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CHEBI:65401 - ambiguine I

ChEBI IDCHEBI:65401
ChEBI Nameambiguine I
Stars
DefinitionAn ambiguine that consists of a 5,5,7,10,10-pentamethyl-4,5,5a,6a,6b,7,8,9,9a,10-decahydro-10dH-6-oxa-4-azacyclopropa[6,7]cyclohepta[1,2,3,4-mno]aceanthrylen-10d-ol skeleton with an ethenyl substituent at position 7 and an isocyano group at position 6b (the 5aS,6aR,6bR,7R,9aR,10dR stereoisomer). An antimicrobial agent isolated from the cyanobacterium strain Fischerella.
Last Modified15 August 2018
DownloadsMolfile
FormulaC26H30N2O2
Net Charge0
Average Mass402.538
Monoisotopic Mass402.23073
SMILES[H][C@]12O[C@@]1([H])C(C)(C)c1nc3cccc4c3c1[C@@]1(O)[C@@]2([N+]#[C-])[C@@](C)(C=C)CC[C@]1([H])C4(C)C
InChIInChI=1S/C26H30N2O2/c1-8-24(6)13-12-16-22(2,3)14-10-9-11-15-17(14)18-19(28-15)23(4,5)20-21(30-20)26(24,27-7)25(16,18)29/h8-11,16,20-21,28-29H,1,12-13H2,2-6H3/t16-,20-,21+,24+,25-,26+/m1/s1
InChIKeyRVIIZRJMWFSNER-LJCLWVHTSA-N
Species of MetaboliteComponentSourceComments
Fischerella (ncbitaxon:1190) - PubMed (17315959) MeOH-Water extract (7:3) of Cyanobacterium culture
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
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)
ambiguine I (CHEBI:65401) has role antibacterial agent (CHEBI:33282)
ambiguine I (CHEBI:65401) has role antifungal agent (CHEBI:35718)
ambiguine I (CHEBI:65401) has role bacterial metabolite (CHEBI:76969)
ambiguine I (CHEBI:65401) is a ambiguine (CHEBI:141618)
ambiguine I (CHEBI:65401) is a epoxide (CHEBI:32955)
ambiguine I (CHEBI:65401) is a isocyanide (CHEBI:35353)
ambiguine I (CHEBI:65401) is a organic heterohexacyclic compound (CHEBI:51914)
ambiguine I (CHEBI:65401) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(5aS,6aR,6bR,7R,9aR,10dR)-7-ethenyl-6b-isocyano-5,5,7,10,10-pentamethyl-4,5,5a,6a,6b,7,8,9,9a,10-decahydro-10dH-6-oxa-4-azacyclopropa[6,7]cyclohepta[1,2,3,4-mno]aceanthrylen-10d-ol
Synonym  Source
ambiguine I isonitrileChEBI
Manual XrefsDatabases
17214461ChemSpider
Registry NumbersSources
Reaxys:18851758Reaxys
Citations