thalianol

CHEBI:52317 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKey	DGAGPZOBTQYNRE-VMSIWEJCSA-N
SMILES	C[C@H](CC/C=C(\C)/CCC=C(C)C)[C@]1(CCC2=C1CC[C@@H]3[C@@]2(CC[C@@H](C3(C)C)O)C)C
Stereochemistry	fully defined
Cross-references	pubchem:25229600

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
Arabidopsis thaliana NCBITaxon:3702	BGC_CHARACTERIZED	mibig:BGC0000670	DOI:10.1126/science.1154990

Occurrences 0

None cited.

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000670	Arabidopsis thaliana NCBITaxon:3702	CLUSTER_DEMONSTRATED	genbank:NC_003076.8

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	Thalianol synthase 1 UniProtKB:Q9FI37	RHEA:26160	CHEBI:15441 → CHEBI:52317	DOI:10.1021/ja0318784

Step 1: Arabidopsis thaliana THAS1/At5g48010 cyclizes (S)-2,3-epoxysqualene to thalianol, the first committed cyclization step in the thalianol triterpene gene cluster.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Partial Arabidopsis thaliana thalianol biosynthesis graph for THAS1-catalyzed cyclization of (S)-2,3-epoxysqualene to thalianol.

Subject	Predicate	Object	Notes	Evidence
(S)-2,3-epoxysqualene	is cyclized by	THAS1		DOI:10.1021/ja0318784 reference DOI:10.1021/ja0318784 evidence type PRIMARY_EXPERIMENT snippet was shown to convert 3(S)-oxidosqualene to the previously unknown triterpene alcohol (3S,13S,14R)-malabarica-8,17,21-trien-3-ol, which we named thalianol notes UniProtKB:Q9FI37 resolves to the Arabidopsis thaliana THAS1/At5g48010 gene product, maps to EMBL AY327541 protein AAP92117.1, and annotates RHEA:26160 for the cyclization of (S)-2,3-epoxysqualene to thalianol.
THAS1	forms	thalianol		DOI:10.1021/ja0318784 reference DOI:10.1021/ja0318784 evidence type PRIMARY_EXPERIMENT snippet was shown to convert 3(S)-oxidosqualene to the previously unknown triterpene alcohol (3S,13S,14R)-malabarica-8,17,21-trien-3-ol, which we named thalianol notes UniProtKB:Q9FI37 resolves to the Arabidopsis thaliana THAS1/At5g48010 gene product, maps to EMBL AY327541 protein AAP92117.1, and annotates RHEA:26160 for the cyclization of (S)-2,3-epoxysqualene to thalianol.

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

Causal graph — biosynthesis 4 nodes, 3 edges

MITE-reported THAH hydroxylation consuming exact thalianol, represented separately from the existing A.thaliana THAS1 synthesis pathway. The sequence-verified D7MKC1 reference is A.lyrata subsp. lyrata donor MN47, not A.thaliana as implied by the MITE prose. Database function is not an independently inspected primary assay. Product identity/stereo remains unresolved; no producer upgrade or full-record sign-off.

Subject	Predicate	Object	Notes	Evidence
Database-named THAH A.lyrata MN47 reference	is_database_reported_catalyst_of	MITE-reported THAH substrate hydroxylation	Functional attribution is MITE's, while independent sequences establish the explicitly named A.lyrata reference despite the inconsistent source prose. No native heme/iron occupancy, electron donor, assay, knockout phenotype, binding site, kinetics or complex is adopted.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000133.json https://www.uniprot.org/uniprotkb/D7MKC1 https://www.ncbi.nlm.nih.gov/protein/EFH41844.1 https://www.ncbi.nlm.nih.gov/nuccore/GL348720.1?from=10405500&to=10409700 reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000133.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes MITE0000133 version3, active, names THAH/D7MKC1/EFH41844.1. Its heterologous-expression evidence code remains a database assertion; the primary paper was inaccessible. The prose organism name is inconsistent with both independent sequence records, which identify Arabidopsis lyrata subsp. lyrata, not A.thaliana. Retired BGC0002857 was removed from this version. snippet Hydroxylates Thalianol reference https://www.uniprot.org/uniprotkb/D7MKC1 evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Current TrEMBL75/sequence1,477aa, ARALYDRAFT_684148/taxon81972; direct EMBL GL348720/EFH41844.1 cross-reference, cv.MN47. No FUNCTION or CATALYTIC ACTIVITY comment. Automated P450, GO, cofactor, membrane and binding annotations are not thalianol assay evidence. reference https://www.ncbi.nlm.nih.gov/protein/EFH41844.1 evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes Complete477-residue predicted reference, Arabidopsis lyrata subsp. lyrata/taxon81972, NASC<UK> donor MN47, locusARALYDRAFT_684148. Full coded_by inspected; no historical assay-stock or construct mapping. reference https://www.ncbi.nlm.nih.gov/nuccore/GL348720.1?from=10405500&to=10409700 evidence type CURATOR_INFERENCE retrieved on 2026-10-07 notes Complete1434-nt eight-exon minus-strand CDS spans10405619..10409607 in forward4201-bp window10405500..10409700. Codon1/default table1 translation equals native annotation, independent EFH41844.1 and current D7MKC1, all477aa. All exact absolute coded_by exon coordinates map to native window features and identical DNA; donor/taxon agree. Full-CDS window, not full genome; sequence identity only.
thalianol	is_database_example_substrate_of	MITE-reported THAH substrate hydroxylation	Pinned example substrate matches full key DGAGPZOBTQYNRE-VMSIWEJCSA-N and complete stereo in the repository-helper/RDKit2026.03.5 screen. This is a substrate-consumption context, not a new thalianol production claim, and not an independently mapped native assay substrate.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000133.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000133.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes MITE0000133 version3, active, names THAH/D7MKC1/EFH41844.1. Its heterologous-expression evidence code remains a database assertion; the primary paper was inaccessible. The prose organism name is inconsistent with both independent sequence records, which identify Arabidopsis lyrata subsp. lyrata, not A.thaliana. Retired BGC0002857 was removed from this version.
MITE-reported THAH substrate hydroxylation	has_database_example_product	Database-encoded hydroxylated thalianol intermediate	The hydroxylated example is marked intermediate. Its encoded product omits side-chain double-bond stereo present in the substrate, so no exact external product identity or complete product stereo is asserted. No downstream order or pathway finality. Preserve the separate A.thaliana THAS1/Q9FI37 pathway/graph and BGC0000670, existing BGC_CHARACTERIZED/CLUSTER_DEMONSTRATED grades and SEEDED status; no retired BGC transfer.	https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000133.json reference https://github.com/mite-standard/mite_data/blob/6eacd913b2036376031072f69cbb33908f132998/mite_data/data/MITE0000133.json evidence type DATABASE_ASSERTION retrieved on 2026-10-07 notes MITE0000133 version3, active, names THAH/D7MKC1/EFH41844.1. Its heterologous-expression evidence code remains a database assertion; the primary paper was inaccessible. The prose organism name is inconsistent with both independent sequence records, which identify Arabidopsis lyrata subsp. lyrata, not A.thaliana. Retired BGC0002857 was removed from this version.

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

Explore across X-Mech

AntibioticMech (thalianol) ↗ MediaIngredientMech (CHEBI:52317) ↗ TaxonMech: Arabidopsis thaliana (NCBITaxon:3702) ↗ PathwayMech (mibig:BGC0000670) ↗

Provenance

Source concept	Source	Version
BGC0000670	MIBIG	4
CHEBI:52317	CHEBI	3-star

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