(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone

CHEBI:70653 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 3, 5 and 7 and methyl groups at positions 6 and 8 (the 2S,3S-stereoisomer). It has been isolated from the buds of Cleistocalyx operculatus and 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:2468 CHEBI:2468
CHEBI:38739 CHEBI:38739
CHEBI:48039 CHEBI:48039

Chemical structure

Computed structure properties
Molecular formula	C17H16O5
Charge	0
Average mass	300.31 Da
Monoisotopic mass	300.09977 Da
Source	ChEBI
InChIKey	HDEMWSJTNCFIGR-WBVHZDCISA-N

SMILES

Cc1c(O)c(C)c2c(c1O)C(=O)[C@@H](O)[C@H](c1ccccc1)O2

InChI

InChI=1S/C17H16O5/c1-8-12(18)9(2)16-11(13(8)19)14(20)15(21)17(22-16)10-6-4-3-5-7-10/h3-7,15,17-19,21H,1-2H3/t15-,17+/m1/s1

Also called

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

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:70653`	(2S,3S)-3,5,7-trihydroxy-6,8-dimethylflavanone	`antibioticmech:chebi-79748ff3f9`	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.