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glionitrin A
A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring. It is an antibiotic isolated from the microbial strains Sphingomonas and Aspergillus fumigatus, and exhibits cytotoxic activity against four human cancer cell lines: HCT-116, A549, AGS, and DU145.


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07. Part of Biological Source of Chemical: unspecified structure [PO:0000004]
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03. Biological Effects of Specific Chemicals: antimicrobial agent [CHEBI:33281] > antibiotic [CHEBI:22582] > glionitrin A [CHEBI:65967]
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more general categories    information about this item
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) 
 glionitrin A [CHEBI:65967] (1)
 antimicrobial agent [CHEBI:33281] (927) 
 antibiotic [CHEBI:22582] (193) 
 glionitrin A [CHEBI:65967] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antineoplastic agent [CHEBI:35610] (760) 
 glionitrin A [CHEBI:65967] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Archaea, Cyanobacteria and Bacteria (302) 
 Eubacteria (239) 
 Proteobacteria (23) 
 alpha-Proteobacteria (3) 
 Sphingomonadales (2) 
 Sphingomonadaceae (2) 
 Sphingomonas (2)
 Fungi, Yeasts, Molds and Mildews (348) 
 Deuteromycotina (255) 
 Hyphomycetes (137) 
 Aspergillus (96) 
 Aspergillus fumigatus (12)
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) 
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 organonitrogen compound [CHEBI:35352] (6705) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 pyrazinoindole [CHEBI:64130] (2) 
 glionitrin A [CHEBI:65967] (1)
 nitro compound [CHEBI:35715] (192) 
 C-nitro compound [CHEBI:35716] (171) 
 glionitrin A [CHEBI:65967] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 sulfur molecular entity [CHEBI:26835] (1541) 
 organosulfur compound [CHEBI:33261] (1005) 
 organic disulfide [CHEBI:35489] (36) 
 glionitrin A [CHEBI:65967] (1)
 disulfide [CHEBI:48343] (41) 
 organic disulfide [CHEBI:35489] (36) 
 glionitrin A [CHEBI:65967] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organosulfur compound [CHEBI:33261] (1005) 
 organic disulfide [CHEBI:35489] (36) 
 glionitrin A [CHEBI:65967] (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) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 pyrazinoindole [CHEBI:64130] (2) 
 glionitrin A [CHEBI:65967] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 glionitrin A [CHEBI:65967] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 pyrazinoindole [CHEBI:64130] (2) 
 glionitrin A [CHEBI:65967] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organosulfur compound [CHEBI:33261] (1005) 
 organic disulfide [CHEBI:35489] (36) 
 glionitrin A [CHEBI:65967] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 pyrazinoindole [CHEBI:64130] (2) 
 glionitrin A [CHEBI:65967] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 glionitrin A [CHEBI:65967] (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 heterotetracyclic compound [CHEBI:38163] (128) 
 glionitrin A [CHEBI:65967] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 pyrazinoindole [CHEBI:64130] (2) 
 glionitrin A [CHEBI:65967] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 glionitrin A [CHEBI:65967] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 pyrazinoindole [CHEBI:64130] (2) 
 glionitrin A [CHEBI:65967] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 glionitrin A [CHEBI:65967] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 glionitrin A [CHEBI:65967] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 pyrazinoindole [CHEBI:64130] (2) 
 glionitrin A [CHEBI:65967] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 glionitrin A [CHEBI:65967] (1)
ChEBI Compound Accession Identifier  [CHEBI:65967]
ChEBI Compound Description  A pyrazinoindole with a disulfide bridge spanning a dioxo-substituted pyrazine ring. It is an antibiotic isolated from the microbial strains Sphingomonas and Aspergillus fumigatus, and exhibits cytotoxic activity against four human cancer cell lines: HCT-116, A549, AGS, and DU145.
ChEBI Compound Identification Number  65967
ChEBI InChI Value  InChI=1S/C13H11N3O5S2/c1-14-10(18)12-5-7-2-3-8(16(20)21)4-9(7)15(12)11(19)13(14,6-17)23-22-12/h2-4,17H,5-6H2,1H3/t12-,13-/m0/s1
ChEBI InChIKey Value  VRFJINVAZRAFHH-STQMWFEESA-N
ChEBI Compound Name  glionitrin A
ChEBI SMILES Value  CN1C(=O)[C@@]23Cc4ccc(cc4N2C(=O)[C@]1(CO)SS3)[N+]([O-])=O
ChEBI Substance ID  160710074
ChEBI URL  ChEBI:65967
ChemSpider ID  NS
Ontomatica Chemical Accession Key (OnChAKey)  VRFJINVAZRAFHH_STQMWFEESA_N_000_000000
PubChem Compound ID  25243252