(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone

CHEBI:70661 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A monohydroxyflavanone that is (2S)-flavanone substituted by a hydroxy group at position 5, a methoxy group at position 7, a methyl group at position 6 and a formyl group at position 8. Isolated from Cleistocalyx operculatus, it has been shown to exhibit inhibitory effects on the viral neuraminidases from two influenza viral strains, H1N1 and H9N2. — 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:17478 CHEBI:17478
CHEBI:38738 CHEBI:38738
CHEBI:38748 CHEBI:38748

Chemical structure

Computed structure properties
Molecular formula	C18H16O5
Charge	0
Average mass	312.321 Da
Monoisotopic mass	312.09977 Da
Source	ChEBI
InChIKey	QJQJKEWQUOORFC-AWEZNQCLSA-N

SMILES

COc1c(C)c(O)c2c(c1C=O)O[C@H](c1ccccc1)CC2=O

InChI

InChI=1S/C18H16O5/c1-10-16(21)15-13(20)8-14(11-6-4-3-5-7-11)23-18(15)12(9-19)17(10)22-2/h3-7,9,14,21H,8H2,1-2H3/t14-/m0/s1

Also called

(2S)-5-hydroxy-7-methoxy-6-methyl-4-oxo-2-phenyl-3,4-dihydro-2H-chromene-8-carbaldehyde (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:10367824

Activity roles

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

CHEBI:52425 CHEBI:52425

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:70661`	(2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone	`antibioticmech:chebi-28e22606ff`	2026-08-30

Mechanism summary

Mode of action: VIRAL_RELEASE_INHIBITION host shared target — Assigned from ChEBI role CHEBI:52425 (EC 3.2.1.18 (exo-α-sialidase) inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

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.