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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:47:38 UTC

Update Date

2022-03-07 02:56:54 UTC

HMDB ID

HMDB0041140

Secondary Accession Numbers

HMDB41140

Metabolite Identification

Common Name

Prenyl cis-caffeate

Description

Prenyl cis-caffeate 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. Based on a literature review very few articles have been published on Prenyl cis-caffeate.

Structure

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

HMDB0041140
     RDKit          3D
Prenyl cis-caffeate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.9411   -0.7610    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4779    0.6211    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1338    1.7179    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4869    0.8893   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8353   -0.2186   -1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -0.3592   -1.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    0.7018   -1.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    1.7683   -1.8079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111    0.6307   -1.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2827   -0.4845   -0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7020   -0.6075   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383   -1.8177    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -2.0334    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3756   -1.0445    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7215   -1.2658    0.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    0.1586   -0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.1378   -0.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    0.3510   -0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514   -1.4655    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8445   -0.8346    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2874   -1.1487   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1849    1.4473    1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5903    2.0075    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2357    2.5734    0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157    1.9059   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3187   -1.1692   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -0.0419   -2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.4683   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -1.3103   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.6209    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293   -2.9574    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4140   -0.5583    0.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6760    2.0294   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    1.2905   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
M  END

  Mrv0541 02241216492D          

 18 18  0  0  0  0            999 V2000
    1.7640    0.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422    0.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -0.6409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2878    0.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858    0.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858   -0.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4007   -1.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4007   -1.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -0.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    0.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224    0.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8442    0.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5660    0.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2878    0.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224    1.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8442    1.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5660    1.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2878    1.8439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041140

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O4/c1-10(2)7-8-18-14(17)6-4-11-3-5-12(15)13(16)9-11/h3-7,9,15-16H,8H2,1-2H3/b6-4+

> <INCHI_KEY>
TTYOHMFLCXENHR-GQCTYLIASA-N

> <FORMULA>
C14H16O4

> <MOLECULAR_WEIGHT>
248.2744

> <EXACT_MASS>
248.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.74437991648594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methylbut-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
3.2694290956666667

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612463352255247

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208618521642132

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283760878432916

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.909

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prenyl caffeate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041140
     RDKit          3D
Prenyl cis-caffeate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.9411   -0.7610    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4779    0.6211    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1338    1.7179    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4869    0.8893   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8353   -0.2186   -1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -0.3592   -1.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    0.7018   -1.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    1.7683   -1.8079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111    0.6307   -1.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2827   -0.4845   -0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7020   -0.6075   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383   -1.8177    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -2.0334    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3756   -1.0445    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7215   -1.2658    0.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    0.1586   -0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.1378   -0.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    0.3510   -0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514   -1.4655    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8445   -0.8346    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2874   -1.1487   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1849    1.4473    1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5903    2.0075    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2357    2.5734    0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157    1.9059   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3187   -1.1692   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -0.0419   -2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.4683   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -1.3103   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.6209    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293   -2.9574    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4140   -0.5583    0.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6760    2.0294   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    1.2905   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.293   1.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.945   0.301   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.945  -1.196   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.137   1.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.640   0.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.640  -1.346   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.748  -3.442   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.748  -1.945   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.598  -1.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.598   0.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.095   1.196   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.443   0.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.790   1.196   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.137   0.450   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.095   2.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.443   3.442   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.790   2.693   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.137   3.442   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5                                                            
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   13   16   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0041140
HETATM    1  C1  UNL     1      -4.941  -0.761   0.465  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.478   0.621   0.277  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.134   1.718   1.017  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.487   0.889  -0.542  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.835  -0.219  -1.280  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.466  -0.359  -1.015  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.621   0.702  -1.310  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.077   1.768  -1.808  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.811   0.631  -1.061  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.283  -0.484  -0.542  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.702  -0.608  -0.274  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.138  -1.818   0.278  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.454  -2.033   0.567  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.376  -1.044   0.313  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.722  -1.266   0.609  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.995   0.159  -0.228  1.00  0.00           C  
HETATM   17  O4  UNL     1       5.942   1.138  -0.475  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.648   0.351  -0.513  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.151  -1.465   0.804  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.845  -0.835   1.109  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.287  -1.149  -0.533  1.00  0.00           H  
HETATM   22  H4  UNL     1      -6.185   1.447   1.318  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.590   2.008   1.935  1.00  0.00           H  
HETATM   24  H6  UNL     1      -5.236   2.573   0.296  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.116   1.906  -0.708  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.319  -1.169  -1.021  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.039  -0.042  -2.362  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.433   1.468  -1.302  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.595  -1.310  -0.316  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.429  -2.621   0.491  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.829  -2.957   0.995  1.00  0.00           H  
HETATM   32  H14 UNL     1       7.414  -0.558   0.432  1.00  0.00           H  
HETATM   33  H15 UNL     1       5.676   2.029  -0.873  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.358   1.290  -0.934  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    4
CONECT    3   22   23   24
CONECT    4    5   25
CONECT    5    6   26   27
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   18
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   16
CONECT   15   32
CONECT   16   17   18   18
CONECT   17   33
CONECT   18   34
END

HMDB0041140
     RDKit          3D
Prenyl cis-caffeate
 34 34  0  0  0  0  0  0  0  0999 V2000
   -4.9411   -0.7610    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4779    0.6211    0.2771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1338    1.7179    1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4869    0.8893   -0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8353   -0.2186   -1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4659   -0.3592   -1.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    0.7018   -1.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    1.7683   -1.8079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111    0.6307   -1.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2827   -0.4845   -0.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7020   -0.6075   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1383   -1.8177    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -2.0334    0.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3756   -1.0445    0.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7215   -1.2658    0.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954    0.1586   -0.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9421    1.1378   -0.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6481    0.3510   -0.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1514   -1.4655    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8445   -0.8346    1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2874   -1.1487   -0.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1849    1.4473    1.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5903    2.0075    1.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2357    2.5734    0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1157    1.9059   -0.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3187   -1.1692   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -0.0419   -2.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.4683   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -1.3103   -0.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.6209    0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293   -2.9574    0.9955 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4140   -0.5583    0.4316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6760    2.0294   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581    1.2905   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Prenyl cis-caffeic acid	Generator
1,1-Dacae	HMDB
1,1-Dimethylallyl caffeic acid ester	HMDB
3-Methyl-2-butenyl caffeate	HMDB
Cinnamic acid, 3,4-dihydroxy-, 3-methyl-2-butenyl ester	HMDB
Isoprenyl caffeate	HMDB
Prenyl cafeate	HMDB
Prenyl caffeate	HMDB
3-Methyl-3-butenyl caffeate	MeSH, HMDB
Prenyl caffeic acid	Generator
Prenyl trans-caffeic acid	Generator

Chemical Formula

C₁₄H₁₆O₄

Average Molecular Weight

248.2744

Monoisotopic Molecular Weight

248.104859

IUPAC Name

3-methylbut-2-en-1-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

prenyl caffeate

CAS Registry Number

118971-61-2

SMILES

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

InChI Identifier

InChI=1S/C14H16O4/c1-10(2)7-8-18-14(17)6-4-11-3-5-12(15)13(16)9-11/h3-7,9,15-16H,8H2,1-2H3/b6-4+

InChI Key

TTYOHMFLCXENHR-GQCTYLIASA-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

hydroxycinnamic acid (CHEBI:8393 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041140)
Cell membrane (HMDB: HMDB0041140)

Source

Exogenous

Exogenous (HMDB: HMDB0041140)

Food

Food (HMDB: HMDB0041140)

Endogenous

Plant

Plant (HMDB: HMDB0041140)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0041140)

Biological role

Nutrient (HMDB: HMDB0041140)

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	169.3 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.24	ALOGPS
logP	3.27	ChemAxon
logS	-3.2	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	5	ChemAxon
Refractivity	70.91 m³·mol⁻¹	ChemAxon
Polarizability	26.74 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.079	30932474
DeepCCS	[M-H]-	157.721	30932474
DeepCCS	[M-2H]-	190.607	30932474
DeepCCS	[M+Na]+	166.173	30932474
AllCCS	[M+H]+	156.3	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	160.0	32859911
AllCCS	[M+Na-2H]-	160.1	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prenyl cis-caffeate	CC(C)=CCOC(=O)\C=C\C1=CC=C(O)C(O)=C1	3694.0	Standard polar	33892256
Prenyl cis-caffeate	CC(C)=CCOC(=O)\C=C\C1=CC=C(O)C(O)=C1	2199.0	Standard non polar	33892256
Prenyl cis-caffeate	CC(C)=CCOC(=O)\C=C\C1=CC=C(O)C(O)=C1	2271.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prenyl cis-caffeate,1TMS,isomer #1	CC(C)=CCOC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	2314.2	Semi standard non polar	33892256
Prenyl cis-caffeate,1TMS,isomer #2	CC(C)=CCOC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	2312.0	Semi standard non polar	33892256
Prenyl cis-caffeate,2TMS,isomer #1	CC(C)=CCOC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	2354.3	Semi standard non polar	33892256
Prenyl cis-caffeate,1TBDMS,isomer #1	CC(C)=CCOC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2584.1	Semi standard non polar	33892256
Prenyl cis-caffeate,1TBDMS,isomer #2	CC(C)=CCOC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2570.2	Semi standard non polar	33892256
Prenyl cis-caffeate,2TBDMS,isomer #1	CC(C)=CCOC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2845.7	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 - Prenyl cis-caffeate GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ti-7900000000-3ed0c0ad01e411fd28c8	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prenyl cis-caffeate GC-MS (2 TMS) - 70eV, Positive	splash10-016r-9056000000-1dbb4b42a01fde6d0dc2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prenyl cis-caffeate 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 - Prenyl cis-caffeate 10V, Positive-QTOF	splash10-00kb-6790000000-ed23dd50a310cc877094	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 20V, Positive-QTOF	splash10-014i-9510000000-7e53c3d2adbc9c894000	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 40V, Positive-QTOF	splash10-0gb9-9500000000-e519c212c410c3ccd505	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 10V, Negative-QTOF	splash10-01ot-3970000000-c837750f955bb0d9074f	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 20V, Negative-QTOF	splash10-01t9-2910000000-0817c9c23d196638f009	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 40V, Negative-QTOF	splash10-03di-5900000000-d36e2881a5dd8c672b4b	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 10V, Positive-QTOF	splash10-0292-5690000000-70fde5990c607025ee99	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 20V, Positive-QTOF	splash10-02t9-9600000000-34036ab3dda40672471e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 40V, Positive-QTOF	splash10-00kf-9800000000-dbd82a9abf3af08362ac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 10V, Negative-QTOF	splash10-004r-0900000000-aa4b7b780915083f2035	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 20V, Negative-QTOF	splash10-000i-1910000000-0f298984efbbcb02386c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prenyl cis-caffeate 40V, Negative-QTOF	splash10-000i-0900000000-9277fa58624c58db1048	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

Not Available

METLIN ID

Not Available

PubChem Compound

5281790

PDB ID

PWH

ChEBI ID

8393

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1588961

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Prenyl cis-caffeate (HMDB0041140)

MOL for HMDB0041140 (Prenyl cis-caffeate)

3D MOL for HMDB0041140 (Prenyl cis-caffeate)

3D SDF for HMDB0041140 (Prenyl cis-caffeate)

3D-SDF for HMDB0041140 (Prenyl cis-caffeate)

PDB for HMDB0041140 (Prenyl cis-caffeate)

3D PDB for HMDB0041140 (Prenyl cis-caffeate)

SMILES for HMDB0041140 (Prenyl cis-caffeate)

INCHI for HMDB0041140 (Prenyl cis-caffeate)

Structure for HMDB0041140 (Prenyl cis-caffeate)

3D Structure for HMDB0041140 (Prenyl cis-caffeate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra