avermitilol

CHEBI:63702 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 carbotricyclic compound that consists of decahydro-1H-1H-cyclopropa[a]naphthalene bearing four methyl substituents at position 1, 1, 3a and 7 as well as a hydroxy substituent at position 4 (the (1aR,3aS,4S,7R,7aS,7bR)-diastereomer).

Structure

Standard InChIKey	BLGPPSRDEKNCLT-CDWXYHGHSA-N
SMILES	[H][C@@]12CC[C@]3(C)[C@@H](O)CC[C@@H](C)[C@@]3([H])[C@]1([H])C2(C)C
Stereochemistry	fully defined
Cross-references	npatlas:NPA019411

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
Streptomyces avermitilis MA-4680 = NBRC 14893 NCBITaxon:227882	SOURCE_ASSERTION	mibig:BGC0000683	PMID:20536237

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
Streptomyces avermitilis NCBITaxon:33903	LOTUS	DOI:10.1021/JA103087W

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000683	Streptomyces avermitilis MA-4680 = NBRC 14893 NCBITaxon:227882	CLUSTER_DEMONSTRATED	genbank:BA000030.3

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	Avermitilol synthase UniProtKB:Q82RR7	RHEA:32023	CHEBI:175763 → CHEBI:63702	DOI:10.1021/ja103087w

Step 1: Streptomyces avermitilis SAV_76/Tpc1 cyclizes (2E,6E)-farnesyl diphosphate to avermitilol.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Streptomyces avermitilis avermitilol biosynthesis graph for Tpc1-catalyzed cyclization of (2E,6E)-farnesyl diphosphate to avermitilol.

Subject	Predicate	Object	Notes	Evidence
(2E,6E)-farnesyl diphosphate	is cyclized by	Tpc1		DOI:10.1021/ja103087w https://mibig.secondarymetabolites.org/repository/BGC0000683.3/ https://www.uniprot.org/uniprotkb/Q82RR7 reference DOI:10.1021/ja103087w evidence type PRIMARY_EXPERIMENT snippet Incubation of the recombinant protein, SAV_76, with farnesyl diphosphate notes Recombinant Streptomyces avermitilis SAV_76/Tpc1 cyclized farnesyl diphosphate to avermitilol. reference https://mibig.secondarymetabolites.org/repository/BGC0000683.3/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 3 links BGC0000683 to avermitilol biosynthesis in Streptomyces avermitilis MA-4680. reference https://www.uniprot.org/uniprotkb/Q82RR7 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes UniProtKB:Q82RR7 is the reviewed Streptomyces avermitilis MA-4680 Tpc1/SAV_76 gene product, maps to EMBL BA000030 protein BAC67785.1, and annotates RHEA:32023 for cyclization of farnesyl diphosphate to avermitilol plus diphosphate.
Tpc1	forms	avermitilol		DOI:10.1021/ja103087w https://mibig.secondarymetabolites.org/repository/BGC0000683.3/ https://www.uniprot.org/uniprotkb/Q82RR7 reference DOI:10.1021/ja103087w evidence type PRIMARY_EXPERIMENT snippet Incubation of the recombinant protein, SAV_76, with farnesyl diphosphate notes Recombinant Streptomyces avermitilis SAV_76/Tpc1 cyclized farnesyl diphosphate to avermitilol. reference https://mibig.secondarymetabolites.org/repository/BGC0000683.3/ evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG entry version 3 links BGC0000683 to avermitilol biosynthesis in Streptomyces avermitilis MA-4680. reference https://www.uniprot.org/uniprotkb/Q82RR7 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes UniProtKB:Q82RR7 is the reviewed Streptomyces avermitilis MA-4680 Tpc1/SAV_76 gene product, maps to EMBL BA000030 protein BAC67785.1, and annotates RHEA:32023 for cyclization of farnesyl diphosphate to avermitilol plus diphosphate.

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

Explore across X-Mech

AntibioticMech (avermitilol) ↗ MediaIngredientMech (CHEBI:63702) ↗ TaxonMech: Streptomyces avermitilis MA-4680 = NBRC 14893 (NCBITaxon:227882) ↗ PathwayMech (mibig:BGC0000683) ↗

Provenance

Source concept	Source	Version
BGC0000683	MIBIG	3
CHEBI:63702	CHEBI	3-star

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