ilicicolin H

CHEBI:77772 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT REVIEWED

An aromatic ketone in which the ketone carbonyl group is attached to a (1R,2R,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl group and a 4-hydroxy-5-(4-hydroxyphenyl)-2-oxo-1,2-dihydropyridin-3-yl group. Isolated from the from the "imperfect" fungus Cylindrocladium iliciola strain MFC-870. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:138397
ilicicolin CHEBI:146212
Label unavailable CHEBI:33853
Label unavailable CHEBI:36785
Label unavailable CHEBI:38182
Label unavailable CHEBI:38183
Label unavailable CHEBI:76224

Chemical structure

Computed structure properties
Molecular formula	C27H31NO4
Charge	0
Average mass	433.548 Da
Monoisotopic mass	433.22531 Da
Source	ChEBI
InChIKey	BYVVOONSAAQMKI-RFKCMYLBSA-N

SMILES

[H][C@]12CC[C@H](C)C[C@]1([H])[C@@H](/C=C/C)[C@H](C(=O)c1c(O)c(-c3ccc(O)cc3)cnc1=O)C=C2C

InChI

InChI=1S/C27H31NO4/c1-4-5-20-21-12-15(2)6-11-19(21)16(3)13-22(20)25(30)24-26(31)23(14-28-27(24)32)17-7-9-18(29)10-8-17/h4-5,7-10,13-15,19-22,29H,6,11-12H2,1-3H3,(H2,28,31,32)/b5-4+/t15-,19+,20+,21-,22+/m0/s1

Also called

3-({(1R,2S,4aS,7S,8aR)-4,7-dimethyl-1-[(1E)-prop-1-en-1-yl]-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl}carbonyl)-4-hydroxy-5-(4-hydroxyphenyl)pyridin-2(1H)-one (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.

knapsack:C00028381
reaxys:1631061

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

patent:CN101260418

Activity roles

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

antimicrobial agent CHEBI:33281

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:77772`	ilicicolin H	`antibioticmech:chebi-64a16b7763`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

cytochrome bc1 complex Qn site PROTEIN_COMPLEX DIRECT_BINDING_TARGET

Electron-transfer assays, spectral titration, and stoichiometry established one ilicicolin-H molecule per yeast Qn site; cross-species assays quantified selective binding. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2003-12; 2007-11 (retrieved 2026-09-02).

Saccharomyces cerevisiae NCBITaxon:4932

PMID:14670947 (Primary yeast bc1 Qn-site binding and inhibition study (DOI:10.1074/jbc.M311805200).)
PMID:18022381 (Primary yeast, bovine, and bacterial bc1 selectivity comparison (DOI:10.1016/j.bbabio.2007.10.011).)

Mechanism summary

Mode of action: ENERGY_METABOLISM_INHIBITION host shared target — CURATOR: PMID:14670947 measured nanomolar inhibition and stoichiometric binding of ilicicolin H at the Qn site of the Saccharomyces cerevisiae cytochrome bc1 complex. PMID:18022381 compared yeast, bovine, and bacterial complexes and showed strong species dependence, so the conserved respiratory target is host-shared despite marked selectivity.

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Producer organisms
Organism	BGC	Cluster link evidence	Source	Quality	Note	Evidence
Talaromyces variabilis NCBITaxon:28576	BGC0002093	Enzymatic assays; Heterologous expression compound specific	MIBIG 4.0.1 (entry 2)	questionable	MIBiG active entry; compound 'ilicicolin H' joined by exact Standard InChIKey.	PMID:30905148 (MIBiG's first legacy reference for the entry, inherited rather than attached to the compound. It supports that the entry exists; it is NOT established as evidence for this specific producer/compound link.)

Record-level evidence

PMID:14670947 (Primary ilicicolin-H yeast bc1 target study.)
PMID:18022381 (Primary cross-species bc1 inhibitor comparison.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, antibiotic role, and unspecified filing class; added respiratory energy-metabolism inhibition and direct, species-selective binding to the host-shared cytochrome-bc1 Qn site.
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (ilicicolin H) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Talaromyces variabilis)