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CHEBI:65967 - glionitrin A

ChEBI IDCHEBI:65967
ChEBI Nameglionitrin A
Stars
DefinitionA 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.
Last Modified27 October 2016
DownloadsMolfile
FormulaC13H11N3O5S2
Net Charge0
Average Mass353.381
Monoisotopic Mass353.01401
SMILESCN1C(=O)[C@@]23Cc4ccc([N+](=O)[O-])cc4N2C(=O)[C@]1(CO)SS3
InChIInChI=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
InChIKeyVRFJINVAZRAFHH-STQMWFEESA-N
Species of MetaboliteComponentSourceComments
Aspergillus fumigatus (ncbitaxon:746128) - PubMed (19159274) Strain: KMC 901
Sphingomonas sp. (ncbitaxon:28214) - PubMed (19159274) Strain: KMK-001
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
glionitrin A (CHEBI:65967) has role Aspergillus metabolite (CHEBI:76956)
glionitrin A (CHEBI:65967) has role antimicrobial agent (CHEBI:33281)
glionitrin A (CHEBI:65967) has role antineoplastic agent (CHEBI:35610)
glionitrin A (CHEBI:65967) is a C-nitro compound (CHEBI:35716)
glionitrin A (CHEBI:65967) is a organic disulfide (CHEBI:35489)
glionitrin A (CHEBI:65967) is a organic heterotetracyclic compound (CHEBI:38163)
glionitrin A (CHEBI:65967) is a pyrazinoindole (CHEBI:64130)
IUPAC Name 
(3S,10aS)-3-(hydroxymethyl)-2-methyl-7-nitro-2,3-dihydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Registry NumbersSources
Reaxys:19154490Reaxys
CAS:1116153-15-1Reaxys
Citations