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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:11:44 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033462

Secondary Accession Numbers

HMDB33462

Metabolite Identification

Common Name

4-Coumaroyl-2-hydroxyputrescine

Description

4-Coumaroyl-2-hydroxyputrescine 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-Coumaroyl-2-hydroxyputrescine has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and wheats (Triticum). This could make 4-coumaroyl-2-hydroxyputrescine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Coumaroyl-2-hydroxyputrescine.

Structure

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

HMDB0033462
     RDKit          3D
4-Coumaroyl-2-hydroxyputrescine
 36 36  0  0  0  0  0  0  0  0999 V2000
    6.4134    0.3334   -0.8047 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9599    0.2651   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4817   -0.4655    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -0.5645    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.2561    1.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    0.7847    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    0.6061    0.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -0.0000   -0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -0.4115   -1.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119   -0.1794   -0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349    0.2200    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    0.0585    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554   -0.5199   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4473   -0.6462   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1148   -0.1900    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5088   -0.3400    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368    0.4010    1.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    0.5196    1.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7680    0.0466    0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7165    1.3101   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5267    1.2987   -0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7163   -0.3113   -1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7790    0.0337    1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614   -1.5027    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -1.1221   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -1.7990    1.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5389    1.2944   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    1.3921    1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134    0.9685    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122   -0.6557   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    0.7049    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.8997   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9754   -1.1097   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0023   -0.0078    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9883    0.7605    2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5370    0.9832    2.2009 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 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
 18 12  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv0541 02241207482D          

 18 18  0  0  0  0            999 V2000
   -0.7145    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.2375    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  9 11  2  0  0  0  0
 11 12  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033462

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCC(O)CNC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O3/c14-8-7-12(17)9-15-13(18)6-3-10-1-4-11(16)5-2-10/h1-6,12,16-17H,7-9,14H2,(H,15,18)/b6-3+

> <INCHI_KEY>
XBVRGBGSLROQIA-ZZXKWVIFSA-N

> <FORMULA>
C13H18N2O3

> <MOLECULAR_WEIGHT>
250.2936

> <EXACT_MASS>
250.131742452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.51702961868573

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-(4-amino-2-hydroxybutyl)-3-(4-hydroxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
-0.8399410572139917

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.805904439316095

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.169523821617782

> <JCHEM_PKA_STRONGEST_BASIC>
9.778236999448103

> <JCHEM_POLAR_SURFACE_AREA>
95.58

> <JCHEM_REFRACTIVITY>
70.5374

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-(4-amino-2-hydroxybutyl)-3-(4-hydroxyphenyl)prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033462
     RDKit          3D
4-Coumaroyl-2-hydroxyputrescine
 36 36  0  0  0  0  0  0  0  0999 V2000
    6.4134    0.3334   -0.8047 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9599    0.2651   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4817   -0.4655    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -0.5645    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.2561    1.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    0.7847    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    0.6061    0.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -0.0000   -0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -0.4115   -1.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119   -0.1794   -0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349    0.2200    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    0.0585    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554   -0.5199   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4473   -0.6462   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1148   -0.1900    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5088   -0.3400    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368    0.4010    1.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    0.5196    1.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7680    0.0466    0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7165    1.3101   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5267    1.2987   -0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7163   -0.3113   -1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7790    0.0337    1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614   -1.5027    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -1.1221   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -1.7990    1.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5389    1.2944   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    1.3921    1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134    0.9685    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122   -0.6557   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    0.7049    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.8997   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9754   -1.1097   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0023   -0.0078    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9883    0.7605    2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5370    0.9832    2.2009 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 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
 18 12  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  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  N   UNK     0      -1.334   0.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.667   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -8.002   0.770   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001  -1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    1    9   10                                                  
CONECT    8    3                                                            
CONECT    9    7   11                                                       
CONECT   10    7                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0033462
HETATM    1  N1  UNL     1       6.413   0.333  -0.805  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.960   0.265  -0.898  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.482  -0.466   0.312  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.966  -0.565   0.249  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.500  -1.256   1.388  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.338   0.785   0.305  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.878   0.606   0.295  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.222  -0.000  -0.788  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.851  -0.412  -1.798  1.00  0.00           O  
HETATM   10  C6  UNL     1      -1.212  -0.179  -0.792  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.935   0.220   0.217  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.384   0.059   0.254  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.055  -0.520  -0.769  1.00  0.00           C  
HETATM   14  C10 UNL     1      -5.447  -0.646  -0.674  1.00  0.00           C  
HETATM   15  C11 UNL     1      -6.115  -0.190   0.438  1.00  0.00           C  
HETATM   16  O3  UNL     1      -7.509  -0.340   0.484  1.00  0.00           O  
HETATM   17  C12 UNL     1      -5.437   0.401   1.485  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.074   0.520   1.381  1.00  0.00           C  
HETATM   19  H1  UNL     1       6.768   0.047   0.129  1.00  0.00           H  
HETATM   20  H2  UNL     1       6.716   1.310  -0.970  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.527   1.299  -0.992  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.716  -0.311  -1.794  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.779   0.034   1.262  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.861  -1.503   0.249  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.655  -1.122  -0.637  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.231  -1.799   1.739  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.539   1.294  -0.670  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.644   1.392   1.162  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.413   0.968   1.153  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.712  -0.656  -1.648  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.486   0.705   1.103  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.592  -0.900  -1.671  1.00  0.00           H  
HETATM   33  H15 UNL     1      -5.975  -1.110  -1.496  1.00  0.00           H  
HETATM   34  H16 UNL     1      -8.002  -0.008   1.296  1.00  0.00           H  
HETATM   35  H17 UNL     1      -5.988   0.761   2.367  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.537   0.983   2.201  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5    6   25
CONECT    5   26
CONECT    6    7   27   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11   11   30
CONECT   11   12   31
CONECT   12   13   13   18
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   17
CONECT   16   34
CONECT   17   18   18   35
CONECT   18   36
END

HMDB0033462
     RDKit          3D
4-Coumaroyl-2-hydroxyputrescine
 36 36  0  0  0  0  0  0  0  0999 V2000
    6.4134    0.3334   -0.8047 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9599    0.2651   -0.8984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4817   -0.4655    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9665   -0.5645    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5005   -1.2561    1.3875 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    0.7847    0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8776    0.6061    0.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218   -0.0000   -0.7885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8510   -0.4115   -1.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119   -0.1794   -0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349    0.2200    0.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3839    0.0585    0.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0554   -0.5199   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4473   -0.6462   -0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1148   -0.1900    0.4378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5088   -0.3400    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4368    0.4010    1.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    0.5196    1.3812 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7680    0.0466    0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7165    1.3101   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5267    1.2987   -0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7163   -0.3113   -1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7790    0.0337    1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614   -1.5027    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545   -1.1221   -0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2305   -1.7990    1.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5389    1.2944   -0.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6445    1.3921    1.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4134    0.9685    1.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7122   -0.6557   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855    0.7049    1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5916   -0.8997   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9754   -1.1097   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0023   -0.0078    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9883    0.7605    2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5370    0.9832    2.2009 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
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 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
 18 12  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 11 31  1  0
 13 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2E)-N-(4-Amino-2-hydroxybutyl)-3-(4-hydroxyphenyl)prop-2-enimidate	HMDB

Chemical Formula

C₁₃H₁₈N₂O₃

Average Molecular Weight

250.2936

Monoisotopic Molecular Weight

250.131742452

IUPAC Name

(2E)-N-(4-amino-2-hydroxybutyl)-3-(4-hydroxyphenyl)prop-2-enamide

Traditional Name

(2E)-N-(4-amino-2-hydroxybutyl)-3-(4-hydroxyphenyl)prop-2-enamide

CAS Registry Number

24177-22-8

SMILES

NCCC(O)CNC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C13H18N2O3/c14-8-7-12(17)9-15-13(18)6-3-10-1-4-11(16)5-2-10/h1-6,12,16-17H,7-9,14H2,(H,15,18)/b6-3+

InChI Key

XBVRGBGSLROQIA-ZZXKWVIFSA-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
1,3-aminoalcohol
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033462)
Cytoplasm (HMDB: HMDB0033462)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033462)

Source

Exogenous

Exogenous (HMDB: HMDB0033462)

Food

Food (HMDB: HMDB0033462)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Wheat (FooDB: FOOD00561)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Plant (HMDB: HMDB0033462)
Poaceae (HMDB: HMDB0033462)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033462)

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	18380 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	-0.84	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	95.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	70.54 m³·mol⁻¹	ChemAxon
Polarizability	27.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	160.916	30932474
DeepCCS	[M-H]-	158.558	30932474
DeepCCS	[M-2H]-	191.444	30932474
DeepCCS	[M+Na]+	167.01	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.5	32859911
AllCCS	[M-H]-	160.5	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	161.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.48 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2546 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.73 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	290.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	453.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	228.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	102.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	254.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	263.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	842.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	612.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	84.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	670.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	709.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	524.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	164.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Coumaroyl-2-hydroxyputrescine	NCCC(O)CNC(=O)\C=C\C1=CC=C(O)C=C1	3901.9	Standard polar	33892256
4-Coumaroyl-2-hydroxyputrescine	NCCC(O)CNC(=O)\C=C\C1=CC=C(O)C=C1	2553.0	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine	NCCC(O)CNC(=O)\C=C\C1=CC=C(O)C=C1	2922.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Coumaroyl-2-hydroxyputrescine,1TMS,isomer #1	C[Si](C)(C)OC(CCN)CNC(=O)/C=C/C1=CC=C(O)C=C1	2727.6	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(O)CCN)C=C1	2749.8	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,1TMS,isomer #3	C[Si](C)(C)NCCC(O)CNC(=O)/C=C/C1=CC=C(O)C=C1	2821.3	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,1TMS,isomer #4	C[Si](C)(C)N(CC(O)CCN)C(=O)/C=C/C1=CC=C(O)C=C1	2733.3	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(CCN)O[Si](C)(C)C)C=C1	2756.5	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TMS,isomer #2	C[Si](C)(C)NCCC(CNC(=O)/C=C/C1=CC=C(O)C=C1)O[Si](C)(C)C	2893.3	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TMS,isomer #3	C[Si](C)(C)OC(CCN)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C	2784.9	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TMS,isomer #4	C[Si](C)(C)NCCC(O)CNC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1	2941.6	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(O)CCN)[Si](C)(C)C)C=C1	2729.5	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TMS,isomer #6	C[Si](C)(C)N(CCC(O)CNC(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C	3005.9	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TMS,isomer #7	C[Si](C)(C)NCCC(O)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C	2870.2	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #1	C[Si](C)(C)NCCC(CNC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2839.6	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #1	C[Si](C)(C)NCCC(CNC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2872.5	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN)O[Si](C)(C)C)[Si](C)(C)C)C=C1	2741.1	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN)O[Si](C)(C)C)[Si](C)(C)C)C=C1	2756.9	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #3	C[Si](C)(C)OC(CCN([Si](C)(C)C)[Si](C)(C)C)CNC(=O)/C=C/C1=CC=C(O)C=C1	3010.5	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #3	C[Si](C)(C)OC(CCN([Si](C)(C)C)[Si](C)(C)C)CNC(=O)/C=C/C1=CC=C(O)C=C1	3006.3	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #4	C[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C)O[Si](C)(C)C	2849.8	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #4	C[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C)O[Si](C)(C)C	2937.8	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(O)CCN([Si](C)(C)C)[Si](C)(C)C)C=C1	3069.3	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(O)CCN([Si](C)(C)C)[Si](C)(C)C)C=C1	3094.4	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #6	C[Si](C)(C)NCCC(O)CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2816.4	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #6	C[Si](C)(C)NCCC(O)CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	2851.5	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #7	C[Si](C)(C)N(CC(O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)/C=C/C1=CC=C(O)C=C1	2992.6	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TMS,isomer #7	C[Si](C)(C)N(CC(O)CCN([Si](C)(C)C)[Si](C)(C)C)C(=O)/C=C/C1=CC=C(O)C=C1	3046.5	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(CCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2999.5	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(CCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1	2993.7	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #2	C[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C)O[Si](C)(C)C	2837.1	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #2	C[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C)O[Si](C)(C)C	2859.7	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #3	C[Si](C)(C)OC(CCN([Si](C)(C)C)[Si](C)(C)C)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C	2995.5	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #3	C[Si](C)(C)OC(CCN([Si](C)(C)C)[Si](C)(C)C)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C	3066.7	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C=C1	2970.6	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(O)CCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)C=C1	2987.6	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C)C=C1	2997.9	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C)C=C1	2970.1	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CCN)CNC(=O)/C=C/C1=CC=C(O)C=C1	2969.1	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(O)CCN)C=C1	3017.7	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC(O)CNC(=O)/C=C/C1=CC=C(O)C=C1	3082.3	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CC(O)CCN)C(=O)/C=C/C1=CC=C(O)C=C1	2952.0	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(CCN)O[Si](C)(C)C(C)(C)C)C=C1	3279.2	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(CNC(=O)/C=C/C1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C	3387.9	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CCN)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3243.8	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC(O)CNC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	3459.0	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(O)CCN)[Si](C)(C)C(C)(C)C)C=C1	3240.4	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(CCC(O)CNC(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3460.2	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NCCC(O)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3332.9	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(CNC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3601.0	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(CNC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3505.1	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3477.7	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3366.1	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CNC(=O)/C=C/C1=CC=C(O)C=C1	3693.8	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CNC(=O)/C=C/C1=CC=C(O)C=C1	3590.4	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3559.3	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3531.1	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3785.3	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3640.1	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCCC(O)CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3581.9	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NCCC(O)CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3448.6	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CC(O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)/C=C/C1=CC=C(O)C=C1	3667.8	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(CC(O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)/C=C/C1=CC=C(O)C=C1	3594.3	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3924.7	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NCC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1	3738.4	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3780.8	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(CN(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3619.6	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3879.1	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CN(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3796.2	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3903.2	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3688.1	Standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4095.5	Semi standard non polar	33892256
4-Coumaroyl-2-hydroxyputrescine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	3836.4	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-Coumaroyl-2-hydroxyputrescine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9510000000-8272d84d65aed3347dce	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine GC-MS (2 TMS) - 70eV, Positive	splash10-003r-9438000000-ccf61932e82ca2793b04	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 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-Coumaroyl-2-hydroxyputrescine 10V, Positive-QTOF	splash10-0f89-3390000000-ba2f4e1217faa267e3db	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 20V, Positive-QTOF	splash10-000i-9530000000-d56c31842bfae248e490	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 40V, Positive-QTOF	splash10-000i-9300000000-5a46857ecd6c25b4f048	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 10V, Negative-QTOF	splash10-0002-0390000000-8adf4f00f41fb804e893	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 20V, Negative-QTOF	splash10-01pn-3950000000-082b7fb0e04cc7b6fe17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 40V, Negative-QTOF	splash10-0006-9400000000-49da193da4b3f0a5bef3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 10V, Positive-QTOF	splash10-001i-0390000000-bc0a7b647b59f89bc451	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 20V, Positive-QTOF	splash10-00l2-1960000000-806c5258d12c93a4d87d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 40V, Positive-QTOF	splash10-014i-4900000000-53a7cb9e90253e71b095	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 10V, Negative-QTOF	splash10-0002-0190000000-1c392b7b41ed80971c18	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 20V, Negative-QTOF	splash10-067i-1940000000-1cd810980ced06b24dcb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Coumaroyl-2-hydroxyputrescine 40V, Negative-QTOF	splash10-014i-2900000000-04d8014449ff6a0fda75	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB011504

KNApSAcK ID

C00054893

Chemspider ID

35013608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101755293

PDB ID

Not Available

ChEBI ID

173781

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1835841

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.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

4-Coumaroyl-2-hydroxyputrescine → (2E)-N-[4-amino-2-(sulfooxy)butyl]-3-(4-hydroxyphenyl)prop-2-enimidic acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4-Coumaroyl-2-hydroxyputrescine → 6-{4-[(1E)-2-[(4-amino-2-hydroxybutyl)-C-hydroxycarbonimidoyl]eth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

4-Coumaroyl-2-hydroxyputrescine → (2E)-N-(4-amino-2-hydroxybutyl)-3-[4-(sulfooxy)phenyl]prop-2-enimidic acid	details

Showing metabocard for 4-Coumaroyl-2-hydroxyputrescine (HMDB0033462)

MOL for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

3D MOL for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

3D SDF for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

3D-SDF for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

PDB for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

3D PDB for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

SMILES for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

INCHI for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

Structure for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

3D Structure for HMDB0033462 (4-Coumaroyl-2-hydroxyputrescine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions