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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:29 UTC

Update Date

2022-03-07 02:52:06 UTC

HMDB ID

HMDB0029293

Secondary Accession Numbers

HMDB29293

Metabolite Identification

Common Name

4-p-Coumaroyl-1,5-quinolactone

Description

4-p-Coumaroyl-1,5-quinolactone, also known as 4-coumaroylquinic acid lactone, belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Based on a literature review very few articles have been published on 4-p-Coumaroyl-1,5-quinolactone.

Structure

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

HMDB0029293
     RDKit          3D
4-p-Coumaroyl-1,5-quinolactone
 39 41  0  0  0  0  0  0  0  0999 V2000
    0.9510    0.7518   -2.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2744    0.5034   -1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    0.5823   -1.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250    0.3232   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706    0.3698   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9971    0.0756    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3800    0.1029    0.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1535    0.4348   -0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5446    0.4648   -0.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5589    0.7321   -1.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.6993   -1.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.1578   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.0786   -0.5699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7343   -1.3123   -0.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6378   -1.9790    0.3061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897   -1.4939    0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0194   -0.3971    1.6867 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4075   -0.8834    2.9050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139    0.4042    1.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7581    1.1092    0.4567 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1196    1.4634    0.3437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099    0.6399    1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1437    0.7573    1.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7243    0.8535   -2.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522    0.0514    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4307   -0.1949    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8741   -0.1296    1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1281   -0.3237   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1095    1.0003   -2.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7297    0.9364   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343    0.3371   -1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128   -1.8680   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -2.9178    0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -2.4635    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.5104    0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623   -0.1320    3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276    1.1062    2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8895   -0.2963    1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    1.9668    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 11  5  1  0
 20 13  1  0
 22 17  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  6
 14 32  1  6
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  1
M  END

Structure #1
  Mrv0541 02241212092D          

 23 25  0  0  1  0            999 V2000
   -0.0292   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0292   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -3.7838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3998   -4.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998   -5.0213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6853   -5.4338    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2549   -3.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689   -2.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2713   -4.2552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -3.1518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6853   -6.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7437   -5.4338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6777   -7.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3883   -7.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406   -7.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0481   -8.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7663   -8.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -9.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4922   -9.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2028   -9.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9211   -9.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952   -8.6891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770   -8.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  1  0  0  0
  3 10  1  6  0  0  0
  4  5  1  0  0  0  0
  5  9  1  1  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  6 11  1  6  0  0  0
  1 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 23  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029293

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O7/c17-10-4-1-9(2-5-10)3-6-13(19)23-14-11(18)7-16(21)8-12(14)22-15(16)20/h1-6,11-12,14,17-18,21H,7-8H2/b6-3+/t11-,12-,14-,16+/m1/s1

> <INCHI_KEY>
PZLNXMHSYFPCAE-OTCYKTEZSA-N

> <FORMULA>
C16H16O7

> <MOLECULAR_WEIGHT>
320.294

> <EXACT_MASS>
320.089602866

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.962364448446635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3R,4R,5R)-1,3-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.6995066883333331

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.179822561200126

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.397865033418228

> <JCHEM_PKA_STRONGEST_BASIC>
-3.246877410527289

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
77.76160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,5R)-1,3-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029293
     RDKit          3D
4-p-Coumaroyl-1,5-quinolactone
 39 41  0  0  0  0  0  0  0  0999 V2000
    0.9510    0.7518   -2.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2744    0.5034   -1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    0.5823   -1.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250    0.3232   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706    0.3698   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9971    0.0756    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3800    0.1029    0.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1535    0.4348   -0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5446    0.4648   -0.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5589    0.7321   -1.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.6993   -1.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.1578   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.0786   -0.5699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7343   -1.3123   -0.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6378   -1.9790    0.3061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897   -1.4939    0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0194   -0.3971    1.6867 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4075   -0.8834    2.9050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139    0.4042    1.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7581    1.1092    0.4567 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1196    1.4634    0.3437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099    0.6399    1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1437    0.7573    1.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7243    0.8535   -2.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522    0.0514    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4307   -0.1949    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8741   -0.1296    1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1281   -0.3237   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1095    1.0003   -2.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7297    0.9364   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343    0.3371   -1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128   -1.8680   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -2.9178    0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -2.4635    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.5104    0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623   -0.1320    3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276    1.1062    2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8895   -0.2963    1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    1.9668    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 11  5  1  0
 20 13  1  0
 22 17  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  6
 14 32  1  6
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.055  -9.373   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.055  -7.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.279  -7.063   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.613  -7.833   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.613  -9.373   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.279 -10.143   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.342  -5.883   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.555  -4.800   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.240  -7.943   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.289  -5.883   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.279 -11.683   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.388 -10.143   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.265 -13.189   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.591 -13.971   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.076 -13.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.090 -15.486   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.430 -16.244   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.445 -17.784   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.785 -18.542   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.112 -17.760   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.453 -18.517   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.098 -16.220   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.757 -15.462   0.000  0.00  0.00           C+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7   10                                             
CONECT    4    3    5                                                       
CONECT    5    4    9    6                                                  
CONECT    6    1    5   11                                                  
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    5    7                                                       
CONECT   10    3                                                            
CONECT   11    6   13                                                       
CONECT   12    1                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   17   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0029293
HETATM    1  O1  UNL     1       0.951   0.752  -2.796  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.274   0.503  -1.770  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.203   0.582  -1.805  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.925   0.323  -0.733  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.371   0.370  -0.655  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.997   0.076   0.530  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.380   0.103   0.668  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.153   0.435  -0.415  1.00  0.00           C  
HETATM    9  O2  UNL     1      -7.545   0.465  -0.286  1.00  0.00           O  
HETATM   10  C8  UNL     1      -5.559   0.732  -1.606  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.163   0.699  -1.726  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.905   0.158  -0.613  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.339   0.079  -0.570  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.734  -1.312  -0.266  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.638  -1.979   0.306  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.890  -1.494   0.672  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.019  -0.397   1.687  1.00  0.00           C  
HETATM   18  O5  UNL     1       4.408  -0.883   2.905  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.714   0.404   1.796  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.758   1.109   0.457  1.00  0.00           C  
HETATM   21  O6  UNL     1       4.120   1.463   0.344  1.00  0.00           O  
HETATM   22  C16 UNL     1       4.910   0.640   1.130  1.00  0.00           C  
HETATM   23  O7  UNL     1       6.144   0.757   1.327  1.00  0.00           O  
HETATM   24  H1  UNL     1      -1.724   0.854  -2.709  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.352   0.051   0.164  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.431  -0.195   1.424  1.00  0.00           H  
HETATM   27  H4  UNL     1      -5.874  -0.130   1.605  1.00  0.00           H  
HETATM   28  H5  UNL     1      -8.128  -0.324  -0.454  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.110   1.000  -2.494  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.730   0.936  -2.669  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.734   0.337  -1.584  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.913  -1.868  -1.234  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.973  -2.918   0.465  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.843  -2.464   1.210  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.819  -1.510   0.066  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.762  -0.132   3.444  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.828   1.106   2.642  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.890  -0.296   1.900  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.080   1.967   0.403  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6   11
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   10
CONECT    9   28
CONECT   10   11   11   29
CONECT   11   30
CONECT   12   13
CONECT   13   14   20   31
CONECT   14   15   16   32
CONECT   15   33
CONECT   16   17   34   35
CONECT   17   18   19   22
CONECT   18   36
CONECT   19   20   37   38
CONECT   20   21   39
CONECT   21   22
CONECT   22   23   23
END

HMDB0029293
     RDKit          3D
4-p-Coumaroyl-1,5-quinolactone
 39 41  0  0  0  0  0  0  0  0999 V2000
    0.9510    0.7518   -2.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2744    0.5034   -1.7704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025    0.5823   -1.8055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250    0.3232   -0.7326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3706    0.3698   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9971    0.0756    0.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3800    0.1029    0.6681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1535    0.4348   -0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5446    0.4648   -0.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5589    0.7321   -1.6064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1629    0.6993   -1.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050    0.1578   -0.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.0786   -0.5699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7343   -1.3123   -0.2658 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6378   -1.9790    0.3061 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8897   -1.4939    0.6720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0194   -0.3971    1.6867 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4075   -0.8834    2.9050 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7139    0.4042    1.7956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7581    1.1092    0.4567 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1196    1.4634    0.3437 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9099    0.6399    1.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1437    0.7573    1.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7243    0.8535   -2.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3522    0.0514    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4307   -0.1949    1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8741   -0.1296    1.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1281   -0.3237   -0.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1095    1.0003   -2.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7297    0.9364   -2.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343    0.3371   -1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128   -1.8680   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9728   -2.9178    0.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -2.4635    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8187   -1.5104    0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623   -0.1320    3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8276    1.1062    2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8895   -0.2963    1.9003 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    1.9668    0.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 11  5  1  0
 20 13  1  0
 22 17  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  6
 14 32  1  6
 15 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Coumaroyl-1,5-lactone	HMDB
4-Coumaroyl-1,5-quinide	HMDB
4-Coumaroylquinic acid lactone	HMDB
(1S,3R,4R,5R)-1,3-Dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acid	HMDB

Chemical Formula

C₁₆H₁₆O₇

Average Molecular Weight

320.294

Monoisotopic Molecular Weight

320.089602866

IUPAC Name

(1S,3R,4R,5R)-1,3-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

(1S,3R,4R,5R)-1,3-dihydroxy-7-oxo-6-oxabicyclo[3.2.1]octan-4-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H16O7/c17-10-4-1-9(2-5-10)3-6-13(19)23-14-11(18)7-16(21)8-12(14)22-15(16)20/h1-6,11-12,14,17-18,21H,7-8H2/b6-3+/t11-,12-,14-,16+/m1/s1

InChI Key

PZLNXMHSYFPCAE-OTCYKTEZSA-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
Coumaric acid or derivatives
Cinnamic acid ester
Caprolactone
Styrene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Oxepane
Phenol
Fatty acyl
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029293)
Cytoplasm (HMDB: HMDB0029293)

