Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:53:54 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038574

Secondary Accession Numbers

HMDB38574

Metabolite Identification

Common Name

Lansiumamide A

Description

Lansiumamide A belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Lansiumamide A has been detected, but not quantified in, fruits. This could make lansiumamide a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lansiumamide A.

Structure

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

HMDB0038574
     RDKit          3D
Lansiumamide A
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.8016    1.2708   -2.9983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428    1.4137   -1.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446    0.6337   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -0.1361   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0692   -0.9254   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -1.7215   -0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -2.4940   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -2.4941    1.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -1.7041    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449   -0.9319    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734    2.1908   -1.3666 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788    2.9597   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    2.6166   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604    1.2950   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    0.1380   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0736   -1.0809    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.1365    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929    0.0282    0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.2044    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138    0.7000    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -0.1621   -2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -1.7596   -1.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -3.0975   -0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -3.1073    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6819   -1.7057    2.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826   -0.3240    1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    2.5431   -2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147    4.1139   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573    3.4882   -0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220    0.1055   -0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4932   -1.9908   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7714   -2.0833    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9531    0.0354    1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    2.1178    0.7642 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  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
 10  5  1  0
 19 14  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 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 02241212062D          

 19 20  0  0  0  0            999 V2000
    0.6813   -1.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0397   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0397   -2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813   -2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249   -0.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447   -0.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031    0.2402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    1.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6813    2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4031    2.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249    2.2452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1249    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0404    1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6813    1.5234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4031    1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1249    1.5234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038574

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(N\C=C/C1=CC=CC=C1)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO/c19-17(12-11-15-7-3-1-4-8-15)18-14-13-16-9-5-2-6-10-16/h1-14H,(H,18,19)/b12-11+,14-13-

> <INCHI_KEY>
DAZFHZLCFLDNPG-WCYNZMGESA-N

> <FORMULA>
C17H15NO

> <MOLECULAR_WEIGHT>
249.3071

> <EXACT_MASS>
249.115364107

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.366849523878393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
3.6606330793333335

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.176289791665422

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1068941053359134

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
79.23949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038574
     RDKit          3D
Lansiumamide A
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.8016    1.2708   -2.9983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428    1.4137   -1.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446    0.6337   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -0.1361   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0692   -0.9254   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -1.7215   -0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -2.4940   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -2.4941    1.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -1.7041    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449   -0.9319    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734    2.1908   -1.3666 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788    2.9597   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    2.6166   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604    1.2950   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    0.1380   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0736   -1.0809    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.1365    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929    0.0282    0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.2044    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138    0.7000    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -0.1621   -2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -1.7596   -1.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -3.0975   -0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -3.1073    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6819   -1.7057    2.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826   -0.3240    1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    2.5431   -2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147    4.1139   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573    3.4882   -0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220    0.1055   -0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4932   -1.9908   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7714   -2.0833    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9531    0.0354    1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    2.1178    0.7642 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  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
 10  5  1  0
 19 14  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 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                                 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       1.272  -1.945   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.074  -2.694   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.074  -4.191   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.272  -4.940   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.619  -4.191   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.619  -2.694   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.966  -1.796   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.817  -0.299   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.619   0.448   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.619   1.945   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.272   2.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.272   4.191   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.619   4.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.966   4.191   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.966   2.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.075   2.095   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.272   2.844   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.619   2.095   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.966   2.844   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   18                                                       
CONECT   10   11   15                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   11   17                                                       
CONECT   17   16   18                                                       
CONECT   18    9   17   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0038574
HETATM    1  O1  UNL     1       0.802   1.271  -2.998  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.443   1.414  -1.797  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.245   0.634  -0.780  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.235  -0.136  -1.166  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.069  -0.925  -0.275  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.062  -1.721  -0.822  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.896  -2.494  -0.017  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.765  -2.494   1.350  1.00  0.00           C  
HETATM    9  C8  UNL     1       3.779  -1.704   1.904  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.945  -0.932   1.092  1.00  0.00           C  
HETATM   11  N1  UNL     1      -0.573   2.191  -1.367  1.00  0.00           N  
HETATM   12  C10 UNL     1      -1.579   2.960  -0.941  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.704   2.617  -0.373  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.160   1.295  -0.052  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.500   0.138  -0.277  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.074  -1.081   0.091  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.306  -1.137   0.683  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.993   0.028   0.921  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.418   1.204   0.556  1.00  0.00           C  
HETATM   20  H1  UNL     1       1.014   0.700   0.270  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.420  -0.162  -2.254  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.209  -1.760  -1.902  1.00  0.00           H  
HETATM   23  H4  UNL     1       5.653  -3.098  -0.493  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.425  -3.107   1.967  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.682  -1.706   2.978  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.183  -0.324   1.564  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.905   2.543  -2.661  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.515   4.114  -1.039  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.357   3.488  -0.126  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.522   0.106  -0.749  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.493  -1.991  -0.115  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.771  -2.083   0.979  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.953   0.035   1.376  1.00  0.00           H  
HETATM   34  H15 UNL     1      -5.001   2.118   0.764  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   20
CONECT    4    5   21
CONECT    5    6    6   10
CONECT    6    7   22
CONECT    7    8    8   23
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   26
CONECT   11   12   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

HMDB0038574
     RDKit          3D
Lansiumamide A
 34 35  0  0  0  0  0  0  0  0999 V2000
    0.8016    1.2708   -2.9983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428    1.4137   -1.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2446    0.6337   -0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -0.1361   -1.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0692   -0.9254   -0.2753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -1.7215   -0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -2.4940   -0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651   -2.4941    1.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7792   -1.7041    1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9449   -0.9319    1.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5734    2.1908   -1.3666 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788    2.9597   -0.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7041    2.6166   -0.3727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1604    1.2950   -0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4997    0.1380   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0736   -1.0809    0.0913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3060   -1.1365    0.6833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9929    0.0282    0.9209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.2044    0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138    0.7000    0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -0.1621   -2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086   -1.7596   -1.9019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6527   -3.0975   -0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -3.1073    1.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6819   -1.7057    2.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826   -0.3240    1.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9045    2.5431   -2.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5147    4.1139   -1.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573    3.4882   -0.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5220    0.1055   -0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4932   -1.9908   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7714   -2.0833    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9531    0.0354    1.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0011    2.1178    0.7642 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  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
 10  5  1  0
 19 14  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 10 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
N-cis-Styrylcinnamamide	HMDB
(2E)-3-Phenyl-N-[(Z)-2-phenylethenyl]prop-2-enimidate	Generator

Chemical Formula

C₁₇H₁₅NO

Average Molecular Weight

249.3071

Monoisotopic Molecular Weight

249.115364107

IUPAC Name

(2E)-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

Traditional Name

(2E)-3-phenyl-N-[(Z)-2-phenylethenyl]prop-2-enamide

CAS Registry Number

121817-36-5

SMILES

O=C(N\C=C/C1=CC=CC=C1)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H15NO/c19-17(12-11-15-7-3-1-4-8-15)18-14-13-16-9-5-2-6-10-16/h1-14H,(H,18,19)/b12-11+,14-13-

InChI Key

DAZFHZLCFLDNPG-WCYNZMGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid amides

Direct Parent

Cinnamic acid amides

Alternative Parents

Substituents

Cinnamic acid amide
Styrene
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038574)

Cellular substructure

Membrane (HMDB: HMDB0038574)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038574)

Source

Exogenous

Food

Food (HMDB: HMDB0038574)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0038574)

Not Available

Nutrient (HMDB: HMDB0038574)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	121 - 123 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0021 g/L	ALOGPS
logP	3.66	ALOGPS
logP	3.66	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	14.18	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.24 m³·mol⁻¹	ChemAxon
Polarizability	28.37 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
DeepCCS	[M+H]+	158.171	30932474
DeepCCS	[M-H]-	155.775	30932474
DeepCCS	[M-2H]-	188.659	30932474
DeepCCS	[M+Na]+	164.201	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	155.7	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	163.9	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lansiumamide A	O=C(N\C=C/C1=CC=CC=C1)\C=C\C1=CC=CC=C1	3612.9	Standard polar	33892256
Lansiumamide A	O=C(N\C=C/C1=CC=CC=C1)\C=C\C1=CC=CC=C1	1930.7	Standard non polar	33892256
Lansiumamide A	O=C(N\C=C/C1=CC=CC=C1)\C=C\C1=CC=CC=C1	2683.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lansiumamide A,1TMS,isomer #1	C[Si](C)(C)N(/C=C\C1=CC=CC=C1)C(=O)/C=C/C1=CC=CC=C1	2609.6	Semi standard non polar	33892256
Lansiumamide A,1TMS,isomer #1	C[Si](C)(C)N(/C=C\C1=CC=CC=C1)C(=O)/C=C/C1=CC=CC=C1	2667.2	Standard non polar	33892256
Lansiumamide A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(/C=C\C1=CC=CC=C1)C(=O)/C=C/C1=CC=CC=C1	2822.9	Semi standard non polar	33892256
Lansiumamide A,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(/C=C\C1=CC=CC=C1)C(=O)/C=C/C1=CC=CC=C1	2869.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lansiumamide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uea-1940000000-8b7119315175bf238115	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lansiumamide A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lansiumamide A 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 - Lansiumamide A 10V, Positive-QTOF	splash10-0gb9-0940000000-914d063f07e8aa4742a8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 20V, Positive-QTOF	splash10-014i-0900000000-a9fd11546fdfb78b0649	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 40V, Positive-QTOF	splash10-0gbc-5900000000-1ba103ff24ad28965133	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 10V, Negative-QTOF	splash10-0002-0290000000-d43726d4837d96cbd8dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 20V, Negative-QTOF	splash10-0002-1950000000-4eb448661659a3535622	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 40V, Negative-QTOF	splash10-0006-8900000000-9122f796b6f19b0ae8c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 10V, Negative-QTOF	splash10-0002-0090000000-3c404c608b5ed5b071d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 20V, Negative-QTOF	splash10-0005-4390000000-02c51ac01fecf8fc27f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 40V, Negative-QTOF	splash10-0006-9450000000-a5fbb1f8714d267d452f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 10V, Positive-QTOF	splash10-0udi-0290000000-f26b73d5b2ccc2c7fa50	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 20V, Positive-QTOF	splash10-0udi-1940000000-f120b6851f5cf5941ed4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lansiumamide A 40V, Positive-QTOF	splash10-0udl-3900000000-5d0f3dbd6c896f0a77c7	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

FDB017964

KNApSAcK ID

C00056656

Chemspider ID

9588895

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11414008

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Lansiumamide A (HMDB0038574)

MOL for HMDB0038574 (Lansiumamide A)

3D MOL for HMDB0038574 (Lansiumamide A)

3D SDF for HMDB0038574 (Lansiumamide A)

3D-SDF for HMDB0038574 (Lansiumamide A)

PDB for HMDB0038574 (Lansiumamide A)

3D PDB for HMDB0038574 (Lansiumamide A)

SMILES for HMDB0038574 (Lansiumamide A)

INCHI for HMDB0038574 (Lansiumamide A)

Structure for HMDB0038574 (Lansiumamide A)

3D Structure for HMDB0038574 (Lansiumamide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra