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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

HMDB0029282

Secondary Accession Numbers

HMDB29282

Metabolite Identification

Common Name

Avenanthramide 1p

Description

Avenanthramide 1p 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 1p.

Structure

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

HMDB0029282
     RDKit          3D
Avenanthramide 1p
 34 35  0  0  0  0  0  0  0  0999 V2000
   -1.0058    0.6569   -2.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704    0.3299   -1.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    0.3737   -1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174    0.0742   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9793    0.1232   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363    0.4987   -1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2271    0.5386   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7783    0.1913    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1566    0.2145    0.6049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9105   -0.1866    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -0.2244    1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349   -0.0598   -0.3874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432   -0.1423   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -0.0644   -1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206   -0.1977   -1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6087   -0.4140   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -0.4988    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644   -0.3634    0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.4311    2.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8087   -0.2936    2.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8372   -0.6694    3.1480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    0.6892   -2.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -0.2392    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    0.7809   -1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907    0.8375   -1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5352    1.0982    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3747   -0.4601    2.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785   -0.5218    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828   -0.3455    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145    0.0970   -2.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4038   -0.1233   -2.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6896   -0.5136   -0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5497   -0.6727    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.0819    3.3400 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  2  0
  2 12  1  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
 18 19  1  0
 19 20  2  0
 19 21  1  0
 11  5  1  0
 18 13  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 21 34  1  0
M  END


  Mrv0541 02241221192D          

 21 22  0  0  0  0            999 V2000
   -3.3295    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -1.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -1.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3295   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -2.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0439   -2.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9005   -1.5321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4716   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861   -0.2946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718   -1.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -2.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718   -2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -2.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.5321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1008   -2.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029282

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13NO4/c18-12-8-5-11(6-9-12)7-10-15(19)17-14-4-2-1-3-13(14)16(20)21/h1-10,18H,(H,17,19)(H,20,21)/b10-7+

> <INCHI_KEY>
INBHLTYBRKASIZ-JXMROGBWSA-N

> <FORMULA>
C16H13NO4

> <MOLECULAR_WEIGHT>
283.2787

> <EXACT_MASS>
283.084457909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.163824016927453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.574405743999999

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.418418749304905

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5528396369176254

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0496242909443296

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
80.57430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029282
     RDKit          3D
Avenanthramide 1p
 34 35  0  0  0  0  0  0  0  0999 V2000
   -1.0058    0.6569   -2.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704    0.3299   -1.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    0.3737   -1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174    0.0742   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9793    0.1232   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363    0.4987   -1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2271    0.5386   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7783    0.1913    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1566    0.2145    0.6049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9105   -0.1866    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -0.2244    1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349   -0.0598   -0.3874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432   -0.1423   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -0.0644   -1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206   -0.1977   -1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6087   -0.4140   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -0.4988    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644   -0.3634    0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.4311    2.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8087   -0.2936    2.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8372   -0.6694    3.1480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    0.6892   -2.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -0.2392    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    0.7809   -1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907    0.8375   -1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5352    1.0982    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3747   -0.4601    2.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785   -0.5218    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828   -0.3455    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145    0.0970   -2.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4038   -0.1233   -2.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6896   -0.5136   -0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5497   -0.6727    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.0819    3.3400 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  2  0
  2 12  1  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
 18 19  1  0
 19 20  2  0
 19 21  1  0
 11  5  1  0
 18 13  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 21 34  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      -6.215   0.220   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.549  -0.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.549  -2.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.215  -2.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.881  -2.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.881  -0.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.215  -4.400   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.881  -5.170   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -7.549  -5.170   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -3.548  -2.860   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -2.214  -2.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.880  -2.860   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.214  -0.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.453  -2.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.787  -2.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.121  -2.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.787  -4.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.121  -5.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.454  -4.400   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.454  -2.860   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.788  -5.170   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   20                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   16                                                       
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0029282
HETATM    1  O1  UNL     1      -1.006   0.657  -2.545  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.570   0.330  -1.424  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.877   0.374  -1.250  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.517   0.074  -0.170  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.979   0.123  -0.009  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.836   0.499  -1.005  1.00  0.00           C  
HETATM    7  C6  UNL     1       5.227   0.539  -0.830  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.778   0.191   0.380  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.157   0.214   0.605  1.00  0.00           O  
HETATM   10  C8  UNL     1       4.911  -0.187   1.382  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.545  -0.224   1.206  1.00  0.00           C  
HETATM   12  N1  UNL     1      -1.435  -0.060  -0.387  1.00  0.00           N  
HETATM   13  C10 UNL     1      -2.843  -0.142  -0.450  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.548  -0.064  -1.632  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.921  -0.198  -1.674  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.609  -0.414  -0.513  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.960  -0.499   0.680  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.564  -0.363   0.732  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.003  -0.431   2.055  1.00  0.00           C  
HETATM   20  O3  UNL     1      -1.809  -0.294   2.325  1.00  0.00           O  
HETATM   21  O4  UNL     1      -3.837  -0.669   3.148  1.00  0.00           O  
HETATM   22  H1  UNL     1       1.499   0.689  -2.107  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.940  -0.239   0.692  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.456   0.781  -1.974  1.00  0.00           H  
HETATM   25  H4  UNL     1       5.891   0.838  -1.627  1.00  0.00           H  
HETATM   26  H5  UNL     1       7.535   1.098   0.955  1.00  0.00           H  
HETATM   27  H6  UNL     1       5.375  -0.460   2.342  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.878  -0.522   1.997  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.983  -0.345   0.530  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.015   0.097  -2.555  1.00  0.00           H  
HETATM   31  H10 UNL     1      -5.404  -0.123  -2.649  1.00  0.00           H  
HETATM   32  H11 UNL     1      -6.690  -0.514  -0.594  1.00  0.00           H  
HETATM   33  H12 UNL     1      -5.550  -0.673   1.582  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.656  -0.082   3.340  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4   22
CONECT    4    5   23
CONECT    5    6    6   11
CONECT    6    7   24
CONECT    7    8    8   25
CONECT    8    9   10
CONECT    9   26
CONECT   10   11   11   27
CONECT   11   28
CONECT   12   13   29
CONECT   13   14   14   18
CONECT   14   15   30
CONECT   15   16   16   31
CONECT   16   17   32
CONECT   17   18   18   33
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   34
END

HMDB0029282
     RDKit          3D
Avenanthramide 1p
 34 35  0  0  0  0  0  0  0  0999 V2000
   -1.0058    0.6569   -2.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704    0.3299   -1.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8769    0.3737   -1.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174    0.0742   -0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9793    0.1232   -0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8363    0.4987   -1.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2271    0.5386   -0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7783    0.1913    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1566    0.2145    0.6049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9105   -0.1866    1.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -0.2244    1.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4349   -0.0598   -0.3874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8432   -0.1423   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5483   -0.0644   -1.6324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206   -0.1977   -1.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6087   -0.4140   -0.5133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9604   -0.4988    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5644   -0.3634    0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -0.4311    2.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8087   -0.2936    2.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8372   -0.6694    3.1480 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    0.6892   -2.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9404   -0.2392    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    0.7809   -1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907    0.8375   -1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5352    1.0982    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3747   -0.4601    2.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8785   -0.5218    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828   -0.3455    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0145    0.0970   -2.5553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4038   -0.1233   -2.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6896   -0.5136   -0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5497   -0.6727    1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6562   -0.0819    3.3400 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  2  0
  2 12  1  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
 18 19  1  0
 19 20  2  0
 19 21  1  0
 11  5  1  0
 18 13  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
 21 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Avenanthramide D	HMDB
N-[4-Hydroxy-(e)-cinnamoyl]-anthranilic acid	HMDB
2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}benzoate	HMDB

Chemical Formula

C₁₆H₁₃NO₄

Average Molecular Weight

283.2787

Monoisotopic Molecular Weight

283.084457909

IUPAC Name

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

Traditional Name

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

CAS Registry Number

115610-36-1

SMILES

OC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C1

InChI Identifier

InChI=1S/C16H13NO4/c18-12-8-5-11(6-9-12)7-10-15(19)17-14-4-2-1-3-13(14)16(20)21/h1-10,18H,(H,17,19)(H,20,21)/b10-7+

InChI Key

INBHLTYBRKASIZ-JXMROGBWSA-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
Coumaric acid or derivatives
Cinnamic acid amide
Benzoic acid or derivatives
Benzoic acid
Anilide
Styrene
N-arylamide
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
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: HMDB0029282)

Membrane (HMDB: HMDB0029282)
Cell membrane (HMDB: HMDB0029282)

Source

Endogenous

Endogenous (HMDB: HMDB0029282)

Plant

Plant (HMDB: HMDB0029282)

Exogenous

Food

Food (HMDB: HMDB0029282)

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	3.17	ALOGPS
logP	3.57	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.57 m³·mol⁻¹	ChemAxon
Polarizability	29.16 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]+	165.748	30932474
DeepCCS	[M-H]-	163.39	30932474
DeepCCS	[M-2H]-	197.119	30932474
DeepCCS	[M+Na]+	172.346	30932474
AllCCS	[M+H]+	165.4	32859911
AllCCS	[M+H-H2O]+	161.7	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.7	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	166.0	32859911
AllCCS	[M+HCOO]-	165.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 1p	OC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C1	4670.3	Standard polar	33892256
Avenanthramide 1p	OC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C1	2696.2	Standard non polar	33892256
Avenanthramide 1p	OC(=O)C1=C(NC(=O)\C=C\C2=CC=C(O)C=C2)C=CC=C1	3158.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 1p,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C1	2986.9	Semi standard non polar	33892256
Avenanthramide 1p,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1	2985.1	Semi standard non polar	33892256
Avenanthramide 1p,1TMS,isomer #3	C[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C1=CC=CC=C1C(=O)O	2829.6	Semi standard non polar	33892256
Avenanthramide 1p,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=C1	2978.0	Semi standard non polar	33892256
Avenanthramide 1p,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C	2778.1	Semi standard non polar	33892256
Avenanthramide 1p,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)C=C1	2826.6	Semi standard non polar	33892256
Avenanthramide 1p,3TMS,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=C1)[Si](C)(C)C	2838.8	Semi standard non polar	33892256
Avenanthramide 1p,3TMS,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=C1)[Si](C)(C)C	2808.2	Standard non polar	33892256
Avenanthramide 1p,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1NC(=O)/C=C/C1=CC=C(O)C=C1	3245.9	Semi standard non polar	33892256
Avenanthramide 1p,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)C=C1	3280.2	Semi standard non polar	33892256
Avenanthramide 1p,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)/C=C/C1=CC=C(O)C=C1)C1=CC=CC=C1C(=O)O	3117.6	Semi standard non polar	33892256
Avenanthramide 1p,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=C1	3498.7	Semi standard non polar	33892256
Avenanthramide 1p,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1N(C(=O)/C=C/C1=CC=C(O)C=C1)[Si](C)(C)C(C)(C)C	3307.3	Semi standard non polar	33892256
Avenanthramide 1p,2TBDMS,isomer #3	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=C1	3373.1	Semi standard non polar	33892256
Avenanthramide 1p,3TBDMS,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=C1)[Si](C)(C)C(C)(C)C	3548.5	Semi standard non polar	33892256
Avenanthramide 1p,3TBDMS,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=C1)[Si](C)(C)C(C)(C)C	3380.7	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 1p GC-MS (Non-derivatized) - 70eV, Positive	splash10-014s-0970000000-a566f728fa7183881de4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 1p GC-MS (2 TMS) - 70eV, Positive	splash10-0072-6839200000-233811b6b290dbe57d6c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 1p 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 1p 10V, Positive-QTOF	splash10-0019-0890000000-04ad40c92e259a7d11d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Positive-QTOF	splash10-000i-1920000000-44906bb2b5721bdec1ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Positive-QTOF	splash10-0f79-9800000000-ad6fc6f94bf65f268a8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 10V, Negative-QTOF	splash10-001r-0190000000-4ee1473cdcf98c48a16e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Negative-QTOF	splash10-000i-1490000000-f60605812a47a3f42c41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Negative-QTOF	splash10-0006-8900000000-d19f83c6414c2312c761	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 10V, Negative-QTOF	splash10-001i-0090000000-0786f2d6ceb295d228c4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Negative-QTOF	splash10-014r-1790000000-d3cc0cd017bee4c03d71	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Negative-QTOF	splash10-014i-1910000000-79dcee6fd90a20fbd59a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 10V, Positive-QTOF	splash10-0002-0900000000-061a828162cdf954fd23	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 20V, Positive-QTOF	splash10-00kb-1900000000-7a1597345127828215e4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1p 40V, Positive-QTOF	splash10-014i-4900000000-9c1631c53579bbdd3f75	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

530

FooDB ID

FDB000281

KNApSAcK ID

Not Available

Chemspider ID

4947061

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443019

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1808141

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 1p (HMDB0029282)

MOL for HMDB0029282 (Avenanthramide 1p)

3D MOL for HMDB0029282 (Avenanthramide 1p)

3D SDF for HMDB0029282 (Avenanthramide 1p)

3D-SDF for HMDB0029282 (Avenanthramide 1p)

PDB for HMDB0029282 (Avenanthramide 1p)

3D PDB for HMDB0029282 (Avenanthramide 1p)

SMILES for HMDB0029282 (Avenanthramide 1p)

INCHI for HMDB0029282 (Avenanthramide 1p)

Structure for HMDB0029282 (Avenanthramide 1p)

3D Structure for HMDB0029282 (Avenanthramide 1p)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra