verongamine (CHEBI:66355)

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ChEBI Name	verongamine

ChEBI ID	CHEBI:66355

Definition	A monocarboxylic acid amide that is N-[2-(1H-imidazol-4-yl)ethyl]propanamide substituted by a hydroxyimino group at position 2 and a 3-bromo-4-methoxyphenyl group at position 3. A bromotyrosine derivative isolated from the marine sponge Verongula gigantea, it exhibits histamine-H₃ antagonist activity.

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

Supplier Information

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Formula

C15H17BrN4O3

Net Charge

Average Mass

381.22400

Monoisotopic Mass

380.04840

InChI

InChI=1S/C15H17BrN4O3/c1-23-14-3-2-10(6-12(14)16)7-13(20-22)15(21)18-5-4-11-8-17-9-19-11/h2-3,6,8-9,22H,4-5,7H2,1H3,(H,17,19)(H,18,21)/b20-13+

InChIKey

MFMMJKGZEGTTSV-DEDYPNTBSA-N

SMILES

COc1ccc(C\C(=N/O)C(=O)NCCc2c[nH]cn2)cc1Br

Metabolite of Species	Details
Verongula gigantea (NCBI:txid289407)	See: PubMed

Roles Classification
Biological Role(s):	marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. H3-receptor antagonist A histamine antagonist that selectively binds to but does not activate histamine H3 receptors, thereby blocking the actions of endogenous histamine. animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

Application(s):	H3-receptor antagonist A histamine antagonist that selectively binds to but does not activate histamine H3 receptors, thereby blocking the actions of endogenous histamine.

ChEBI Ontology
Outgoing	verongamine (CHEBI:66355) has role animal metabolite (CHEBI:75767) verongamine (CHEBI:66355) has role H₃-receptor antagonist (CHEBI:64176) verongamine (CHEBI:66355) has role marine metabolite (CHEBI:76507) verongamine (CHEBI:66355) is a bromobenzenes (CHEBI:37149) verongamine (CHEBI:66355) is a imidazoles (CHEBI:24780) verongamine (CHEBI:66355) is a ketoxime (CHEBI:24983) verongamine (CHEBI:66355) is a monocarboxylic acid amide (CHEBI:29347) verongamine (CHEBI:66355) is a monomethoxybenzene (CHEBI:25235)

IUPAC Name

(2E)-3-(3-bromo-4-methoxyphenyl)-2-(hydroxyimino)-N-[2-(1H-imidazol-4-yl)ethyl]propanamide

Synonym	Source
(E)-3-bromo-α-(hydroxyimino)-N-(2-(1H-imidazol-4-yl)ethyl)-4-methoxy-benzenepropanamide	ChemIDplus

Citation	Type	Source
8158162	PubMed citation	Europe PMC

Last Modified

27 November 2014