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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 17:03:57 UTC

Update Date

2021-09-23 17:03:57 UTC

HMDB ID

HMDB0302344

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Caffeic acid ester

Description

Caffeic acid ester, also known as caffeic acid phenethyl ester or cape, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Caffeic acid ester is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Caffeic acid ester can be found in corn, flaxseed, oat, and peach, which makes caffeic acid ester a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302344
     RDKit          3D
Caffeic acid ester
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.7547   -1.6277   -1.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551   -0.9916   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -0.9976   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.3152    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -0.2971   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135   -0.9508   -1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -0.8900   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3396   -0.1432   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7164   -0.0592   -0.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6257    0.5433    0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    1.2849    1.8314 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2543    0.4583    0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199   -0.2734    0.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -0.1839    0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609    0.4102   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1782    0.4444   -0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015    1.5384    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0268    1.6194    0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8178    0.5348    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220   -0.5921   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9854   -0.6259   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445   -1.5810   -1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6187    0.2412    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8028   -1.5396   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.4094   -1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2593   -0.5349   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8419    1.7883    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7227    0.9999    1.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1509    0.5167    1.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -1.1416    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865   -0.1778   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4182    1.4649   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729    2.3952    0.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4576    2.4682    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8640    0.5692    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9635   -1.4334   -0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5808   -1.5121   -1.0190 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12  5  1  0
 21 16  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

  Mrv0541 05041410072D          

 23 24  0  0  0  0            999 V2000
   -5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    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
   -2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
 11 10  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17  9  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  2  0  0  0  0
 21 11  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  1  0  0  0  0
 23  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302344

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+

> <INCHI_KEY>
SWUARLUWKZWEBQ-VQHVLOKHSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.3065

> <EXACT_MASS>
284.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.743755265936063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-phenylethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
3.9213173283333336

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612490717820709

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208642931081249

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283759959158108

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
81.15839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caffeic acid phenethyl ester

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302344
     RDKit          3D
Caffeic acid ester
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.7547   -1.6277   -1.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551   -0.9916   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -0.9976   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.3152    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -0.2971   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135   -0.9508   -1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -0.8900   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3396   -0.1432   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7164   -0.0592   -0.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6257    0.5433    0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    1.2849    1.8314 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2543    0.4583    0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199   -0.2734    0.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -0.1839    0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609    0.4102   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1782    0.4444   -0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015    1.5384    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0268    1.6194    0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8178    0.5348    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220   -0.5921   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9854   -0.6259   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445   -1.5810   -1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6187    0.2412    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8028   -1.5396   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.4094   -1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2593   -0.5349   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8419    1.7883    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7227    0.9999    1.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1509    0.5167    1.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -1.1416    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865   -0.1778   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4182    1.4649   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729    2.3952    0.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4576    2.4682    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8640    0.5692    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9635   -1.4334   -0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5808   -1.5121   -1.0190 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12  5  1  0
 21 16  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   13                                                       
CONECT    5    3   13                                                       
CONECT    6    8   14                                                       
CONECT    7    9   14   22                                                  
CONECT    8    6   15                                                       
CONECT    9    7   17   23                                                  
CONECT   10   11   13                                                       
CONECT   11   10   21                                                       
CONECT   12   14   16                                                       
CONECT   13    4    5   10                                                  
CONECT   14    6    7   12                                                  
CONECT   15    8   16   18                                                  
CONECT   16   12   15   19                                                  
CONECT   17    9   20   21                                                  
CONECT   18   15                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   11   17                                                       
CONECT   22    7                                                            
CONECT   23    9                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0302344
HETATM    1  O1  UNL     1      -0.755  -1.628  -1.494  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.055  -0.992  -0.697  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.412  -0.998  -0.827  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.135  -0.315   0.030  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.578  -0.297  -0.066  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.313  -0.951  -1.006  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.700  -0.890  -1.040  1.00  0.00           C  
HETATM    8  C7  UNL     1       6.340  -0.143  -0.089  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.716  -0.059  -0.091  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.626   0.543   0.894  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.337   1.285   1.831  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.254   0.458   0.894  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.620  -0.273   0.316  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.989  -0.184   0.550  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.761   0.410  -0.620  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.178   0.444  -0.237  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.702   1.538   0.394  1.00  0.00           C  
HETATM   18  C14 UNL     1      -6.027   1.619   0.775  1.00  0.00           C  
HETATM   19  C15 UNL     1      -6.818   0.535   0.488  1.00  0.00           C  
HETATM   20  C16 UNL     1      -6.322  -0.592  -0.151  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.985  -0.626  -0.513  1.00  0.00           C  
HETATM   22  H1  UNL     1       1.845  -1.581  -1.648  1.00  0.00           H  
HETATM   23  H2  UNL     1       1.619   0.241   0.821  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.803  -1.540  -1.755  1.00  0.00           H  
HETATM   25  H4  UNL     1       6.261  -1.409  -1.785  1.00  0.00           H  
HETATM   26  H5  UNL     1       8.259  -0.535  -0.776  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.842   1.788   2.549  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.723   1.000   1.666  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.151   0.517   1.409  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.457  -1.142   0.847  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.586  -0.178  -1.552  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.418   1.465  -0.738  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.073   2.395   0.620  1.00  0.00           H  
HETATM   34  H13 UNL     1      -6.458   2.468   1.271  1.00  0.00           H  
HETATM   35  H14 UNL     1      -7.864   0.569   0.775  1.00  0.00           H  
HETATM   36  H15 UNL     1      -6.964  -1.433  -0.366  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.581  -1.512  -1.019  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6    6   12
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   12   12
CONECT   11   27
CONECT   12   28
CONECT   13   14
CONECT   14   15   29   30
CONECT   15   16   31   32
CONECT   16   17   17   21
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20   35
CONECT   20   21   21   36
CONECT   21   37
END

