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ilicicolin H

CHEBI:77772 EXACT SEEDED antifungalantimicrobial unspecifiedcytotoxicenzyme inhibitor

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

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 InChIKeyBYVVOONSAAQMKI-RFKCMYLBSA-N
SMILESC/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
Stereochemistryfully defined
Cross-referencespubchem: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.

TaxonBasisClusterEvidence
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.

TaxonSourceReference
Calonectria pyrochroa
NCBITaxon:57139		 LOTUS DOI:10.1016/S0040-4039(00)93121-6

Biosynthetic gene clusters 2

AccessionHostLocus evidenceGenome
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.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

StepEnzymeReactionSubstrate → productEvidence
1 IccE NADH-dependent flavin oxidoreductase
UniProtKB:A0A482N8M8		 RHEA:64564 CHEBI:155888 → CHEBI:77772 DOI:10.1021/jacs.9b02204

Step 1: Talaromyces variabilis HXQ-H-1 IccE epimerizes 8-epi-ilicicolin H to ilicicolin H; upstream IccA-IccD assembly is left unexpanded.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 2 producers (0 causal) 1 cited occurrence BIOSYNTHETIC LOCUS 2 gene clusters 1 curated pathway step NATURAL PRODUCT ilicicolin H CHEBI:77772 Alkaloids TARGETS & BIOACTIVITY 0 molecular targets 17 bioactivities · 1 graph

Causal graph — biosynthesis 3 nodes, 2 edges

Talaromyces variabilis HXQ-H-1 IccE epimerizes 8-epi-ilicicolin H to form ilicicolin H.

SubjectPredicateObjectNotesEvidence
8-epi-ilicicolin H is epimerized by IccE IccE catalyzes the RHEA:64564 epimerization from 8-epi-ilicicolin H.
DOI:10.1021/jacs.9b02204
https://www.ncbi.nlm.nih.gov/nuccore/MK539848.1
https://www.uniprot.org/uniprotkb/A0A482N8M8
https://www.rhea-db.org/rhea/64564
  • reference
    DOI:10.1021/jacs.9b02204
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Zhang et al. characterized the Penicillium variabile, synonymous with Talaromyces variabilis, icc pathway and showed that IccE converts 8-epi-ilicicolin H to ilicicolin H in heterologous reconstitution and in vitro epimerization experiments.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/MK539848.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    GenBank MK539848.1 is the Talaromyces variabilis HXQ-H-1 ilicicolin H cluster sequence and places iccE at protein_id QBQ83707.1.
  • reference
    https://www.uniprot.org/uniprotkb/A0A482N8M8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:A0A482N8M8 is the Talaromyces variabilis IccE / QBQ83707.1 gene product and annotates the RHEA:64564 catalytic activity of 8-epi-ilicicolin H epimerization.
  • reference
    https://www.rhea-db.org/rhea/64564
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    RHEA:64564 is the 8-epi-ilicicolin H to ilicicolin H epimerization; the left-to-right RHEA:64565 direction maps to UniProtKB:A0A482N8M8.
IccE forms ilicicolin H IccE forms ilicicolin H as the final product of the Talaromyces variabilis icc pathway.
DOI:10.1021/jacs.9b02204
https://www.ncbi.nlm.nih.gov/nuccore/MK539848.1
https://www.uniprot.org/uniprotkb/A0A482N8M8
https://www.rhea-db.org/rhea/64564
  • reference
    DOI:10.1021/jacs.9b02204
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Zhang et al. characterized the Penicillium variabile, synonymous with Talaromyces variabilis, icc pathway and showed that IccE converts 8-epi-ilicicolin H to ilicicolin H in heterologous reconstitution and in vitro epimerization experiments.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/MK539848.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    GenBank MK539848.1 is the Talaromyces variabilis HXQ-H-1 ilicicolin H cluster sequence and places iccE at protein_id QBQ83707.1.
  • reference
    https://www.uniprot.org/uniprotkb/A0A482N8M8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:A0A482N8M8 is the Talaromyces variabilis IccE / QBQ83707.1 gene product and annotates the RHEA:64564 catalytic activity of 8-epi-ilicicolin H epimerization.
  • reference
    https://www.rhea-db.org/rhea/64564
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    RHEA:64564 is the 8-epi-ilicicolin H to ilicicolin H epimerization; the left-to-right RHEA:64565 direction maps to UniProtKB:A0A482N8M8.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Bioactivities 17

Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.

AssayResultTarget enzymeSource detail
Anti-Fungal Single Agen: CaCi2 Measured in Microorganism System Using Plate Reader - 2148-01_Inhibitor_Dose_DryPowder_Activity_Set4OTHER 4.81 uM; ACTIVENot recorded
pubchem.aid:624006
assay
Anti-Fungal Single Agen: CaCi2 Measured in Microorganism System Using Plate Reader - 2148-01_Inhibitor_Dose_DryPowder_Activity_Set4
evidence
  • reference
    pubchem.aid:624006
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 624006, deposited by Broad Institute; assay type Confirmatory. Source endpoint: AC50.
call
ACTIVE
measurement type
OTHER
value
4.81
units
uM
activity class
ANTIFUNGAL
Anti-Fungal Single Agent: C.glabrata growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-04_Inhibitor_Dose_DryPowder_Activity_Set3OTHER 2.94 uM; ACTIVENot recorded
pubchem.aid:623965
assay
Anti-Fungal Single Agent: C.glabrata growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-04_Inhibitor_Dose_DryPowder_Activity_Set3
evidence
  • reference
    pubchem.aid:623965
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 623965, deposited by Broad Institute; assay type Confirmatory. Source endpoint: AC50.
call
ACTIVE
measurement type
OTHER
value
2.94
units
uM
activity class
ANTIFUNGAL
Anti-Fungal Single Agent: C.glabrata growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-04_Inhibitor_Dose_DryPowder_Activity_Set4OTHER 2.45 uM; ACTIVENot recorded
pubchem.aid:624014
assay
Anti-Fungal Single Agent: C.glabrata growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-04_Inhibitor_Dose_DryPowder_Activity_Set4
evidence
  • reference
    pubchem.aid:624014
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 624014, deposited by Broad Institute; assay type Confirmatory. Source endpoint: AC50.
call
ACTIVE
measurement type
OTHER
value
2.45
units
uM
activity class
ANTIFUNGAL
Anti-Fungal Single Agent: S.cerevisiae growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-06_Inhibitor_Dose_DryPowder_Activity_Set3OTHER 0.0335 uM; ACTIVENot recorded
pubchem.aid:623969
assay
Anti-Fungal Single Agent: S.cerevisiae growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-06_Inhibitor_Dose_DryPowder_Activity_Set3
evidence
  • reference
    pubchem.aid:623969
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 623969, deposited by Broad Institute; assay type Confirmatory. Source endpoint: AC50.
call
ACTIVE
measurement type
OTHER
value
0.0335
units
uM
activity class
ANTIFUNGAL
Anti-Fungal Single Agent: S.cerevisiae growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-06_Inhibitor_Dose_DryPowder_Activity_Set4OTHER 0.0275 uM; ACTIVENot recorded
pubchem.aid:624012
assay
Anti-Fungal Single Agent: S.cerevisiae growth, Glycerol Measured in Microorganism System Using Plate Reader - 2148-06_Inhibitor_Dose_DryPowder_Activity_Set4
evidence
  • reference
    pubchem.aid:624012
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 624012, deposited by Broad Institute; assay type Confirmatory. Source endpoint: AC50.
call
ACTIVE
measurement type
OTHER
value
0.0275
units
uM
activity class
ANTIFUNGAL
HPAF-II Cancer Cell Toxicity qHTS against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
HPAF-II Cancer Cell Toxicity qHTS against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347346, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
KB-3-1 Cancer Cell Toxicity qHTS against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
KB-3-1 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347366, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
KB-8-5-11 Cancer Cell Toxicity qHTS against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
KB-8-5-11 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347364, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
OV-SAHO Cancer Cell Toxicity qHTS against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
OV-SAHO Cancer Cell Toxicity qHTS against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347348, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
Primary screen NINDS Rhodamine qHTS for Zika virus inhibitorsACTIVENot recorded
PMID:33229545
assay
Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors
evidence
  • reference
    PMID:33229545
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347160, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
SW1088 Cancer Cell Toxicity qHTS against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
SW1088 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347350, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
UWB1.289 Cancer Cell Toxicity qHTS against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
UWB1.289 Cancer Cell Toxicity qHTS against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347347, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
CYTOTOXIC
Vero-766 cells viability qHTS against the NCATS CANVASS Library: Counterscreen for Zika virus inhibition assayACTIVENot recorded
PMID:30648156
assay
Vero-766 cells viability qHTS against the NCATS CANVASS Library: Counterscreen for Zika virus inhibition assay
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347394, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
qHTS assay for small molecule disruptors of mitochondrial membrane potential screened against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
qHTS assay for small molecule disruptors of mitochondrial membrane potential screened against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347389, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347374, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
qHTS for Hypoxia signaling pathway (HIF-1) antagonists against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347374, deposited by NCGC; assay type Confirmatory. Target accession AAC68568 was left ungrounded because PubChem did not provide a UniProtKB accession.
call
ACTIVE
qHTS for inhibitors of ER calcium dysfunction: SERCaMP assay screened against the NCATS CANVASS LibraryACTIVENot recorded
PMID:30648156
assay
qHTS for inhibitors of ER calcium dysfunction: SERCaMP assay screened against the NCATS CANVASS Library
evidence
  • reference
    PMID:30648156
    evidence type
    DATABASE_ASSERTION
    notes
    PubChem BioAssay AID 1347393, deposited by NCGC; assay type Confirmatory.
call
ACTIVE
activity class
ENZYME_INHIBITOR

Elsewhere in the fleet

Explore across X-Mech

AntibioticMech (ilicicolin H) ↗ MediaIngredientMech (CHEBI:77772) ↗ TaxonMech: Neonectria sp. DH2 (NCBITaxon:1735992) ↗ TaxonMech: Talaromyces variabilis (NCBITaxon:28576) ↗ PathwayMech (mibig:BGC0002035) ↗ PathwayMech (mibig:BGC0002093) ↗

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 conceptSourceVersion
BGC0002035MIBIG3
BGC0002093MIBIG2
CHEBI:77772CHEBI3-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.