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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-02-26 19:01:51 UTC

Update Date

2022-03-07 03:17:35 UTC

HMDB ID

HMDB0059747

Secondary Accession Numbers

HMDB59747

Metabolite Identification

Common Name

4-Hydroxy-3-methoxy-cinnamoylglycine

Description

4-Hydroxy-3-methoxy-cinnamoylglycine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. 4-Hydroxy-3-methoxy-cinnamoylglycine is an extremely weak basic (essentially neutral) compound (based on its pKa). These are organic compounds containing a glycine residue with the N-atom attached to another moiety through an N-ester bond.

Structure

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

HMDB0059747
     RDKit          3D
4-Hydroxy-3-methoxy-cinnamoylglycine
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.0708   -2.1057    3.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417   -2.3006    2.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947   -1.7792    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -1.0351    1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -0.4784    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342    0.2982   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    0.8855   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.6592   -1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176    2.1707   -2.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307    1.8810   -0.2370 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    2.6658   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    2.0251   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172    0.9738   -1.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    2.6094   -1.7834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -0.6825   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -1.4419   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -1.9916    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328   -2.7507    0.6097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555   -2.4720    3.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120   -1.0358    4.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4033   -2.6773    4.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -0.8444    2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6110    0.4258    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496    0.7624   -2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3128    1.4714    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    2.7724    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260    3.6720   -0.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286    2.0624   -2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -0.2690   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431   -1.6075   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3207   -2.8632   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
M  END

 
  Mrv0541 02271201342D          
 
 18 18  0  0  0  0            999 V2000
   12.7875   -8.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7875   -9.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5019  -10.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2165   -9.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2165   -8.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5019   -8.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9419   -8.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6521   -8.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9419  -10.1952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0730   -8.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3585   -8.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6441   -8.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9296   -8.9512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2151   -8.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5007   -8.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7862   -8.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6441   -7.7137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5007   -9.7762    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  2  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
 15 16  1  0  0  0  0
 12 17  2  0  0  0  0
 15 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059747

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO5/c1-18-10-6-8(2-4-9(10)14)3-5-11(15)13-7-12(16)17/h2-6,14H,7H2,1H3,(H,13,15)(H,16,17)/b5-3+

> <INCHI_KEY>
CLGNQAIRBLDHIN-HWKANZROSA-N

> <FORMULA>
C12H13NO5

> <MOLECULAR_WEIGHT>
251.2353

> <EXACT_MASS>
251.079372531

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.08577441397712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]acetic acid

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
0.5695664330000001

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.888752600251673

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3151077633790575

> <JCHEM_PKA_STRONGEST_BASIC>
0.5277319894207635

> <JCHEM_POLAR_SURFACE_AREA>
95.85999999999999

> <JCHEM_REFRACTIVITY>
64.3075

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-feruloylglycine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059747
     RDKit          3D
4-Hydroxy-3-methoxy-cinnamoylglycine
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.0708   -2.1057    3.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417   -2.3006    2.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947   -1.7792    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -1.0351    1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -0.4784    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342    0.2982   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    0.8855   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.6592   -1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176    2.1707   -2.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307    1.8810   -0.2370 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    2.6658   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    2.0251   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172    0.9738   -1.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    2.6094   -1.7834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -0.6825   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -1.4419   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -1.9916    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328   -2.7507    0.6097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555   -2.4720    3.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120   -1.0358    4.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4033   -2.6773    4.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -0.8444    2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6110    0.4258    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496    0.7624   -2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3128    1.4714    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    2.7724    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260    3.6720   -0.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286    2.0624   -2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -0.2690   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431   -1.6075   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3207   -2.8632   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      23.870 -16.709   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      23.870 -18.249   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.204 -19.019   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.537 -18.249   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.537 -16.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.204 -15.939   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      27.892 -15.927   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      29.217 -16.692   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      27.892 -19.031   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      22.536 -15.939   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.203 -16.709   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.869 -15.939   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      18.535 -16.709   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      17.202 -15.939   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.868 -16.709   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.534 -15.939   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      19.869 -14.399   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      15.868 -18.249   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    4                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0059747
HETATM    1  C1  UNL     1      -2.071  -2.106   3.816  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.942  -2.301   2.712  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.695  -1.779   1.469  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.562  -1.035   1.264  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.259  -0.478   0.015  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.034   0.298  -0.113  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.395   0.886  -1.207  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.631   1.659  -1.303  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.918   2.171  -2.431  1.00  0.00           O  
HETATM   10  N1  UNL     1       2.531   1.881  -0.237  1.00  0.00           N  
HETATM   11  C8  UNL     1       3.747   2.666  -0.412  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.601   2.025  -1.443  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.217   0.974  -1.995  1.00  0.00           O  
HETATM   14  O4  UNL     1       5.828   2.609  -1.783  1.00  0.00           O  
HETATM   15  C10 UNL     1      -2.126  -0.682  -1.049  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.256  -1.442  -0.787  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.562  -1.992   0.433  1.00  0.00           C  
HETATM   18  O5  UNL     1      -4.733  -2.751   0.610  1.00  0.00           O  
HETATM   19  H1  UNL     1      -1.055  -2.472   3.493  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.012  -1.036   4.095  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.403  -2.677   4.704  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.851  -0.844   2.058  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.611   0.426   0.757  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.250   0.762  -2.092  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.313   1.471   0.691  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.248   2.772   0.559  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.426   3.672  -0.809  1.00  0.00           H  
HETATM   28  H10 UNL     1       6.529   2.062  -2.278  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.920  -0.269  -2.014  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.943  -1.608  -1.618  1.00  0.00           H  
HETATM   31  H13 UNL     1      -5.321  -2.863  -0.198  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   22
CONECT    5    6   15   15
CONECT    6    7    7   23
CONECT    7    8   24
CONECT    8    9    9   10
CONECT   10   11   25
CONECT   11   12   26   27
CONECT   12   13   13   14
CONECT   14   28
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   18
CONECT   18   31
END

HMDB0059747
     RDKit          3D
4-Hydroxy-3-methoxy-cinnamoylglycine
 31 31  0  0  0  0  0  0  0  0999 V2000
   -2.0708   -2.1057    3.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417   -2.3006    2.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947   -1.7792    1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -1.0351    1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2592   -0.4784    0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342    0.2982   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951    0.8855   -1.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6311    1.6592   -1.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176    2.1707   -2.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5307    1.8810   -0.2370 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    2.6658   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    2.0251   -1.4430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2172    0.9738   -1.9951 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284    2.6094   -1.7834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1262   -0.6825   -1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2558   -1.4419   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5615   -1.9916    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7328   -2.7507    0.6097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555   -2.4720    3.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0120   -1.0358    4.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4033   -2.6773    4.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8513   -0.8444    2.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6110    0.4258    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2496    0.7624   -2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3128    1.4714    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2482    2.7724    0.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260    3.6720   -0.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5286    2.0624   -2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9200   -0.2690   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9431   -1.6075   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3207   -2.8632   -0.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
  5 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17  3  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[3-(4-Hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]glycine	Kegg

Chemical Formula

C₁₂H₁₃NO₅

Average Molecular Weight

251.2353

Monoisotopic Molecular Weight

251.079372531

IUPAC Name

2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]acetic acid

Traditional Name

N-feruloylglycine

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C12H13NO5/c1-18-10-6-8(2-4-9(10)14)3-5-11(15)13-7-12(16)17/h2-6,14H,7H2,1H3,(H,13,15)(H,16,17)/b5-3+

InChI Key

CLGNQAIRBLDHIN-HWKANZROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cinnamic acid amide
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:17691 )

Ontology

Not Available

Urine (PMID: 2338430)

Source

Exogenous

Exogenous (HMDB: HMDB0059747)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	1.59	ALOGPS
logP	0.57	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	0.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.31 m³·mol⁻¹	ChemAxon
Polarizability	25.09 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]+	158.194	30932474
DeepCCS	[M-H]-	155.836	30932474
DeepCCS	[M-2H]-	188.916	30932474
DeepCCS	[M+Na]+	164.287	30932474
AllCCS	[M+H]+	156.1	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.4	32859911
AllCCS	[M+Na]+	160.4	32859911
AllCCS	[M-H]-	156.7	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	157.3	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.	3.45 minutes	32390414
Predicted by Siyang on May 30, 2022	9.881 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.05 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1362.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	237.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	107.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	69.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	333.6 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	315.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	174.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	763.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	308.8 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	988.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	218.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	266.6 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	98.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methoxy-cinnamoylglycine	COC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O	4172.0	Standard polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine	COC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O	2374.5	Standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine	COC1=CC(\C=C\C(=O)NCC(O)=O)=CC=C1O	2662.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methoxy-cinnamoylglycine,1TMS,isomer #1	COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C)=CC=C1O	2611.0	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TMS,isomer #2	COC1=CC(/C=C/C(=O)NCC(=O)O)=CC=C1O[Si](C)(C)C	2622.6	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TMS,isomer #3	COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C)=CC=C1O	2593.0	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TMS,isomer #1	COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2665.8	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TMS,isomer #2	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2553.4	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TMS,isomer #3	COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2627.8	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TMS,isomer #1	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2610.7	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TMS,isomer #1	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2573.0	Standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TMS,isomer #1	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2833.6	Standard polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2895.8	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)NCC(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2902.2	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,1TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O	2843.8	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3195.6	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	3047.4	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,2TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3143.1	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3315.6	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3223.3	Standard non polar	33892256
4-Hydroxy-3-methoxy-cinnamoylglycine,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3079.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-2940000000-68fbe21644bff52199f5	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-9047000000-45f1efb450d6ad556284	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 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-Hydroxy-3-methoxy-cinnamoylglycine 10V, Positive-QTOF	splash10-0fk9-9160000000-744298d87bf18ec4b6a2	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Positive-QTOF	splash10-00fr-9210000000-bbf4a1d1d2d84d84d856	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Positive-QTOF	splash10-00fr-9200000000-da8639fc4456a4a8c583	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 10V, Negative-QTOF	splash10-0udi-0190000000-88aa56e4cca7e999df41	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Negative-QTOF	splash10-0ue9-3590000000-c2a725902a93090b41ba	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Negative-QTOF	splash10-00di-9500000000-1171a97ac3b7e5d27949	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 10V, Negative-QTOF	splash10-0pba-1490000000-0d82c19a854d2bdc8f21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Negative-QTOF	splash10-001i-2900000000-f762ab31918e815cf322	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Negative-QTOF	splash10-001r-1900000000-1dcba79c43f68112702f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 10V, Positive-QTOF	splash10-0fb9-0890000000-866638cae32d314727ff	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 20V, Positive-QTOF	splash10-002b-1910000000-e3ec4df22d23ae6158c0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-cinnamoylglycine 40V, Positive-QTOF	splash10-004j-6900000000-3032f20b6908622bbdb0	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	2338430	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

4444158

KEGG Compound ID

C02564

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280527

PDB ID

Not Available

ChEBI ID

17691

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

Not Available

Showing metabocard for 4-Hydroxy-3-methoxy-cinnamoylglycine (HMDB0059747)

MOL for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

3D MOL for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

3D SDF for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

3D-SDF for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

PDB for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

3D PDB for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

SMILES for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

INCHI for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

Structure for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

3D Structure for HMDB0059747 (4-Hydroxy-3-methoxy-cinnamoylglycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra