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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:59:15 UTC

Update Date

2022-03-07 02:56:58 UTC

HMDB ID

HMDB0041319

Secondary Accession Numbers

HMDB41319

Metabolite Identification

Common Name

Cinnamyl anthranilate

Description

Cinnamyl anthranilate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Cinnamyl anthranilate is a balsam, fruity, and grape tasting compound. Based on a literature review very few articles have been published on Cinnamyl anthranilate.

Structure

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

HMDB0041319
     RDKit          3D
Cinnamyl anthranilate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.0418    2.0007   -0.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464    0.6193   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2492   -0.0532   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2861   -1.4130    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1535   -2.0806    0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9692   -1.3499    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9122   -0.0169    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    0.7034    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455    1.9271    0.1023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708    0.1403    0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357    0.8621    0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    1.4733   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    1.1908   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045    0.2425   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6220    0.4925   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736   -0.3507   -0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135   -1.4992    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.7762    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903   -0.9096    0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7427    2.3769   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564    2.6738    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1697    0.4230   -0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2293   -1.9575   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467   -3.1223    0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -1.9095    0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.3568    1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742    1.7774    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299    2.2485   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    1.7748   -1.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.4052   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6675   -0.1078   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -2.1988    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179   -2.7018    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021   -1.2414    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7  2  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END


  Mrv0541 05061312342D          

 19 20  0  0  0  0            999 V2000
    0.7145    4.5375    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
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    8.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    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  4  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  9  6  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  2  0  0  0  0
 19 12  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041319

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO2/c17-15-11-5-4-10-14(15)16(18)19-12-6-9-13-7-2-1-3-8-13/h1-11H,12,17H2/b9-6-

> <INCHI_KEY>
GABQNAFEZZDSCM-TWGQIWQCSA-N

> <FORMULA>
C16H15NO2

> <MOLECULAR_WEIGHT>
253.2958

> <EXACT_MASS>
253.110278729

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.083932977869598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
4.132185616666667

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.390839665845853

> <JCHEM_PKA_STRONGEST_BASIC>
2.146031644801402

> <JCHEM_POLAR_SURFACE_AREA>
52.32000000000001

> <JCHEM_REFRACTIVITY>
77.7149

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041319
     RDKit          3D
Cinnamyl anthranilate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.0418    2.0007   -0.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464    0.6193   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2492   -0.0532   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2861   -1.4130    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1535   -2.0806    0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9692   -1.3499    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9122   -0.0169    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    0.7034    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455    1.9271    0.1023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708    0.1403    0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357    0.8621    0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    1.4733   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    1.1908   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045    0.2425   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6220    0.4925   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736   -0.3507   -0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135   -1.4992    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.7762    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903   -0.9096    0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7427    2.3769   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564    2.6738    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1697    0.4230   -0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2293   -1.9575   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467   -3.1223    0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -1.9095    0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.3568    1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742    1.7774    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299    2.2485   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    1.7748   -1.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.4052   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6675   -0.1078   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -2.1988    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179   -2.7018    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021   -1.2414    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7  2  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  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       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  15.400   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.668  16.170   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       6.668  11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    7                                                       
CONECT    3    1    8                                                       
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6    9   12                                                       
CONECT    7    2   13                                                       
CONECT    8    3   13                                                       
CONECT    9    6   13                                                       
CONECT   10    4   14                                                       
CONECT   11    5   15                                                       
CONECT   12    6   19                                                       
CONECT   13    7    8    9                                                  
CONECT   14   10   15   16                                                  
CONECT   15   11   14   17                                                  
CONECT   16   14   18   19                                                  
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0041319
HETATM    1  N1  UNL     1      -4.042   2.001  -0.459  1.00  0.00           N  
HETATM    2  C1  UNL     1      -4.046   0.619  -0.132  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.249  -0.053  -0.245  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.286  -1.413   0.070  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.153  -2.081   0.485  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.969  -1.350   0.580  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.912  -0.017   0.277  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.669   0.703   0.388  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.646   1.927   0.102  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.471   0.140   0.793  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.736   0.862   0.895  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.210   1.473  -0.347  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.334   1.191  -0.912  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.304   0.243  -0.468  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.622   0.493  -0.891  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.674  -0.351  -0.645  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.414  -1.499   0.055  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.142  -1.776   0.481  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.090  -0.910   0.220  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.743   2.377  -1.382  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.356   2.674   0.269  1.00  0.00           H  
HETATM   22  H3  UNL     1      -6.170   0.423  -0.566  1.00  0.00           H  
HETATM   23  H4  UNL     1      -6.229  -1.957  -0.015  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.147  -3.122   0.734  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.096  -1.910   0.911  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.449   0.357   1.518  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.374   1.777   1.573  1.00  0.00           H  
HETATM   28  H9  UNL     1       0.530   2.248  -0.834  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.537   1.775  -1.870  1.00  0.00           H  
HETATM   30  H11 UNL     1       4.868   1.405  -1.456  1.00  0.00           H  
HETATM   31  H12 UNL     1       6.668  -0.108  -0.994  1.00  0.00           H  
HETATM   32  H13 UNL     1       6.213  -2.199   0.277  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.918  -2.702   1.048  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.102  -1.241   0.538  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    7
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   26   27
CONECT   12   13   13   28
CONECT   13   14   29
CONECT   14   15   15   19
CONECT   15   16   30
CONECT   16   17   17   31
CONECT   17   18   32
CONECT   18   19   19   33
CONECT   19   34
END

HMDB0041319
     RDKit          3D
Cinnamyl anthranilate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.0418    2.0007   -0.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0464    0.6193   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2492   -0.0532   -0.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2861   -1.4130    0.0699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1535   -2.0806    0.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9692   -1.3499    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9122   -0.0169    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    0.7034    0.3876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455    1.9271    0.1023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708    0.1403    0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357    0.8621    0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2097    1.4733   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    1.1908   -0.9125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045    0.2425   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6220    0.4925   -0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736   -0.3507   -0.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4135   -1.4992    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1423   -1.7762    0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903   -0.9096    0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7427    2.3769   -1.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3564    2.6738    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1697    0.4230   -0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2293   -1.9575   -0.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1467   -3.1223    0.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960   -1.9095    0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4493    0.3568    1.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742    1.7774    1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299    2.2485   -0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    1.7748   -1.8696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675    1.4052   -1.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6675   -0.1078   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -2.1988    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9179   -2.7018    1.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021   -1.2414    0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  7  2  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cinnamyl anthranilic acid	Generator
2-Aminobenzoic acid 3-phenyl-2-propenyl ester	HMDB
2-Propen-1-ol, 3-phenyl-, 1-(2-aminobenzoate)	HMDB
2-Propen-1-ol, 3-phenyl-, 2-aminobenzoate	HMDB
3-Phenyl-2-propen-1-ol 2-aminobenzoate	HMDB
3-Phenyl-2-propen-1-yl 2-aminobenzoate	HMDB
3-Phenyl-2-propen-1-yl anthranilate	HMDB
3-Phenyl-2-propenyl anthranilate	HMDB
3-Phenyl-2-propenylanthranilate	HMDB
Anthranilic acid, cinnamyl ester	HMDB
Benzoic acid, 2-amino-, 3-phenyl-2-propenyl ester	HMDB
Cinnamyl 2-aminobenzoate	HMDB
Cinnamyl alcohol, anthranilate	HMDB
Cinnamyl anthranylate	HMDB
Cinnamyl O-aminobenzoate	HMDB
Cinnamylester kyseliny anthranilove	HMDB
FEMA 2295	HMDB
(2Z)-3-Phenylprop-2-en-1-yl 2-aminobenzoic acid	Generator
3-Phenyl-2-propenyl-2-aminobenzoate	MeSH
Cinnamyl anthranilate	MeSH

Chemical Formula

C₁₆H₁₅NO₂

Average Molecular Weight

253.2958

Monoisotopic Molecular Weight

253.110278729

IUPAC Name

(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

Traditional Name

(2Z)-3-phenylprop-2-en-1-yl 2-aminobenzoate

CAS Registry Number

87-29-6

SMILES

NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H15NO2/c17-15-11-5-4-10-14(15)16(18)19-12-6-9-13-7-2-1-3-8-13/h1-11H,12,17H2/b9-6-

InChI Key

GABQNAFEZZDSCM-TWGQIWQCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Styrene
Vinylogous amide
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	64 °C	Not Available
Boiling Point	322.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	2.03 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.474 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.54	ALOGPS
logP	4.13	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	19.39	ChemAxon
pKa (Strongest Basic)	2.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.71 m³·mol⁻¹	ChemAxon
Polarizability	28.08 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
DarkChem	[M+H]+	159.212	31661259
DarkChem	[M-H]-	157.227	31661259
DeepCCS	[M+H]+	157.556	30932474
DeepCCS	[M-H]-	155.198	30932474
DeepCCS	[M-2H]-	188.152	30932474
DeepCCS	[M+Na]+	163.649	30932474
AllCCS	[M+H]+	159.8	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	163.4	32859911
AllCCS	[M+Na]+	164.5	32859911
AllCCS	[M-H]-	163.0	32859911
AllCCS	[M+Na-2H]-	162.7	32859911
AllCCS	[M+HCOO]-	162.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinnamyl anthranilate	NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1	3585.3	Standard polar	33892256
Cinnamyl anthranilate	NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1	2280.2	Standard non polar	33892256
Cinnamyl anthranilate	NC1=CC=CC=C1C(=O)OC\C=C/C1=CC=CC=C1	2337.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cinnamyl anthranilate,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1	2486.6	Semi standard non polar	33892256
Cinnamyl anthranilate,1TMS,isomer #1	C[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1	2464.1	Standard non polar	33892256
Cinnamyl anthranilate,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C	2410.5	Semi standard non polar	33892256
Cinnamyl anthranilate,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C	2402.8	Standard non polar	33892256
Cinnamyl anthranilate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1	2702.4	Semi standard non polar	33892256
Cinnamyl anthranilate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1	2681.9	Standard non polar	33892256
Cinnamyl anthranilate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2852.2	Semi standard non polar	33892256
Cinnamyl anthranilate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OC/C=C\C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2866.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnamyl anthranilate GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-6900000000-c67918c6b47914e2e6d4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnamyl anthranilate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnamyl anthranilate 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 - Cinnamyl anthranilate 10V, Positive-QTOF	splash10-0uy0-0690000000-85d2f32c193a1ae02a01	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Positive-QTOF	splash10-014i-0910000000-3b4c9b53b568b901061c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Positive-QTOF	splash10-0v4i-9700000000-85c51499b0bd22ea95da	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 10V, Negative-QTOF	splash10-0udi-2590000000-679d958bba4686930ee8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Negative-QTOF	splash10-000f-7910000000-cce12f47044d49554746	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Negative-QTOF	splash10-0006-9500000000-0dd8d9c87d13e6219d3a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 10V, Positive-QTOF	splash10-00xr-0910000000-840743942c1c7339d58c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Positive-QTOF	splash10-00xu-2900000000-cefd8fe63dfd9522d9df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Positive-QTOF	splash10-00r6-7900000000-bf1164f59e89ddffff9c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 10V, Negative-QTOF	splash10-0f7c-4390000000-4a5270f5d52a19bcd107	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 20V, Negative-QTOF	splash10-0006-9310000000-183323bd99f2d5d6838c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl anthranilate 40V, Negative-QTOF	splash10-0006-9000000000-f142da8ca3951731a32c	2021-09-25	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

FDB021238

KNApSAcK ID

Not Available

Chemspider ID

30777557

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54603882

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1015441

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 Cinnamyl anthranilate (HMDB0041319)

MOL for HMDB0041319 (Cinnamyl anthranilate)

3D MOL for HMDB0041319 (Cinnamyl anthranilate)

3D SDF for HMDB0041319 (Cinnamyl anthranilate)

3D-SDF for HMDB0041319 (Cinnamyl anthranilate)

PDB for HMDB0041319 (Cinnamyl anthranilate)

3D PDB for HMDB0041319 (Cinnamyl anthranilate)

SMILES for HMDB0041319 (Cinnamyl anthranilate)

INCHI for HMDB0041319 (Cinnamyl anthranilate)

Structure for HMDB0041319 (Cinnamyl anthranilate)

3D Structure for HMDB0041319 (Cinnamyl anthranilate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra