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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 23:53:57 UTC

Update Date

2022-03-07 02:55:49 UTC

HMDB ID

HMDB0038575

Secondary Accession Numbers

HMDB38575

Metabolite Identification

Common Name

(Z)-N-Feruloyl-5-hydroxyanthranilic acid

Description

(Z)-N-Feruloyl-5-hydroxyanthranilic acid, also known as avenanthramide 1, 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 (Z)-N-Feruloyl-5-hydroxyanthranilic acid is found, on average, in the highest concentration within oats (Avena sativa). This could make (Z)-N-feruloyl-5-hydroxyanthranilic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (Z)-N-Feruloyl-5-hydroxyanthranilic acid.

Structure

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

HMDB0038575
     RDKit          3D
(Z)-N-Feruloyl-5-hydroxyanthranilic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.6180   -0.3317   -1.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8758   -0.3663   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -0.3089    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -0.2192   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102   -0.1633    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249   -0.0695    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460   -0.0293   -0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    0.0651   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8530    0.0883   -2.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    0.1235   -0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159    0.2144   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6591    0.2595   -2.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9864    0.3485   -2.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9323    0.3956   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2829    0.4856   -1.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5406    0.3538   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1924    0.2634    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    0.2272    1.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9123    0.2802    2.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6982    0.1423    2.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -0.2000    2.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9757   -0.2868    2.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266   -0.3415    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -0.4304    2.2287 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    0.5611   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -1.2689   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502   -0.2779   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3436   -0.1972   -1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398   -0.0298    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310   -0.0692   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.0953    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9404    0.2243   -2.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.3807   -3.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7463    1.3923   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109    0.3927    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502   -0.7797    2.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594   -0.1550    2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -0.3142    3.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5204   -0.4548    3.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 24 39  1  0
M  END


  Mrv0541 02241211492D          

 24 25  0  0  0  0            999 V2000
   -2.4835   -1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823   -0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9611   -1.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1599   -0.7608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413    0.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4835    0.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1246   -0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9258   -1.1615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4419    2.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413    1.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400    1.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624    0.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4835    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046    0.1206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9258    0.6006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0413   -2.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0413    1.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624    1.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4835    1.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046    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 20  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 21  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 23  2  0  0  0  0
 18 19  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038575

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO6/c1-24-15-8-10(2-6-14(15)20)3-7-16(21)18-13-5-4-11(19)9-12(13)17(22)23/h2-9,19-20H,1H3,(H,18,21)(H,22,23)/b7-3+

> <INCHI_KEY>
JXFZHMCSCYADIX-XVNBXDOJSA-N

> <FORMULA>
C17H15NO6

> <MOLECULAR_WEIGHT>
329.3041

> <EXACT_MASS>
329.089937217

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.11806579679511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
3.1131691566666664

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.348574592076714

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3071193313077347

> <JCHEM_PKA_STRONGEST_BASIC>
-2.031672753251153

> <JCHEM_POLAR_SURFACE_AREA>
116.09000000000002

> <JCHEM_REFRACTIVITY>
89.01839999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038575
     RDKit          3D
(Z)-N-Feruloyl-5-hydroxyanthranilic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.6180   -0.3317   -1.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8758   -0.3663   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -0.3089    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -0.2192   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102   -0.1633    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249   -0.0695    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460   -0.0293   -0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    0.0651   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8530    0.0883   -2.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    0.1235   -0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159    0.2144   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6591    0.2595   -2.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9864    0.3485   -2.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9323    0.3956   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2829    0.4856   -1.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5406    0.3538   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1924    0.2634    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    0.2272    1.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9123    0.2802    2.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6982    0.1423    2.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -0.2000    2.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9757   -0.2868    2.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266   -0.3415    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -0.4304    2.2287 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    0.5611   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -1.2689   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502   -0.2779   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3436   -0.1972   -1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398   -0.0298    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310   -0.0692   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.0953    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9404    0.2243   -2.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.3807   -3.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7463    1.3923   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109    0.3927    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502   -0.7797    2.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594   -0.1550    2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -0.3142    3.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5204   -0.4548    3.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 24 39  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      -4.636  -2.168   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.140  -1.420   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.794  -2.168   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.298  -1.420   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -1.944   0.971   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -3.140   0.225   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.636   0.971   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.833   0.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.833  -1.420   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -7.328  -2.168   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.692   3.813   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.944   2.467   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.448   2.467   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.298   1.121   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.944   1.121   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.290   0.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.636   1.121   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.982   0.225   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.328   1.121   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.944  -3.813   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.944   2.617   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.290   3.365   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.636   2.617   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.982   3.365   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4   20                                                  
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   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    3                                                            
CONECT   21   15   22                                                       
CONECT   22   21   23                                                       
CONECT   23   17   22   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0038575
HETATM    1  C1  UNL     1       5.618  -0.332  -1.821  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.876  -0.366  -0.426  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.791  -0.309   0.437  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.473  -0.219  -0.038  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.410  -0.163   0.831  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.025  -0.070   0.366  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.646  -0.029  -0.875  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.745   0.065  -1.357  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.853   0.088  -2.606  1.00  0.00           O  
HETATM   10  N1  UNL     1      -1.848   0.124  -0.489  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.216   0.214  -0.812  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.659   0.259  -2.127  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.986   0.348  -2.510  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.932   0.396  -1.521  1.00  0.00           C  
HETATM   15  O3  UNL     1      -7.283   0.486  -1.868  1.00  0.00           O  
HETATM   16  C12 UNL     1      -5.541   0.354  -0.208  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.192   0.263   0.177  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.909   0.227   1.589  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.912   0.280   2.402  1.00  0.00           O  
HETATM   20  O5  UNL     1      -2.698   0.142   2.228  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.710  -0.200   2.181  1.00  0.00           C  
HETATM   22  C16 UNL     1       3.976  -0.287   2.693  1.00  0.00           C  
HETATM   23  C17 UNL     1       5.027  -0.342   1.793  1.00  0.00           C  
HETATM   24  O6  UNL     1       6.340  -0.430   2.229  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.001   0.561  -2.020  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.091  -1.269  -2.159  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.550  -0.278  -2.408  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.344  -0.197  -1.093  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.240  -0.030   1.130  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.431  -0.069  -1.623  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.613   0.095   0.528  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.940   0.224  -2.926  1.00  0.00           H  
HETATM   33  H9  UNL     1      -5.281   0.381  -3.555  1.00  0.00           H  
HETATM   34  H10 UNL     1      -7.746   1.392  -1.990  1.00  0.00           H  
HETATM   35  H11 UNL     1      -6.311   0.393   0.554  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.450  -0.780   2.615  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.859  -0.155   2.863  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.189  -0.314   3.756  1.00  0.00           H  
HETATM   39  H15 UNL     1       6.520  -0.455   3.219  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   28
CONECT    5    6   21   21
CONECT    6    7    7   29
CONECT    7    8   30
CONECT    8    9    9   10
CONECT   10   11   31
CONECT   11   12   12   17
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15   16
CONECT   15   34
CONECT   16   17   17   35
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   36
CONECT   21   22   37
CONECT   22   23   23   38
CONECT   23   24
CONECT   24   39
END

HMDB0038575
     RDKit          3D
(Z)-N-Feruloyl-5-hydroxyanthranilic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.6180   -0.3317   -1.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8758   -0.3663   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -0.3089    0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -0.2192   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102   -0.1633    0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0249   -0.0695    0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460   -0.0293   -0.8755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7449    0.0651   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8530    0.0883   -2.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8475    0.1235   -0.4888 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159    0.2144   -0.8121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6591    0.2595   -2.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9864    0.3485   -2.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9323    0.3956   -1.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2829    0.4856   -1.8682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5406    0.3538   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1924    0.2634    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    0.2272    1.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9123    0.2802    2.4017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6982    0.1423    2.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7102   -0.2000    2.1809 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9757   -0.2868    2.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266   -0.3415    1.7931 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -0.4304    2.2287 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    0.5611   -2.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -1.2689   -2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5502   -0.2779   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3436   -0.1972   -1.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2398   -0.0298    1.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310   -0.0692   -1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6131    0.0953    0.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9404    0.2243   -2.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2814    0.3807   -3.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7463    1.3923   -1.9901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3109    0.3927    0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502   -0.7797    2.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8594   -0.1550    2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1886   -0.3142    3.7558 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5204   -0.4548    3.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  5 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23  3  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
  7 30  1  0
 10 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 24 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid	ChEBI
Avenanthramide 1	ChEBI
Avenanthramide 2F	ChEBI
Avenanthramide BF	ChEBI
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxyanthranilic acid	ChEBI
N-Feruloyl-5-hydroxyanthranilic acid	ChEBI
5-Hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoate	Generator
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxyanthranilate	Generator
N-Feruloyl-5-hydroxyanthranilate	Generator
(Z)-N-Feruloyl-5-hydroxyanthranilate	Generator
Avenanthramide b	HMDB
5-Hydroxy-2-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}benzoate	Generator

Chemical Formula

C₁₇H₁₅NO₆

Average Molecular Weight

329.3041

Monoisotopic Molecular Weight

329.089937217

IUPAC Name

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

Traditional Name

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

CAS Registry Number

108605-69-2

SMILES

COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1

InChI Identifier

InChI=1S/C17H15NO6/c1-24-15-8-10(2-6-14(15)20)3-7-16(21)18-13-5-4-11(19)9-12(13)17(22)23/h2-9,19-20H,1H3,(H,18,21)(H,22,23)/b7-3+

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Membrane (HMDB: HMDB0038575)

Source

Exogenous

Exogenous (HMDB: HMDB0038575)

Food

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Oat (FooDB: FOOD00022)

Cereals and cereal products (FooDB: FOOD00858)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	246 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	2.89	ALOGPS
logP	3.11	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.02 m³·mol⁻¹	ChemAxon
Polarizability	33.12 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]+	183.651	30932474
DeepCCS	[M-H]-	181.293	30932474
DeepCCS	[M-2H]-	215.793	30932474
DeepCCS	[M+Na]+	192.049	30932474
AllCCS	[M+H]+	176.5	32859911
AllCCS	[M+H-H2O]+	173.2	32859911
AllCCS	[M+NH4]+	179.5	32859911
AllCCS	[M+Na]+	180.4	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.8	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.	5.03 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6316 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.64 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1711.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	204.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	107.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	149.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	432.2 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	441.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	814.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	326.0 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	1219.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	391.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	262.1 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	136.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-N-Feruloyl-5-hydroxyanthranilic acid	COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1	5504.1	Standard polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid	COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1	3217.7	Standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid	COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1	3589.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)=CC=C1O[Si](C)(C)C	3407.5	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)=CC=C1O	3414.6	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TMS,isomer #3	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)=CC=C1O	3415.8	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TMS,isomer #4	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)=CC=C1O	3284.9	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)=CC=C1O[Si](C)(C)C	3406.0	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3388.8	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3214.2	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TMS,isomer #4	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C)C=C2C(=O)O[Si](C)(C)C)=CC=C1O	3397.7	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TMS,isomer #5	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)[Si](C)(C)C)=CC=C1O	3204.3	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TMS,isomer #6	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O	3147.6	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C)C=C2C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3414.4	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TMS,isomer #2	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3215.7	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3136.3	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TMS,isomer #4	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O	3157.0	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,4TMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3230.9	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,4TMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3159.5	Standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3720.3	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)=CC=C1O	3730.9	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TBDMS,isomer #3	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3718.8	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,1TBDMS,isomer #4	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O	3592.7	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3990.1	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3948.5	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3809.9	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TBDMS,isomer #4	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3937.1	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TBDMS,isomer #5	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O	3808.8	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,2TBDMS,isomer #6	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	3746.5	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4154.7	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TBDMS,isomer #2	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4030.2	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3930.8	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,3TBDMS,isomer #4	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O	3927.8	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,4TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4157.9	Semi standard non polar	33892256
(Z)-N-Feruloyl-5-hydroxyanthranilic acid,4TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3854.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0imi-0924000000-c3f6c91375c93d0a5c9c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid GC-MS (3 TMS) - 70eV, Positive	splash10-001i-1080590000-6045db6c80549a228c2d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid , positive-QTOF	splash10-004i-0900000000-7cbaf29a9a688b59419b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid , positive-QTOF	splash10-004i-0901000000-0163c92dd87682f74e49	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 10V, Positive-QTOF	splash10-0ue9-0927000000-26acbd87ed1c4c7e9ca9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 20V, Positive-QTOF	splash10-0udi-0911000000-78ce1bd1e9a10fec28aa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 40V, Positive-QTOF	splash10-0zgi-2900000000-0c8824e0e7d9498b9b47	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 10V, Negative-QTOF	splash10-0059-0298000000-02ccc213e8295d0379f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 20V, Negative-QTOF	splash10-00o0-0592000000-35fd0a16d32cdcf0bf2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 40V, Negative-QTOF	splash10-0pb9-0910000000-fb965f111b5f23f3029f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 10V, Negative-QTOF	splash10-004i-0039000000-df10e0e447b7cc8a8f0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 20V, Negative-QTOF	splash10-0159-0691000000-7f0a6fbb5ad61a39ab8e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 40V, Negative-QTOF	splash10-0059-0893000000-cd7163d8f0ff7a58fde9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 10V, Positive-QTOF	splash10-01u0-0925000000-ab8d5673204674843b25	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 20V, Positive-QTOF	splash10-001j-0961000000-e93728b9e83ed1cfbf37	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-N-Feruloyl-5-hydroxyanthranilic acid 40V, Positive-QTOF	splash10-0a4i-0910000000-dbd82e0cb572a5afa4a5	2021-09-23	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

534

FooDB ID

FDB000285

KNApSAcK ID

Not Available

Chemspider ID

8263492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10087955

PDB ID

Not Available

ChEBI ID

167489

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 (Z)-N-Feruloyl-5-hydroxyanthranilic acid (HMDB0038575)

MOL for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

3D MOL for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

3D SDF for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

3D-SDF for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

PDB for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

3D PDB for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

SMILES for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

INCHI for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

Structure for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

3D Structure for HMDB0038575 ((Z)-N-Feruloyl-5-hydroxyanthranilic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra