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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:14:55 UTC

Update Date

2022-03-07 02:54:49 UTC

HMDB ID

HMDB0036189

Secondary Accession Numbers

HMDB36189

Metabolite Identification

Common Name

Tetrahydrofurfuryl cinnamate

Description

Tetrahydrofurfuryl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. Tetrahydrofurfuryl cinnamate is a sweet, balsam, and cortex tasting compound. Based on a literature review a significant number of articles have been published on Tetrahydrofurfuryl cinnamate.

Structure

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

HMDB0036189
     RDKit          3D
Tetrahydrofurfuryl cinnamate
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.8369    0.8786   -2.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806    0.7921   -1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363    0.3827   -1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959    0.2670   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -0.1287    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023   -0.4370   -1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3373   -0.8122   -0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8755   -0.8838    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505   -0.5716    1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582   -0.2106    1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    1.0754   -0.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3344    1.4670   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2718    0.4325   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -0.8281    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4467   -0.9248    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9685    0.5033    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5785    0.8476   -0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    0.1701   -2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232    0.4933    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5846   -0.3821   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9696   -1.0524   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -1.1751    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797   -0.6292    2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329    0.0281    2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566    2.3893   -0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858    1.6560    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625    0.2043   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8979   -1.7193   -0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059   -0.7550    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -1.1431    1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1190   -1.6136    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    1.1635    1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0769    0.5159    0.7209 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
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 10  5  1  0
 17 13  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
M  END


  Mrv0541 05061308562D          

 17 18  0  0  0  0            999 V2000
    2.7512    5.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    6.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7360   -0.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    5.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9910    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110   -0.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    3.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6561    0.6910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    2.4134    0.0000 O   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
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  4  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036189

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(OCC1CCCO1)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O3/c15-14(17-11-13-7-4-10-16-13)9-8-12-5-2-1-3-6-12/h1-3,5-6,8-9,13H,4,7,10-11H2/b9-8+

> <INCHI_KEY>
QCMSQCLNALBZOD-CMDGGOBGSA-N

> <FORMULA>
C14H16O3

> <MOLECULAR_WEIGHT>
232.275

> <EXACT_MASS>
232.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.78070278664615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
oxolan-2-ylmethyl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.9339026776666657

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.159780700877198

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
66.08370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxolan-2-ylmethyl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036189
     RDKit          3D
Tetrahydrofurfuryl cinnamate
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.8369    0.8786   -2.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806    0.7921   -1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363    0.3827   -1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959    0.2670   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -0.1287    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023   -0.4370   -1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3373   -0.8122   -0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8755   -0.8838    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505   -0.5716    1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582   -0.2106    1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    1.0754   -0.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3344    1.4670   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2718    0.4325   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -0.8281    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4467   -0.9248    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9685    0.5033    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5785    0.8476   -0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    0.1701   -2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232    0.4933    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5846   -0.3821   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9696   -1.0524   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -1.1751    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797   -0.6292    2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329    0.0281    2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566    2.3893   -0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858    1.6560    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625    0.2043   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8979   -1.7193   -0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059   -0.7550    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -1.1431    1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1190   -1.6136    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    1.1635    1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0769    0.5159    0.7209 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
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 10  5  1  0
 17 13  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.136  10.665   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.136   9.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.469  11.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.574  -0.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.469   8.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.803  10.665   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.050   1.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.137   8.355   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.137   6.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.034  -0.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.804   3.735   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.803   9.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.804   2.195   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.470   6.045   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.804   6.815   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.558   1.290   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.470   4.505   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    7   10                                                       
CONECT    5    2   12                                                       
CONECT    6    3   12                                                       
CONECT    7    4   13                                                       
CONECT    8    9   12                                                       
CONECT    9    8   14                                                       
CONECT   10    4   16                                                       
CONECT   11   13   17                                                       
CONECT   12    5    6    8                                                  
CONECT   13    7   11   16                                                  
CONECT   14    9   15   17                                                  
CONECT   15   14                                                            
CONECT   16   10   13                                                       
CONECT   17   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036189
HETATM    1  O1  UNL     1      -0.837   0.879  -2.370  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.281   0.792  -1.248  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.136   0.383  -1.211  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.796   0.267  -0.077  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.187  -0.129   0.051  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.002  -0.437  -1.008  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.337  -0.812  -0.816  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.875  -0.884   0.447  1.00  0.00           C  
HETATM    9  C8  UNL     1       5.050  -0.572   1.523  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.758  -0.211   1.305  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.995   1.075  -0.122  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.334   1.467  -0.073  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.272   0.432  -0.661  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.130  -0.828   0.135  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.447  -0.925   0.844  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.969   0.503   0.686  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.578   0.848  -0.596  1.00  0.00           O  
HETATM   18  H1  UNL     1       1.656   0.170  -2.129  1.00  0.00           H  
HETATM   19  H2  UNL     1       1.223   0.493   0.814  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.585  -0.382  -1.999  1.00  0.00           H  
HETATM   21  H4  UNL     1       5.970  -1.052  -1.656  1.00  0.00           H  
HETATM   22  H5  UNL     1       6.917  -1.175   0.617  1.00  0.00           H  
HETATM   23  H6  UNL     1       5.480  -0.629   2.523  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.133   0.028   2.152  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.457   2.389  -0.677  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.586   1.656   0.986  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.962   0.204  -1.715  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.898  -1.719  -0.482  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.306  -0.755   0.891  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.348  -1.143   1.909  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.119  -1.614   0.299  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.510   1.164   1.431  1.00  0.00           H  
HETATM   33  H16 UNL     1      -6.077   0.516   0.721  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   18
CONECT    4    5   19
CONECT    5    6    6   10
CONECT    6    7   20
CONECT    7    8    8   21
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   24
CONECT   11   12
CONECT   12   13   25   26
CONECT   13   14   17   27
CONECT   14   15   28   29
CONECT   15   16   30   31
CONECT   16   17   32   33
END

HMDB0036189
     RDKit          3D
Tetrahydrofurfuryl cinnamate
 33 34  0  0  0  0  0  0  0  0999 V2000
   -0.8369    0.8786   -2.3695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2806    0.7921   -1.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363    0.3827   -1.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959    0.2670   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867   -0.1287    0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0023   -0.4370   -1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3373   -0.8122   -0.8162 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8755   -0.8838    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0505   -0.5716    1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582   -0.2106    1.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951    1.0754   -0.1219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3344    1.4670   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2718    0.4325   -0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -0.8281    0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4467   -0.9248    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9685    0.5033    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5785    0.8476   -0.5960 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6557    0.1701   -2.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232    0.4933    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5846   -0.3821   -1.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9696   -1.0524   -1.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -1.1751    0.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4797   -0.6292    2.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329    0.0281    2.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566    2.3893   -0.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5858    1.6560    0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625    0.2043   -1.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8979   -1.7193   -0.4819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3059   -0.7550    0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3481   -1.1431    1.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1190   -1.6136    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5102    1.1635    1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0769    0.5159    0.7209 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
  9 10  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 10  5  1  0
 17 13  1  0
  3 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tetrahydrofurfuryl cinnamic acid	Generator
FEMA 3320	HMDB
Oxolan-2-ylmethyl 3-phenylprop-2-enoate	HMDB
(Oxolan-2-yl)methyl (2E)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₁₄H₁₆O₃

Average Molecular Weight

232.275

Monoisotopic Molecular Weight

232.109944378

IUPAC Name

oxolan-2-ylmethyl (2E)-3-phenylprop-2-enoate

Traditional Name

oxolan-2-ylmethyl (2E)-3-phenylprop-2-enoate

CAS Registry Number

65505-25-1

SMILES

O=C(OCC1CCCO1)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H16O3/c15-14(17-11-13-7-4-10-16-13)9-8-12-5-2-1-3-6-12/h1-3,5-6,8-9,13H,4,7,10-11H2/b9-8+

InChI Key

QCMSQCLNALBZOD-CMDGGOBGSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0036189)
Cell membrane (HMDB: HMDB0036189)

Source

Exogenous

Exogenous (HMDB: HMDB0036189)

Food

Food (HMDB: HMDB0036189)

Endogenous

Plant

Plant (HMDB: HMDB0036189)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036189)

Biological role

Nutrient (HMDB: HMDB0036189)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	390.00 to 391.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	102.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.211 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.93	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	66.08 m³·mol⁻¹	ChemAxon
Polarizability	25.78 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.917	31661259
DarkChem	[M-H]-	153.616	31661259
DeepCCS	[M+H]+	154.114	30932474
DeepCCS	[M-H]-	151.756	30932474
DeepCCS	[M-2H]-	185.025	30932474
DeepCCS	[M+Na]+	160.207	30932474
AllCCS	[M+H]+	154.3	32859911
AllCCS	[M+H-H2O]+	150.3	32859911
AllCCS	[M+NH4]+	158.0	32859911
AllCCS	[M+Na]+	159.1	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	158.0	32859911
AllCCS	[M+HCOO]-	158.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.3 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0409 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2634.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	471.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	186.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	250.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	668.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	713.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1422.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	498.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1395.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	373.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	410.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydrofurfuryl cinnamate	O=C(OCC1CCCO1)\C=C\C1=CC=CC=C1	2762.5	Standard polar	33892256
Tetrahydrofurfuryl cinnamate	O=C(OCC1CCCO1)\C=C\C1=CC=CC=C1	1873.3	Standard non polar	33892256
Tetrahydrofurfuryl cinnamate	O=C(OCC1CCCO1)\C=C\C1=CC=CC=C1	2022.6	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 - Tetrahydrofurfuryl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ffx-9410000000-07cc54c9a2c70c534661	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrofurfuryl cinnamate 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 - Tetrahydrofurfuryl cinnamate 10V, Positive-QTOF	splash10-001i-7790000000-1dbec697c1fe29131b85	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 20V, Positive-QTOF	splash10-0019-9710000000-4cdbd2e5a9af45ad3861	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 40V, Positive-QTOF	splash10-0kal-9500000000-5886b267c886b0a30677	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 10V, Negative-QTOF	splash10-003s-0940000000-cad5e8535e61cd2856ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 20V, Negative-QTOF	splash10-002b-2900000000-278f617184fe7939bf97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 40V, Negative-QTOF	splash10-0fba-3900000000-9928262dc2c45f763399	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 10V, Positive-QTOF	splash10-001i-0590000000-aad6be2d579043c533a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 20V, Positive-QTOF	splash10-0f89-2920000000-bda41313e59704043edd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 40V, Positive-QTOF	splash10-0udr-6900000000-c30f1e787c14a3e03199	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 10V, Negative-QTOF	splash10-001i-3690000000-71fe923045836915d6cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 20V, Negative-QTOF	splash10-0udi-1920000000-70e2ac5e7853e3dec5c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl cinnamate 40V, Negative-QTOF	splash10-0fb9-9500000000-7251ed6f2cee33036dba	2021-09-22	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

FDB015043

KNApSAcK ID

Not Available

Chemspider ID

4855215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6232217

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035861

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 Tetrahydrofurfuryl cinnamate (HMDB0036189)

MOL for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

3D MOL for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

3D SDF for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

3D-SDF for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

PDB for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

3D PDB for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

SMILES for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

INCHI for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

Structure for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

3D Structure for HMDB0036189 (Tetrahydrofurfuryl cinnamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra