CHEBI:132668 - icajine

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ChEBI Name icajine
ChEBI ID CHEBI:132668
Definition A monoterpenoid indole alkaloid with formula C22H24N2O3, originallly isolated from the leaves of Strychnos icaja.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
Supplier Information
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Formula C22H24N2O3
Net Charge 0
Average Mass 364.438
Monoisotopic Mass 364.17869
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
SMILES [C@@]123[C@@]4([C@]5([C@@](CC1=O)(C(CN(CC2)C)=CCO[C@]5(CC(N4C6=C3C=CC=C6)=O)[H])[H])[H])[H]
Metabolite of Species Details
Strychnos icaja (NCBI:txid1040889) Found in leaf (BTO:0000713). See: PubMed
Strychnos nux-vomica (NCBI:txid28545) Found in seed (BTO:0001226). See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing icajine (CHEBI:132668) has role plant metabolite (CHEBI:76924)
icajine (CHEBI:132668) has role sodium channel blocker (CHEBI:38633)
icajine (CHEBI:132668) is a δ-lactam (CHEBI:77727)
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)
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 Types Sources
1093794 Reaxys Registry Number Reaxys
5525-31-5 CAS Registry Number ChemIDplus
59544 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11509972 PubMed citation Europe PMC
15280006 PubMed citation Europe PMC
16317898 PubMed citation Europe PMC
19235686 PubMed citation Europe PMC
21616062 PubMed citation Europe PMC
21756423 PubMed citation Europe PMC
25594733 PubMed citation Europe PMC
4954818 PubMed citation Europe PMC
7779278 PubMed citation Europe PMC
7912074 PubMed citation Europe PMC
Last Modified
10 January 2017