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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:17:32 UTC

Update Date

2022-03-07 02:56:00 UTC

HMDB ID

HMDB0038944

Secondary Accession Numbers

HMDB38944

Metabolite Identification

Common Name

Avenanthramide E

Description

Avenanthramide E belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid. Avenanthramide E has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and oats (Avena sativa). This could make avenanthramide e a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Avenanthramide E.

Structure

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

HMDB0038944
     RDKit          3D
Avenanthramide E
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.9966   -1.0828   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5938    0.1263   -0.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    0.6129   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027   -0.0607    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247    0.4053    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.2265    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2114   -0.5091    1.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -0.2158    0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    0.2541   -0.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565   -0.5092    0.9251 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0726   -0.3001   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.5512   -1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052    0.7879   -1.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1065    0.2016   -1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3361   -0.6375   -0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   -0.9060    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6140   -1.8426    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7749   -2.2180    2.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9170   -2.3625    1.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8709    1.5776    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6783    2.2803   -0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9211    1.7850   -0.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221    2.4920   -1.8408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274   -1.8673   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9692   -1.3640   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -0.8797    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019   -0.9917    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -0.5312    2.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.9988    2.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803   -0.8756    1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9307    1.0553   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    1.4552   -2.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9129    0.4149   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3122   -1.0868   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1069   -3.1788    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283    2.0887    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    3.2053   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4277    3.3512   -2.2703 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
M  END


  Mrv0541 02241210462D          

 23 24  0  0  0  0            999 V2000
    1.4398    2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987    1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8396    2.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5806    1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1814   -1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405   -2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996   -1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816   -0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4405   -0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5225    0.4111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8396    0.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0987    0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4398    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816    0.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414    2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    1.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7816    0.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241    0.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9224    0.4111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396   -0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5806   -0.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  2  0  0  0  0
  2  3  1  0  0  0  0
  2 13  2  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  2  0  0  0  0
  5 22  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  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  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038944

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C/C(=O)NC2=C(C=CC=C2)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO5/c1-23-15-10-11(6-8-14(15)19)7-9-16(20)18-13-5-3-2-4-12(13)17(21)22/h2-10,19H,1H3,(H,18,20)(H,21,22)/b9-7-

> <INCHI_KEY>
FSKJPXSYWQUVGO-CLFYSBASSA-N

> <FORMULA>
C17H15NO5

> <MOLECULAR_WEIGHT>
313.3047

> <EXACT_MASS>
313.095022595

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.958614953524958

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.416734478333332

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.887085422259442

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.55284001361007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0497187568321467

> <JCHEM_POLAR_SURFACE_AREA>
95.85999999999999

> <JCHEM_REFRACTIVITY>
87.03749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038944
     RDKit          3D
Avenanthramide E
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.9966   -1.0828   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5938    0.1263   -0.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    0.6129   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027   -0.0607    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247    0.4053    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.2265    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2114   -0.5091    1.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -0.2158    0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    0.2541   -0.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565   -0.5092    0.9251 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0726   -0.3001   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.5512   -1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052    0.7879   -1.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1065    0.2016   -1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3361   -0.6375   -0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   -0.9060    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6140   -1.8426    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7749   -2.2180    2.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9170   -2.3625    1.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8709    1.5776    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6783    2.2803   -0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9211    1.7850   -0.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221    2.4920   -1.8408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274   -1.8673   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9692   -1.3640   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -0.8797    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019   -0.9917    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -0.5312    2.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.9988    2.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803   -0.8756    1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9307    1.0553   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    1.4552   -2.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9129    0.4149   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3122   -1.0868   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1069   -3.1788    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283    2.0887    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    3.2053   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4277    3.3512   -2.2703 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  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       2.688   3.841   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.918   3.073   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.301   3.841   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.684   3.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.072  -1.535   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.072  -3.072   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.689  -3.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.306  -3.072   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.459  -1.535   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.689  -0.767   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.842   0.767   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       5.301   0.767   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.918   1.535   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.688   0.767   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.459   1.690   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.305   3.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.077   3.841   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.306   3.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.459   1.535   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.232   0.461   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.455   0.767   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.301  -0.767   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.684  -1.535   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    6   10   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10   19                                                       
CONECT   12   13                                                            
CONECT   13    2   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16    1   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   11   18   20                                                  
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22    5   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0038944
HETATM    1  C1  UNL     1       5.997  -1.083  -0.076  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.594   0.126  -0.687  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.317   0.613  -0.370  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.503  -0.061   0.495  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.225   0.405   0.826  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.474  -0.226   1.853  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.211  -0.509   1.864  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.654  -0.216   0.732  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.260   0.254  -0.346  1.00  0.00           O  
HETATM   10  N1  UNL     1      -2.056  -0.509   0.925  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.073  -0.300  -0.023  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.860   0.551  -1.105  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.905   0.788  -1.978  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.107   0.202  -1.777  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.336  -0.637  -0.721  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.304  -0.906   0.188  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.614  -1.843   1.246  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.775  -2.218   2.096  1.00  0.00           O  
HETATM   19  O4  UNL     1      -5.917  -2.363   1.335  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.871   1.578   0.220  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.678   2.280  -0.662  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.921   1.785  -0.959  1.00  0.00           C  
HETATM   23  O5  UNL     1       4.722   2.492  -1.841  1.00  0.00           O  
HETATM   24  H1  UNL     1       5.227  -1.867  -0.201  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.969  -1.364  -0.564  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.153  -0.880   1.013  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.802  -0.992   0.970  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.034  -0.531   2.794  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.242  -0.999   2.775  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.280  -0.876   1.866  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.931   1.055  -1.307  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.718   1.455  -2.816  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.913   0.415  -2.492  1.00  0.00           H  
HETATM   34  H11 UNL     1      -6.312  -1.087  -0.596  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.107  -3.179   1.871  1.00  0.00           H  
HETATM   36  H13 UNL     1       0.928   2.089   0.463  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.308   3.205  -1.098  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.428   3.351  -2.270  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   27
CONECT    5    6   20   20
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9    9   10
CONECT   10   11   30
CONECT   11   12   12   16
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   35
CONECT   20   21   36
CONECT   21   22   22   37
CONECT   22   23
CONECT   23   38
END

HMDB0038944
     RDKit          3D
Avenanthramide E
 38 39  0  0  0  0  0  0  0  0999 V2000
    5.9966   -1.0828   -0.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5938    0.1263   -0.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    0.6129   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5027   -0.0607    0.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2247    0.4053    0.8259 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   -0.2265    1.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2114   -0.5091    1.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6541   -0.2158    0.7318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2597    0.2541   -0.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0565   -0.5092    0.9251 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0726   -0.3001   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.5512   -1.1049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052    0.7879   -1.9775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1065    0.2016   -1.7771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3361   -0.6375   -0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   -0.9060    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6140   -1.8426    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7749   -2.2180    2.0960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9170   -2.3625    1.3349 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8709    1.5776    0.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6783    2.2803   -0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9211    1.7850   -0.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7221    2.4920   -1.8408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274   -1.8673   -0.2013 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9692   -1.3640   -0.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1534   -0.8797    1.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8019   -0.9917    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0339   -0.5312    2.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418   -0.9988    2.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2803   -0.8756    1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9307    1.0553   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    1.4552   -2.8162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9129    0.4149   -2.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3122   -1.0868   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1069   -3.1788    1.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283    2.0887    0.4634 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    3.2053   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4277    3.3512   -2.2703 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22  3  1  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  7 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Feruloylanthranilic acid	HMDB
2-{[(2Z)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}benzoate	Generator

Chemical Formula

C₁₇H₁₅NO₅

Average Molecular Weight

313.3047

Monoisotopic Molecular Weight

313.095022595

IUPAC Name

2-[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid

Traditional Name

2-[(2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid

CAS Registry Number

93755-77-2

SMILES

COC1=C(O)C=CC(\C=C/C(=O)NC2=C(C=CC=C2)C(O)=O)=C1

InChI Identifier

InChI=1S/C17H15NO5/c1-23-15-10-11(6-8-14(15)19)7-9-16(20)18-13-5-3-2-4-12(13)17(21)22/h2-10,19H,1H3,(H,18,20)(H,21,22)/b9-7-

InChI Key

FSKJPXSYWQUVGO-CLFYSBASSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Avenanthramides

Alternative Parents

Substituents

Avenanthramide
N-cinnamoylanthranilic acid
Acylaminobenzoic acid or derivatives
Cinnamic acid amide
Methoxyphenol
Benzoic acid or derivatives
Benzoic acid
Anilide
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Styrene
N-arylamide
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038944)

Cellular substructure

Membrane (HMDB: HMDB0038944)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038944)

Source

Exogenous

Food

Food (HMDB: HMDB0038944)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Oat (FooDB: FOOD00022)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Plant (HMDB: HMDB0038944)
Poaceae (HMDB: HMDB0038944)

Not Available

Nutrient (HMDB: HMDB0038944)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 °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	0.011 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.42	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-2	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	87.04 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	181.125	30932474
DeepCCS	[M-H]-	178.767	30932474
DeepCCS	[M-2H]-	212.897	30932474
DeepCCS	[M+Na]+	189.119	30932474
AllCCS	[M+H]+	173.0	32859911
AllCCS	[M+H-H2O]+	169.6	32859911
AllCCS	[M+NH4]+	176.2	32859911
AllCCS	[M+Na]+	177.1	32859911
AllCCS	[M-H]-	173.6	32859911
AllCCS	[M+Na-2H]-	173.3	32859911
AllCCS	[M+HCOO]-	173.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide E	COC1=C(O)C=CC(\C=C/C(=O)NC2=C(C=CC=C2)C(O)=O)=C1	5011.5	Standard polar	33892256
Avenanthramide E	COC1=C(O)C=CC(\C=C/C(=O)NC2=C(C=CC=C2)C(O)=O)=C1	3006.0	Standard non polar	33892256
Avenanthramide E	COC1=C(O)C=CC(\C=C/C(=O)NC2=C(C=CC=C2)C(O)=O)=C1	3236.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide E,1TMS,isomer #1	COC1=CC(/C=C\C(=O)NC2=CC=CC=C2C(=O)O)=CC=C1O[Si](C)(C)C	3162.3	Semi standard non polar	33892256
Avenanthramide E,1TMS,isomer #2	COC1=CC(/C=C\C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=CC=C1O	3113.4	Semi standard non polar	33892256
Avenanthramide E,1TMS,isomer #3	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC=C1O	2954.3	Semi standard non polar	33892256
Avenanthramide E,2TMS,isomer #1	COC1=CC(/C=C\C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3137.8	Semi standard non polar	33892256
Avenanthramide E,2TMS,isomer #2	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2943.4	Semi standard non polar	33892256
Avenanthramide E,2TMS,isomer #3	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O	2891.1	Semi standard non polar	33892256
Avenanthramide E,3TMS,isomer #1	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2947.9	Semi standard non polar	33892256
Avenanthramide E,3TMS,isomer #1	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2929.5	Standard non polar	33892256
Avenanthramide E,1TBDMS,isomer #1	COC1=CC(/C=C\C(=O)NC2=CC=CC=C2C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3440.6	Semi standard non polar	33892256
Avenanthramide E,1TBDMS,isomer #2	COC1=CC(/C=C\C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3367.1	Semi standard non polar	33892256
Avenanthramide E,1TBDMS,isomer #3	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O	3239.4	Semi standard non polar	33892256
Avenanthramide E,2TBDMS,isomer #1	COC1=CC(/C=C\C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3625.7	Semi standard non polar	33892256
Avenanthramide E,2TBDMS,isomer #2	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3471.9	Semi standard non polar	33892256
Avenanthramide E,2TBDMS,isomer #3	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	3395.0	Semi standard non polar	33892256
Avenanthramide E,3TBDMS,isomer #1	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=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	3628.1	Semi standard non polar	33892256
Avenanthramide E,3TBDMS,isomer #1	COC1=CC(/C=C\C(=O)N(C2=CC=CC=C2C(=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	3496.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide E GC-MS (Non-derivatized) - 70eV, Positive	splash10-000b-0980000000-83af92007cce3a3f6258	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide E GC-MS (2 TMS) - 70eV, Positive	splash10-006x-8568900000-8b1c8bce90fc3313ac7b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide E 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 - Avenanthramide E 10V, Positive-QTOF	splash10-01p9-0944000000-37da69947a7599ed75d7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 20V, Positive-QTOF	splash10-000i-1920000000-7d2f6e421a78c3b4603e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 40V, Positive-QTOF	splash10-0f79-6900000000-978fde2751f9b46ee40b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 10V, Negative-QTOF	splash10-03xr-0296000000-ceff7584db93fcf5c226	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 20V, Negative-QTOF	splash10-0gb9-1491000000-dcee909a8a4dcb165993	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 40V, Negative-QTOF	splash10-0006-6910000000-897815d4e566f76bbc38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 10V, Positive-QTOF	splash10-004j-0941000000-ff48ab51281499f5c605	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 20V, Positive-QTOF	splash10-0002-0950000000-dbcc81c4f3543543ad85	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 40V, Positive-QTOF	splash10-00dj-1920000000-714dc57c8adcd73662c2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 10V, Negative-QTOF	splash10-03di-1279000000-eb2f0335aae650a9d87e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 20V, Negative-QTOF	splash10-0udi-1290000000-c55b04336b14df32aba4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide E 40V, Negative-QTOF	splash10-0f8a-1960000000-47f08c35ff018789e74e	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB018420

KNApSAcK ID

C00054326

Chemspider ID

30777307

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13041878

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Avenanthramide E (HMDB0038944)

MOL for HMDB0038944 (Avenanthramide E)

3D MOL for HMDB0038944 (Avenanthramide E)

3D SDF for HMDB0038944 (Avenanthramide E)

3D-SDF for HMDB0038944 (Avenanthramide E)

PDB for HMDB0038944 (Avenanthramide E)

3D PDB for HMDB0038944 (Avenanthramide E)

SMILES for HMDB0038944 (Avenanthramide E)

INCHI for HMDB0038944 (Avenanthramide E)

Structure for HMDB0038944 (Avenanthramide E)

3D Structure for HMDB0038944 (Avenanthramide E)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra