humulone

CHEBI:5769 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An optically active cyclic ketone consisting of 3,5,6-trihydroxycyclohexa-2,4-dien-1-one bearing two 3-methylbut-2-en-1-yl substituents at positions 4 and 6 as well as a 3-methylbutanoyl group at the 2-position. — 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:139592 CHEBI:139592
CHEBI:27136 CHEBI:27136
CHEBI:3992 CHEBI:3992
CHEBI:46640 CHEBI:46640
CHEBI:76224 CHEBI:76224

Chemical structure

Computed structure properties
Molecular formula	C21H30O5
Charge	0
Average mass	362.466 Da
Monoisotopic mass	362.20932 Da
Source	ChEBI
InChIKey	VMSLCPKYRPDHLN-OAQYLSRUSA-N

SMILES

CC(C)=CCC1=C(O)[C@](O)(CC=C(C)C)C(=O)C(C(=O)CC(C)C)=C1O

InChI

InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m1/s1

Also called

(6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one (EXACT_SYNONYM)— chebi
(6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone (EXACT_SYNONYM)— chebi
Humulone (EXACT_SYNONYM)— chebi
humulon (EXACT_SYNONYM)— chebi
α-humulon (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:23510-81-8
cas:26472-41-3
kegg.compound:C10695
knapsack:C00002697
patent:CN101134719
patent:DE102007028397
patent:US2011021610
patent:WO2009114939
reaxys:3221160

Activity roles

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

CHEBI:36047 CHEBI:36047

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:5769`	humulone	`antibioticmech:chebi-2ae7899770`	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.