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ambiguine I Isonitrile
Isonitrile containing indole alkaloid 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.

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03. Biological Effects of Specific Chemicals: antimicrobial agent [CHEBI:33281] > antifungal agent [CHEBI:35718] > ambiguine I Isonitrile [CHEBI:65401]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antibacterial agent [CHEBI:33282] (317) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 antifungal agent [CHEBI:35718] (130) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Archaea, Cyanobacteria and Bacteria (302) 
 Cyanobacteria (63) 
 Stigonematales (2) 
 Fischerella (2)
07. Part of Biological Source of Chemical 
07. Part of Biological Source of Chemical
 unspecified structure [PO:0000004] (703)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 tertiary alcohol [CHEBI:26878] (183) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 indole alkaloid [CHEBI:38958] (144) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 isocyanide [CHEBI:35353] (5) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 tertiary alcohol [CHEBI:26878] (183) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterohexacyclic compound [CHEBI:51914] (33) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 indole alkaloid [CHEBI:38958] (144) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 isocyanide [CHEBI:35353] (5) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 tertiary alcohol [CHEBI:26878] (183) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterohexacyclic compound [CHEBI:51914] (33) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 polycyclic compound [CHEBI:33635] (4078) 
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterohexacyclic compound [CHEBI:51914] (33) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterohexacyclic compound [CHEBI:51914] (33) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterohexacyclic compound [CHEBI:51914] (33) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterohexacyclic compound [CHEBI:51914] (33) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 cyclic ether [CHEBI:37407] (314) 
 epoxide [CHEBI:32955] (145) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterohexacyclic compound [CHEBI:51914] (33) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 tertiary alcohol [CHEBI:26878] (183) 
 ambiguine I Isonitrile [CHEBI:65401] (1)
ChEBI Compound Accession Identifier:   [CHEBI:65401]
ChEBI Compound Description:   Isonitrile containing indole alkaloid 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.
ChEBI Compound Identification Number:   65401
ChEBI InChI Value:   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
ChEBI InChIKey Value:   RVIIZRJMWFSNER-LJCLWVHTSA-N
ChEBI Compound Name:   ambiguine I Isonitrile
ChEBI SMILES Value:   [H][C@@]12O[C@]1([H])[C@]1([N+]#[C-])[C@](C)(CC[C@]3([H])C(C)(C)c4cccc5[nH]c(c(c45)[C@@]13O)C2(C)C)C=C
ChEBI Substance ID:   160644832
ChEBI URL:   ChEBI:65401
ChemSpider ID:   17214461
Ontomatica Chemical Accession Key (OnChAKey):   RVIIZRJMWFSNER_LJCLWVHTSA_N_000_000000
PubChem Compound ID:   16109784