glandicoline B

CHEBI:134347 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An indole alkaloid with a tetracyclic skeleton that is isolated from Penicillium chrysogenum. — 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:24780 CHEBI:24780
CHEBI:24995 CHEBI:24995
CHEBI:33823 CHEBI:33823
CHEBI:38163 CHEBI:38163
CHEBI:38958 CHEBI:38958
CHEBI:78840 CHEBI:78840

Chemical structure

Computed structure properties
Molecular formula	C22H21N5O4
Charge	0
Average mass	419.441 Da
Monoisotopic mass	419.15935 Da
Source	ChEBI
InChIKey	YEVSOYBNHBOQJZ-GCTRCSCRSA-N

SMILES

C=CC(C)(C)[C@]12C=C(O)C(=O)N3/C(=C/c4cncn4)C(=O)N[C@@]31N(O)c1ccccc12

InChI

InChI=1S/C22H21N5O4/c1-4-20(2,3)21-10-17(28)19(30)26-16(9-13-11-23-12-24-13)18(29)25-22(21,26)27(31)15-8-6-5-7-14(15)21/h4-12,28,31H,1H2,2-3H3,(H,23,24)(H,25,29)/b16-9+/t21-,22-/m1/s1

Also called

(3E,7aS,12aR)-6,12-dihydroxy-3-[(1H-imidazol-4-yl)methylidene]-7a-(2-methylbut-3-en-2-yl)-7a,12-dihydro-1H,5H-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3H)-dione (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

metacyc.compound:CPD-17390

Activity roles

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

CHEBI:33282 CHEBI:33282

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:134347`	glandicoline B	`antibioticmech:chebi-50fc8a18fe`	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.