CHEBI:141616 - hapalindole-type alkaloid

ChEBI IDCHEBI:141616
ChEBI Namehapalindole-type alkaloid
Stars
DefinitionAny member of a structurally diverse group of hybrid isoprenoid-indole alkaloids, produced solely by members of the Subsection V cyanobacterial strains. The major classes of hapalindole-type molecules include hapalindoles, fischerindoles, welwitindolinones and ambiguines that share a common molecular feature where an indole and an isonitrile group are connected by a carbon-carbon motif (C10-C11) that is appended with a monoterpene unit. Fusion of the exomethylene carbon C-16 with indole backbones in the tricyclic hapalindoles provides tetracyclic hapalindoles and fischerindoles that, on rearrangement, can also lead to the bridged tetracyclic welwitindolinones. Decoration of tetracyclic hapalindoles with a tert-prenyl group at C-2 of the indole ring results in ambiguines, of which many have a fused pentacyclic 6-6-6-5-7 or 6-6-6-5-6 ring system.
Last Modified15 August 2018
SubmitterGareth Owen
Roles Classification
Biological Role:
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)
hapalindole-type alkaloid (CHEBI:141616) is a indole alkaloid (CHEBI:38958)
Incoming Relation(s)
ambiguine (CHEBI:141618) is a hapalindole-type alkaloid (CHEBI:141616)
fischerindole alkaloid (CHEBI:141619) is a hapalindole-type alkaloid (CHEBI:141616)
hapalindole (CHEBI:141617) is a hapalindole-type alkaloid (CHEBI:141616)
Synonym  Source
hapalindole-type alkaloidsChEBI
Citations