avenanthramide B (CHEBI:167489)

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ChEBI Name	avenanthramide B

ChEBI ID	CHEBI:167489

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C17H15NO6

Net Charge

Average Mass

329.308

Monoisotopic Mass

329.08994

InChI

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+

InChIKey

JXFZHMCSCYADIX-XVNBXDOJSA-N

SMILES

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

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	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(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	avenanthramide B (CHEBI:167489) has functional parent 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	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	Sources
5-hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid	ChEBI
avenanthramide 1	ChemIDplus
avenanthramide 2F	ChemIDplus
avenanthramide BF	ChemIDplus
N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid	ChEBI
N-feruloyl-5-hydroxyanthranilic acid	FooDB

Last Modified

15 February 2021