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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:49:51 UTC

Update Date

2021-09-26 22:50:42 UTC

HMDB ID

HMDB0243580

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide

Description

(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 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. Based on a literature review very few articles have been published on (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). (e)-3-(4-chlorophenyl)-n-(4-methoxyphenyl)prop-2-enamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0243580
     RDKit          3D
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide
 34 35  0  0  0  0  0  0  0  0999 V2000
    6.5826    0.5796   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0655   -0.3763   -1.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -0.3125   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8688    0.6176   -1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460    0.6620   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923   -0.2676   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -0.1982    0.1458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929   -0.7335    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799   -1.3542    2.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205   -0.6103    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.0062    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.1284    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4764    0.7973   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449    0.9416   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5502    0.4256    0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2923    0.6190    1.0308 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.8270   -0.2438    1.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -0.3884    1.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8026   -1.2006    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1773   -1.2357    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3822    1.6255   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6840    0.4615   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970    0.4073   -2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3014    1.3317   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9242    1.4262   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    0.3280   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9685   -1.0586    2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308    0.4484   -0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338    1.2149   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4235    1.4724   -0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3723   -0.6494    2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233   -0.9189    2.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -1.9296    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7645   -2.0033    0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1652309102122502D          

 20 21  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724  -11.1375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 10  1  4  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243580

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(NC(=O)C=CC2=CC=C(Cl)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14ClNO2/c1-20-15-9-7-14(8-10-15)18-16(19)11-4-12-2-5-13(17)6-3-12/h2-11H,1H3,(H,18,19)

> <INCHI_KEY>
LYIXDMRSDTZYCF-UHFFFAOYSA-N

> <FORMULA>
C16H14ClNO2

> <MOLECULAR_WEIGHT>
287.74

> <EXACT_MASS>
287.0713064

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.752996855155715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
4.016761568333333

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.272634611129153

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9259195659003563

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
82.6052

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243580
     RDKit          3D
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide
 34 35  0  0  0  0  0  0  0  0999 V2000
    6.5826    0.5796   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0655   -0.3763   -1.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -0.3125   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8688    0.6176   -1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460    0.6620   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923   -0.2676   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -0.1982    0.1458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929   -0.7335    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799   -1.3542    2.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205   -0.6103    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.0062    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.1284    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4764    0.7973   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449    0.9416   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5502    0.4256    0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2923    0.6190    1.0308 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.8270   -0.2438    1.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -0.3884    1.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8026   -1.2006    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1773   -1.2357    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3822    1.6255   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6840    0.4615   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970    0.4073   -2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3014    1.3317   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9242    1.4262   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    0.3280   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9685   -1.0586    2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308    0.4484   -0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338    1.2149   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4235    1.4724   -0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3723   -0.6494    2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233   -0.9189    2.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -1.9296    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7645   -2.0033    0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.001 -11.550   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       6.668 -20.790   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0243580
HETATM    1  C1  UNL     1       6.583   0.580  -1.914  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.065  -0.376  -1.007  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.694  -0.312  -0.727  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.869   0.618  -1.287  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.546   0.662  -1.002  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.992  -0.268  -0.108  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.606  -0.198   0.146  1.00  0.00           N  
HETATM    8  C6  UNL     1      -0.093  -0.733   1.244  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.580  -1.354   2.137  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.520  -0.610   1.400  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.279  -0.006   0.558  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.746   0.128   0.704  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.476   0.797  -0.257  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.845   0.942  -0.152  1.00  0.00           C  
HETATM   15  C12 UNL     1      -6.550   0.426   0.915  1.00  0.00           C  
HETATM   16 CL1  UNL     1      -8.292   0.619   1.031  1.00  0.00          CL  
HETATM   17  C13 UNL     1      -5.827  -0.244   1.878  1.00  0.00           C  
HETATM   18  C14 UNL     1      -4.437  -0.388   1.769  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.803  -1.201   0.457  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.177  -1.236   0.152  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.382   1.626  -1.544  1.00  0.00           H  
HETATM   22  H2  UNL     1       7.684   0.461  -2.017  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.097   0.407  -2.883  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.301   1.332  -1.976  1.00  0.00           H  
HETATM   25  H5  UNL     1       1.924   1.426  -1.476  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.057   0.328  -0.615  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.968  -1.059   2.285  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.831   0.448  -0.338  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.934   1.215  -1.113  1.00  0.00           H  
HETATM   30  H10 UNL     1      -6.423   1.472  -0.915  1.00  0.00           H  
HETATM   31  H11 UNL     1      -6.372  -0.649   2.715  1.00  0.00           H  
HETATM   32  H12 UNL     1      -3.923  -0.919   2.548  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.394  -1.930   1.133  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.765  -2.003   0.637  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   20
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   19
CONECT    7    8   26
CONECT    8    9    9   10
CONECT   10   11   11   27
CONECT   11   12   28
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   17   18   18   31
CONECT   18   32
CONECT   19   20   20   33
CONECT   20   34
END

HMDB0243580
     RDKit          3D
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide
 34 35  0  0  0  0  0  0  0  0999 V2000
    6.5826    0.5796   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0655   -0.3763   -1.0073 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6942   -0.3125   -0.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8688    0.6176   -1.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460    0.6620   -1.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9923   -0.2676   -0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -0.1982    0.1458 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929   -0.7335    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5799   -1.3542    2.1369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5205   -0.6103    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -0.0062    0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.1284    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4764    0.7973   -0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8449    0.9416   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5502    0.4256    0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2923    0.6190    1.0308 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.8270   -0.2438    1.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4371   -0.3884    1.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8026   -1.2006    0.4568 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1773   -1.2357    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3822    1.6255   -1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6840    0.4615   -2.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0970    0.4073   -2.8827 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3014    1.3317   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9242    1.4262   -1.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    0.3280   -0.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9685   -1.0586    2.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8308    0.4484   -0.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9338    1.2149   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4235    1.4724   -0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3723   -0.6494    2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9233   -0.9189    2.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942   -1.9296    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7645   -2.0033    0.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  6 19  1  0
 19 20  2  0
 20  3  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄ClNO₂

Average Molecular Weight

287.74

Monoisotopic Molecular Weight

287.0713064

IUPAC Name

3-(4-chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide

Traditional Name

3-(4-chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide

CAS Registry Number

Not Available

SMILES

COC1=CC=C(NC(=O)C=CC2=CC=C(Cl)C=C2)C=C1

InChI Identifier

InChI=1S/C16H14ClNO2/c1-20-15-9-7-14(8-10-15)18-16(19)11-4-12-2-5-13(17)6-3-12/h2-11H,1H3,(H,18,19)

InChI Key

LYIXDMRSDTZYCF-UHFFFAOYSA-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
Methoxyaniline
Anilide
Phenoxy compound
Anisole
Methoxybenzene
N-arylamide
Styrene
Phenol ether
Alkyl aryl ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Benzenoid
Monocyclic benzene moiety
Secondary carboxylic acid amide
Carboxamide group
Ether
Carboxylic acid derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.09	ALOGPS
logP	4.02	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	15.27	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.61 m³·mol⁻¹	ChemAxon
Polarizability	30.75 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]+	170.485	30932474
DeepCCS	[M-H]-	168.127	30932474
DeepCCS	[M-2H]-	201.013	30932474
DeepCCS	[M+Na]+	176.578	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide	COC1=CC=C(NC(=O)C=CC2=CC=C(Cl)C=C2)C=C1	3931.4	Standard polar	33892256
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide	COC1=CC=C(NC(=O)C=CC2=CC=C(Cl)C=C2)C=C1	2619.7	Standard non polar	33892256
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide	COC1=CC=C(NC(=O)C=CC2=CC=C(Cl)C=C2)C=C1	2836.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide,1TMS,isomer #1	COC1=CC=C(N(C(=O)C=CC2=CC=C(Cl)C=C2)[Si](C)(C)C)C=C1	2690.8	Semi standard non polar	33892256
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide,1TMS,isomer #1	COC1=CC=C(N(C(=O)C=CC2=CC=C(Cl)C=C2)[Si](C)(C)C)C=C1	2607.8	Standard non polar	33892256
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide,1TMS,isomer #1	COC1=CC=C(N(C(=O)C=CC2=CC=C(Cl)C=C2)[Si](C)(C)C)C=C1	3237.1	Standard polar	33892256
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide,1TBDMS,isomer #1	COC1=CC=C(N(C(=O)C=CC2=CC=C(Cl)C=C2)[Si](C)(C)C(C)(C)C)C=C1	2922.4	Semi standard non polar	33892256
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide,1TBDMS,isomer #1	COC1=CC=C(N(C(=O)C=CC2=CC=C(Cl)C=C2)[Si](C)(C)C(C)(C)C)C=C1	2826.9	Standard non polar	33892256
(E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide,1TBDMS,isomer #1	COC1=CC=C(N(C(=O)C=CC2=CC=C(Cl)C=C2)[Si](C)(C)C(C)(C)C)C=C1	3287.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xr-0930000000-7e8de822caa63f3c48c5	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 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 - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 10V, Positive-QTOF	splash10-00kr-0690000000-0758cb30ae20508fc65b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 20V, Positive-QTOF	splash10-00kr-0940000000-f2fd336c3014e0284bc7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 40V, Positive-QTOF	splash10-000i-1900000000-f04d7f5ac2b044075b24	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 10V, Negative-QTOF	splash10-000i-0190000000-08727240b225b839200b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 20V, Negative-QTOF	splash10-000i-2590000000-cc6fe7f948c7d5d81e22	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide 40V, Negative-QTOF	splash10-001i-9400000000-eeed047d9878b539301c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

603307

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

692413

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide (HMDB0243580)

MOL for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

3D MOL for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

3D SDF for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

3D-SDF for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

PDB for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

3D PDB for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

SMILES for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

INCHI for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

Structure for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

3D Structure for HMDB0243580 ((E)-3-(4-Chlorophenyl)-N-(4-methoxyphenyl)prop-2-enamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra