trichobrasilenol

CHEBI:167379 EXACT SEEDED

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

A carbobicyclic compound that is (3aS,7aS)-octahydro-1H-indene substituted by a methyl group at positions 1S, 6 and 6, and by a 1-hydroxypropan-2-ylidene group at position 4. It is a sesquiterpenoid produced by a Trichoderma terpene cyclase.

Structure

Standard InChIKey	DJBXKQSFHIRXRM-JRYBIPSHSA-N
SMILES	C/C(CO)=C1/CC(C)(C)C[C@H]2[C@@H](C)CC[C@H]12
Stereochemistry	fully defined
Cross-references	npatlas:NPA025694, pubchem:146682173

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
Annulohypoxylon truncatum NCBITaxon:327061	SOURCE_ASSERTION	mibig:BGC0002260	PMID:32936132

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
Trichoderma atroviride NCBITaxon:63577	LOTUS	DOI:10.1002/ANIE.201907964

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0002260	Annulohypoxylon truncatum NCBITaxon:327061	CLUSTER_DEMONSTRATED	genbank:MT383109.1

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	TaTC6 native FKI-3849 reference UniProtKB:A0A5S9I252	RHEA:66644	ungrounded → CHEBI:167379	https://www.uniprot.org/uniprotkb/A0A5S9I252
2	BraB native CBS140778 reference UniProtKB:P9WER1		CHEBI:167379 → ungrounded	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000202.json

Step 1: UniProtKB:A0A5S9I252 / RHEA:66644-reported conversion of (2E,6E)-farnesyl diphosphate to trichobrasilenol (CHEBI:167379) by Trichoderma atroviride FKI-3849 TaTC6 (BBK61014.1 on LC484924.1). Synchronizes biosynthetic_pathway with the existing database-backed causal_graph without upgrading producer or locus evidence grades.

Step 2: MITE0000202-reported glycosylation of trichobrasilenol (CHEBI:167379) with a putative UDP-GlcNAc donor to brasilane A by Annulohypoxylon truncatum CBS 140778 BraB (UniProtKB:P9WER1, QOE88884.1 on MT383109.1, BGC0002260). Synchronizes biosynthetic_pathway with the existing MITE-backed causal_graph without upgrading producer or locus evidence grades.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Database-reported BraB glycosylation consumes exact trichobrasilenol. BraB is the sequence-verified native Annulohypoxylon truncatum CBS140778 reference, not a Trichoderma terpene cyclase or an identified historical assay construct. The primary paper was inaccessible, so functional evidence remains database-level. Product stereochemistry is incomplete; donor and pathway-finality limits remain explicit. No native producer-grade upgrade or change to SEEDED status.

Subject	Predicate	Object	Notes	Evidence
BraB native CBS140778 reference	is_database_reported_catalyst_of	MITE-reported BraB glycosylation	MITE and reviewed UniProt supply functional attribution at database level. Native sequence equality proves reference correspondence, not historical assay-stock or construct identity. UniProt qualifies UDP-GlcNAc as a putative sugar donor; this graph does not assert a measured donor preference, kinetics, protein-alone assay or physical complex. No native producer upgrade follows from heterologous-expression database codes.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000202.json https://www.uniprot.org/uniprotkb/P9WER1 https://www.ncbi.nlm.nih.gov/protein/QOE88884.1 https://www.ncbi.nlm.nih.gov/nuccore/MT383109.1 reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000202.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Active MITE0000202 version2 names BraB/P9WER1/QOE88884.1/BGC0002260. Its single example consumes trichobrasilenol and labels the product brasilane A. Heterologous expression and in vitro assay are source evidence codes, not independently inspected primary experiments. The cited DOI10.1039/D0CC03950K/PMID32936132 returned403 at the first publisher full-text attempt. No alternate paper or SI was inspected. reference https://www.uniprot.org/uniprotkb/P9WER1 evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Reviewed entry7/sequence1,421aa, braB, A.truncatum/tax327061; genomic-reference strain provenance DSM103480/CBS140778 and EMBL MT383109/QOE88884.1 agree. Its function narrative attributes trichobrasilenol glycosylation to BraB, with UDP-GlcNAc a putative donor and later BraC transformations of brasilane A. Broad promiscuity and downstream claims are not adopted as independently inspected experiments. reference https://www.ncbi.nlm.nih.gov/protein/QOE88884.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Independent complete421-aa N-acetylglucosamine transferase, gene braB, A.truncatum/tax327061, culture_collectionCBS:140778. coded_by is complement(MT383109.1:2625..3890). Native reference identity, not a measured assay construct; PMID32936132 is bibliographic linkage, not direct paper inspection. reference https://www.ncbi.nlm.nih.gov/nuccore/MT383109.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-07 notes Complete1266-nt reverse CDS2625..3890, codon1/defaulttable1, translates to native annotation, independent GenPept and current UniProt, all421aa. Independent coded_by DNA/coordinates and CBS140778/taxon327061 agree. Complete17473-bp cluster retained; source metadata and target CDS inspected, not a whole-cluster functional audit. No historical assay-stock or heterologous construct sequence inferred.
trichobrasilenol	is_database_example_substrate_of	MITE-reported BraB glycosylation	Pinned RDKit2026.03.5 and the repository identity helper match the MITE substrate to full owner key DJBXKQSFHIRXRM-JRYBIPSHSA-N with complete stereochemistry. BraB consumes the owner compound; it is not its terpene synthase. This does not equate the owner's Trichoderma occurrence/ChEBI definition context with the native A.truncatum reference or upgrade the imported SOURCE_ASSERTION producer claim. All source-owned contexts remain unchanged.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000202.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000202.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Active MITE0000202 version2 names BraB/P9WER1/QOE88884.1/BGC0002260. Its single example consumes trichobrasilenol and labels the product brasilane A. Heterologous expression and in vitro assay are source evidence codes, not independently inspected primary experiments. The cited DOI10.1039/D0CC03950K/PMID32936132 returned403 at the first publisher full-text attempt. No alternate paper or SI was inspected.
MITE-reported BraB glycosylation	has_database_example_product	Brasilane A, stereo-incomplete database model	MITE's brasilane A model leaves anomeric and alkene stereochemistry unspecified; repository chemistry checks mark it stereo-incomplete. It remains externally ungrounded, with no exact stereoisomer or historical structure assignment substituted. MITE marks isIntermediate false, but UniProt describes later BraC transformations. That source flag does not prove pathway finality; no downstream graph or final-product claim is adopted.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000202.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000202.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Active MITE0000202 version2 names BraB/P9WER1/QOE88884.1/BGC0002260. Its single example consumes trichobrasilenol and labels the product brasilane A. Heterologous expression and in vitro assay are source evidence codes, not independently inspected primary experiments. The cited DOI10.1039/D0CC03950K/PMID32936132 returned403 at the first publisher full-text attempt. No alternate paper or SI was inspected. snippet Brasilane A formation

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

Causal graph — biosynthesis 3 nodes, 2 edges

Database-reported TaTC6 formation of trichobrasilenol as the main product. A0A5S9I252 denotes the sequence-verified native Trichoderma atroviride FKI-3849 reference, not a verified full assayed construct. Functional and stereochemical product attribution remain database-level. No native producer, BGC membership, physical complex or measured Mg-binding claim is added.

Subject	Predicate	Object	Notes	Evidence
TaTC6 native FKI-3849 reference	is_database_reported_catalyst_of	Database-reported TaTC6 FPP conversion	The native reference mapping does not establish historical assay-stock or full construct/tag identity. UniProt separately reports a koraiol disruption phenotype; its applicability is unresolved and no phenotype edge is adopted. Its homodimer and Mg-binding assertions are homology-based and are not adopted here.	https://www.uniprot.org/uniprotkb/A0A5S9I252 https://www.ncbi.nlm.nih.gov/protein/BBK61014.1 https://www.ncbi.nlm.nih.gov/nuccore/LC484924.1 reference https://www.uniprot.org/uniprotkb/A0A5S9I252 evidence type DATABASE_ASSERTION retrieved on 2026-10-09 notes Reviewed entry 21/sequence 1 assigns RHEA:66644 to tatc6 and explicitly names CHEBI:167379 as product of FPP plus water; RHEA:66645 is annotated left-to-right. The function narrative calls trichobrasilenol the main product and pristinol a side product. These are adopted UniProt assertions, not independently inspected experiments. PMID31418991 / DOI10.1002/anie.201907964 is the database-cited bibliography; the primary paper and supplementary information were inaccessible and were not inspected. reference https://www.ncbi.nlm.nih.gov/protein/BBK61014.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-09 notes Complete 386-aa native Trichoderma atroviride FKI-3849 reference, taxon63577, gene tatc6. GenPept annotates trichobrasilenol synthesis from FPP; it does not independently establish pristinol formation. Its in-vitro-assay code is a deposit annotation, not a newly inspected assay. reference https://www.ncbi.nlm.nih.gov/nuccore/LC484924.1 evidence type CURATOR_INFERENCE retrieved on 2026-10-09 notes Independent translation of the complete six-exon CDS join(1..242,308..434,497..515,569..1035,1100..1326,1385..1463), codon_start1/default table1: 1161 nt including stop equals 386-aa annotated translation, GenPept BBK61014.1 and UniProt A0A5S9I252. Independent GenPept coded_by accession, coordinates and orientation agree; both deposits name FKI-3849/taxon63577. This is native reference correspondence, not experimental construct equivalence.
Database-reported TaTC6 FPP conversion	has_database_reported_product	trichobrasilenol	The explicit UniProt reaction product CURIE CHEBI:167379 matches this owner, whose unchanged full InChIKey is DJBXKQSFHIRXRM-JRYBIPSHSA-N. This is database product mapping, not an independent spectrum or primary-paper stereochemical analysis. No exclusive specificity, product percentage or native production is asserted. This synthase graph is separate from Annulohypoxylon BraB glycosylation and does not place TaTC6 in BGC0002260 or upgrade the existing Trichoderma occurrence to production.	https://www.uniprot.org/uniprotkb/A0A5S9I252 reference https://www.uniprot.org/uniprotkb/A0A5S9I252 evidence type DATABASE_ASSERTION retrieved on 2026-10-09 notes Reviewed entry 21/sequence 1 assigns RHEA:66644 to tatc6 and explicitly names CHEBI:167379 as product of FPP plus water; RHEA:66645 is annotated left-to-right. The function narrative calls trichobrasilenol the main product and pristinol a side product. These are adopted UniProt assertions, not independently inspected experiments. PMID31418991 / DOI10.1002/anie.201907964 is the database-cited bibliography; the primary paper and supplementary information were inaccessible and were not inspected. snippet The main product is trichobrasilenol

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

Explore across X-Mech

AntibioticMech (trichobrasilenol) ↗ MediaIngredientMech (CHEBI:167379) ↗ TaxonMech: Annulohypoxylon truncatum (NCBITaxon:327061) ↗ PathwayMech (mibig:BGC0002260) ↗

Provenance

Source concept	Source	Version
BGC0002260	MIBIG	3
CHEBI:167379	CHEBI	3-star

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