Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

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

HMDB0029286

Secondary Accession Numbers

HMDB29286

Metabolite Identification

Common Name

Avenanthramide 2s

Description

Avenanthramide 2s 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 2s.

Structure

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


  Mrv0541 02271201072D          

 26 27  0  0  0  0            999 V2000
   -2.5929    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639   -0.5009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495    0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374   -0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084   -2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -2.9759    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
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 16  1  0  0  0  0
 17 12  2  0  0  0  0
 12 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

HMDB0029286
     RDKit          3D
Avenanthramide 2s
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.9655    3.2888    1.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7923    2.2443    1.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    1.1201    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879    0.9984    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493   -0.1178    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873   -0.1842    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -1.1870   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4527   -1.2999   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9121   -2.3774   -0.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521   -0.2422   -0.0150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6690   -0.2948   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3670   -1.4626   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7657   -1.5424   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4803   -0.4171    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8732   -0.4764    0.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7971    0.7424    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975    0.8615    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139    2.1538    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6032    3.1301    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    2.4573    0.4541 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405   -1.1311   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3376   -1.0253   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -2.0408   -0.8404 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5689   -3.2118   -1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9534    0.0938    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.2187    0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    3.8236    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208    3.9798    2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    2.8321    2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    1.8022    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335    0.6824    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5729   -2.0403   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7481    0.5870    0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8972   -2.4059   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2803   -2.4731   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3599   -0.2926   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3628    1.6484    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393    3.2258    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -2.0276   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -3.6374   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0956   -3.0429   -2.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3605   -3.9908   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7660    1.0310    0.5671 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  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 25  3  1  0
 17 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
 26 43  1  0
M  END


  Mrv0541 02271201072D          

 26 27  0  0  0  0            999 V2000
   -2.5929    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1639   -0.5009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4494   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2650   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495    0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3073   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084   -1.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374   -0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374   -1.7384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4084   -2.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8374    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -2.9759    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
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 16  1  0  0  0  0
 17 12  2  0  0  0  0
 12 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029286

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO7/c1-25-14-7-10(8-15(26-2)17(14)22)3-6-16(21)19-13-5-4-11(20)9-12(13)18(23)24/h3-9,20,22H,1-2H3,(H,19,21)(H,23,24)/b6-3+

> <INCHI_KEY>
IYRNSMDETLBKHB-ZZXKWVIFSA-N

> <FORMULA>
C18H17NO7

> <MOLECULAR_WEIGHT>
359.3301

> <EXACT_MASS>
359.100501903

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.11927069201966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.9554978909999994

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.091047371875181

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3071189945767605

> <JCHEM_PKA_STRONGEST_BASIC>
-2.031824183268591

> <JCHEM_POLAR_SURFACE_AREA>
125.32000000000002

> <JCHEM_REFRACTIVITY>
95.48159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.52e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029286
     RDKit          3D
Avenanthramide 2s
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.9655    3.2888    1.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7923    2.2443    1.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    1.1201    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879    0.9984    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493   -0.1178    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873   -0.1842    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -1.1870   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4527   -1.2999   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9121   -2.3774   -0.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521   -0.2422   -0.0150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6690   -0.2948   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3670   -1.4626   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7657   -1.5424   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4803   -0.4171    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8732   -0.4764    0.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7971    0.7424    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975    0.8615    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139    2.1538    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6032    3.1301    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    2.4573    0.4541 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405   -1.1311   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3376   -1.0253   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -2.0408   -0.8404 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5689   -3.2118   -1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9534    0.0938    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.2187    0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    3.8236    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208    3.9798    2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    2.8321    2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    1.8022    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335    0.6824    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5729   -2.0403   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7481    0.5870    0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8972   -2.4059   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2803   -2.4731   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3599   -0.2926   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3628    1.6484    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393    3.2258    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -2.0276   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -3.6374   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0956   -3.0429   -2.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3605   -3.9908   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7660    1.0310    0.5671 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  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 25  3  1  0
 17 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
 26 43  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.840   2.145   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.174   1.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.174  -0.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.840  -0.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.506  -0.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.506   1.375   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.173  -0.935   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.839  -0.165   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.495  -0.935   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.839   1.375   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.828  -0.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.162  -0.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.840  -2.475   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.506  -3.245   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -6.174  -3.245   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -7.507   2.145   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.496  -0.165   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.162  -2.475   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.496  -3.245   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.829  -2.475   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.829  -0.935   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.163  -0.165   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.163  -3.245   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.496  -4.785   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.163   1.375   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.829  -5.555   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11   17   18                                                  
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2                                                            
CONECT   17   12   21                                                       
CONECT   18   12   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   17   20   22                                                  
CONECT   22   21   25                                                       
CONECT   23   20                                                            
CONECT   24   19   26                                                       
CONECT   25   22                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0029286
HETATM    1  C1  UNL     1       3.965   3.289   1.602  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.792   2.244   1.123  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.162   1.120   0.608  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.788   0.998   0.552  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.149  -0.118   0.041  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.687  -0.184   0.011  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.000  -1.187  -0.449  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.453  -1.300  -0.500  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.912  -2.377  -0.995  1.00  0.00           O  
HETATM   10  N1  UNL     1      -2.252  -0.242  -0.015  1.00  0.00           N  
HETATM   11  C8  UNL     1      -3.669  -0.295  -0.030  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.367  -1.463  -0.267  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.766  -1.542  -0.229  1.00  0.00           C  
HETATM   14  C11 UNL     1      -6.480  -0.417   0.055  1.00  0.00           C  
HETATM   15  O3  UNL     1      -7.873  -0.476   0.098  1.00  0.00           O  
HETATM   16  C12 UNL     1      -5.797   0.742   0.290  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.398   0.861   0.260  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.814   2.154   0.491  1.00  0.00           C  
HETATM   19  O4  UNL     1      -4.603   3.130   0.758  1.00  0.00           O  
HETATM   20  O5  UNL     1      -2.499   2.457   0.454  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.941  -1.131  -0.423  1.00  0.00           C  
HETATM   22  C16 UNL     1       4.338  -1.025  -0.375  1.00  0.00           C  
HETATM   23  O6  UNL     1       5.154  -2.041  -0.840  1.00  0.00           O  
HETATM   24  C17 UNL     1       4.569  -3.212  -1.377  1.00  0.00           C  
HETATM   25  C18 UNL     1       4.953   0.094   0.138  1.00  0.00           C  
HETATM   26  O7  UNL     1       6.328   0.219   0.195  1.00  0.00           O  
HETATM   27  H1  UNL     1       3.452   3.824   0.784  1.00  0.00           H  
HETATM   28  H2  UNL     1       4.621   3.980   2.198  1.00  0.00           H  
HETATM   29  H3  UNL     1       3.249   2.832   2.331  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.178   1.802   0.921  1.00  0.00           H  
HETATM   31  H5  UNL     1       0.134   0.682   0.407  1.00  0.00           H  
HETATM   32  H6  UNL     1       0.573  -2.040  -0.840  1.00  0.00           H  
HETATM   33  H7  UNL     1      -1.748   0.587   0.385  1.00  0.00           H  
HETATM   34  H8  UNL     1      -3.897  -2.406  -0.486  1.00  0.00           H  
HETATM   35  H9  UNL     1      -6.280  -2.473  -0.420  1.00  0.00           H  
HETATM   36  H10 UNL     1      -8.360  -0.293  -0.783  1.00  0.00           H  
HETATM   37  H11 UNL     1      -6.363   1.648   0.519  1.00  0.00           H  
HETATM   38  H12 UNL     1      -2.039   3.226   0.026  1.00  0.00           H  
HETATM   39  H13 UNL     1       2.535  -2.028  -0.834  1.00  0.00           H  
HETATM   40  H14 UNL     1       3.781  -3.637  -0.708  1.00  0.00           H  
HETATM   41  H15 UNL     1       4.096  -3.043  -2.361  1.00  0.00           H  
HETATM   42  H16 UNL     1       5.360  -3.991  -1.542  1.00  0.00           H  
HETATM   43  H17 UNL     1       6.766   1.031   0.567  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   30
CONECT    5    6   21   21
CONECT    6    7    7   31
CONECT    7    8   32
CONECT    8    9    9   10
CONECT   10   11   33
CONECT   11   12   12   17
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   16
CONECT   15   36
CONECT   16   17   17   37
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   38
CONECT   21   22   39
CONECT   22   23   25   25
CONECT   23   24
CONECT   24   40   41   42
CONECT   25   26
CONECT   26   43
END

HMDB0029286
     RDKit          3D
Avenanthramide 2s
 43 44  0  0  0  0  0  0  0  0999 V2000
    3.9655    3.2888    1.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7923    2.2443    1.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1621    1.1201    0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7879    0.9984    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493   -0.1178    0.0410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873   -0.1842    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -1.1870   -0.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4527   -1.2999   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9121   -2.3774   -0.9949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2521   -0.2422   -0.0150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6690   -0.2948   -0.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3670   -1.4626   -0.2668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7657   -1.5424   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4803   -0.4171    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8732   -0.4764    0.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7971    0.7424    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3975    0.8615    0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8139    2.1538    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6032    3.1301    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    2.4573    0.4541 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405   -1.1311   -0.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3376   -1.0253   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1537   -2.0408   -0.8404 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5689   -3.2118   -1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9534    0.0938    0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3278    0.2187    0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4516    3.8236    0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6208    3.9798    2.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    2.8321    2.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1780    1.8022    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1335    0.6824    0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5729   -2.0403   -0.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7481    0.5870    0.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8972   -2.4059   -0.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2803   -2.4731   -0.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3599   -0.2926   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3628    1.6484    0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393    3.2258    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -2.0276   -0.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7813   -3.6374   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0956   -3.0429   -2.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3605   -3.9908   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7660    1.0310    0.5671 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  1  0
 23 24  1  0
 22 25  2  0
 25 26  1  0
 25  3  1  0
 17 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 20 38  1  0
 21 39  1  0
 24 40  1  0
 24 41  1  0
 24 42  1  0
 26 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₈H₁₇NO₇

Average Molecular Weight

359.3301

Monoisotopic Molecular Weight

359.100501903

IUPAC Name

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

Traditional Name

5-hydroxy-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=C(O)C=C2C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C18H17NO7/c1-25-14-7-10(8-15(26-2)17(14)22)3-6-16(21)19-13-5-4-11(20)9-12(13)18(23)24/h3-9,20,22H,1-2H3,(H,19,21)(H,23,24)/b6-3+

InChI Key

IYRNSMDETLBKHB-ZZXKWVIFSA-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
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Benzoic acid or derivatives
Anilide
Benzoic acid
Phenoxy compound
Benzoyl
Anisole
Styrene
Methoxybenzene
Phenol ether
N-arylamide
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
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

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	0.035 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.96	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.32 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.48 m³·mol⁻¹	ChemAxon
Polarizability	36.12 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]+	176.784	30932474
DeepCCS	[M-H]-	174.388	30932474
DeepCCS	[M-2H]-	208.717	30932474
DeepCCS	[M+Na]+	184.291	30932474
AllCCS	[M+H]+	183.8	32859911
AllCCS	[M+H-H2O]+	180.8	32859911
AllCCS	[M+NH4]+	186.6	32859911
AllCCS	[M+Na]+	187.4	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	183.3	32859911
AllCCS	[M+HCOO]-	183.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 2s	COC1=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=CC(OC)=C1O	5908.9	Standard polar	33892256
Avenanthramide 2s	COC1=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=CC(OC)=C1O	3378.9	Standard non polar	33892256
Avenanthramide 2s	COC1=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=CC(OC)=C1O	3816.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Avenanthramide 2s,1TMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)=CC(OC)=C1O	3579.6	Semi standard non polar	33892256
Avenanthramide 2s,1TMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)=CC(OC)=C1O	3574.9	Semi standard non polar	33892256
Avenanthramide 2s,1TMS,isomer #3	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C	3553.4	Semi standard non polar	33892256
Avenanthramide 2s,1TMS,isomer #4	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O	3366.0	Semi standard non polar	33892256
Avenanthramide 2s,2TMS,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(OC)=C1O	3531.0	Semi standard non polar	33892256
Avenanthramide 2s,2TMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C	3509.7	Semi standard non polar	33892256
Avenanthramide 2s,2TMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O	3264.6	Semi standard non polar	33892256
Avenanthramide 2s,2TMS,isomer #4	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3485.8	Semi standard non polar	33892256
Avenanthramide 2s,2TMS,isomer #5	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O	3220.1	Semi standard non polar	33892256
Avenanthramide 2s,2TMS,isomer #6	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3263.4	Semi standard non polar	33892256
Avenanthramide 2s,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(OC)=C1O[Si](C)(C)C	3496.9	Semi standard non polar	33892256
Avenanthramide 2s,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)[Si](C)(C)C)=CC(OC)=C1O	3233.1	Semi standard non polar	33892256
Avenanthramide 2s,3TMS,isomer #3	COC1=CC(/C=C/C(=O)N(C2=CC=C(O[Si](C)(C)C)C=C2C(=O)O)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3258.7	Semi standard non polar	33892256
Avenanthramide 2s,3TMS,isomer #4	COC1=CC(/C=C/C(=O)N(C2=CC=C(O)C=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1O[Si](C)(C)C	3193.5	Semi standard non polar	33892256
Avenanthramide 2s,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(OC)=C1O[Si](C)(C)C	3278.7	Semi standard non polar	33892256
Avenanthramide 2s,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(OC)=C1O[Si](C)(C)C	3233.4	Standard non polar	33892256
Avenanthramide 2s,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)=CC(OC)=C1O	3896.3	Semi standard non polar	33892256
Avenanthramide 2s,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	3865.2	Semi standard non polar	33892256
Avenanthramide 2s,1TBDMS,isomer #3	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3831.1	Semi standard non polar	33892256
Avenanthramide 2s,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(OC)=C1O	3696.3	Semi standard non polar	33892256
Avenanthramide 2s,2TBDMS,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(OC)=C1O	4059.6	Semi standard non polar	33892256
Avenanthramide 2s,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2C(=O)O)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4069.7	Semi standard non polar	33892256
Avenanthramide 2s,2TBDMS,isomer #3	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(OC)=C1O	3899.4	Semi standard non polar	33892256
Avenanthramide 2s,2TBDMS,isomer #4	COC1=CC(/C=C/C(=O)NC2=CC=C(O)C=C2C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	4017.2	Semi standard non polar	33892256
Avenanthramide 2s,2TBDMS,isomer #5	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(OC)=C1O	3818.8	Semi standard non polar	33892256
Avenanthramide 2s,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)=CC(OC)=C1O[Si](C)(C)C(C)(C)C	3845.1	Semi standard non polar	33892256
Avenanthramide 2s,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(OC)=C1O[Si](C)(C)C(C)(C)C	4221.6	Semi standard non polar	33892256
Avenanthramide 2s,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)[Si](C)(C)C(C)(C)C)=CC(OC)=C1O	4019.0	Semi standard non polar	33892256
Avenanthramide 2s,3TBDMS,isomer #3	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(OC)=C1O[Si](C)(C)C(C)(C)C	4075.9	Semi standard non polar	33892256
Avenanthramide 2s,3TBDMS,isomer #4	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(OC)=C1O[Si](C)(C)C(C)(C)C	3963.2	Semi standard non polar	33892256
Avenanthramide 2s,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(OC)=C1O[Si](C)(C)C(C)(C)C	4194.7	Semi standard non polar	33892256
Avenanthramide 2s,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(OC)=C1O[Si](C)(C)C(C)(C)C	3870.9	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 2s GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-0917000000-8a8fe3466b148db2e1c1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 2s GC-MS (3 TMS) - 70eV, Positive	splash10-03di-0060190000-8121e3fa449f7e3d1dd0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Avenanthramide 2s 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 2s 10V, Positive-QTOF	splash10-0w29-0809000000-58a85c2fc48a429d3f51	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 20V, Positive-QTOF	splash10-0udi-0912000000-0a048db6efbe4739382d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 40V, Positive-QTOF	splash10-0zgi-2900000000-c634ab41e0a919127b44	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 10V, Negative-QTOF	splash10-0bt9-0129000000-de66cb2cecd76f73d4b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 20V, Negative-QTOF	splash10-0bta-0598000000-d0eb276330504a5c280a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 40V, Negative-QTOF	splash10-0pb9-0910000000-51e16d367f68b4c71856	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 10V, Positive-QTOF	splash10-0btc-0049000000-b4cc55661becf0f7f8a1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 20V, Positive-QTOF	splash10-08fu-0349000000-0519c687f62fc49a356a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 40V, Positive-QTOF	splash10-0zj0-0931000000-7c7889203fa9e3f43291	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 10V, Negative-QTOF	splash10-03dj-0059000000-7ef42b242e04c609832d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 20V, Negative-QTOF	splash10-001j-0492000000-ec00d73b50bbf5294368	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Avenanthramide 2s 40V, Negative-QTOF	splash10-0ac0-0190000000-e9d0d0d8e4bd63b6e277	2021-09-23	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

537

FooDB ID

FDB000288

KNApSAcK ID

Not Available

Chemspider ID

9199961

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11024779

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 2s (HMDB0029286)

MOL for HMDB0029286 (Avenanthramide 2s)

3D MOL for HMDB0029286 (Avenanthramide 2s)

3D SDF for HMDB0029286 (Avenanthramide 2s)

3D-SDF for HMDB0029286 (Avenanthramide 2s)

PDB for HMDB0029286 (Avenanthramide 2s)

3D PDB for HMDB0029286 (Avenanthramide 2s)

SMILES for HMDB0029286 (Avenanthramide 2s)

INCHI for HMDB0029286 (Avenanthramide 2s)

Structure for HMDB0029286 (Avenanthramide 2s)

3D Structure for HMDB0029286 (Avenanthramide 2s)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra