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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:11:40 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033461

Secondary Accession Numbers

HMDB33461

Metabolite Identification

Common Name

4-Coumaroylputrescine

Description

4-Coumaroylputrescine belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 4-Coumaroylputrescine has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, fats and oils, fruits, and garden tomatoes (Solanum lycopersicum). This could make 4-coumaroylputrescine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Coumaroylputrescine.

Structure

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

HMDB0033461
     RDKit          3D
4-Coumaroylputrescine
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6595    0.3576   -0.0342 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -0.1531   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757    0.9373   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052    1.6068    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897    0.6519    1.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3073    0.0275    1.2893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2720   -0.8753    2.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -1.0561    3.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -1.6325    2.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -1.6142    1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -0.8120    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056    0.5104   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    1.1196   -1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0440    0.4287   -2.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136    1.0703   -3.5330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -0.9265   -2.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1427   -1.5123   -0.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456   -0.3273    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041    0.5685   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -0.5374   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424   -0.9595    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    0.5464   -1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673    1.6994   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4195    2.4818    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894    1.9747    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -0.1791    1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1801    2.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    0.3359    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -2.4128    3.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2591   -2.3779    1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.1328    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3546    2.1920   -1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5419    0.6012   -4.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6889   -1.4652   -3.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3759   -2.5817   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
M  END

  Mrv0541 02241216522D          

 17 17  0  0  0  0            999 V2000
   -0.7380   -2.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7380   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -2.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769   -0.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157   -0.3698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157    0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948    1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559    2.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    1.6004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9022   -0.2056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -0.4511    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
  3 17  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 10  1  0  0  0  0
  9 16  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033461

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O2/c14-9-1-2-10-15-13(17)8-5-11-3-6-12(16)7-4-11/h3-8,16H,1-2,9-10,14H2,(H,15,17)/b8-5-

> <INCHI_KEY>
CJHDBEPXEKGBDW-YVMONPNESA-N

> <FORMULA>
C13H18N2O2

> <MOLECULAR_WEIGHT>
234.2942

> <EXACT_MASS>
234.13682783

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.418677649063316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
0.22419931278505054

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.232370935440716

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.29683990242163

> <JCHEM_PKA_STRONGEST_BASIC>
10.027301810332872

> <JCHEM_POLAR_SURFACE_AREA>
75.35

> <JCHEM_REFRACTIVITY>
69.21950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033461
     RDKit          3D
4-Coumaroylputrescine
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6595    0.3576   -0.0342 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -0.1531   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757    0.9373   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052    1.6068    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897    0.6519    1.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3073    0.0275    1.2893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2720   -0.8753    2.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -1.0561    3.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -1.6325    2.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -1.6142    1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -0.8120    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056    0.5104   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    1.1196   -1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0440    0.4287   -2.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136    1.0703   -3.5330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -0.9265   -2.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1427   -1.5123   -0.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456   -0.3273    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041    0.5685   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -0.5374   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424   -0.9595    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    0.5464   -1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673    1.6994   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4195    2.4818    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894    1.9747    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -0.1791    1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1801    2.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    0.3359    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -2.4128    3.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2591   -2.3779    1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.1328    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3546    2.1920   -1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5419    0.6012   -4.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6889   -1.4652   -3.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3759   -2.5817   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  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      -1.378  -3.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.757  -3.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.757  -1.608   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.378  -0.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.152  -1.608   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.152  -3.141   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.224  -3.907   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.604  -2.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.757  -1.455   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.136  -0.690   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.136   0.842   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.757   1.608   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.604   3.141   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.224   3.907   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.001   2.987   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       1.684  -0.384   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.136  -0.842   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    9                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0033461
HETATM    1  N1  UNL     1       4.660   0.358  -0.034  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.398  -0.153  -0.522  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.376   0.937  -0.639  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.105   1.607   0.685  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.590   0.652   1.722  1.00  0.00           C  
HETATM    6  N2  UNL     1       0.307   0.028   1.289  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.272  -0.875   2.152  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.457  -1.056   3.240  1.00  0.00           O  
HETATM    9  C6  UNL     1      -1.462  -1.633   2.130  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.444  -1.614   1.304  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.675  -0.812   0.154  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.406   0.510  -0.002  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.587   1.120  -1.224  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.044   0.429  -2.326  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.214   1.070  -3.533  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.329  -0.927  -2.193  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.143  -1.512  -0.975  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.146  -0.327   0.608  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.304   0.569  -0.802  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.598  -0.537  -1.562  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.042  -0.960   0.118  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.447   0.546  -1.079  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.767   1.699  -1.362  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.420   2.482   0.562  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.089   1.975   1.059  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.306  -0.179   1.832  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.421   1.180   2.678  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.030   0.336   0.336  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.590  -2.413   3.000  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.259  -2.378   1.554  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.078   1.133   0.851  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.355   2.192  -1.302  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.542   0.601  -4.349  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.689  -1.465  -3.067  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.376  -2.582  -0.898  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28
CONECT    7    8    8    9
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   12   17
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   15   16
CONECT   15   33
CONECT   16   17   17   34
CONECT   17   35
END

HMDB0033461
     RDKit          3D
4-Coumaroylputrescine
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.6595    0.3576   -0.0342 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3983   -0.1531   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3757    0.9373   -0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1052    1.6068    0.6855 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897    0.6519    1.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3073    0.0275    1.2893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2720   -0.8753    2.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -1.0561    3.2399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620   -1.6325    2.1298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -1.6142    1.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -0.8120    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4056    0.5104   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    1.1196   -1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0440    0.4287   -2.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136    1.0703   -3.5330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -0.9265   -2.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1427   -1.5123   -0.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1456   -0.3273    0.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3041    0.5685   -0.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980   -0.5374   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0424   -0.9595    0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    0.5464   -1.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673    1.6994   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4195    2.4818    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0894    1.9747    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061   -0.1791    1.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212    1.1801    2.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0301    0.3359    0.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -2.4128    3.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2591   -2.3779    1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.1328    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3546    2.1920   -1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5419    0.6012   -4.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6889   -1.4652   -3.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3759   -2.5817   -0.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-N-(4-Aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide	HMDB
4-Hydroxycinnamoylputrescine	HMDB
(2Z)-N-(4-Aminobutyl)-3-(4-hydroxyphenyl)prop-2-enimidate	Generator

Chemical Formula

C₁₃H₁₈N₂O₂

Average Molecular Weight

234.2942

Monoisotopic Molecular Weight

234.13682783

IUPAC Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

Traditional Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

CAS Registry Number

34136-53-3

SMILES

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

InChI Identifier

InChI=1S/C13H18N2O2/c14-9-1-2-10-15-13(17)8-5-11-3-6-12(16)7-4-11/h3-8,16H,1-2,9-10,14H2,(H,15,17)/b8-5-

InChI Key

CJHDBEPXEKGBDW-YVMONPNESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid amide
Coumaric acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Primary amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033461)
Cytoplasm (HMDB: HMDB0033461)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033461)

Source

Exogenous

Exogenous (HMDB: HMDB0033461)

Food

Food (HMDB: HMDB0033461)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Fruit

Fruits (FooDB: FOOD00871)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0033461)
Poaceae (HMDB: HMDB0033461)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033461)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 - 183.5 °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	0.3 g/L	ALOGPS
logP	1.12	ALOGPS
logP	0.22	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	10.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.22 m³·mol⁻¹	ChemAxon
Polarizability	26.42 Å³	ChemAxon
Number of Rings	1	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]+	159.046	30932474
DeepCCS	[M-H]-	156.688	30932474
DeepCCS	[M-2H]-	189.573	30932474
DeepCCS	[M+Na]+	165.139	30932474
AllCCS	[M+H]+	153.5	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	156.8	32859911
AllCCS	[M+Na]+	157.7	32859911
AllCCS	[M-H]-	158.4	32859911
AllCCS	[M+Na-2H]-	158.9	32859911
AllCCS	[M+HCOO]-	159.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Coumaroylputrescine	NCCCCNC(=O)\C=C/C1=CC=C(O)C=C1	3576.1	Standard polar	33892256
4-Coumaroylputrescine	NCCCCNC(=O)\C=C/C1=CC=C(O)C=C1	2481.5	Standard non polar	33892256
4-Coumaroylputrescine	NCCCCNC(=O)\C=C/C1=CC=C(O)C=C1	2710.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Coumaroylputrescine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)NCCCCN)C=C1	2557.9	Semi standard non polar	33892256
4-Coumaroylputrescine,1TMS,isomer #2	C[Si](C)(C)NCCCCNC(=O)/C=C\C1=CC=C(O)C=C1	2656.5	Semi standard non polar	33892256
4-Coumaroylputrescine,1TMS,isomer #3	C[Si](C)(C)N(CCCCN)C(=O)/C=C\C1=CC=C(O)C=C1	2543.4	Semi standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #1	C[Si](C)(C)NCCCCNC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1	2742.5	Semi standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #1	C[Si](C)(C)NCCCCNC(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1	2904.5	Standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN)[Si](C)(C)C)C=C1	2534.6	Semi standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN)[Si](C)(C)C)C=C1	2642.2	Standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #3	C[Si](C)(C)N(CCCCNC(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C	2840.1	Semi standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #3	C[Si](C)(C)N(CCCCNC(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C	3005.3	Standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #4	C[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C	2715.8	Semi standard non polar	33892256
4-Coumaroylputrescine,2TMS,isomer #4	C[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C	2845.0	Standard non polar	33892256
4-Coumaroylputrescine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)NCCCCN([Si](C)(C)C)[Si](C)(C)C)C=C1	2901.6	Semi standard non polar	33892256
4-Coumaroylputrescine,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)NCCCCN([Si](C)(C)C)[Si](C)(C)C)C=C1	2989.6	Standard non polar	33892256
4-Coumaroylputrescine,3TMS,isomer #2	C[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2663.9	Semi standard non polar	33892256
4-Coumaroylputrescine,3TMS,isomer #2	C[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2775.2	Standard non polar	33892256
4-Coumaroylputrescine,3TMS,isomer #3	C[Si](C)(C)N(CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)/C=C\C1=CC=C(O)C=C1	2864.4	Semi standard non polar	33892256
4-Coumaroylputrescine,3TMS,isomer #3	C[Si](C)(C)N(CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)/C=C\C1=CC=C(O)C=C1	2938.6	Standard non polar	33892256
4-Coumaroylputrescine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C=C1	2870.5	Semi standard non polar	33892256
4-Coumaroylputrescine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C=C1	2850.6	Standard non polar	33892256
4-Coumaroylputrescine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)NCCCCN)C=C1	2845.9	Semi standard non polar	33892256
4-Coumaroylputrescine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCCNC(=O)/C=C\C1=CC=C(O)C=C1	2913.6	Semi standard non polar	33892256
4-Coumaroylputrescine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCN)C(=O)/C=C\C1=CC=C(O)C=C1	2788.8	Semi standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCCNC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3295.0	Semi standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCCNC(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3300.5	Standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN)[Si](C)(C)C(C)(C)C)C=C1	3088.9	Semi standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN)[Si](C)(C)C(C)(C)C)C=C1	3022.4	Standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCNC(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3311.3	Semi standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCNC(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3408.4	Standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3186.5	Semi standard non polar	33892256
4-Coumaroylputrescine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3229.7	Standard non polar	33892256
4-Coumaroylputrescine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)NCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3620.0	Semi standard non polar	33892256
4-Coumaroylputrescine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)NCCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3563.4	Standard non polar	33892256
4-Coumaroylputrescine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3421.4	Semi standard non polar	33892256
4-Coumaroylputrescine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCCCN(C(=O)/C=C\C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3337.4	Standard non polar	33892256
4-Coumaroylputrescine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)/C=C\C1=CC=C(O)C=C1	3536.2	Semi standard non polar	33892256
4-Coumaroylputrescine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)/C=C\C1=CC=C(O)C=C1	3519.4	Standard non polar	33892256
4-Coumaroylputrescine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3776.6	Semi standard non polar	33892256
4-Coumaroylputrescine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C\C(=O)N(CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3569.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaroylputrescine GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-7900000000-686237486111ca5377af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaroylputrescine GC-MS (1 TMS) - 70eV, Positive	splash10-0089-9250000000-900eeaeab8dd59948443	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaroylputrescine 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 - 4-Coumaroylputrescine 10V, Positive-QTOF	splash10-000i-9160000000-b8ce2e2ef1c5286c2f95	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 20V, Positive-QTOF	splash10-0079-9100000000-5af7143169e20606b8f4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 40V, Positive-QTOF	splash10-05fr-9100000000-7f95a937c75ff8841457	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 10V, Negative-QTOF	splash10-001i-1290000000-1f10ea35bb3bd001c098	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 20V, Negative-QTOF	splash10-02ar-5960000000-9c5fabd9beb41d115306	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 40V, Negative-QTOF	splash10-0006-9400000000-ba6c955f19e1fc83670c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 10V, Negative-QTOF	splash10-001i-0490000000-43b971f3023135c78a90	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 20V, Negative-QTOF	splash10-015c-3930000000-20ce8d0f262f21e170f5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 40V, Negative-QTOF	splash10-014i-3900000000-fd0dfe6e4df61c6b7fdd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 10V, Positive-QTOF	splash10-000i-0190000000-3e66517a03ea06856d51	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 20V, Positive-QTOF	splash10-00r2-8970000000-9fe9a3682f05ba645258	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroylputrescine 40V, Positive-QTOF	splash10-06di-6900000000-b9ec2c186f420c521546	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB011503

KNApSAcK ID

C00053637

Chemspider ID

30777004

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751428

PDB ID

Not Available

ChEBI ID

168929

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 4-Coumaroylputrescine (HMDB0033461)

MOL for HMDB0033461 (4-Coumaroylputrescine)

3D MOL for HMDB0033461 (4-Coumaroylputrescine)

3D SDF for HMDB0033461 (4-Coumaroylputrescine)

3D-SDF for HMDB0033461 (4-Coumaroylputrescine)

PDB for HMDB0033461 (4-Coumaroylputrescine)

3D PDB for HMDB0033461 (4-Coumaroylputrescine)

SMILES for HMDB0033461 (4-Coumaroylputrescine)

INCHI for HMDB0033461 (4-Coumaroylputrescine)

Structure for HMDB0033461 (4-Coumaroylputrescine)

3D Structure for HMDB0033461 (4-Coumaroylputrescine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra