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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:33:35 UTC

Update Date

2021-09-26 23:09:31 UTC

HMDB ID

HMDB0255031

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nalpha-Cinnamoylhistamine

Description

cinnamoylhistamine 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. cinnamoylhistamine is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Nalpha-cinnamoylhistamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nalpha-Cinnamoylhistamine 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

HMDB0255031
     RDKit          3D
Nalpha-Cinnamoylhistamine
 33 34  0  0  0  0  0  0  0  0999 V2000
    0.6442   -1.1429   -0.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864   -0.0285   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    0.0736   -0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.0011   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5900   -0.9751   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2999   -2.1836   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6716   -2.2329   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3490   -1.0350   -0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6634    0.1595   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667    0.2156   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305    1.1584   -0.4723 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    1.1409   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242    0.4651    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    0.5022    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092    1.4694    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509    1.1216    0.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3676   -0.0634   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0705   -0.4341   -0.0924 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    1.0405   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005   -1.9578   -0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664   -3.1245   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2139   -3.1739   -0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4387   -1.0642    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2154    1.0953   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158    1.1912   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3427    2.0759   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057    2.1529   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    0.5977   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.0833    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948   -0.5683    0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244    2.3718    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3427    1.6701    0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2096   -0.5998   -0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 10  5  1  0
 18 14  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END


  Mrv1533004231518452D          

 18 19  0  0  0  0            999 V2000
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0405   -2.9644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5925   -3.5775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1800   -4.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3731   -4.1205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
 11  2  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255031

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C(NCCC1=CNC=N1)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H15N3O/c18-14(7-6-12-4-2-1-3-5-12)16-9-8-13-10-15-11-17-13/h1-7,10-11H,8-9H2,(H,15,17)(H,16,18)

> <INCHI_KEY>
HCENGXRZXKAJLN-UHFFFAOYSA-N

> <FORMULA>
C14H15N3O

> <MOLECULAR_WEIGHT>
241.294

> <EXACT_MASS>
241.121512115

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.78784512762479

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(1H-imidazol-4-yl)ethyl]-3-phenylprop-2-enamide

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.4773074329999996

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.937845415070218

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.10079883741044

> <JCHEM_PKA_STRONGEST_BASIC>
6.550011065788746

> <JCHEM_POLAR_SURFACE_AREA>
57.78

> <JCHEM_REFRACTIVITY>
71.52340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(1H-imidazol-4-yl)ethyl]-3-phenylprop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255031
     RDKit          3D
Nalpha-Cinnamoylhistamine
 33 34  0  0  0  0  0  0  0  0999 V2000
    0.6442   -1.1429   -0.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864   -0.0285   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    0.0736   -0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.0011   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5900   -0.9751   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2999   -2.1836   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6716   -2.2329   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3490   -1.0350   -0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6634    0.1595   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667    0.2156   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305    1.1584   -0.4723 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    1.1409   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242    0.4651    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    0.5022    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092    1.4694    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509    1.1216    0.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3676   -0.0634   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0705   -0.4341   -0.0924 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    1.0405   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005   -1.9578   -0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664   -3.1245   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2139   -3.1739   -0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4387   -1.0642    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2154    1.0953   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158    1.1912   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3427    2.0759   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057    2.1529   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    0.5977   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.0833    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948   -0.5683    0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244    2.3718    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3427    1.6701    0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2096   -0.5998   -0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 10  5  1  0
 18 14  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.409  -5.534   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      10.439  -6.678   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.669  -8.012   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       8.163  -7.692   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    2   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0255031
HETATM    1  O1  UNL     1       0.644  -1.143  -0.433  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.086  -0.028  -0.417  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.392   0.074  -0.338  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.144  -1.001  -0.283  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.590  -0.975  -0.205  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.300  -2.184  -0.151  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.672  -2.233  -0.075  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.349  -1.035  -0.054  1.00  0.00           C  
HETATM    9  C8  UNL     1      -5.663   0.159  -0.106  1.00  0.00           C  
HETATM   10  C9  UNL     1      -4.267   0.216  -0.183  1.00  0.00           C  
HETATM   11  N1  UNL     1       0.830   1.158  -0.472  1.00  0.00           N  
HETATM   12  C10 UNL     1       2.258   1.141  -0.546  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.824   0.465   0.679  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.317   0.502   0.509  1.00  0.00           C  
HETATM   15  C13 UNL     1       5.209   1.469   0.917  1.00  0.00           C  
HETATM   16  N2  UNL     1       6.451   1.122   0.571  1.00  0.00           N  
HETATM   17  C14 UNL     1       6.368  -0.063  -0.058  1.00  0.00           C  
HETATM   18  N3  UNL     1       5.070  -0.434  -0.092  1.00  0.00           N  
HETATM   19  H1  UNL     1      -1.869   1.041  -0.324  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.601  -1.958  -0.300  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.766  -3.125  -0.168  1.00  0.00           H  
HETATM   22  H4  UNL     1      -6.214  -3.174  -0.034  1.00  0.00           H  
HETATM   23  H5  UNL     1      -7.439  -1.064   0.006  1.00  0.00           H  
HETATM   24  H6  UNL     1      -6.215   1.095  -0.088  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.816   1.191  -0.220  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.343   2.076  -0.460  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.706   2.153  -0.634  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.628   0.598  -1.465  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.589   1.083   1.592  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.495  -0.568   0.784  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.924   2.372   1.440  1.00  0.00           H  
HETATM   32  H14 UNL     1       7.343   1.670   0.754  1.00  0.00           H  
HETATM   33  H15 UNL     1       7.210  -0.600  -0.454  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   19
CONECT    4    5   20
CONECT    5    6    6   10
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   25
CONECT   11   12   26
CONECT   12   13   27   28
CONECT   13   14   29   30
CONECT   14   15   15   18
CONECT   15   16   31
CONECT   16   17   32
CONECT   17   18   18   33
END

HMDB0255031
     RDKit          3D
Nalpha-Cinnamoylhistamine
 33 34  0  0  0  0  0  0  0  0999 V2000
    0.6442   -1.1429   -0.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0864   -0.0285   -0.4167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    0.0736   -0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.0011   -0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5900   -0.9751   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2999   -2.1836   -0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6716   -2.2329   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3490   -1.0350   -0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6634    0.1595   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2667    0.2156   -0.1831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305    1.1584   -0.4723 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    1.1409   -0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242    0.4651    0.6790 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    0.5022    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092    1.4694    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4509    1.1216    0.5713 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3676   -0.0634   -0.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0705   -0.4341   -0.0924 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8685    1.0405   -0.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6005   -1.9578   -0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7664   -3.1245   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2139   -3.1739   -0.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4387   -1.0642    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2154    1.0953   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8158    1.1912   -0.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3427    2.0759   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057    2.1529   -0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6283    0.5977   -1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886    1.0833    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4948   -0.5683    0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244    2.3718    1.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3427    1.6701    0.7536 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2096   -0.5998   -0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  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  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 10  5  1  0
 18 14  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[2-(1H-Imidazol-5-yl)ethyl]-3-phenylprop-2-enimidate	Generator

Chemical Formula

C₁₄H₁₅N₃O

Average Molecular Weight

241.294

Monoisotopic Molecular Weight

241.121512115

IUPAC Name

N-[2-(1H-imidazol-4-yl)ethyl]-3-phenylprop-2-enamide

Traditional Name

N-[2-(1H-imidazol-4-yl)ethyl]-3-phenylprop-2-enamide

CAS Registry Number

Not Available

SMILES

O=C(NCCC1=CNC=N1)C=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C14H15N3O/c18-14(7-6-12-4-2-1-3-5-12)16-9-8-13-10-15-11-17-13/h1-7,10-11H,8-9H2,(H,15,17)(H,16,18)

InChI Key

HCENGXRZXKAJLN-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
Styrene
Monocyclic benzene moiety
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

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	1.34	ALOGPS
logP	1.48	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.1	ChemAxon
pKa (Strongest Basic)	6.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.52 m³·mol⁻¹	ChemAxon
Polarizability	26.79 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
DeepCCS	[M+H]+	154.37	30932474
DeepCCS	[M-H]-	152.012	30932474
DeepCCS	[M-2H]-	185.031	30932474
DeepCCS	[M+Na]+	160.463	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	161.8	32859911
AllCCS	[M+Na]+	162.8	32859911
AllCCS	[M-H]-	159.4	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	159.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nalpha-Cinnamoylhistamine	O=C(NCCC1=CNC=N1)C=CC1=CC=CC=C1	3682.7	Standard polar	33892256
Nalpha-Cinnamoylhistamine	O=C(NCCC1=CNC=N1)C=CC1=CC=CC=C1	2236.1	Standard non polar	33892256
Nalpha-Cinnamoylhistamine	O=C(NCCC1=CNC=N1)C=CC1=CC=CC=C1	2843.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nalpha-Cinnamoylhistamine,1TMS,isomer #1	C[Si](C)(C)N(CCC1=C[NH]C=N1)C(=O)C=CC1=CC=CC=C1	2557.8	Semi standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TMS,isomer #1	C[Si](C)(C)N(CCC1=C[NH]C=N1)C(=O)C=CC1=CC=CC=C1	2609.2	Standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TMS,isomer #1	C[Si](C)(C)N(CCC1=C[NH]C=N1)C(=O)C=CC1=CC=CC=C1	3146.5	Standard polar	33892256
Nalpha-Cinnamoylhistamine,1TMS,isomer #2	C[Si](C)(C)N1C=NC(CCNC(=O)C=CC2=CC=CC=C2)=C1	2778.5	Semi standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TMS,isomer #2	C[Si](C)(C)N1C=NC(CCNC(=O)C=CC2=CC=CC=C2)=C1	2588.9	Standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TMS,isomer #2	C[Si](C)(C)N1C=NC(CCNC(=O)C=CC2=CC=CC=C2)=C1	3185.0	Standard polar	33892256
Nalpha-Cinnamoylhistamine,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C=N1)C(=O)C=CC1=CC=CC=C1	2697.2	Semi standard non polar	33892256
Nalpha-Cinnamoylhistamine,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C=N1)C(=O)C=CC1=CC=CC=C1	2637.3	Standard non polar	33892256
Nalpha-Cinnamoylhistamine,2TMS,isomer #1	C[Si](C)(C)N(CCC1=CN([Si](C)(C)C)C=N1)C(=O)C=CC1=CC=CC=C1	2985.2	Standard polar	33892256
Nalpha-Cinnamoylhistamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C=N1)C(=O)C=CC1=CC=CC=C1	2788.4	Semi standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C=N1)C(=O)C=CC1=CC=CC=C1	2824.7	Standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=C[NH]C=N1)C(=O)C=CC1=CC=CC=C1	3216.0	Standard polar	33892256
Nalpha-Cinnamoylhistamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(CCNC(=O)C=CC2=CC=CC=C2)=C1	3006.4	Semi standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(CCNC(=O)C=CC2=CC=CC=C2)=C1	2782.8	Standard non polar	33892256
Nalpha-Cinnamoylhistamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=NC(CCNC(=O)C=CC2=CC=CC=C2)=C1	3274.2	Standard polar	33892256
Nalpha-Cinnamoylhistamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)C=CC1=CC=CC=C1	3099.1	Semi standard non polar	33892256
Nalpha-Cinnamoylhistamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)C=CC1=CC=CC=C1	2998.2	Standard non polar	33892256
Nalpha-Cinnamoylhistamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CN([Si](C)(C)C(C)(C)C)C=N1)C(=O)C=CC1=CC=CC=C1	3148.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nalpha-Cinnamoylhistamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-6910000000-2870e6c69573ecf2f053	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalpha-Cinnamoylhistamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

280288

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 Nalpha-Cinnamoylhistamine (HMDB0255031)

MOL for HMDB0255031 (Nalpha-Cinnamoylhistamine)

3D MOL for HMDB0255031 (Nalpha-Cinnamoylhistamine)

3D SDF for HMDB0255031 (Nalpha-Cinnamoylhistamine)

3D-SDF for HMDB0255031 (Nalpha-Cinnamoylhistamine)

PDB for HMDB0255031 (Nalpha-Cinnamoylhistamine)

3D PDB for HMDB0255031 (Nalpha-Cinnamoylhistamine)

SMILES for HMDB0255031 (Nalpha-Cinnamoylhistamine)

INCHI for HMDB0255031 (Nalpha-Cinnamoylhistamine)

Structure for HMDB0255031 (Nalpha-Cinnamoylhistamine)

3D Structure for HMDB0255031 (Nalpha-Cinnamoylhistamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra