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(+)-(2S,3R,9R)-pristinol

CHEBI:138165 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 bicyclic sesquiterpenoid that is 2,3,5,6,7,8,9,9a-octahydro-1H-cyclopenta[8]annulen-6-ol carrying four additional methyl substiuents at positions 1, 4, 8 and 8.

Structure

Standard InChIKeyPXKJCWZAMAFFIW-GLBIRDDMSA-N
SMILESC[C@@H]1CC/C/2=C(/C[C@@H](CC(C[C@@H]12)(C)C)O)\C
Stereochemistryfully defined

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
Streptomyces pristinaespiralis ATCC 25486
NCBITaxon:457429		 SOURCE_ASSERTION mibig:BGC0001746 PMID:27403888

Occurrences 2

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
Streptomyces pristinaespiralis
NCBITaxon:38300		 CHEBI PMID:27403888
Streptomyces pristinaespiralis
NCBITaxon:457429		 LOTUS DOI:10.1002/ANIE.201605425

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0001746 Streptomyces pristinaespiralis ATCC 25486
NCBITaxon:457429 		CLUSTER_DEMONSTRATED genbank:NZ_CM000950.1

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 Pristinol synthase
UniProtKB:B5H7H3		 RHEA:54372 CHEBI:175763 → CHEBI:138165 DOI:10.1002/anie.201605425

Step 1: Streptomyces pristinaespiralis ATCC 25486 pristinol synthase cyclizes (2E,6E)-farnesyl diphosphate with water to (+)-(2S,3R,9R)-pristinol and diphosphate.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (0 causal) 2 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 1 curated pathway step NATURAL PRODUCT (+)-(2S,3R,9R)-pristinol CHEBI:138165 Terpenoids TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 2 graphs

Causal graph — biosynthesis 4 nodes, 3 edges

Streptomyces pristinaespiralis ATCC 25486 pristinol synthase cyclizes (2E,6E)-farnesyl diphosphate to form (+)-(2S,3R,9R)-pristinol.

SubjectPredicateObjectNotesEvidence
BGC0001746 pristinol biosynthetic gene cluster encodes Pristinol synthase BGC0001746 contains SSDG_RS31275, the WP_005320742.1-encoded pristinol synthase.
https://mibig.secondarymetabolites.org/repository/BGC0001746.3/BGC0001746.gbk
https://www.uniprot.org/uniprotkb/B5H7H3
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0001746.3/BGC0001746.gbk
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    MIBiG BGC0001746.3 maps the Streptomyces pristinaespiralis ATCC 25486 pristinol core CDS SSDG_RS31275 to RefSeq protein WP_005320742.1.
  • reference
    https://www.uniprot.org/uniprotkb/B5H7H3
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:B5H7H3 is the 372 aa Streptomyces pristinaespiralis ATCC 25486 pristinol synthase, cross-references RefSeq WP_005320742.1 on NZ_CM000950.1, and annotates RHEA:54372 from PMID:27403888.
(2E,6E)-farnesyl diphosphate is cyclized by Pristinol synthase Pristinol synthase abstracts diphosphate from FPP and catalyzes the rearranged sesquiterpenol-forming cyclization.
DOI:10.1002/anie.201605425
https://www.uniprot.org/uniprotkb/B5H7H3
https://www.rhea-db.org/rhea/54372
  • reference
    DOI:10.1002/anie.201605425
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    synthase for (+)-(2S,3S,9R)-pristinol
    notes
    Klapschinski et al. characterized the Streptomyces pristinaespiralis ATCC 25486 terpene cyclase for pristinol; Rhea and IUBMB normalize the enzymatic product to (+)-(2S,3R,9R)-pristinol.
  • reference
    https://www.uniprot.org/uniprotkb/B5H7H3
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:B5H7H3 is the 372 aa Streptomyces pristinaespiralis ATCC 25486 pristinol synthase, cross-references RefSeq WP_005320742.1 on NZ_CM000950.1, and annotates RHEA:54372 from PMID:27403888.
  • reference
    https://www.rhea-db.org/rhea/54372
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    RHEA:54372 is the (2E,6E)-farnesyl diphosphate plus H2O to (+)-(2S,3R,9R)-pristinol plus diphosphate reaction; RHEA:54373 is the left-to-right direction mapped to UniProtKB:B5H7H3 in Swiss-Prot.
Pristinol synthase produces (+)-(2S,3R,9R)-pristinol Pristinol synthase produces (+)-(2S,3R,9R)-pristinol via the RHEA:54372 reaction.
DOI:10.1002/anie.201605425
https://www.uniprot.org/uniprotkb/B5H7H3
https://www.rhea-db.org/rhea/54372
  • reference
    DOI:10.1002/anie.201605425
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    synthase for (+)-(2S,3S,9R)-pristinol
    notes
    Klapschinski et al. characterized the Streptomyces pristinaespiralis ATCC 25486 terpene cyclase for pristinol; Rhea and IUBMB normalize the enzymatic product to (+)-(2S,3R,9R)-pristinol.
  • reference
    https://www.uniprot.org/uniprotkb/B5H7H3
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:B5H7H3 is the 372 aa Streptomyces pristinaespiralis ATCC 25486 pristinol synthase, cross-references RefSeq WP_005320742.1 on NZ_CM000950.1, and annotates RHEA:54372 from PMID:27403888.
  • reference
    https://www.rhea-db.org/rhea/54372
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    RHEA:54372 is the (2E,6E)-farnesyl diphosphate plus H2O to (+)-(2S,3R,9R)-pristinol plus diphosphate reaction; RHEA:54373 is the left-to-right direction mapped to UniProtKB:B5H7H3 in Swiss-Prot.

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 (+)-(2S,3R,9R)-pristinol as a side 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.

SubjectPredicateObjectNotesEvidence
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:54372 to tatc6 and explicitly names CHEBI:138165 as product of FPP plus water; RHEA:54373 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 (+)-(2S,3R,9R)-pristinol The explicit UniProt reaction product CURIE CHEBI:138165 matches this owner, whose unchanged full InChIKey is PXKJCWZAMAFFIW-GLBIRDDMSA-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 fungal side-product graph is separate from the existing Streptomyces B5H7H3/BGC0001746 mechanism; its historical naming/stereochemistry notes are preserved without a new adjudication.
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:54372 to tatc6 and explicitly names CHEBI:138165 as product of FPP plus water; RHEA:54373 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
    (2E,6E)-farnesyl diphosphate + H2O = (+)-(2S,3R,9R)-pristinol + diphosphate

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

Explore across X-Mech

AntibioticMech ((+)-(2S,3R,9R)-pristinol) ↗ MediaIngredientMech (CHEBI:138165) ↗ TaxonMech: Streptomyces pristinaespiralis ATCC 25486 (NCBITaxon:457429) ↗ PathwayMech (mibig:BGC0001746) ↗

Provenance

Source conceptSourceVersion
BGC0001746MIBIG3
CHEBI:138165CHEBI3-star

This page is generated from data/natural_products/terpenoids/2s-3r-9r-pristinol.yaml, which is generated from the committed inventories. Neither is edited by hand.