH4]+	166.459	32859911
AllCCS	[M-H]-	160.327	32859911
AllCCS	[M+Na-2H]-	160.009	32859911
AllCCS	[M+HCOO]-	159.791	32859911
DeepCCS	[M+H]+	167.887	30932474
DeepCCS	[M-H]-	165.529	30932474
DeepCCS	[M-2H]-	198.873	30932474
DeepCCS	[M+Na]+	175.153	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3093 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1558.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	305.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	429.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	391.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	103.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1042.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	365.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1133.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	350.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	280.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.6 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-coumaroyltriacetic acid lactone,2TMS,isomer #1	C[Si](C)(C)OC(C=CC1=CC=C(O[Si](C)(C)C)C=C1)=CC1=CC([O-])=CC(=O)O1	2969.4	Semi standard non polar	33892256
p-coumaroyltriacetic acid lactone,2TMS,isomer #1	C[Si](C)(C)OC(C=CC1=CC=C(O[Si](C)(C)C)C=C1)=CC1=CC([O-])=CC(=O)O1	2879.6	Standard non polar	33892256
p-coumaroyltriacetic acid lactone,2TMS,isomer #1	C[Si](C)(C)OC(C=CC1=CC=C(O[Si](C)(C)C)C=C1)=CC1=CC([O-])=CC(=O)O1	3068.2	Standard polar	33892256
p-coumaroyltriacetic acid lactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)=CC1=CC([O-])=CC(=O)O1	3499.8	Semi standard non polar	33892256
p-coumaroyltriacetic acid lactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)=CC1=CC([O-])=CC(=O)O1	3282.7	Standard non polar	33892256
p-coumaroyltriacetic acid lactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C=CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)=CC1=CC([O-])=CC(=O)O1	3193.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-coumaroyltriacetic acid lactone 10V, Negative-QTOF	splash10-004i-0190000000-726e110b953977a7422a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-coumaroyltriacetic acid lactone 20V, Negative-QTOF	splash10-002f-5290000000-5a134482a2f01c868616	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-coumaroyltriacetic acid lactone 40V, Negative-QTOF	splash10-0ar3-5960000000-57854277a2b1be21dff2	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB031079

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for p-coumaroyltriacetic acid lactone (HMDB0304447)

MOL for HMDB0304447 (p-coumaroyltriacetic acid lactone)

3D MOL for HMDB0304447 (p-coumaroyltriacetic acid lactone)

3D SDF for HMDB0304447 (p-coumaroyltriacetic acid lactone)

3D-SDF for HMDB0304447 (p-coumaroyltriacetic acid lactone)

PDB for HMDB0304447 (p-coumaroyltriacetic acid lactone)

3D PDB for HMDB0304447 (p-coumaroyltriacetic acid lactone)

SMILES for HMDB0304447 (p-coumaroyltriacetic acid lactone)

INCHI for HMDB0304447 (p-coumaroyltriacetic acid lactone)

Structure for HMDB0304447 (p-coumaroyltriacetic acid lactone)

3D Structure for HMDB0304447 (p-coumaroyltriacetic acid lactone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra