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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 23:54:00 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038576

Secondary Accession Numbers

HMDB38576

Metabolite Identification

Common Name

Avenanthramide C

Description

Avenanthramide C 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 C is found, on average, in the highest concentration within oats (Avena sativa). This could make avenanthramide C a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Avenanthramide C.

Structure

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

HMDB0038576
     RDKit          3D
Avenanthramide C
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.1826    0.9748   -2.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029    0.5428   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623    0.5467   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    0.1331   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    0.1462    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    0.5926   -0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1371    0.5775   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7461    0.1123    0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1386    0.1062    0.4015 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.3364    1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5029   -0.8128    2.4860 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535   -0.3184    1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5169    0.0803   -0.0740 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    0.0589   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    0.7281   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0188    0.7513   -1.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7221    0.1147   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1246    0.1342   -0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0167   -0.5497    0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6229   -0.5864    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -1.3605    1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7955   -1.9122    2.8127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899   -1.6086    2.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    0.9259   -1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -0.2434    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039    0.9631   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7635    0.9317   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7198    0.4367   -0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4805   -0.8567    2.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -0.6786    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0446   -0.2583    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1979    1.2709   -1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5720    1.2795   -1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6288    0.6306   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6154   -1.0534    1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -1.4627    3.0734 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
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  5  1  0
 20 14  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 23 36  1  0
M  END


  Mrv0541 02241209002D          

 23 24  0  0  0  0            999 V2000
   -2.1231   -1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218   -0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6006   -1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1999   -0.7609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6807    0.5205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3218    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1231    0.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641   -0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5654   -1.1615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    2.0429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6807    1.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1198    1.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5205    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4019    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8443    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5654    0.1206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6807   -2.0429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4019    1.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    1.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8443    1.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5654    1.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  2  0  0  0  0
  3 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 12  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
 11 12  2  0  0  0  0
 12 13  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
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 22  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038576

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+

> <INCHI_KEY>
IDUUXROOZBOOPH-QHHAFSJGSA-N

> <FORMULA>
C16H13NO6

> <MOLECULAR_WEIGHT>
315.2775

> <EXACT_MASS>
315.074287153

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.962789502308034

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.967275100666667

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.035637921119847

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.307118911932904

> <JCHEM_PKA_STRONGEST_BASIC>
-2.032265536964912

> <JCHEM_POLAR_SURFACE_AREA>
127.09000000000002

> <JCHEM_REFRACTIVITY>
84.53609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038576
     RDKit          3D
Avenanthramide C
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.1826    0.9748   -2.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029    0.5428   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623    0.5467   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    0.1331   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    0.1462    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    0.5926   -0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1371    0.5775   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7461    0.1123    0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1386    0.1062    0.4015 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.3364    1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5029   -0.8128    2.4860 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535   -0.3184    1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5169    0.0803   -0.0740 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    0.0589   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    0.7281   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0188    0.7513   -1.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7221    0.1147   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1246    0.1342   -0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0167   -0.5497    0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6229   -0.5864    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -1.3605    1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7955   -1.9122    2.8127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899   -1.6086    2.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    0.9259   -1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -0.2434    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039    0.9631   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7635    0.9317   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7198    0.4367   -0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4805   -0.8567    2.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -0.6786    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0446   -0.2583    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1979    1.2709   -1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5720    1.2795   -1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6288    0.6306   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6154   -1.0534    1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -1.4627    3.0734 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
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  5  1  0
 20 14  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 23 36  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.963  -2.168   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.467  -1.420   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.121  -2.168   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.373  -1.420   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -1.271   0.972   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.467   0.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.963   0.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.160   0.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.160  -1.420   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.655  -2.168   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.019   3.813   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.271   2.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.224   2.467   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.972   1.121   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.617   1.121   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.963   0.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.309   1.121   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.655   0.225   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.271  -3.813   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.617   2.617   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.963   3.365   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.309   2.617   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.655   3.365   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3                                                            
CONECT    5    6   12                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    5   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22                                                       
CONECT   22   17   21   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0038576
HETATM    1  O1  UNL     1      -1.183   0.975  -2.183  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.703   0.543  -1.125  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.762   0.547  -1.043  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.463   0.133  -0.016  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.934   0.146   0.045  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.743   0.593  -0.967  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.137   0.578  -0.844  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.746   0.112   0.300  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.139   0.106   0.401  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.936  -0.336   1.317  1.00  0.00           C  
HETATM   11  O3  UNL     1       5.503  -0.813   2.486  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.553  -0.318   1.189  1.00  0.00           C  
HETATM   13  N1  UNL     1      -1.517   0.080  -0.074  1.00  0.00           N  
HETATM   14  C10 UNL     1      -2.909   0.059  -0.092  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.620   0.728  -1.059  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.019   0.751  -1.042  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.722   0.115  -0.072  1.00  0.00           C  
HETATM   18  O4  UNL     1      -7.125   0.134  -0.049  1.00  0.00           O  
HETATM   19  C14 UNL     1      -5.017  -0.550   0.887  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.623  -0.586   0.890  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.022  -1.360   1.941  1.00  0.00           C  
HETATM   22  O5  UNL     1      -3.796  -1.912   2.813  1.00  0.00           O  
HETATM   23  O6  UNL     1      -1.690  -1.609   2.160  1.00  0.00           O  
HETATM   24  H1  UNL     1       1.323   0.926  -1.910  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.897  -0.243   0.844  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.304   0.963  -1.876  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.764   0.932  -1.648  1.00  0.00           H  
HETATM   28  H5  UNL     1       7.720   0.437  -0.349  1.00  0.00           H  
HETATM   29  H6  UNL     1       6.480  -0.857   2.651  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.910  -0.679   2.005  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.045  -0.258   0.811  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.198   1.271  -1.861  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.572   1.280  -1.807  1.00  0.00           H  
HETATM   34  H11 UNL     1      -7.629   0.631  -0.767  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.615  -1.053   1.657  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.311  -1.463   3.073  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    6   12
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9   10
CONECT    9   28
CONECT   10   11   12   12
CONECT   11   29
CONECT   12   30
CONECT   13   14   31
CONECT   14   15   15   20
CONECT   15   16   32
CONECT   16   17   17   33
CONECT   17   18   19
CONECT   18   34
CONECT   19   20   20   35
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   36
END

HMDB0038576
     RDKit          3D
Avenanthramide C
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.1826    0.9748   -2.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7029    0.5428   -1.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623    0.5467   -1.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628    0.1331   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    0.1462    0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7432    0.5926   -0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1371    0.5775   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7461    0.1123    0.3002 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1386    0.1062    0.4015 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.3364    1.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5029   -0.8128    2.4860 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535   -0.3184    1.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5169    0.0803   -0.0740 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9089    0.0589   -0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6202    0.7281   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0188    0.7513   -1.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7221    0.1147   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1246    0.1342   -0.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0167   -0.5497    0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6229   -0.5864    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -1.3605    1.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7955   -1.9122    2.8127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899   -1.6086    2.1599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232    0.9259   -1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971   -0.2434    0.8442 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3039    0.9631   -1.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7635    0.9317   -1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7198    0.4367   -0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4805   -0.8567    2.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -0.6786    2.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0446   -0.2583    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1979    1.2709   -1.8613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5720    1.2795   -1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6288    0.6306   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6154   -1.0534    1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3115   -1.4627    3.0734 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
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 12  5  1  0
 20 14  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 23 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(3,4-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid	HMDB
Avenanthramide	MeSH, HMDB
Avenanthramide 2C	MeSH, HMDB
Avenanthramide-c	MeSH, HMDB
N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid	MeSH, HMDB
Avenanthramide-2C	MeSH, HMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoate	Generator

Chemical Formula

C₁₆H₁₃NO₆

Average Molecular Weight

315.2775

Monoisotopic Molecular Weight

315.074287153

IUPAC Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

Traditional Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+

InChI Key

IDUUXROOZBOOPH-QHHAFSJGSA-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
Hydroxybenzoic acid
Anilide
Benzoic acid or derivatives
Benzoic acid
Styrene
N-arylamide
Catechol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen 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: HMDB0000051)
Cell membrane (HMDB: HMDB0000051)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000051)

Source

Exogenous

Exogenous (HMDB: HMDB0000051)

Food

Food (HMDB: HMDB0000051)

Cereal and cereal product

Cereal

Oat (FooDB: FOOD00022)

Endogenous

Plant

Plant (HMDB: HMDB0000051)
Poaceae (HMDB: HMDB0000051)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0000051)

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	0.086 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.97	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.54 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]+	172.899	30932474
DeepCCS	[M-H]-	170.542	30932474
DeepCCS	[M-2H]-	204.424	30932474
DeepCCS	[M+Na]+	179.651	30932474
AllCCS	[M+H]+	172.1	32859911
AllCCS	[M+H-H2O]+	168.7	32859911
AllCCS	[M+NH4]+	175.2	32859911
AllCCS	[M+Na]+	176.1	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	170.8	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.	4.49 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2717 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.16 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	81.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1388.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	202.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	84.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	141.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	401.2 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	397.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	177.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	667.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	247.6 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	1171.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	232.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	462.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	292.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	232.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide C	OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1	5525.8	Standard polar	33892256
Avenanthramide C	OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1	3157.6	Standard non polar	33892256
Avenanthramide C	OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1	3614.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide C,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C1	3490.8	Semi standard non polar	33892256
Avenanthramide C,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(C(=O)O)=C1	3448.6	Semi standard non polar	33892256
Avenanthramide C,1TMS,isomer #3	C[Si](C)(C)OC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)=CC=C1O	3418.1	Semi standard non polar	33892256
Avenanthramide C,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)C=C1O	3444.1	Semi standard non polar	33892256
Avenanthramide C,1TMS,isomer #5	C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)C1=CC=C(O)C=C1C(=O)O	3383.4	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C1	3402.0	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #10	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)C=C1O	3220.7	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	3419.0	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	3397.2	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C	3277.0	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(C(=O)O)=C1	3420.4	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(C(=O)O)=C1	3394.6	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #7	C[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O)C(O)=C2)[Si](C)(C)C)C(C(=O)O)=C1	3285.6	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)C=C1O[Si](C)(C)C	3403.6	Semi standard non polar	33892256
Avenanthramide C,2TMS,isomer #9	C[Si](C)(C)OC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)=CC=C1O	3221.3	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1	3411.6	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #10	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)C=C1O[Si](C)(C)C	3225.0	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1	3389.8	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C	3164.5	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3390.3	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #5	C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	3139.8	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #6	C[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	3143.5	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #7	C[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(C(=O)O)=C1	3417.1	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #8	C[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)[Si](C)(C)C)C(C(=O)O)=C1	3200.6	Semi standard non polar	33892256
Avenanthramide C,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C(C(=O)O)=C1	3209.6	Semi standard non polar	33892256
Avenanthramide C,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	3433.2	Semi standard non polar	33892256
Avenanthramide C,4TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	3208.2	Semi standard non polar	33892256
Avenanthramide C,4TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	3214.5	Semi standard non polar	33892256
Avenanthramide C,4TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(O)=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	3176.0	Semi standard non polar	33892256
Avenanthramide C,4TMS,isomer #5	C[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)[Si](C)(C)C)C(C(=O)O)=C1	3258.6	Semi standard non polar	33892256
Avenanthramide C,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=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	3295.4	Semi standard non polar	33892256
Avenanthramide C,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C)=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	3103.0	Standard non polar	33892256
Avenanthramide C,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C1	3778.2	Semi standard non polar	33892256
Avenanthramide C,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(C(=O)O)=C1	3754.6	Semi standard non polar	33892256
Avenanthramide C,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)=CC=C1O	3736.2	Semi standard non polar	33892256
Avenanthramide C,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)C=C1O	3768.8	Semi standard non polar	33892256
Avenanthramide C,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)C1=CC=C(O)C=C1C(=O)O	3683.5	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O)=C1	3965.7	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C1O	3856.4	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	4005.4	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	3982.7	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	3865.9	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(C(=O)O)=C1	4047.4	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(C(=O)O)=C1	4022.4	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O)C(O)=C2)[Si](C)(C)C(C)(C)C)C(C(=O)O)=C1	3871.0	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	3998.9	Semi standard non polar	33892256
Avenanthramide C,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O	3857.6	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	4201.7	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	4027.2	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1NC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	4175.3	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N(C(=O)/C=C/C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	3977.1	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=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	4161.9	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=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	3977.1	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=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	3971.9	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC=C(NC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(C(=O)O)=C1	4224.5	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)[Si](C)(C)C(C)(C)C)C(C(=O)O)=C1	4080.8	Semi standard non polar	33892256
Avenanthramide C,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C(C(=O)O)=C1	4064.0	Semi standard non polar	33892256
Avenanthramide C,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=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	4351.6	Semi standard non polar	33892256
Avenanthramide C,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=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	4190.0	Semi standard non polar	33892256
Avenanthramide C,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=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	4164.0	Semi standard non polar	33892256
Avenanthramide C,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O)=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	4140.8	Semi standard non polar	33892256
Avenanthramide C,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(N(C(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)[Si](C)(C)C(C)(C)C)C(C(=O)O)=C1	4249.5	Semi standard non polar	33892256
Avenanthramide C,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=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	4371.4	Semi standard non polar	33892256
Avenanthramide C,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=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	3927.6	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 C GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kk-0961000000-44dbc62c555f06b47f7f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide C GC-MS (4 TMS) - 70eV, Positive	splash10-000i-1001090000-53a821e1e639ff675118	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide C 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 C 10V, Positive-QTOF	splash10-0uxr-0944000000-5e5598cbbeecb8348ac7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 20V, Positive-QTOF	splash10-0udi-0920000000-1b9e5ede80b19281ed06	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 40V, Positive-QTOF	splash10-0zfr-3900000000-46e41c6f4643f73a7a96	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 10V, Negative-QTOF	splash10-03k9-0296000000-14b2323a1e6e5ff7cbad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 20V, Negative-QTOF	splash10-0h90-0691000000-8b8e4683c02f3c041f74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 40V, Negative-QTOF	splash10-0a4i-1900000000-314538513f94732d5b12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 10V, Positive-QTOF	splash10-03di-0932000000-5d3591a255d5d5cbfa17	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 20V, Positive-QTOF	splash10-03dj-0940000000-0f1360efb2b43e67087f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 40V, Positive-QTOF	splash10-00ks-0910000000-1e8610c76ae0ea403063	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 10V, Negative-QTOF	splash10-00di-0392000000-43f87b14905d03692265	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 20V, Negative-QTOF	splash10-000i-0920000000-5e17ae5c4582f4714289	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide C 40V, Negative-QTOF	splash10-0543-2920000000-c1737d3db456bb532dfc	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

533

FooDB ID

FDB000284

KNApSAcK ID

Not Available

Chemspider ID

9897916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11723200

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 C (HMDB0038576)

MOL for HMDB0038576 (Avenanthramide C)

3D MOL for HMDB0038576 (Avenanthramide C)

3D SDF for HMDB0038576 (Avenanthramide C)

3D-SDF for HMDB0038576 (Avenanthramide C)

PDB for HMDB0038576 (Avenanthramide C)

3D PDB for HMDB0038576 (Avenanthramide C)

SMILES for HMDB0038576 (Avenanthramide C)

INCHI for HMDB0038576 (Avenanthramide C)

Structure for HMDB0038576 (Avenanthramide C)

3D Structure for HMDB0038576 (Avenanthramide C)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra