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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:31:27 UTC

Update Date

2022-03-07 02:54:54 UTC

HMDB ID

HMDB0036387

Secondary Accession Numbers

HMDB36387

Metabolite Identification

Common Name

3-Phenylpropyl cinnamate

Description

3-Phenylpropyl cinnamate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 3-Phenylpropyl cinnamate is a sweet, apricot, and balsam tasting compound. Based on a literature review very few articles have been published on 3-Phenylpropyl cinnamate.

Structure

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

HMDB0036387
     RDKit          3D
3-Phenylpropyl cinnamate
 38 39  0  0  0  0  0  0  0  0999 V2000
    0.3122    0.2821   -2.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9786    0.5664   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.0598   -0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030    0.3237    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604   -0.1451    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448    0.2117    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4416   -0.2080    1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1089   -0.9940    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -1.3403   -0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1395   -0.9194   -0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4170    1.3409   -0.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    1.8705   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927    0.7686   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843    1.3703   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    0.3161   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245   -0.2063    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7954   -1.1888    0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2850   -1.6661   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186   -1.1758   -1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8454   -0.1913   -1.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779   -0.5560   -1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    0.9396    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    0.8211    2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750    0.0749    2.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1126   -1.3274    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9441   -1.9493   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570   -1.2227   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159    2.3751    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763    2.5971   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    0.1995   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8277    0.1411    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    1.9113    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    2.0959   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4349    0.1734    1.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1403   -1.5526    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0552   -2.4455   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1883   -1.5354   -2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881    0.1848   -2.3245 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061309062D          

 20 21  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  1  0  0  0  0
 14 13  2  0  0  0  0
 15  7  1  0  0  0  0
 16  8  2  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036387

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(OCCCC1=CC=CC=C1)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O2/c19-18(14-13-17-10-5-2-6-11-17)20-15-7-12-16-8-3-1-4-9-16/h1-6,8-11,13-14H,7,12,15H2/b14-13+

> <INCHI_KEY>
LYRAHIUDQRJGGZ-BUHFOSPRSA-N

> <FORMULA>
C18H18O2

> <MOLECULAR_WEIGHT>
266.3343

> <EXACT_MASS>
266.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.77825103228634

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenylpropyl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
4.973016636666666

> <ALOGPS_LOGS>
-5.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.8089721191714645

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
81.79759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.34e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenylpropyl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036387
     RDKit          3D
3-Phenylpropyl cinnamate
 38 39  0  0  0  0  0  0  0  0999 V2000
    0.3122    0.2821   -2.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9786    0.5664   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.0598   -0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030    0.3237    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604   -0.1451    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448    0.2117    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4416   -0.2080    1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1089   -0.9940    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -1.3403   -0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1395   -0.9194   -0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4170    1.3409   -0.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    1.8705   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927    0.7686   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843    1.3703   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    0.3161   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245   -0.2063    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7954   -1.1888    0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2850   -1.6661   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186   -1.1758   -1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8454   -0.1913   -1.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779   -0.5560   -1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    0.9396    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    0.8211    2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750    0.0749    2.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1126   -1.3274    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9441   -1.9493   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570   -1.2227   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159    2.3751    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763    2.5971   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    0.1995   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8277    0.1411    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    1.9113    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    2.0959   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4349    0.1734    1.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1403   -1.5526    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0552   -2.4455   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1883   -1.5354   -2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881    0.1848   -2.3245 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.006   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.673   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.006   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.339   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.339   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      17.338   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.004   3.080   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    8                                                       
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7   12   15                                                       
CONECT    8    3   16                                                       
CONECT    9    4   16                                                       
CONECT   10    5   17                                                       
CONECT   11    6   17                                                       
CONECT   12    7   16                                                       
CONECT   13   14   17                                                       
CONECT   14   13   18                                                       
CONECT   15    7   20                                                       
CONECT   16    8    9   12                                                  
CONECT   17   10   11   13                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0036387
HETATM    1  O1  UNL     1       0.312   0.282  -2.113  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.979   0.566  -1.098  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.343   0.060  -1.000  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.103   0.324   0.048  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.460  -0.145   0.210  1.00  0.00           C  
HETATM    6  C5  UNL     1       5.145   0.212   1.370  1.00  0.00           C  
HETATM    7  C6  UNL     1       6.442  -0.208   1.576  1.00  0.00           C  
HETATM    8  C7  UNL     1       7.109  -0.994   0.645  1.00  0.00           C  
HETATM    9  C8  UNL     1       6.434  -1.340  -0.489  1.00  0.00           C  
HETATM   10  C9  UNL     1       5.140  -0.919  -0.691  1.00  0.00           C  
HETATM   11  O2  UNL     1       0.417   1.341  -0.108  1.00  0.00           O  
HETATM   12  C10 UNL     1      -0.890   1.870  -0.117  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.893   0.769  -0.170  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.284   1.370  -0.174  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.327   0.316  -0.225  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.825  -0.206   0.964  1.00  0.00           C  
HETATM   17  C15 UNL     1      -5.795  -1.189   0.951  1.00  0.00           C  
HETATM   18  C16 UNL     1      -6.285  -1.666  -0.241  1.00  0.00           C  
HETATM   19  C17 UNL     1      -5.819  -1.176  -1.422  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.845  -0.191  -1.385  1.00  0.00           C  
HETATM   21  H1  UNL     1       2.778  -0.556  -1.795  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.624   0.940   0.810  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.687   0.821   2.137  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.975   0.075   2.489  1.00  0.00           H  
HETATM   25  H5  UNL     1       8.113  -1.327   0.788  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.944  -1.949  -1.216  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.657  -1.223  -1.604  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.016   2.375   0.884  1.00  0.00           H  
HETATM   29  H9  UNL     1      -0.976   2.597  -0.936  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.755   0.199  -1.094  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.828   0.141   0.741  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.414   1.911   0.788  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.403   2.096  -0.985  1.00  0.00           H  
HETATM   34  H14 UNL     1      -4.435   0.173   1.921  1.00  0.00           H  
HETATM   35  H15 UNL     1      -6.140  -1.553   1.907  1.00  0.00           H  
HETATM   36  H16 UNL     1      -7.055  -2.446  -0.245  1.00  0.00           H  
HETATM   37  H17 UNL     1      -6.188  -1.535  -2.367  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.488   0.185  -2.325  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   21
CONECT    4    5   22
CONECT    5    6    6   10
CONECT    6    7   23
CONECT    7    8    8   24
CONECT    8    9   25
CONECT    9   10   10   26
CONECT   10   27
CONECT   11   12
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   15   32   33
CONECT   15   16   16   20
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   38
END

