glionitrin A

CHEBI:65967 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:35489 CHEBI:35489
CHEBI:35716 CHEBI:35716
CHEBI:38163 CHEBI:38163
CHEBI:64130 CHEBI:64130

Chemical structure

Computed structure properties
Molecular formula	C13H11N3O5S2
Charge	0
Average mass	353.381 Da
Monoisotopic mass	353.01401 Da
Source	ChEBI
InChIKey	VRFJINVAZRAFHH-STQMWFEESA-N

SMILES

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

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

Also called

(3S,10aS)-3-(hydroxymethyl)-2-methyl-7-nitro-2,3-dihydro-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:1116153-15-1
reaxys:19154490

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:65967`	glionitrin A	`antibioticmech:chebi-983837d3a8`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.