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8α-hydroxy-6-protoilludene

naturalproductmech:mibig-32b7a54e39 MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.
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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKeyXTXSLQPVMVDDTB-ZRQNBYAXSA-N
SMILESCC1=C2CC[C@]2(C)[C@H]2CC(C)(C)C[C@H]2[C@@H]1O
Stereochemistryfully defined
Cross-referencesnpatlas:NPA033501

Filing pathway

Terpenoids — 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 terpene, from MIBiG.

Producer organisms 1

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
Armillaria gallica
NCBITaxon:47427		 SOURCE_ASSERTION mibig:BGC0002445 PMID:33191459

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
Armillaria gallica
NCBITaxon:47427		 LOTUS DOI:10.1007/S00253-020-11006-Y

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0002445 Armillaria gallica
NCBITaxon:47427 		CLUSTER_DEMONSTRATED genbank:MT277003.1

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 6-protoilludene synthase
UniProtKB:A0A7U3MPB9		 RHEA:34695 CHEBI:175763 → CHEBI:68655 DOI:10.1074/jbc.M110.165845
2 CYP-Arm3
UniProtKB:A0A7S5T363		 CHEBI:68655 → naturalproductmech:mibig-32b7a54e39 DOI:10.1007/s00253-020-11006-y

Step 1: Armillaria gallica Pro1 cyclizes (2E,6E)-farnesyl diphosphate to Delta(6)-protoilludene. UniProtKB:A0A7U3MPB9 resolves to the BGC0002445 MT277003.1 Pro1 sequence, while the earlier functional assay established A. gallica Pro1 sesquiterpene synthase activity.

Step 2: Armillaria gallica CYP-Arm3 hydroxylates Delta(6)-protoilludene to 8α-hydroxy-6-protoilludene.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (0 causal) 1 cited occurrence BIOSYNTHETIC LOCUS 1 gene cluster 2 curated pathway steps NATURAL PRODUCT 8α-hydroxy-6-protoilludene naturalproductmech:mibig-32b7a54e39 Terpenoids TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 3 graphs

Causal graph — biosynthesis 5 nodes, 4 edges

Armillaria gallica 8α-hydroxy-6-protoilludene biosynthesis graph for Pro1 cyclization of farnesyl diphosphate followed by CYP-Arm3 hydroxylation.

SubjectPredicateObjectNotesEvidence
(2E,6E)-farnesyl diphosphate is cyclized by Pro1
DOI:10.1074/jbc.M110.165845
DOI:10.1007/s00253-020-11006-y
https://www.ncbi.nlm.nih.gov/protein/QJQ03973.1
  • reference
    DOI:10.1074/jbc.M110.165845
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    farnesyl diphosphate to produce protoilludene
    notes
    The earlier A. gallica Pro1 cDNA study experimentally established that Pro1 catalyzes farnesyl diphosphate cyclization to Delta(6)-protoilludene.
  • reference
    DOI:10.1007/s00253-020-11006-y
    evidence type
    PRIMARY_EXPERIMENT
    notes
    The Armillaria BGC study identified the MT277003.1 gene cluster and annotated GenPept QJQ03973.1 as the BGC0002445 Pro1 protein.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/QJQ03973.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    NCBI resolves GenPept QJQ03973.1 to the MT277003.1 coding sequence for the Armillaria gallica 6-protoilludene synthase Pro1.
Pro1 forms Delta(6)-protoilludene
DOI:10.1074/jbc.M110.165845
DOI:10.1007/s00253-020-11006-y
https://www.ncbi.nlm.nih.gov/protein/QJQ03973.1
  • reference
    DOI:10.1074/jbc.M110.165845
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    farnesyl diphosphate to produce protoilludene
    notes
    The earlier A. gallica Pro1 cDNA study experimentally established that Pro1 catalyzes farnesyl diphosphate cyclization to Delta(6)-protoilludene.
  • reference
    DOI:10.1007/s00253-020-11006-y
    evidence type
    PRIMARY_EXPERIMENT
    notes
    The Armillaria BGC study identified the MT277003.1 gene cluster and annotated GenPept QJQ03973.1 as the BGC0002445 Pro1 protein.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/QJQ03973.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    NCBI resolves GenPept QJQ03973.1 to the MT277003.1 coding sequence for the Armillaria gallica 6-protoilludene synthase Pro1.
Delta(6)-protoilludene is hydroxylated by CYP-Arm3
DOI:10.1007/s00253-020-11006-y
https://www.ncbi.nlm.nih.gov/protein/QJQ03972.1
  • reference
    DOI:10.1007/s00253-020-11006-y
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    8α-hydroxy-6-protoilludene intermediate produced by CYP-Arm3
    notes
    Armillaria gallica CYP-Arm3 hydroxylated Delta(6)-protoilludene to 8α-hydroxy-6-protoilludene in yeast feeding and coexpression experiments.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/QJQ03972.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    NCBI resolves GenPept QJQ03972.1 to the MT277003.1 coding sequence for Armillaria gallica CYP-Arm3.
CYP-Arm3 forms 8α-hydroxy-6-protoilludene
DOI:10.1007/s00253-020-11006-y
https://www.ncbi.nlm.nih.gov/protein/QJQ03972.1
  • reference
    DOI:10.1007/s00253-020-11006-y
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    8α-hydroxy-6-protoilludene intermediate produced by CYP-Arm3
    notes
    Armillaria gallica CYP-Arm3 hydroxylated Delta(6)-protoilludene to 8α-hydroxy-6-protoilludene in yeast feeding and coexpression experiments.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/QJQ03972.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    NCBI resolves GenPept QJQ03972.1 to the MT277003.1 coding sequence for Armillaria gallica CYP-Arm3.

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

Causal graph — biosynthesis 2 nodes, 1 edge

Native reference in Armillaria gallica FU02472/BGC0002445. The complete CDS is a deposited gene model, not an independently verified experimental transcript. The annotated mRNA boundaries are partial. Native reference identity does not establish the sequence of the 2023 assay construct, mature processing or experimental heme occupancy.

SubjectPredicateObjectNotesEvidence
CYP-Arm2 CDS (MT277003.1, 12 reverse-strand exons) encodes the native protein reference CYPArm2 (FU02472 native-reference example) FU02472, taxon 47427; complete 1542-nt CDS including stop, 513-residue reference. The CDS spans MT277003.1 positions 17425..19546 with 12 reverse-strand exons.
https://www.ncbi.nlm.nih.gov/nuccore/MT277003.1
https://www.ncbi.nlm.nih.gov/protein/QJQ03971.1
https://www.uniprot.org/uniprotkb/A0A7S5T5B1/entry
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/MT277003.1
    evidence type
    DATABASE_ASSERTION
    notes
    GenBank assigns gene CYP-Arm2 and protein QJQ03971.1 to the spliced CDS.
    retrieved on
    2026-10-08
    snippet
    /gene="CYP-Arm2"
  • reference
    https://www.ncbi.nlm.nih.gov/protein/QJQ03971.1
    evidence type
    DATABASE_ASSERTION
    notes
    The separate 513-residue GenPept record identifies FU02472 and the same 12-exon reverse-strand CDS.
    retrieved on
    2026-10-08
  • reference
    https://www.uniprot.org/uniprotkb/A0A7S5T5B1/entry
    evidence type
    CURATOR_INFERENCE
    notes
    Unreviewed entry version 22, sequence version 1. CDS-aware translation, deposited translation, GenPept QJQ03971.1 and A0A7S5T5B1 agree over all 513 residues. This is native-reference identity only. UniProt has no specific FUNCTION or CATALYTIC ACTIVITY comment.
    retrieved on
    2026-10-08

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

Causal graph — biosynthesis 4 nodes, 3 edges

Partial downstream-consumption graph: the 2023 abstract names 8α-hydroxy-6-protoilludene as a CYPArm2 substrate and reports an NMR-identified dihydroxylated product. This is not another route producing this owner and does not extend its existing two-step biosynthetic_pathway. The protein is a qualified native reference example, not a sequence-verified assay construct. Only the returned abstract was read, not full text or supplements. The MITE model lacks C8 stereochemistry; no complete product structure, ChEBI/Rhea assignment, assembly or kinetic claim is adopted.

