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CHEBI:167489 - avenanthramide B

ChEBI IDCHEBI:167489
ChEBI Nameavenanthramide B
Stars
DefinitionA monohydroxybenzoic acid resulting from the formal condensation of the carboxy group of ferulic acid with the amino group of 2-amino-5-hydroxybenzoic acid. It is an oat phytoalexin produced in response to pathogen attack and elicitation.
Last Modified15 February 2021
SubmitterAdnan
DownloadsMolfile
FormulaC17H15NO6
Net Charge0
Average Mass329.308
Monoisotopic Mass329.08994
SMILESCOc1cc(/C=C/C(=O)Nc2ccc(O)cc2C(=O)O)ccc1O
InChIInChI=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+
InChIKeyJXFZHMCSCYADIX-XVNBXDOJSA-N
Species of MetaboliteComponentSourceComments
Avena sativa (ncbitaxon:4498)
seed (BTO:0001226) PubMed (10739096)
leaf (BTO:0000713) DOI (10.1111/j.1365-313X.2004.02163.x)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
phytoalexin  A toxin made by a plant that acts against an organism attacking it.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
avenanthramide B (CHEBI:167489) has functional parent trans-ferulic acid (CHEBI:17620)
avenanthramide B (CHEBI:167489) has role antineoplastic agent (CHEBI:35610)
avenanthramide B (CHEBI:167489) has role apoptosis inducer (CHEBI:68495)
avenanthramide B (CHEBI:167489) has role phytoalexin (CHEBI:26115)
avenanthramide B (CHEBI:167489) is a amidobenzoic acid (CHEBI:48470)
avenanthramide B (CHEBI:167489) is a cinnamamides (CHEBI:23247)
avenanthramide B (CHEBI:167489) is a monohydroxybenzoic acid (CHEBI:25389)
avenanthramide B (CHEBI:167489) is a monomethoxybenzene (CHEBI:25235)
avenanthramide B (CHEBI:167489) is a phenols (CHEBI:33853)
avenanthramide B (CHEBI:167489) is a secondary carboxamide (CHEBI:140325)
avenanthramide B (CHEBI:167489) is conjugate acid of avenanthramide B(1−) (CHEBI:167465)
Incoming Relation(s)
avenanthramide B(1−) (CHEBI:167465) is conjugate base of avenanthramide B (CHEBI:167489)
IUPAC Name 
5-hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino}benzoic acid
Synonyms  Source
avenanthramide 1ChemIDplus
avenanthramide BFChemIDplus
avenanthramide 2FChemIDplus
5-hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acidChEBI
N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-5-hydroxyanthranilic acidChEBI
N-feruloyl-5-hydroxyanthranilic acidFooDB
Manual XrefsDatabases
HMDB0038575HMDB
FDB000285FooDB
8263492ChemSpider
Registry NumbersSources
Reaxys:3625397Reaxys
CAS:108605-69-2ChemIDplus
Citations