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

CHEBI:70664 ·resolve ·ANTIVIRAL ·EXACT SEEDED

A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 5 and 7 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.

Label unavailable CHEBI:38749

Chemical structure

Computed structure properties
Molecular formula	C17H16O4
Charge	0
Average mass	284.311 Da
Monoisotopic mass	284.10486 Da
Source	ChEBI
InChIKey	HAIHGFWQOPJMPV-ZDUSSCGKSA-N

SMILES

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

InChI

InChI=1S/C17H16O4/c1-9-15(19)10(2)17-14(16(9)20)12(18)8-13(21-17)11-6-4-3-5-7-11/h3-7,13,19-20H,8H2,1-2H3/t13-/m0/s1

Also called

(2S)-5,7-dihydroxy-6,8-dimethyl-2-phenyl-2,3-dihydro-4H-chromen-4-one (EXACT_SYNONYM)— chebi
(2S)-2,3-dihydro-5,7-dihydroxy-6,8-dimethyl-2-phenyl-4H-1-benzopyran-4-one (EXACT_SYNONYM)— chebi
(−)-demethoxymatteucinol (EXACT_SYNONYM)— chebi
6,8-dimethylpinocembrin (EXACT_SYNONYM)— chebi
demethoxymatteucinol (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

cas:56297-79-1
reaxys:1290952

Activity roles

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

EC 3.2.1.18 (exo-α-sialidase) inhibitor 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:70664`	(2S)-5,7-dihydroxy-6,8-dimethylflavanone	`antibioticmech:chebi-29f2e13209`	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 (YAML).

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