HMDB0302344
     RDKit          3D
Caffeic acid ester
 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.7547   -1.6277   -1.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551   -0.9916   -0.6970 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123   -0.9976   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1349   -0.3152    0.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5782   -0.2971   -0.0659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135   -0.9508   -1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -0.8900   -1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3396   -0.1432   -0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7164   -0.0592   -0.0907 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6257    0.5433    0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3366    1.2849    1.8314 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2543    0.4583    0.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6199   -0.2734    0.3157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9894   -0.1839    0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609    0.4102   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1782    0.4444   -0.2370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015    1.5384    0.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0268    1.6194    0.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8178    0.5348    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220   -0.5921   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9854   -0.6259   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445   -1.5810   -1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6187    0.2412    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8028   -1.5396   -1.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2612   -1.4094   -1.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2593   -0.5349   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8419    1.7883    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7227    0.9999    1.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1509    0.5167    1.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -1.1416    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5865   -0.1778   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4182    1.4649   -0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729    2.3952    0.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4576    2.4682    1.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8640    0.5692    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9635   -1.4334   -0.3656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5808   -1.5121   -1.0190 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 12  5  1  0
 21 16  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylate	ChEBI
2-Phenylethyl caffeate	ChEBI
Caffeic acid phenethyl ester	ChEBI
CAPE	ChEBI
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)acrylic acid	Generator
2-Phenylethyl caffeic acid	Generator
Caffeate phenethyl ester	Generator
Phenethyl caffeic acid	Generator
CAPE compound	MeSH
CAPEEE	MeSH
Caffeic acid phenyl ester	MeSH
Phenyl caffeate	MeSH
Caffeate ester	Generator
Phenethyl caffeate	MeSH

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.3065

Monoisotopic Molecular Weight

284.104859

IUPAC Name

2-phenylethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

caffeic acid phenethyl ester

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+

InChI Key

SWUARLUWKZWEBQ-VQHVLOKHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alkyl caffeate ester (CHEBI:8062 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302344)

Food

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Fruit

Drupe

Peach (FooDB: FOOD00149)

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	3.65	ALOGPS
logP	3.92	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	81.16 m³·mol⁻¹	ChemAxon
Polarizability	30.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	166.337	32859911
AllCCS	[M+H-H2O]+	162.802	32859911
AllCCS	[M+Na]+	170.558	32859911
AllCCS	[M+NH4]+	169.615	32859911
AllCCS	[M-H]-	169.879	32859911
AllCCS	[M+Na-2H]-	169.402	32859911
AllCCS	[M+HCOO]-	169.005	32859911
DeepCCS	[M+H]+	169.353	30932474
DeepCCS	[M-H]-	166.995	30932474
DeepCCS	[M-2H]-	201.18	30932474
DeepCCS	[M+Na]+	176.301	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Caffeic acid ester GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-3900000000-62548c49c8e49f1179de	2017-07-27	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 - Caffeic acid ester 10V, Positive-QTOF	splash10-000i-0970000000-3ead949a4b33ddf83a47	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 20V, Positive-QTOF	splash10-0bt9-0910000000-edce37422aca70f6e004	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 40V, Positive-QTOF	splash10-0a4i-5900000000-7a448f8c4402b3836f79	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 10V, Negative-QTOF	splash10-01q9-0970000000-65a7d0af8a3310ebf8f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 20V, Negative-QTOF	splash10-03fr-0910000000-4bdc18e559b25d305c03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 40V, Negative-QTOF	splash10-03g3-6900000000-8270b803edf414dd7802	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 10V, Positive-QTOF	splash10-000i-0390000000-ce73056df2bcf6d3c1f4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 20V, Positive-QTOF	splash10-06ri-1930000000-dfff28b8878e5d52b8c9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 40V, Positive-QTOF	splash10-0a4r-2900000000-c94cd4513f24a8bba089	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 10V, Negative-QTOF	splash10-003r-0690000000-3387ce31518f152b80ad	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 20V, Negative-QTOF	splash10-0019-2940000000-2bcbc9c2181629ef7a4b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caffeic acid ester 40V, Negative-QTOF	splash10-0019-2900000000-4a20e5d83c4c38f6530d	2021-10-21	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caffeic_acid_phenethyl_ester

METLIN ID

Not Available

PubChem Compound

5281787

PDB ID

Not Available

ChEBI ID

8062

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1667051

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Caffeic acid ester (HMDB0302344)

MOL for HMDB0302344 (Caffeic acid ester)

3D MOL for HMDB0302344 (Caffeic acid ester)

3D SDF for HMDB0302344 (Caffeic acid ester)

3D-SDF for HMDB0302344 (Caffeic acid ester)

PDB for HMDB0302344 (Caffeic acid ester)

3D PDB for HMDB0302344 (Caffeic acid ester)

SMILES for HMDB0302344 (Caffeic acid ester)

INCHI for HMDB0302344 (Caffeic acid ester)

Structure for HMDB0302344 (Caffeic acid ester)

3D Structure for HMDB0302344 (Caffeic acid ester)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra