oxetanocin A

CHEBI:86012 EXACT SEEDED antibacterial

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 nucleoside analogue found in Bacillus megaterium in which an adenine moiety is attached to position 2 of a of an oxetane ring which is substituted at positions 3 and 4 by hydroxymethyl groups.

Structure

Standard InChIKey	LMJVXGOFWKVXAW-OXOINMOOSA-N
SMILES	C1=NC2=C(C(=N1)N)N=CN2[C@H]3[C@@H]([C@H](O3)CO)CO
Stereochemistry	fully defined

Filing pathway

Carbohydrates — 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 other, 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
Bacillus megaterium NCBITaxon:1404	SOURCE_ASSERTION	mibig:BGC0001725	DOI:10.7164/antibiotics.39.1623

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.

Taxon	Source	Reference
Bacillus megaterium NCBITaxon:1404	LOTUS	DOI:10.7164/ANTIBIOTICS.39.1626
Bacillus megaterium NCBITaxon:1404	CHEBI	PMID:3025147

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0001725	Bacillus megaterium NCBITaxon:1404	CLUSTER_UNSTATED	genbank:AB005787.1

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	OxsA 4'-phosphooxetanocin A phosphatase UniProtKB:O24769	RHEA:81367	CHEBI:85720 → CHEBI:86012	DOI:10.1073/pnas.1613610113

Step 1: OxsA hydrolyzes 4'-phosphooxetanocin A to oxetanocin A as the terminal dephosphorylation in the Bacillus megaterium NK84-0128 oxetanocin A pathway; this single curated step leaves the upstream OxsB-catalyzed radical ring contraction unexpanded.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Bacillus megaterium NK84-0128 OxsA dephosphorylates 4'-phosphooxetanocin A to form oxetanocin A.

Subject	Predicate	Object	Notes	Evidence
4'-phosphooxetanocin A	is dephosphorylated by	OxsA	OxsA catalyzes the RHEA:81367 hydrolysis of 4'-phosphooxetanocin A to oxetanocin A plus phosphate.	DOI:10.1073/pnas.1613610113 DOI:10.1038/nature21689 https://mibig.secondarymetabolites.org/repository/BGC0001725.3/BGC0001725.gbk https://www.uniprot.org/uniprotkb/O24769 https://www.rhea-db.org/rhea/81367 reference DOI:10.1073/pnas.1613610113 evidence type PRIMARY_EXPERIMENT snippet HD domain phosphohydrolase OxsA, involved in the biosynthesis notes Bridwell-Rabb et al. structurally and biochemically characterized the Bacillus megaterium OxsA phosphohydrolase toward phosphorylated oxetanocin A substrates. reference DOI:10.1038/nature21689 evidence type PRIMARY_EXPERIMENT snippet both the oxsA and oxsB genes are required for the production of OXT-A notes Bridwell-Rabb et al. showed that plasmid-borne Bacillus megaterium oxsA and oxsB are required for oxetanocin A production. reference https://mibig.secondarymetabolites.org/repository/BGC0001725.3/BGC0001725.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0001725.3 places oxsA / BAA21630.1 on the Priestia/Bacillus megaterium NK84-0128 oxetanocin A plasmid pOXTB2. reference https://www.uniprot.org/uniprotkb/O24769 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:O24769 is the 194 aa Priestia megaterium 4'-phosphooxetanocin A phosphatase OxsA, cross-references EMBL AB005787 protein BAA21630.1, and annotates RHEA:81367 / RHEA:81368. reference https://www.rhea-db.org/rhea/81367 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:81367 is the 4'-phosphooxetanocin A plus H2O to oxetanocin A plus phosphate reaction; Rhea maps the master reaction to UniProtKB:O24769 in Swiss-Prot.
OxsA	forms	oxetanocin A	OxsA is the 4'-phosphooxetanocin A phosphatase encoded by the plasmid pOXTB2 oxsA locus.	DOI:10.1073/pnas.1613610113 DOI:10.1038/nature21689 https://mibig.secondarymetabolites.org/repository/BGC0001725.3/BGC0001725.gbk https://www.uniprot.org/uniprotkb/O24769 https://www.rhea-db.org/rhea/81367 reference DOI:10.1073/pnas.1613610113 evidence type PRIMARY_EXPERIMENT snippet HD domain phosphohydrolase OxsA, involved in the biosynthesis notes Bridwell-Rabb et al. structurally and biochemically characterized the Bacillus megaterium OxsA phosphohydrolase toward phosphorylated oxetanocin A substrates. reference DOI:10.1038/nature21689 evidence type PRIMARY_EXPERIMENT snippet both the oxsA and oxsB genes are required for the production of OXT-A notes Bridwell-Rabb et al. showed that plasmid-borne Bacillus megaterium oxsA and oxsB are required for oxetanocin A production. reference https://mibig.secondarymetabolites.org/repository/BGC0001725.3/BGC0001725.gbk evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes MIBiG BGC0001725.3 places oxsA / BAA21630.1 on the Priestia/Bacillus megaterium NK84-0128 oxetanocin A plasmid pOXTB2. reference https://www.uniprot.org/uniprotkb/O24769 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes Reviewed UniProtKB:O24769 is the 194 aa Priestia megaterium 4'-phosphooxetanocin A phosphatase OxsA, cross-references EMBL AB005787 protein BAA21630.1, and annotates RHEA:81367 / RHEA:81368. reference https://www.rhea-db.org/rhea/81367 evidence type DATABASE_ASSERTION retrieved on 2026-09-30 notes RHEA:81367 is the 4'-phosphooxetanocin A plus H2O to oxetanocin A plus phosphate reaction; Rhea maps the master reaction to UniProtKB:O24769 in Swiss-Prot.

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

Elsewhere in the fleet

AntibioticMech — CHEBI:86012 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (oxetanocin A) ↗ MediaIngredientMech (CHEBI:86012) ↗ TaxonMech: Bacillus megaterium (NCBITaxon:1404) ↗ PathwayMech (mibig:BGC0001725) ↗

Provenance

Source concept	Source	Version
BGC0001725	MIBIG	3
CHEBI:86012	CHEBI	3-star

This page is generated from data/natural_products/carbohydrates/oxetanocin-a.yaml, which is generated from the committed inventories. Neither is edited by hand.