SubjectPredicateObjectNotesEvidence
CYPArm2 (FU02472 native-reference example) is reported to catalyze Reported CYPArm2 13-hydroxylation The native accession is an example for the named CYPArm2 activity. The abstract does not establish the exact experimental construct sequence. No claim of native heme occupancy or strict substrate specificity.
DOI:10.1002/cbic.202300179
https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000295.json
  • reference
    DOI:10.1002/cbic.202300179
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract text returned by an official-domain web search before the subsequent PubMed browser-check stop; full text and supplements were not inspected. The abstract reports CYPArm2 as a protoilludene 13-hydroxylase; this is an abstract-level experimental report, not an independently audited full assay.
    retrieved on
    2026-10-08
    snippet
    confirming that CYPArm2 is a protoilludene 13-hydroxylase.
  • reference
    https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000295.json
    evidence type
    DATABASE_ASSERTION
    notes
    Active MITE0000295 version 1 links CYPArm2 to A0A7S5T5B1, QJQ03971.1 and BGC0002445. This is a database association, not independent sequence verification of the 2023 assay stock.
    retrieved on
    2026-10-08
8α-hydroxy-6-protoilludene is reported as a substrate of Reported CYPArm2 13-hydroxylation Owner consumption, not owner production. The abstract explicitly names the 8alpha substrate. MITE's model key XTXSLQPVMVDDTB-SUTJQRNSSA-N is stereo-incomplete and is not asserted equal to this owner's full key XTXSLQPVMVDDTB-ZRQNBYAXSA-N.
DOI:10.1002/cbic.202300179
  • reference
    DOI:10.1002/cbic.202300179
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract text returned by an official-domain web search before the subsequent PubMed browser-check stop; full text and supplements were not inspected. The named accepted substrates include this 8alpha-hydroxylated compound. No reaction ordering is inferred from gene order, and the under-specified MITE structure is not used as exact stereochemical identity evidence.
    retrieved on
    2026-10-08
    snippet
    accepts Δ-6-protoilludene and 8α-hydroxy-6-protoilludene as substrates.
Reported CYPArm2 13-hydroxylation is reported to produce 8α,13-dihydroxy-protoilludene (reported product) Named product only: no stable chemical identifier or full stereochemical structure is assigned. MITE's product model is also stereo-incomplete; its unspecified center is not filled in.
DOI:10.1002/cbic.202300179
  • reference
    DOI:10.1002/cbic.202300179
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract text returned by an official-domain web search before the subsequent PubMed browser-check stop; full text and supplements were not inspected. The abstract reports NMR identification of the named dihydroxylated product after recombinant yeast biosynthesis. No analytical spectra, yield, kinetic values or downstream complete pathway are imported.
    retrieved on
    2026-10-08
    snippet
    identification of 8α,13-dihydroxy-protoilludene

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

Explore across X-Mech

AntibioticMech (8α-hydroxy-6-protoilludene) ↗ MediaIngredientMech (naturalproductmech:mibig-32b7a54e39) ↗ TaxonMech: Armillaria gallica (NCBITaxon:47427) ↗ PathwayMech (mibig:BGC0002445) ↗

Provenance

Source conceptSourceVersion
BGC0002445MIBIG3

This page is generated from data/natural_products/terpenoids/8-hydroxy-6-protoilludene.yaml, which is generated from the committed inventories. Neither is edited by hand.