(2S)-2,7-dihydroxy-5-methoxy-6,8-dimethylflavanone

CHEBI:70654 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A dihydroxyflavanon that is (2S)-flavanone substituted by hydroxy groups at positions 2 and 7, a methoxy group at position 5 and methyl groups at positions 6 and 8. Isolated from the buds of 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:141992 CHEBI:141992
CHEBI:38738 CHEBI:38738
CHEBI:38749 CHEBI:38749

Chemical structure

Computed structure properties
Molecular formula	C18H18O5
Charge	0
Average mass	314.337 Da
Monoisotopic mass	314.11542 Da
Source	ChEBI
InChIKey	BIMVXOYXXZYVJF-SFHVURJKSA-N

SMILES

COc1c(C)c(O)c(C)c2c1C(=O)C[C@@](O)(c1ccccc1)O2

InChI

InChI=1S/C18H18O5/c1-10-15(20)11(2)17-14(16(10)22-3)13(19)9-18(21,23-17)12-7-5-4-6-8-12/h4-8,20-21H,9H2,1-3H3/t18-/m0/s1

Also called

(2S)-2,7-dihydroxy-5-methoxy-6,8-dimethyl-2-phenyl-2,3-dihydro-4H-chromen-4-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:21040402

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:70654`	(2S)-2,7-dihydroxy-5-methoxy-6,8-dimethylflavanone	`antibioticmech:chebi-d262a1595d`	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.