(+)-juniperol(longiborneol)

naturalproductmech:mibig-390b0e4f55 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 InChIKey	MNNFKQAYXGEKFA-MJBFILCRSA-N
SMILES	CC1(CCCC2(C3C1[C@@H](C2(CC3)C)O)C)C
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	pubchem:6432447

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.

Taxon	Basis	Cluster	Evidence
Fusarium graminearum PH-1 NCBITaxon:229533	BGC_CHARACTERIZED	mibig:BGC0002176	PMID:19880637

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
Artemisia argyi NCBITaxon:259893	LOTUS	DOI:10.3390/IJMS131114679

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002176	Fusarium graminearum PH-1 NCBITaxon:229533	CLUSTER_DEMONSTRATED	genbank:CM000574.1

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.

Step	Enzyme	Reaction	Substrate → product	Evidence
1	CLM1 longiborneol synthase UniProtKB:I1S104		CHEBI:175763 → naturalproductmech:mibig-390b0e4f55	DOI:10.1128/AEM.02017-09

Step 1: CLM1/FGSG_10397 cyclizes (2E,6E)-farnesyl diphosphate to the longiborneol represented by this MIBiG record. RHEA:83907 is not used here because it fixes (-)-longiborneol, while this record leaves several longiborneol stereocenters unspecified.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Fusarium graminearum PH-1 CLM1 cyclization of (2E,6E)-farnesyl diphosphate to longiborneol.

Subject	Predicate	Object	Notes	Evidence
(2E,6E)-farnesyl diphosphate	is cyclized by	CLM1 longiborneol synthase		DOI:10.1128/AEM.02017-09 https://mibig.secondarymetabolites.org/repository/BGC0002176.3/ https://www.uniprot.org/uniprotkb/I1S104 https://www.ncbi.nlm.nih.gov/gene/23557306 reference DOI:10.1128/AEM.02017-09 evidence type PRIMARY_EXPERIMENT snippet resulted in the production of a sesquiterpene alcohol, longiborneol notes McCormick et al. expressed fg10397/CLM1 in Saccharomyces cerevisiae and identified longiborneol by GC-MS/NMR; disruption and add-back experiments tied the gene to culmorin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0002176.3/ evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes MIBiG BGC0002176.3 places FGSG_10397 / ESU17105.1 in the Fusarium graminearum PH-1 culmorin/(+)-juniperol(longiborneol) BGC at CM000574.1:10717529-10718727. reference https://www.uniprot.org/uniprotkb/I1S104 evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes UniProtKB reviewed entry I1S104 resolves to the 339 aa Fusarium graminearum PH-1 longiborneol synthase CLM1 and annotates the farnesyl-diphosphate cyclization from PMID:19880637. reference https://www.ncbi.nlm.nih.gov/gene/23557306 evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes NCBI Gene resolves FGSG_10397 in Fusarium graminearum PH-1 and cross-references UniProtKB/Swiss-Prot I1S104.
CLM1 longiborneol synthase	forms	(+)-juniperol(longiborneol)		DOI:10.1128/AEM.02017-09 https://mibig.secondarymetabolites.org/repository/BGC0002176.3/ https://www.uniprot.org/uniprotkb/I1S104 https://www.ncbi.nlm.nih.gov/gene/23557306 reference DOI:10.1128/AEM.02017-09 evidence type PRIMARY_EXPERIMENT snippet resulted in the production of a sesquiterpene alcohol, longiborneol notes McCormick et al. expressed fg10397/CLM1 in Saccharomyces cerevisiae and identified longiborneol by GC-MS/NMR; disruption and add-back experiments tied the gene to culmorin biosynthesis. reference https://mibig.secondarymetabolites.org/repository/BGC0002176.3/ evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes MIBiG BGC0002176.3 places FGSG_10397 / ESU17105.1 in the Fusarium graminearum PH-1 culmorin/(+)-juniperol(longiborneol) BGC at CM000574.1:10717529-10718727. reference https://www.uniprot.org/uniprotkb/I1S104 evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes UniProtKB reviewed entry I1S104 resolves to the 339 aa Fusarium graminearum PH-1 longiborneol synthase CLM1 and annotates the farnesyl-diphosphate cyclization from PMID:19880637. reference https://www.ncbi.nlm.nih.gov/gene/23557306 evidence type DATABASE_ASSERTION retrieved on 2026-09-29 notes NCBI Gene resolves FGSG_10397 in Fusarium graminearum PH-1 and cross-references UniProtKB/Swiss-Prot I1S104.

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

Explore across X-Mech

AntibioticMech ((+)-juniperol(longiborneol)) ↗ MediaIngredientMech (naturalproductmech:mibig-390b0e4f55) ↗ TaxonMech: Fusarium graminearum PH-1 (NCBITaxon:229533) ↗ PathwayMech (mibig:BGC0002176) ↗

Provenance

Source concept	Source	Version
BGC0002176	MIBIG	3

This page is generated from data/natural_products/terpenoids/juniperol-longiborneol.yaml, which is generated from the committed inventories. Neither is edited by hand.