(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone

CHEBI:70655 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 4, 2' and 4', a methoxy group at position 6' and methyl groups at positions 3' and 5'. 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:23086 CHEBI:23086
CHEBI:25235 CHEBI:25235
CHEBI:26195 CHEBI:26195

Chemical structure

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

SMILES

COc1c(C)c(O)c(C)c(O)c1C(=O)/C=C/c1ccc(O)cc1

InChI

InChI=1S/C18H18O5/c1-10-16(21)11(2)18(23-3)15(17(10)22)14(20)9-6-12-4-7-13(19)8-5-12/h4-9,19,21-22H,1-3H3/b9-6+

Also called

(2E)-1-(2,4-dihydroxy-6-methoxy-3,5-dimethylphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

reaxys:21040404

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:70655`	(E)-4,2',4'-trihydroxy-6'-methoxy-3',5'-dimethylchalcone	`antibioticmech:chebi-57a8caee72`	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.