pulcherriminic acid
CHEBI:71599 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 pyrazine N-oxide that is pyrazine-1,4-dioxide substituted at positions 2 and 5 by hydroxy groups and at positions 3 and 6 by isobutyl groups. Formed by oxidative aromatisation of cyclo(L-leucyl-L-leucyl).
Structure
| Standard InChIKey | WXWWNANFOZVVLD-UHFFFAOYSA-N |
|---|---|
| SMILES | CC(C)CC1=C(O)N(=O)=C(CC(C)C)C(O)=N1=O |
| Stereochemistry | fully defined |
| Cross-references | npatlas:NPA012181 |
Filing pathway
Unclassified — 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 2
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 |
|---|---|---|---|
| Metschnikowia aff. pulcherrima NCBITaxon:2163413 |
BGC_CORRELATED | mibig:BGC0002321 | PMID:31081214 |
| Bacillus subtilis subsp. subtilis str. 168 NCBITaxon:224308 |
SOURCE_ASSERTION | mibig:BGC0002103 | DOI:10.1038/s41522-023-00418-z |
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 |
|---|---|---|
| Metschnikowia pulcherrima NCBITaxon:27326 |
LOTUS | DOI:10.1139/V63-021 |
| Caesalpinia pulcherrima NCBITaxon:53846 |
LOTUS | DOI:10.1016/S0031-9422(00)97708-2 |
Biosynthetic gene clusters 2
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0002321 | Metschnikowia aff. pulcherrima NCBITaxon:2163413 |
CLUSTER_CORRELATED | genbank:CP034458.1 |
| mibig:BGC0002103 | Bacillus subtilis subsp. subtilis str. 168 NCBITaxon:224308 |
CLUSTER_DEMONSTRATED | genbank:NC_000964.3 |
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 | YvmC cyclodileucine synthase UniProtKB:O34351 |
RHEA:46452 | ungrounded → CHEBI:67269 | DOI:10.1038/nchembio.175 |
| 2 | CypX pulcherriminic acid synthase UniProtKB:O34926 |
RHEA:35555 | CHEBI:67269 → CHEBI:71599 | DOI:10.1021/bi100910y |
Step 1: Bacillus subtilis 168 yvmC, annotated pchC in MIBiG's NC_000964.3 GenBank record, catalyzes cyclodileucine formation from two L-leucyl-tRNA(Leu) substrates. The full Rhea tRNA participant RHEA-COMP:9622 is not used as a substrate CURIE because RHEA-COMP is not yet a NaturalProductMech grounding prefix.
Step 2: Bacillus subtilis 168 CypX/CYP134A1 oxidizes cyclo(L-leucyl-L-leucyl) toward pulcherriminic acid. RHEA:35555 uses pulcherriminate(2-) CHEBI:77663 as the product participant; CHEBI:71599 is the neutral acid recorded for the same BGC0002103 structure.