Source

Endogenous

Endogenous (HMDB: HMDB0029293)

Plant

Plant (HMDB: HMDB0029293)

Exogenous

Food

Food (HMDB: HMDB0029293)

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
Water Solubility	3.2 g/L	ALOGPS
logP	0.47	ALOGPS
logP	0.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.76 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	3	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]+	174.036	30932474
DeepCCS	[M-H]-	171.641	30932474
DeepCCS	[M-2H]-	204.897	30932474
DeepCCS	[M+Na]+	179.949	30932474
AllCCS	[M+H]+	174.9	32859911
AllCCS	[M+H-H2O]+	171.8	32859911
AllCCS	[M+NH4]+	177.8	32859911
AllCCS	[M+Na]+	178.7	32859911
AllCCS	[M-H]-	173.8	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	173.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-p-Coumaroyl-1,5-quinolactone	O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C=C1	4791.1	Standard polar	33892256
4-p-Coumaroyl-1,5-quinolactone	O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C=C1	2988.1	Standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone	O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)\C=C\C1=CC=C(O)C=C1	3164.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-p-Coumaroyl-1,5-quinolactone,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	2846.7	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,1TMS,isomer #2	C[Si](C)(C)O[C@@]12C[C@@H](O)[C@@H](OC(=O)/C=C/C3=CC=C(O)C=C3)[C@@H](C1)OC2=O	2899.8	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@]3(O)C[C@H]2OC3=O)C=C1	2911.7	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@]2(O[Si](C)(C)C)C[C@@H](OC2=O)[C@@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	2887.8	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H]2[C@H]3C[C@@](O)(C[C@H]2O[Si](C)(C)C)C(=O)O3)C=C1	2921.7	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@]3(O[Si](C)(C)C)C[C@H]2OC3=O)C=C1	2980.0	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H]2[C@H]3C[C@@](O[Si](C)(C)C)(C[C@H]2O[Si](C)(C)C)C(=O)O3)C=C1	2979.1	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@]2(O)C[C@@H](OC2=O)[C@@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	3089.7	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@]12C[C@@H](O)[C@@H](OC(=O)/C=C/C3=CC=C(O)C=C3)[C@@H](C1)OC2=O	3148.9	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@]3(O)C[C@H]2OC3=O)C=C1	3166.4	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@]2(O[Si](C)(C)C(C)(C)C)C[C@@H](OC2=O)[C@@H]1OC(=O)/C=C/C1=CC=C(O)C=C1	3363.5	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H]2[C@H]3C[C@@](O)(C[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)O3)C=C1	3399.4	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H]2[C@H](O)C[C@]3(O[Si](C)(C)C(C)(C)C)C[C@H]2OC3=O)C=C1	3472.3	Semi standard non polar	33892256
4-p-Coumaroyl-1,5-quinolactone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@H]2[C@H]3C[C@@](O[Si](C)(C)C(C)(C)C)(C[C@H]2O[Si](C)(C)C(C)(C)C)C(=O)O3)C=C1	3718.8	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 - 4-p-Coumaroyl-1,5-quinolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-7971000000-fd7c74a3df4f2e2bb737	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone GC-MS (3 TMS) - 70eV, Positive	splash10-01di-3723930000-40c0cac7181ece45fb81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 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 - 4-p-Coumaroyl-1,5-quinolactone 10V, Positive-QTOF	splash10-00dj-0917000000-29f8e654f5e402e60cfb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 20V, Positive-QTOF	splash10-052b-0911000000-3bda04e9ba873e16092a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 40V, Positive-QTOF	splash10-0a4j-2900000000-28d413349b1ff61021b9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 10V, Negative-QTOF	splash10-014i-0829000000-254f67f0cb401c58d11f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 20V, Negative-QTOF	splash10-0cka-0901000000-18f1a13c04cd5cf771df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 40V, Negative-QTOF	splash10-0005-2900000000-ebb30e782f67f1355e8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 10V, Positive-QTOF	splash10-00di-0309000000-402b82c9e011f3ec9e39	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 20V, Positive-QTOF	splash10-06dj-1923000000-dc510a9fdd2119041712	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 40V, Positive-QTOF	splash10-014i-2910000000-c794038a60a20ffa3af0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 10V, Negative-QTOF	splash10-014i-0109000000-604a00d22dcf9e4907b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 20V, Negative-QTOF	splash10-014i-0923000000-42f196a9d03aece69cf0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-p-Coumaroyl-1,5-quinolactone 40V, Negative-QTOF	splash10-014i-4920000000-cd99365e33d26b341bcb	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

548

FooDB ID

FDB000297

KNApSAcK ID

Not Available

Chemspider ID

30776764

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102210473

PDB ID

Not Available

ChEBI ID

175083

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

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Showing metabocard for 4-p-Coumaroyl-1,5-quinolactone (HMDB0029293)

MOL for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

3D MOL for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

3D SDF for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

3D-SDF for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

PDB for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

3D PDB for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

SMILES for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

INCHI for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

Structure for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

3D Structure for HMDB0029293 (4-p-Coumaroyl-1,5-quinolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra