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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:25 UTC

Update Date

2022-03-07 02:52:06 UTC

HMDB ID

HMDB0029284

Secondary Accession Numbers

HMDB29284

Metabolite Identification

Common Name

Avenanthramide 1c

Description

Avenanthramide 1c 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. Based on a literature review very few articles have been published on Avenanthramide 1c.

Structure

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

HMDB0029284
     RDKit          3D
Avenanthramide 1c
 35 36  0  0  0  0  0  0  0  0999 V2000
   -0.9234    2.0597    0.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7705    0.8406    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121    0.2735    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6396    1.0880    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    0.6734    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0381    1.6203    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839    1.2986    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7443   -0.0225    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0593   -0.4565   -0.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502   -0.9761   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0956   -2.3159   -0.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093   -0.6269    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.0760    0.0731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079    0.2623    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239    1.5319    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9620    1.8262    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8918    0.8828    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808   -0.3707   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.7178   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8431   -2.0578   -0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -2.8766   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -2.5800   -0.8759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -0.7830    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.1657    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974    2.6735    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    2.0276    0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3305   -1.4098   -0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -3.0396   -0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973   -1.4353   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -1.1121    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950    2.2760    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216    2.8452    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9412    1.1595    0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2342   -1.1102   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -3.5383   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
 19 14  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 22 35  1  0
M  END

  Mrv0541 02241212132D          

 22 23  0  0  0  0            999 V2000
   -4.3607    1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318   -0.0884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462   -1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752   -1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    0.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  2  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  8 20  2  0  0  0  0
 16 21  1  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029284

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13NO5/c18-13-7-5-10(9-14(13)19)6-8-15(20)17-12-4-2-1-3-11(12)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-6+

> <INCHI_KEY>
LLPIRWBXMYKFQM-SOFGYWHQSA-N

> <FORMULA>
C16H13NO5

> <MOLECULAR_WEIGHT>
299.2781

> <EXACT_MASS>
299.079372531

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.04709951857371

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.270840422333333

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.21985744786933

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.552839278345897

> <JCHEM_PKA_STRONGEST_BASIC>
-2.050336879933771

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
82.55519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029284
     RDKit          3D
Avenanthramide 1c
 35 36  0  0  0  0  0  0  0  0999 V2000
   -0.9234    2.0597    0.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7705    0.8406    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121    0.2735    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6396    1.0880    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    0.6734    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0381    1.6203    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839    1.2986    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7443   -0.0225    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0593   -0.4565   -0.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502   -0.9761   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0956   -2.3159   -0.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093   -0.6269    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.0760    0.0731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079    0.2623    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239    1.5319    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9620    1.8262    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8918    0.8828    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808   -0.3707   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.7178   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8431   -2.0578   -0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -2.8766   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -2.5800   -0.8759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -0.7830    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.1657    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974    2.6735    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    2.0276    0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3305   -1.4098   -0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -3.0396   -0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973   -1.4353   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -1.1121    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950    2.2760    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216    2.8452    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9412    1.1595    0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2342   -1.1102   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -3.5383   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
 19 14  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 22 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.140   2.915   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.474   2.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.474   0.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.140  -0.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.806   0.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.806   2.145   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.473  -0.165   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.139   0.605   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.805  -0.165   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.472   0.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.138  -0.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.196   0.605   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.138  -1.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.196  -2.475   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.529  -1.705   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.529  -0.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.140  -1.705   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.806  -2.475   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -9.474  -2.475   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.139   2.145   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.863   0.605   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.863  -2.475   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   12   15   21                                                  
CONECT   17    4   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8                                                            
CONECT   21   16                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0029284
HETATM    1  O1  UNL     1      -0.923   2.060   0.215  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.770   0.841   0.130  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.612   0.273   0.084  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.640   1.088   0.134  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.030   0.673   0.098  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.038   1.620   0.158  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.384   1.299   0.128  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.744  -0.023   0.035  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.059  -0.456  -0.002  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.750  -0.976  -0.025  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.096  -2.316  -0.120  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.409  -0.627   0.006  1.00  0.00           C  
HETATM   13  N1  UNL     1      -1.837  -0.076   0.073  1.00  0.00           N  
HETATM   14  C10 UNL     1      -3.208   0.262   0.112  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.624   1.532   0.503  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.962   1.826   0.595  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.892   0.883   0.306  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.481  -0.371  -0.081  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.131  -0.718  -0.190  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.843  -2.058  -0.649  1.00  0.00           C  
HETATM   21  O4  UNL     1      -4.821  -2.877  -0.883  1.00  0.00           O  
HETATM   22  O5  UNL     1      -2.612  -2.580  -0.876  1.00  0.00           O  
HETATM   23  H1  UNL     1       0.786  -0.783   0.010  1.00  0.00           H  
HETATM   24  H2  UNL     1       1.420   2.166   0.210  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.797   2.673   0.232  1.00  0.00           H  
HETATM   26  H4  UNL     1       6.167   2.028   0.174  1.00  0.00           H  
HETATM   27  H5  UNL     1       7.330  -1.410  -0.070  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.394  -3.040  -0.166  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.697  -1.435  -0.046  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.567  -1.112   0.023  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.895   2.276   0.744  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.222   2.845   0.908  1.00  0.00           H  
HETATM   33  H11 UNL     1      -6.941   1.160   0.392  1.00  0.00           H  
HETATM   34  H12 UNL     1      -6.234  -1.110  -0.307  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.392  -3.538  -0.611  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6    6   12
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27
CONECT   10   11   12   12
CONECT   11   28
CONECT   12   29
CONECT   13   14   30
CONECT   14   15   15   19
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   35
END

HMDB0029284
     RDKit          3D
Avenanthramide 1c
 35 36  0  0  0  0  0  0  0  0999 V2000
   -0.9234    2.0597    0.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7705    0.8406    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6121    0.2735    0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6396    1.0880    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0297    0.6734    0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0381    1.6203    0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3839    1.2986    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7443   -0.0225    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0593   -0.4565   -0.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502   -0.9761   -0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0956   -2.3159   -0.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4093   -0.6269    0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.0760    0.0731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079    0.2623    0.1120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6239    1.5319    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9620    1.8262    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8918    0.8828    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808   -0.3707   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1309   -0.7178   -0.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8431   -2.0578   -0.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8209   -2.8766   -0.8826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6125   -2.5800   -0.8759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -0.7830    0.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.1657    0.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7974    2.6735    0.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1666    2.0276    0.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3305   -1.4098   -0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -3.0396   -0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6973   -1.4353   -0.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5665   -1.1121    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950    2.2760    0.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2216    2.8452    0.9080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9412    1.1595    0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2342   -1.1102   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3915   -3.5383   -0.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
 19 14  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 22 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[3,4-Dihydroxy-(e)-cinnamoyl]-anthranilic acid	HMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}benzoate	HMDB

Chemical Formula

C₁₆H₁₃NO₅

Average Molecular Weight

299.2781

Monoisotopic Molecular Weight

299.079372531

IUPAC Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid

Traditional Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C16H13NO5/c18-13-7-5-10(9-14(13)19)6-8-15(20)17-12-4-2-1-3-11(12)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-6+

InChI Key

LLPIRWBXMYKFQM-SOFGYWHQSA-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
Anilide
Benzoic acid or derivatives
Benzoic acid
Catechol
Styrene
N-arylamide
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029284)
Cell membrane (HMDB: HMDB0029284)

Source

Endogenous

Endogenous (HMDB: HMDB0029284)

Plant

Plant (HMDB: HMDB0029284)

Exogenous

Food

Food (HMDB: HMDB0029284)

Exogenous (HMDB: HMDB0029284)

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	0.044 g/L	ALOGPS
logP	3.01	ALOGPS
logP	3.27	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.56 m³·mol⁻¹	ChemAxon
Polarizability	30.05 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]+	168.808	30932474
DeepCCS	[M-H]-	166.45	30932474
DeepCCS	[M-2H]-	200.055	30932474
DeepCCS	[M+Na]+	175.282	30932474
AllCCS	[M+H]+	168.8	32859911
AllCCS	[M+H-H2O]+	165.3	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	173.0	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.3	32859911
AllCCS	[M+HCOO]-	168.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 1c	OC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1	4917.9	Standard polar	33892256
Avenanthramide 1c	OC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1	2970.4	Standard non polar	33892256
Avenanthramide 1c	OC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1	3257.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 1c,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C1	3162.3	Semi standard non polar	33892256
Avenanthramide 1c,1TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC=C1O	3142.6	Semi standard non polar	33892256
Avenanthramide 1c,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O	3153.6	Semi standard non polar	33892256
Avenanthramide 1c,1TMS,isomer #4	C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)C1=CC=CC=C1C(=O)O	3024.5	Semi standard non polar	33892256
Avenanthramide 1c,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	3110.7	Semi standard non polar	33892256
Avenanthramide 1c,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	3102.7	Semi standard non polar	33892256
Avenanthramide 1c,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C	2900.6	Semi standard non polar	33892256
Avenanthramide 1c,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O[Si](C)(C)C	3150.4	Semi standard non polar	33892256
Avenanthramide 1c,2TMS,isomer #5	C[Si](C)(C)OC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC=C1O	2923.5	Semi standard non polar	33892256
Avenanthramide 1c,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=C1O	2923.1	Semi standard non polar	33892256
Avenanthramide 1c,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3153.3	Semi standard non polar	33892256
Avenanthramide 1c,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	2909.1	Semi standard non polar	33892256
Avenanthramide 1c,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2922.1	Semi standard non polar	33892256
Avenanthramide 1c,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=C1O[Si](C)(C)C	2968.6	Semi standard non polar	33892256
Avenanthramide 1c,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2998.1	Semi standard non polar	33892256
Avenanthramide 1c,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2896.4	Standard non polar	33892256
Avenanthramide 1c,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C1	3413.0	Semi standard non polar	33892256
Avenanthramide 1c,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC=C1O	3425.1	Semi standard non polar	33892256
Avenanthramide 1c,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O	3435.2	Semi standard non polar	33892256
Avenanthramide 1c,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)C1=CC=CC=C1C(=O)O	3298.3	Semi standard non polar	33892256
Avenanthramide 1c,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	3634.6	Semi standard non polar	33892256
Avenanthramide 1c,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3622.5	Semi standard non polar	33892256
Avenanthramide 1c,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	3429.1	Semi standard non polar	33892256
Avenanthramide 1c,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	3676.4	Semi standard non polar	33892256
Avenanthramide 1c,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O	3487.5	Semi standard non polar	33892256
Avenanthramide 1c,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C1O	3488.4	Semi standard non polar	33892256
Avenanthramide 1c,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	3837.7	Semi standard non polar	33892256
Avenanthramide 1c,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[Si](C)(C)C(C)(C)C	3622.1	Semi standard non polar	33892256
Avenanthramide 1c,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3623.2	Semi standard non polar	33892256
Avenanthramide 1c,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	3695.2	Semi standard non polar	33892256
Avenanthramide 1c,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3838.0	Semi standard non polar	33892256
Avenanthramide 1c,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3618.5	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 1c GC-MS (Non-derivatized) - 70eV, Positive	splash10-03ei-0970000000-0f85089d01f3c6f013ba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 1c GC-MS (3 TMS) - 70eV, Positive	splash10-0pi3-3011930000-9f3c51403a36032bb96c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 1c 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 1c 10V, Positive-QTOF	splash10-0f79-0944000000-572f97b2d1cb962f6090	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Positive-QTOF	splash10-000i-1910000000-99d60d003d66b05a9174	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Positive-QTOF	splash10-0f79-8900000000-9a6c0c6b575ceac4051e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 10V, Negative-QTOF	splash10-0f6t-0190000000-85572801e7260d0ffc48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Negative-QTOF	splash10-0udr-1490000000-186ab994a2d992f6eec2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Negative-QTOF	splash10-0006-8900000000-a4a60e0c0ca8e12f7d50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 10V, Negative-QTOF	splash10-0002-0290000000-50c6639b64e14d58aa91	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Negative-QTOF	splash10-000i-1930000000-d53c4ff0c45696138d0a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Negative-QTOF	splash10-0019-1910000000-00e62c1ff14365cf946e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 10V, Positive-QTOF	splash10-03di-0911000000-62cd227d3ac94469eb85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 20V, Positive-QTOF	splash10-03e9-0930000000-b1f368ebae5203f688ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1c 40V, Positive-QTOF	splash10-000j-1910000000-d5288893d97757e538bb	2021-09-22	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

535

FooDB ID

FDB000286

KNApSAcK ID

Not Available

Chemspider ID

8036787

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9861088

PDB ID

Not Available

ChEBI ID

710546

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

Bratt K, Sunnerheim K, Bryngelsson S, Fagerlund A, Engman L, Andersson RE, Dimberg LH: Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. J Agric Food Chem. 2003 Jan 29;51(3):594-600. [PubMed:12537428 ]
Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Showing metabocard for Avenanthramide 1c (HMDB0029284)

MOL for HMDB0029284 (Avenanthramide 1c)

3D MOL for HMDB0029284 (Avenanthramide 1c)

3D SDF for HMDB0029284 (Avenanthramide 1c)

3D-SDF for HMDB0029284 (Avenanthramide 1c)

PDB for HMDB0029284 (Avenanthramide 1c)

3D PDB for HMDB0029284 (Avenanthramide 1c)

SMILES for HMDB0029284 (Avenanthramide 1c)

INCHI for HMDB0029284 (Avenanthramide 1c)

Structure for HMDB0029284 (Avenanthramide 1c)

3D Structure for HMDB0029284 (Avenanthramide 1c)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra