glionitrin A (CHEBI:65967)

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ChEBI Name	glionitrin A

ChEBI ID	CHEBI:65967

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C13H11N3O5S2

Net Charge

Average Mass

353.37400

Monoisotopic Mass

353.01401

InChI

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

InChIKey

VRFJINVAZRAFHH-STQMWFEESA-N

SMILES

CN1C(=O)[C@@]23Cc4ccc(cc4N2C(=O)[C@]1(CO)SS3)[N+]([O-])=O

Metabolite of Species	Details
Sphingomonas sp. (NCBI:txid28214)	of strain KMK-001 See: PubMed
Aspergillus fumigatus (NCBI:txid746128)	of strain KMC 901 See: PubMed

Roles Classification
Biological Role(s):	Aspergillus metabolite Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus . antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	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

Last Modified

27 October 2016