verongamine (CHEBI:66355)

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CHEBI:66355 - verongamine

ChEBI ID	CHEBI:66355
ChEBI Name	verongamine
Stars
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.
Last Modified	27 November 2014
Downloads	Molfile

Formula	C15H17BrN4O3
Net Charge	0
Average Mass	381.230
Monoisotopic Mass	380.04840
SMILES	COc1ccc(C/C(=N\O)C(=O)NCCc2cncn2)cc1Br
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

Species of Metabolite	Component	Source	Comments
Verongula gigantea (ncbitaxon:289407)	-	PubMed (8158162)

Roles Classification

Biological Roles:

animal metabolite Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.

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.

Application:

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 Relation(s)
	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

Registry Numbers	Sources
Reaxys:8075601	Reaxys
CAS:150036-88-7	ChemIDplus

Citations