icajine (CHEBI:132668)

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CHEBI:132668 - icajine

ChEBI ID	CHEBI:132668
ChEBI Name	icajine
Stars
Definition	A monoterpenoid indole alkaloid with formula C₂₂H₂₄N₂O₃, originallly isolated from the leaves of Strychnos icaja.
Last Modified	10 January 2017
Submitter	liuqingping
Downloads	Molfile

Formula	C22H24N2O3
Net Charge	0
Average Mass	364.445
Monoisotopic Mass	364.17869
SMILES	[H][C@@]12N3C(=O)C[C@]4([H])OCC=C5CN(C)CC[C@]1(C(=O)C[C@]5([H])[C@]24[H])c1ccccc13
InChI	InChI=1S/C22H24N2O3/c1-23-8-7-22-15-4-2-3-5-16(15)24-19(26)11-17-20(21(22)24)14(10-18(22)25)13(12-23)6-9-27-17/h2-6,14,17,20-21H,7-12H2,1H3/t14-,17-,20-,21-,22+/m0/s1
InChIKey	RNZRHJNFQWMXHB-ZXXLSYNSSA-N

Species of Metabolite	Component	Source	Comments
Strychnos nux-vomica (ncbitaxon:28545)	seed (BTO:0001226)	PubMed (16317898)
Strychnos icaja (ncbitaxon:1040889)	leaf (BTO:0000713)	PubMed (4954818)

Roles Classification

Chemical Role:

Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).

Biological Roles:

plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.

sodium channel blocker An agent that inhibits sodium influx through cell membranes.

metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.

ChEBI Ontology

Outgoing Relation(s)
	icajine (CHEBI:132668) has role plant metabolite (CHEBI:76924)
	icajine (CHEBI:132668) has role sodium channel blocker (CHEBI:38633)
	icajine (CHEBI:132668) is a cyclic ketone (CHEBI:3992)
	icajine (CHEBI:132668) is a monoterpenoid indole alkaloid (CHEBI:65323)
	icajine (CHEBI:132668) is a organic heterohexacyclic compound (CHEBI:51914)
	icajine (CHEBI:132668) is a tertiary amino compound (CHEBI:50996)
	icajine (CHEBI:132668) is a δ-lactam (CHEBI:77727)

IUPAC Name
(4aR,6aS,12aS,12bR,12cS)-15-methyl-4a,5,12,12a,12b,12c-hexahydro-11H-6a,4-(ethanoiminomethano)-1-oxa-10b-azacyclohepta[1,2,3-cd]fluoranthene-6,11(2H)-dione

Synonym	Source
19-methyl-16,19-seco-strychnidine-10,16-dione	ChEBI

Registry Numbers	Sources
Reaxys:59544	Reaxys
Reaxys:1093794	Reaxys
CAS:5525-31-5	ChemIDplus

Citations