toyocamycin
CHEBI:134606 EXACT SEEDED antifungalenzyme inhibitor
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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.
An N-glycosylpyrrolopyrimidine that is tubercidin in which the hydrogen at position 5 of the pyrrolopyrimidine moiety has been replaced by a cyano group.
Structure
| Standard InChIKey | XOKJUSAYZUAMGJ-WOUKDFQISA-N |
|---|---|
| SMILES | NC1=NC=NC2=C1C(=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C#N |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA06347, pubchem:11824 |
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 3
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 rimosus NCBITaxon:1927 |
SOURCE_ASSERTION | mibig:BGC0000879 | PMID:18721750 |
| Streptomyces ahygroscopicus subsp. wuzhouensis NCBITaxon:387850 |
SOURCE_ASSERTION | mibig:BGC0000881 | PMID:28342817 |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
SOURCE_ASSERTION | mibig:BGC0001808 | PMID:26790416 |
Occurrences 15
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 diastatochromogenes NCBITaxon:1628 |
CHEBI | PMID:23775805 |
| Streptomyces NCBITaxon:1883 |
LOTUS | DOI:10.1021/NP50077A014 |
| Tolypothrix tenuis NCBITaxon:457083 |
CYANOMETDB | DOI:10.1021/ja01004a076 |
| Tolypothrix tenuis NCBITaxon:457083 |
LOTUS | DOI:10.7164/ANTIBIOTICS.41.1048 |
| Streptomyces toyocaensis NCBITaxon:55952 |
LOTUS | DOI:10.1021/JA01004A076 |
| Streptomyces sparsogenes NCBITaxon:67365 |
LOTUS | DOI:10.1016/S0021-9673(01)83861-9 |
| Streptomyces rimosus NCBITaxon:1927 |
LOTUS | DOI:10.1039/C0OB01054E |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1002/JOBM.201200489 |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1007/S00253-014-5573-2 |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1007/S00253-019-09959-W |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1007/S00284-013-0461-Z |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1007/S00284-018-1529-6 |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1007/S10295-015-1732-4 |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1007/S12223-013-0271-5 |
| Streptomyces diastatochromogenes NCBITaxon:42236 |
LOTUS | DOI:10.1371/JOURNAL.PONE.0203006 |
Biosynthetic gene clusters 3
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000879 | Streptomyces rimosus NCBITaxon:1927 |
CLUSTER_UNSTATED | genbank:EU573979.1 |
| mibig:BGC0000881 | Streptomyces ahygroscopicus subsp. wuzhouensis NCBITaxon:387850 |
CLUSTER_UNSTATED | genbank:JX576291.1 |
| mibig:BGC0001808 | Streptomyces diastatochromogenes NCBITaxon:42236 |
CLUSTER_UNSTATED | genbank:KY022432.1 |
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.
Mechanism & Biosynthesis Overview
Causal graph — bioactivity 2 nodes, 1 edge
Toyocamycin binds Archaeoglobus fulgidus Rio1 kinase in the PDB 3RE4 co-crystal structure.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| toyocamycin | binds | Archaeoglobus fulgidus Rio1 kinase | PubChem AID 977611 maps this InChIKey to an active 0.04 uM Kd row for PDB 3RE4 chain A; RCSB identifies TO1 in 3RE4 as toyocamycin with matching InChIKey XOKJUSAYZUAMGJ-WOUKDFQISA-N; and PDBe maps chains A and B to Archaeoglobus fulgidus UniProtKB:O28471. | DOI:10.1371/journal.pone.0037371 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Bioactivities 1
Entries preserve source qualifiers, targets and evidence. Repeated assay names or values are not independent replications; inspect source detail for differences.
| Assay | Result | Target enzyme | Source detail |
|---|---|---|---|
| Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | KD 0.04 uM; ACTIVE | Not recorded | PMID:22629386
|
Elsewhere in the fleet
- AntibioticMech — CHEBI:134606 (same structure, same inchikey)
Explore across X-Mech
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0000879, BGC0000881, BGC0001808. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000879 | MIBIG | 5 |
| BGC0000881 | MIBIG | 3 |
| BGC0001808 | MIBIG | 5 |
| CHEBI:134606 | CHEBI | 3-star |
This page is generated from data/natural_products/carbohydrates/toyocamycin.yaml, which is generated from the committed inventories. Neither is edited by hand.