5-O-methyl embelin

CHEBI:65842 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A member of the class of monohydroxy-1,4-benzoquinones that is embelin in which the hydroxy group at position 5 is replaced by a methoxy group. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antileishmanial activity as well as inhibitory activity towards hepatitis C protease. — 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:47985
Label unavailable CHEBI:67273

Chemical structure

Computed structure properties
Molecular formula	C18H28O4
Charge	0
Average mass	308.418 Da
Monoisotopic mass	308.19876 Da
Source	ChEBI
InChIKey	KHBJLRRAMCJZLZ-UHFFFAOYSA-N

SMILES

CCCCCCCCCCCC1=C(O)C(=O)C=C(OC)C1=O

InChI

InChI=1S/C18H28O4/c1-3-4-5-6-7-8-9-10-11-12-14-17(20)15(19)13-16(22-2)18(14)21/h13,20H,3-12H2,1-2H3

Also called

2-hydroxy-5-methoxy-3-undecylcyclohexa-2,5-diene-1,4-dione (EXACT_SYNONYM)— chebi
2-hydroxy-5-methoxy-3-undecyl-1,4-benzoquinone (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.

Activity roles

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

antileishmanial agent CHEBI:70868

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:65842`	5-O-methyl embelin	`antibioticmech:chebi-d4efa0e58a`	2026-08-30

Mechanism summary

Mode of action: VIRAL_PROTEASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:64924 (hepatitis C protease inhibitor). ChEBI asserts the role on the compound, but this mechanism belongs to an anti-viral activity while the record is filed as ANTIPROTOZOAL. Either the compound has both activities, or the filing is wrong — the priority table has put azole antifungals under ANTIBACTERIAL before now. A curator should decide which. The role names a target specific to the microbe or virus — 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).

Explore across X-Mech: MediaIngredientMech (5-O-methyl embelin) · CultureMech · NaturalProductMech · PathwayMech · TraitMech