espicufolin

CHEBI:65867 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A naphthochromene that is 4H-naphtho[2,3-h]chromene which is substituted at position 2 by a (2R)-butan-2-yl group, at position 5 by a hydroxymethyl group, at position 11 by a hydroxy group, and at positions 4, 7, and 12 by oxogroups. An antibiotic isolated from Streptomyces sp. cu39, it exerts a potent protecting effect on neuronal cells through suppressing L-glutamate toxicity. — 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:22743 CHEBI:22743
CHEBI:25830 CHEBI:25830
CHEBI:33853 CHEBI:33853
CHEBI:68504 CHEBI:68504

Chemical structure

Computed structure properties
Molecular formula	C22H18O6
Charge	0
Average mass	378.38 Da
Monoisotopic mass	378.11034 Da
Source	ChEBI
InChIKey	HXAZTNIVBVVFJS-SNVBAGLBSA-N

SMILES

CC[C@@H](C)c1cc(=O)c2c(CO)cc3c(c2o1)C(=O)c1c(O)cccc1C3=O

InChI

InChI=1S/C22H18O6/c1-3-10(2)16-8-15(25)17-11(9-23)7-13-19(22(17)28-16)21(27)18-12(20(13)26)5-4-6-14(18)24/h4-8,10,23-24H,3,9H2,1-2H3/t10-/m1/s1

Also called

2-[(2R)-butan-2-yl]-11-hydroxy-5-(hydroxymethyl)-4H-naphtho[2,3-h]chromene-4,7,12-trione (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:8804787

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:65867`	espicufolin	`antibioticmech:chebi-8638a2d4c7`	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.