Mechanism & Biosynthesis Overview
Causal graph — biosynthesis 6 nodes, 6 edges
Bacillus subtilis 168 pchC/yvmC and cypX encode the two enzymes that convert leucyl-tRNA through cyclodileucine into pulcherriminic acid.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| BGC0002103 pulcherriminic acid biosynthetic gene cluster | encodes | YvmC cyclodileucine synthase | BGC0002103 contains the BSU35070 core CDS: pchC in the current GenBank annotation, yvmC in the UniProt entry. | https://mibig.secondarymetabolites.org/repository/BGC0002103.2/BGC0002103.gbk |
| BGC0002103 pulcherriminic acid biosynthetic gene cluster | encodes | CypX pulcherriminic acid synthase | BGC0002103 contains the BSU35060 cypX CDS. | https://mibig.secondarymetabolites.org/repository/BGC0002103.2/BGC0002103.gbk |
| L-leucyl-tRNA(Leu) | is cyclized by | YvmC cyclodileucine synthase | RHEA:46452 consumes two L-leucyl-tRNA(Leu) participants; the full tRNA participant is left ungrounded locally. | DOI:10.1038/nchembio.175 |
| YvmC cyclodileucine synthase | forms | cyclo(L-leucyl-L-leucyl) | YvmC catalyzes cyclo(L-leucyl-L-leucyl) formation as RHEA:46452. | DOI:10.1038/nchembio.175 |
| cyclo(L-leucyl-L-leucyl) | is oxidized by | CypX pulcherriminic acid synthase | CypX/CYP134A1 is the cytochrome P450 that oxidizes cyclo(L-leucyl-L-leucyl) in the pulcherriminic acid pathway. | DOI:10.1021/bi100910y |
| CypX pulcherriminic acid synthase | produces | pulcherriminic acid | CypX produces pulcherriminate(2-) in RHEA:35555; this edge points to the neutral pulcherriminic acid form that grounds the MIBiG BGC0002103 record. | DOI:10.1089/ind.2006.2.66 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — biosynthesis 5 nodes, 4 edges
Database-qualified K. lactis PUL gene regulation and pulcherriminic-acid secretion. PUL4 regulates genes encoding the PUL1/PUL2/PUL3 reference proteins; PUL3 is annotated as required for acid secretion. Gene-expression predicates do not assert protein-protein interactions. All four nodes denote reference proteins, not verified historical assay stocks. No ordered yeast reaction, bacterial leucyl-tRNA/Rhea transfer, direct promoter binding, iron-complex uptake, antimicrobial effect or producer/BGC upgrade is asserted. The existing bacterial pathway is separate and unchanged.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| PUL4 (KLLA0_C19228g; K. lactis reference) | regulates expression of gene encoding | PUL1 (KLLA0_C19184g; K. lactis reference) | Database-reported regulation of the named PUL gene. The object is its reference protein, not a gene identifier or a physical interaction partner. No positive/negative direction, direct promoter binding, binding site, protein abundance measurement or specific transcriptional mechanism is asserted. | https://www.uniprot.org/uniprotkb/Q6CSN1 |
| PUL4 (KLLA0_C19228g; K. lactis reference) | regulates expression of gene encoding | PUL2 (KLLA0_C19206g; K. lactis reference) | Database-reported regulation of the named PUL gene. The object is its reference protein, not a gene identifier or a physical interaction partner. No positive/negative direction, direct promoter binding, binding site, protein abundance measurement or specific transcriptional mechanism is asserted. | https://www.uniprot.org/uniprotkb/Q6CSN1 |
| PUL4 (KLLA0_C19228g; K. lactis reference) | regulates expression of gene encoding | PUL3 (KLLA0_C19250g; K. lactis reference) | Database-reported regulation of the named PUL gene. The object is its reference protein, not a gene identifier or a physical interaction partner. No positive/negative direction, direct promoter binding, binding site, protein abundance measurement or specific transcriptional mechanism is asserted. | https://www.uniprot.org/uniprotkb/Q6CSN1 |
| PUL3 (KLLA0_C19250g; K. lactis reference) | is required for secretion of | pulcherriminic acid | Database requirement statement, not a purified-protein transport assay or a claim about substrate specificity, transport stoichiometry, protonation state or membrane topology. The acid name is represented by this neutral parent owner; the transported ionic species is not established. Separate iron-complex uptake is deliberately not transferred to the unresolved two-Fe pulcherrimin record. | https://www.uniprot.org/uniprotkb/Q6CSN0 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Explore across X-Mech
Open questions 1
shared-structure — This structure is reported by more than one MIBiG entry: BGC0002103, BGC0002321. Confirm they describe the same compound rather than an upstream cross-reference error.
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0002321 | MIBIG | 3 |
| BGC0002103 | MIBIG | 2 |
| CHEBI:71599 | CHEBI | 3-star |
This page is generated from data/natural_products/unclassified/pulcherriminic-acid.yaml, which is generated from the committed inventories. Neither is edited by hand.