xanthohumol

CHEBI:66331 ·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 a prenyl group at position 3'. Isolated from Humulus lupulus, it induces apoptosis in human malignant glioblastoma cells. — 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:26195 CHEBI:26195
CHEBI:35618 CHEBI:35618

Chemical structure

Computed structure properties
Molecular formula	C21H22O5
Charge	0
Average mass	354.402 Da
Monoisotopic mass	354.14672 Da
Source	ChEBI
InChIKey	ORXQGKIUCDPEAJ-YRNVUSSQSA-N

SMILES

COc1cc(O)c(CC=C(C)C)c(O)c1C(=O)/C=C/c1ccc(O)cc1

InChI

InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+

Also called

(2E)-1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-en-1-yl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one (EXACT_SYNONYM)— chebi
2',4,4'-trihydroxy-6'-methoxy-3'-prenylchalcone (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:6754-58-1
hmdb:HMDB0037479
kegg.compound:C16417
knapsack:C00007099
lipidmaps:LMPK12120294
metacyc.compound:CPD-7119
patent:EP2579862
patent:WO2009126320
reaxys:2226282
wikipedia.en:Xanthohumol

Activity roles

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

CHEBI:22587 CHEBI:22587
CHEBI:64947 CHEBI:64947

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:66331`	xanthohumol	`antibioticmech:chebi-c2e6e2f500`	2026-08-30

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.