HMDB0036387
     RDKit          3D
3-Phenylpropyl cinnamate
 38 39  0  0  0  0  0  0  0  0999 V2000
    0.3122    0.2821   -2.1129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9786    0.5664   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    0.0598   -0.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030    0.3237    0.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604   -0.1451    0.2098 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448    0.2117    1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4416   -0.2080    1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1089   -0.9940    0.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4343   -1.3403   -0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1395   -0.9194   -0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4170    1.3409   -0.1084 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8900    1.8705   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8927    0.7686   -0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843    1.3703   -0.1736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    0.3161   -0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245   -0.2063    0.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7954   -1.1888    0.9514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2850   -1.6661   -0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186   -1.1758   -1.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8454   -0.1913   -1.3850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7779   -0.5560   -1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237    0.9396    0.8105 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    0.8211    2.1370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750    0.0749    2.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1126   -1.3274    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9441   -1.9493   -1.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570   -1.2227   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159    2.3751    0.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763    2.5971   -0.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7550    0.1995   -1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8277    0.1411    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    1.9113    0.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4026    2.0959   -0.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4349    0.1734    1.9210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1403   -1.5526    1.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0552   -2.4455   -0.2454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1883   -1.5354   -2.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4881    0.1848   -2.3245 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  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 10  5  1  0
 20 15  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Phenylpropyl cinnamic acid	Generator
2-Propenoic acid, 3-phenyl-, 3-phenylpropyl ester	HMDB
3-Phenyl-2-propenoic acid 3-phenylpropyl ester	HMDB
3-Phenylpropyl 3-phenyl-2-propenoate	HMDB
3-Phenylpropyl beta-phenylacrylate	HMDB
Cinnamic acid, 3-phenylpropyl ester	HMDB
Cinnamic acid, 3-phenylpropyl ester (7ci,8ci)	HMDB
FEMA 2894	HMDB
Hydrocinnamyl 3-phenylpropenoate	HMDB
Hydrocinnamyl cinnamate	HMDB
Phenylpropyl cinnamate	HMDB
3-Phenylpropyl (2E)-3-phenylprop-2-enoic acid	Generator
3-Phenylpropyl cinnamate	MeSH

Chemical Formula

C₁₈H₁₈O₂

Average Molecular Weight

266.3343

Monoisotopic Molecular Weight

266.13067982

IUPAC Name

3-phenylpropyl (2E)-3-phenylprop-2-enoate

Traditional Name

3-phenylpropyl (2E)-3-phenylprop-2-enoate

CAS Registry Number

122-68-9

SMILES

O=C(OCCCC1=CC=CC=C1)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H18O2/c19-18(14-13-17-10-5-2-6-11-17)20-15-7-12-16-8-3-1-4-9-16/h1-6,8-11,13-14H,7,12,15H2/b14-13+

InChI Key

LYRAHIUDQRJGGZ-BUHFOSPRSA-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
Benzenoid
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0036387)
Cell membrane (HMDB: HMDB0036387)

Source

Exogenous

Exogenous (HMDB: HMDB0036387)

Food

Food (HMDB: HMDB0036387)

Endogenous

Plant

Plant (HMDB: HMDB0036387)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036387)

Biological role

Nutrient (HMDB: HMDB0036387)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	300.00 to 301.00 °C. @ 0.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.94 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.023 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00053 g/L	ALOGPS
logP	4.56	ALOGPS
logP	4.97	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.8 m³·mol⁻¹	ChemAxon
Polarizability	30.78 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]+	166.706	31661259
DarkChem	[M-H]-	162.733	31661259
DeepCCS	[M+H]+	164.074	30932474
DeepCCS	[M-H]-	161.716	30932474
DeepCCS	[M-2H]-	194.602	30932474
DeepCCS	[M+Na]+	170.167	30932474
AllCCS	[M+H]+	164.0	32859911
AllCCS	[M+H-H2O]+	160.3	32859911
AllCCS	[M+NH4]+	167.4	32859911
AllCCS	[M+Na]+	168.4	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	168.9	32859911
AllCCS	[M+HCOO]-	168.7	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.	10.06 minutes	32390414
Predicted by Siyang on May 30, 2022	18.7165 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3130.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	611.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	240.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	334.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	454.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	864.4 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	853.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1830.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	708.4 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	1642.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	493.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	404.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	428.6 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Phenylpropyl cinnamate	O=C(OCCCC1=CC=CC=C1)\C=C\C1=CC=CC=C1	3149.5	Standard polar	33892256
3-Phenylpropyl cinnamate	O=C(OCCCC1=CC=CC=C1)\C=C\C1=CC=CC=C1	2157.1	Standard non polar	33892256
3-Phenylpropyl cinnamate	O=C(OCCCC1=CC=CC=C1)\C=C\C1=CC=CC=C1	2298.6	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 - 3-Phenylpropyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-6900000000-29ef2574b1f9d44c6f78	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Phenylpropyl cinnamate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Phenylpropyl 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 - 3-Phenylpropyl cinnamate 10V, Positive-QTOF	splash10-014i-0390000000-aefb892b28da12e790ed	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 20V, Positive-QTOF	splash10-014i-1910000000-c6188b4b969cc7be01a0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 40V, Positive-QTOF	splash10-0fr6-8910000000-f8bcb9b2396fc02dc307	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 10V, Negative-QTOF	splash10-014i-0490000000-79b062077075dc8f8b17	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 20V, Negative-QTOF	splash10-0002-0910000000-206f7d2a25cb6851ef0d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 40V, Negative-QTOF	splash10-0fba-0900000000-76be13d2ea7c6413245b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 10V, Positive-QTOF	splash10-014i-2690000000-15f3102d79ac3282ea6d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 20V, Positive-QTOF	splash10-014i-2930000000-7151edc6cb6720dd9915	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 40V, Positive-QTOF	splash10-0006-9400000000-2266d586dc9c5efd0afd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 10V, Negative-QTOF	splash10-014i-0090000000-49b99ae65a6ecc65d875	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 20V, Negative-QTOF	splash10-0gb9-1960000000-aa7b655d7903f6f6228b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl cinnamate 40V, Negative-QTOF	splash10-0fb9-9500000000-330c1d67c9c180760158	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

FDB015265

KNApSAcK ID

Not Available

Chemspider ID

4478589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320530

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1002221

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 3-Phenylpropyl cinnamate (HMDB0036387)

MOL for HMDB0036387 (3-Phenylpropyl cinnamate)

3D MOL for HMDB0036387 (3-Phenylpropyl cinnamate)

3D SDF for HMDB0036387 (3-Phenylpropyl cinnamate)

3D-SDF for HMDB0036387 (3-Phenylpropyl cinnamate)

PDB for HMDB0036387 (3-Phenylpropyl cinnamate)

3D PDB for HMDB0036387 (3-Phenylpropyl cinnamate)

SMILES for HMDB0036387 (3-Phenylpropyl cinnamate)

INCHI for HMDB0036387 (3-Phenylpropyl cinnamate)

Structure for HMDB0036387 (3-Phenylpropyl cinnamate)

3D Structure for HMDB0036387 (3-Phenylpropyl cinnamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra