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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:29:26 UTC

Update Date

2022-03-07 02:52:06 UTC

HMDB ID

HMDB0029285

Secondary Accession Numbers

HMDB29285

Metabolite Identification

Common Name

Avenanthramide 1s

Description

Avenanthramide 1s 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 1s.

Structure

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

HMDB0029285
     RDKit          3D
Avenanthramide 1s
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.5407    3.0796   -1.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    1.8326   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2678    0.7849   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887    0.9878   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.0070   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    0.2327   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    1.3468   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371    1.5637   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8394    2.6975   -0.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3284    0.5381   -0.0751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404    0.5929   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116    1.6368   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8073    1.6803   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5615    0.6992   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -0.3313    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937   -0.3906    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916   -1.5006    1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -1.7266    1.4626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7453   -2.4966    1.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -1.2174    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4732    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -2.6897    0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -3.7959    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7314   -0.4504   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -0.6563   -0.0979 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357    3.4395   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    2.9421   -2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    3.8118   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5411    1.9694   -0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499   -0.6322    0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    2.1738   -0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115   -0.4084    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795    2.4350   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3254    2.4992   -1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6643    0.7363   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4668   -1.1372    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -2.9317    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297   -1.9886    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969   -4.5497    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1890   -4.2498    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -3.5181    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5040   -1.5426    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 24  3  1  0
 16 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 25 42  1  0
M  END

  Mrv0541 02241212132D          

 25 26  0  0  0  0            999 V2000
   -4.3607    1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9318   -0.0884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5028   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406    0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3550   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3607   -0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6462   -1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0752   -1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2173    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    0.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6406   -2.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -2.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  2  0  0  0  0
 11 13  1  0  0  0  0
 12 16  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  8 20  2  0  0  0  0
 16 21  1  0  0  0  0
 15 22  1  0  0  0  0
 21 23  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029285

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO6/c1-24-14-9-11(10-15(25-2)17(14)21)7-8-16(20)19-13-6-4-3-5-12(13)18(22)23/h3-10,21H,1-2H3,(H,19,20)(H,22,23)/b8-7+

> <INCHI_KEY>
RGFLTMLKBQWTSH-BQYQJAHWSA-N

> <FORMULA>
C18H17NO6

> <MOLECULAR_WEIGHT>
343.3307

> <EXACT_MASS>
343.105587281

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
35.142037485774814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
3.2590632126666663

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.307670912237404

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5528394369083425

> <JCHEM_PKA_STRONGEST_BASIC>
-2.049846190753865

> <JCHEM_POLAR_SURFACE_AREA>
105.09000000000002

> <JCHEM_REFRACTIVITY>
93.5007

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029285
     RDKit          3D
Avenanthramide 1s
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.5407    3.0796   -1.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    1.8326   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2678    0.7849   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887    0.9878   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.0070   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    0.2327   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    1.3468   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371    1.5637   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8394    2.6975   -0.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3284    0.5381   -0.0751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404    0.5929   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116    1.6368   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8073    1.6803   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5615    0.6992   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -0.3313    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937   -0.3906    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916   -1.5006    1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -1.7266    1.4626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7453   -2.4966    1.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -1.2174    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4732    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -2.6897    0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -3.7959    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7314   -0.4504   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -0.6563   -0.0979 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357    3.4395   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    2.9421   -2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    3.8118   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5411    1.9694   -0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499   -0.6322    0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    2.1738   -0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115   -0.4084    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795    2.4350   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3254    2.4992   -1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6643    0.7363   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4668   -1.1372    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -2.9317    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297   -1.9886    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969   -4.5497    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1890   -4.2498    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -3.5181    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5040   -1.5426    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 24  3  1  0
 16 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 25 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -8.140   2.915   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.474   2.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.474   0.605   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.140  -0.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.806   0.605   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.806   2.145   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -5.473  -0.165   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.139   0.605   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.805  -0.165   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.472   0.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.138  -0.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.196   0.605   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.138  -1.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.196  -2.475   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.529  -1.705   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.529  -0.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.140  -1.705   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.806  -2.475   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -9.474  -2.475   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.139   2.145   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.863   0.605   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.863  -2.475   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.197  -0.165   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.196  -4.015   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.530  -4.785   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   16                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   22                                                  
CONECT   16   12   15   21                                                  
CONECT   17    4   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8                                                            
CONECT   21   16   23                                                       
CONECT   22   15                                                            
CONECT   23   21                                                            
CONECT   24   14   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0029285
HETATM    1  C1  UNL     1       4.541   3.080  -1.243  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.079   1.833  -0.862  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.268   0.785  -0.479  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.889   0.988  -0.478  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.002   0.007  -0.113  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.561   0.233  -0.116  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.006   1.347  -0.453  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.437   1.564  -0.453  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.839   2.697  -0.803  1.00  0.00           O  
HETATM   10  N1  UNL     1      -2.328   0.538  -0.075  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.740   0.593  -0.031  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.412   1.637  -0.648  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.807   1.680  -0.670  1.00  0.00           C  
HETATM   14  C11 UNL     1      -6.561   0.699  -0.086  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.905  -0.331   0.524  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.494  -0.391   0.556  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.892  -1.501   1.269  1.00  0.00           C  
HETATM   18  O3  UNL     1      -2.688  -1.727   1.463  1.00  0.00           O  
HETATM   19  O4  UNL     1      -4.745  -2.497   1.845  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.544  -1.217   0.261  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.894  -1.473   0.278  1.00  0.00           C  
HETATM   22  O5  UNL     1       4.380  -2.690   0.652  1.00  0.00           O  
HETATM   23  C17 UNL     1       3.636  -3.796   1.051  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.731  -0.450  -0.098  1.00  0.00           C  
HETATM   25  O6  UNL     1       6.100  -0.656  -0.098  1.00  0.00           O  
HETATM   26  H1  UNL     1       3.936   3.440  -0.366  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.834   2.942  -2.110  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.320   3.812  -1.477  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.541   1.969  -0.782  1.00  0.00           H  
HETATM   30  H5  UNL     1      -0.050  -0.632   0.198  1.00  0.00           H  
HETATM   31  H6  UNL     1       0.636   2.174  -0.755  1.00  0.00           H  
HETATM   32  H7  UNL     1      -1.912  -0.408   0.185  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.880   2.435  -1.135  1.00  0.00           H  
HETATM   34  H9  UNL     1      -6.325   2.499  -1.154  1.00  0.00           H  
HETATM   35  H10 UNL     1      -7.664   0.736  -0.106  1.00  0.00           H  
HETATM   36  H11 UNL     1      -6.467  -1.137   1.002  1.00  0.00           H  
HETATM   37  H12 UNL     1      -5.394  -2.932   1.198  1.00  0.00           H  
HETATM   38  H13 UNL     1       1.830  -1.989   0.548  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.297  -4.550   1.534  1.00  0.00           H  
HETATM   40  H15 UNL     1       3.189  -4.250   0.135  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.837  -3.518   1.770  1.00  0.00           H  
HETATM   42  H17 UNL     1       6.504  -1.543   0.172  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   29
CONECT    5    6   20   20
CONECT    6    7    7   30
CONECT    7    8   31
CONECT    8    9    9   10
CONECT   10   11   32
CONECT   11   12   12   16
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16   36
CONECT   16   17
CONECT   17   18   18   19
CONECT   19   37
CONECT   20   21   38
CONECT   21   22   24   24
CONECT   22   23
CONECT   23   39   40   41
CONECT   24   25
CONECT   25   42
END

HMDB0029285
     RDKit          3D
Avenanthramide 1s
 42 43  0  0  0  0  0  0  0  0999 V2000
    4.5407    3.0796   -1.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    1.8326   -0.8618 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2678    0.7849   -0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887    0.9878   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018    0.0070   -0.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    0.2327   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    1.3468   -0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4371    1.5637   -0.4533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8394    2.6975   -0.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3284    0.5381   -0.0751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404    0.5929   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116    1.6368   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8073    1.6803   -0.6700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5615    0.6992   -0.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9046   -0.3313    0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937   -0.3906    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8916   -1.5006    1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -1.7266    1.4626 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7453   -2.4966    1.8453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5436   -1.2174    0.2608 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4732    0.2780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798   -2.6897    0.6520 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6356   -3.7959    1.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7314   -0.4504   -0.0979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1002   -0.6563   -0.0979 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9357    3.4395   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8336    2.9421   -2.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3203    3.8118   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5411    1.9694   -0.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0499   -0.6322    0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6358    2.1738   -0.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9115   -0.4084    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8795    2.4350   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3254    2.4992   -1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6643    0.7363   -0.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4668   -1.1372    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3939   -2.9317    1.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8297   -1.9886    0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2969   -4.5497    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1890   -4.2498    0.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8365   -3.5181    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5040   -1.5426    0.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  2  0
 24 25  1  0
 24  3  1  0
 16 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  7 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 19 37  1  0
 20 38  1  0
 23 39  1  0
 23 40  1  0
 23 41  1  0
 25 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[4-Hydroxy-3,5-dimethoxy-(e)-cinnamoyl]-anthranilic acid	HMDB
2-{[(2E)-1-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-ylidene]amino}benzoate	HMDB

Chemical Formula

C₁₈H₁₇NO₆

Average Molecular Weight

343.3307

Monoisotopic Molecular Weight

343.105587281

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C18H17NO6/c1-24-14-9-11(10-15(25-2)17(14)21)7-8-16(20)19-13-6-4-3-5-12(13)18(22)23/h3-10,21H,1-2H3,(H,19,20)(H,22,23)/b8-7+

InChI Key

RGFLTMLKBQWTSH-BQYQJAHWSA-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
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Benzoic acid
Anilide
Benzoic acid or derivatives
Phenoxy compound
Anisole
Benzoyl
Styrene
Methoxybenzene
Phenol ether
N-arylamide
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Ether
Organooxygen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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: HMDB0029285)
Cell membrane (HMDB: HMDB0029285)

Source

Endogenous

Endogenous (HMDB: HMDB0029285)

Plant

Plant (HMDB: HMDB0029285)

Exogenous

Food

Food (HMDB: HMDB0029285)

Exogenous (HMDB: HMDB0029285)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	2.76	ALOGPS
logP	3.26	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.09 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	93.5 m³·mol⁻¹	ChemAxon
Polarizability	35.14 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]+	171.168	30932474
DeepCCS	[M-H]-	168.801	30932474
DeepCCS	[M-2H]-	203.101	30932474
DeepCCS	[M+Na]+	178.489	30932474
AllCCS	[M+H]+	180.5	32859911
AllCCS	[M+H-H2O]+	177.3	32859911
AllCCS	[M+NH4]+	183.4	32859911
AllCCS	[M+Na]+	184.3	32859911
AllCCS	[M-H]-	180.9	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 1s	COC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O	5395.1	Standard polar	33892256
Avenanthramide 1s	COC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O	3186.0	Standard non polar	33892256
Avenanthramide 1s	COC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O	3453.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 1s,1TMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=CC(OC)=C1O	3301.3	Semi standard non polar	33892256
Avenanthramide 1s,1TMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C	3314.4	Semi standard non polar	33892256
Avenanthramide 1s,1TMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O	3071.2	Semi standard non polar	33892256
Avenanthramide 1s,2TMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3246.1	Semi standard non polar	33892256
Avenanthramide 1s,2TMS,isomer #2	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	2999.0	Semi standard non polar	33892256
Avenanthramide 1s,2TMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3037.5	Semi standard non polar	33892256
Avenanthramide 1s,3TMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3041.1	Semi standard non polar	33892256
Avenanthramide 1s,3TMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3015.1	Standard non polar	33892256
Avenanthramide 1s,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3546.7	Semi standard non polar	33892256
Avenanthramide 1s,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3577.3	Semi standard non polar	33892256
Avenanthramide 1s,1TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3357.3	Semi standard non polar	33892256
Avenanthramide 1s,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3737.4	Semi standard non polar	33892256
Avenanthramide 1s,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3497.8	Semi standard non polar	33892256
Avenanthramide 1s,2TBDMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3552.5	Semi standard non polar	33892256
Avenanthramide 1s,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3697.5	Semi standard non polar	33892256
Avenanthramide 1s,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3500.7	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 1s GC-MS (Non-derivatized) - 70eV, Positive	splash10-004r-1955000000-564736af845bb0a51278	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 1s GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9243700000-43632e64182dba9bc3d2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 1s 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 1s 10V, Positive-QTOF	splash10-000l-0927000000-e5d58a2a6d94e0c81805	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Positive-QTOF	splash10-000i-1921000000-47b213268a64bc7c0277	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Positive-QTOF	splash10-0f7c-5900000000-f3f4ed879aaefc57398d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 10V, Negative-QTOF	splash10-0007-0197000000-7d69fc260eea4ff9e9dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Negative-QTOF	splash10-000w-1291000000-055f9d8ef39d27d8a689	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Negative-QTOF	splash10-000x-6920000000-02b0a938a9a5166c0f60	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 10V, Positive-QTOF	splash10-0a6r-0694000000-66d11b75dd9029d84131	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Positive-QTOF	splash10-056r-0950000000-f0d118cd615062d02818	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Positive-QTOF	splash10-00di-1940000000-349643528b7f0a3e36c8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 10V, Negative-QTOF	splash10-0006-0049000000-94f6ad9f0e27a9d34656	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 20V, Negative-QTOF	splash10-001i-0091000000-639f7b338d7e724c452d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 1s 40V, Negative-QTOF	splash10-0006-2192000000-a4ac72f382e99750095d	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

536

FooDB ID

FDB000287

KNApSAcK ID

Not Available

Chemspider ID

9123115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10947890

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

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

Showing metabocard for Avenanthramide 1s (HMDB0029285)

MOL for HMDB0029285 (Avenanthramide 1s)

3D MOL for HMDB0029285 (Avenanthramide 1s)

3D SDF for HMDB0029285 (Avenanthramide 1s)

3D-SDF for HMDB0029285 (Avenanthramide 1s)

PDB for HMDB0029285 (Avenanthramide 1s)

3D PDB for HMDB0029285 (Avenanthramide 1s)

SMILES for HMDB0029285 (Avenanthramide 1s)

INCHI for HMDB0029285 (Avenanthramide 1s)

Structure for HMDB0029285 (Avenanthramide 1s)

3D Structure for HMDB0029285 (Avenanthramide 1s)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra