ilicicolin H
CHEBI:77772 EXACT SEEDED antifungalantimicrobial unspecifiedcytotoxicenzyme inhibitor
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.
Structure
| Standard InChIKey | BYVVOONSAAQMKI-RFKCMYLBSA-N |
|---|---|
| SMILES | C/C=C/[C@@H]1[C@H]2C[C@H](CC[C@@H]2C(=C[C@H]1C(=O)C3=C(C(=CNC3=O)C4=CC=C(C=C4)O)O)C)C |
| Stereochemistry | fully defined |
| Cross-references | pubchem:54704283, npatlas:NPA013324 |
Filing pathway
Alkaloids — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is nrps, pks, from MIBiG.
Producer organisms 2
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Neonectria sp. DH2 NCBITaxon:1735992 |
SOURCE_ASSERTION | mibig:BGC0002035 | DOI:10.3390/molecules24122267 |
| Talaromyces variabilis NCBITaxon:28576 |
SOURCE_ASSERTION | mibig:BGC0002093 | DOI:10.3390/molecules24122267 |
Occurrences 1
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Calonectria pyrochroa NCBITaxon:57139 |
LOTUS | DOI:10.1016/S0040-4039(00)93121-6 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0002035 | Neonectria sp. DH2 NCBITaxon:1735992 |
CLUSTER_UNSTATED | genbank:RQWH01000002.1 |
| mibig:BGC0002093 | Talaromyces variabilis NCBITaxon:28576 |
CLUSTER_DEMONSTRATED | genbank:MK539848.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 17
| Assay | Result | Reference |
|---|---|---|
| Anti-Fungal Single Agen: CaCi2 Measured in Microorganism System Using Plate Reader - 2148-01_Inhibitor_Dose_DryPowder_Activity_Set4 | EC50 4.81 uM | pubchem.aid:624006 |
| Anti-Fungal Single Agent: C.glabrata growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-04_Inhibitor_Dose_DryPowder_Activity_Set3 | EC50 2.94 uM | pubchem.aid:623965 |
| Anti-Fungal Single Agent: C.glabrata growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-04_Inhibitor_Dose_DryPowder_Activity_Set4 | EC50 2.45 uM | pubchem.aid:624014 |
| Anti-Fungal Single Agent: S.cerevisiae growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-06_Inhibitor_Dose_DryPowder_Activity_Set3 | EC50 0.0335 uM | pubchem.aid:623969 |
| Anti-Fungal Single Agent: S.cerevisiae growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-06_Inhibitor_Dose_DryPowder_Activity_Set4 | EC50 0.0275 uM | pubchem.aid:624012 |
| HPAF-II Cancer Cell Toxicity qHTS against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| KB-3-1 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| KB-8-5-11 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| OV-SAHO Cancer Cell Toxicity qHTS against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | ACTIVE | PMID:33229545 |
| SW1088 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| UWB1.289 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| Vero-766 cells viability qHTS against the NCATS CANVASS Library: Counterscreen for Zika virus inhibition assay | ACTIVE | PMID:30648156 |
| qHTS assay for small molecule disruptors of mitochondrial membrane potential screened against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
| qHTS for inhibitors of ER calcium dysfunction: SERCaMP assay screened against the NCATS CANVASS Library | ACTIVE | PMID:30648156 |
Elsewhere in the fleet
- AntibioticMech — CHEBI:77772 (same structure, same inchikey)
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0002035, BGC0002093. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0002035 | MIBIG | 3 |
| BGC0002093 | MIBIG | 2 |
| CHEBI:77772 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/ilicicolin-h.yaml, which is generated from the committed inventories. Neither is edited by hand.