CHEBI:65401 - ambiguine I

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ChEBI Name ambiguine I
ChEBI ID CHEBI:65401
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C26H30N2O2
Net Charge 0
Average Mass 402.530
Monoisotopic Mass 402.23073
InChI InChI=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
InChIKey RVIIZRJMWFSNER-LJCLWVHTSA-N
SMILES C=12NC=3C4=C(C=CC3)C([C@]5([H])[C@@](O)(C41)[C@]([C@@](CC5)(C)C=C)([N+]#[C-])[C@@]6([C@@](O6)(C2(C)C)[H])[H])(C)C
Metabolite of Species Details
Fischerella (NCBI:txid1190) MeOH-Water extract (7:3) of Cyanobacterium culture See: PubMed
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
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 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 isonitrile ChEBI
Manual Xref Database
17214461 ChemSpider
View more database links
Registry Number Type Source
18851758 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17315959 PubMed citation Europe PMC
Last Modified
15 August 2018