indigoidine
CHEBI:79296 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 member of the class of pyridone that is a dimeric blue pigment biosynthesised from L-glutamine.
Structure
| Standard InChIKey | ALDIVIWLBSDGGN-ONEGZZNKSA-N |
|---|---|
| SMILES | C\1=C(C(=O)NC(=O)/C1=C/2\C=C(C(=O)NC2=O)N)N |
| Stereochemistry | fully defined |
| Cross-references | pubchem:5492261 |
Filing pathway
Alkaloids — 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 nrps, 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 chromofuscus NCBITaxon:42881 |
SOURCE_ASSERTION | mibig:BGC0000375 | PMID:23053349 |
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 |
|---|---|---|
| Streptomyces lavendulae NCBITaxon:1914 |
CHEBI | PMID:17237222 |
| Streptomyces chromofuscus NCBITaxon:42881 |
LOTUS | DOI:10.1007/S10295-012-1207-9 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000375 | Streptomyces chromofuscus NCBITaxon:42881 |
CLUSTER_UNSTATED | genbank:JX499187.1 |
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 | Sc-IndC indigoidine synthase UniProtKB:K4MP98 |
RHEA:81499 | CHEBI:58210 + CHEBI:58359 + CHEBI:30616 + CHEBI:15379 → CHEBI:79296 + CHEBI:57618 + CHEBI:456215 + CHEBI:33019 + CHEBI:15377 | DOI:10.1007/s10295-012-1207-9 |
Step 1: Streptomyces chromofuscus ATCC 49982 Sc-IndC is the exact indigoidine synthase encoded by the MIBiG BGC0000375 indC CDS. The Sc-IndB coexpression effect is represented separately in the Sc-IndC causal graph; it is not assigned this Rhea-grounded synthase reaction or an additional ordered pathway step.
Mechanism & Biosynthesis Overview
Causal graph — biosynthesis 5 nodes, 4 edges
Streptomyces chromofuscus ATCC 49982 Sc-IndC converts L-glutamine to the blue pigment indigoidine. Sc-IndB is represented as the native reference for a conditional yield-enhancing coexpression effect with Sc-IndC in E. coli BAP1, not as an assigned catalytic step. Additional GlnA coexpression is represented as host engineering; the reported BL21(DE3) protein sequence remains unresolved.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| L-glutamine | is converted to indigoidine by | Sc-IndC | Sc-IndC catalyzes the RHEA:81499 overall conversion from two L-glutamine molecules to indigoidine. | DOI:10.1007/s10295-012-1207-9 |
| Sc-IndC | forms | indigoidine | Heterologous expression of Sc-IndC established it as the indigoidine synthase in the Streptomyces chromofuscus ATCC 49982 BGC0000375 cluster. | DOI:10.1007/s10295-012-1207-9 |
| Sc-IndB (S. chromofuscus native reference) | increases yield of when coexpressed with Sc-IndC | indigoidine | Conditional coexpression effect reported in E. coli BAP1, represented by the exact native Sc-IndB reference. This is not an isolated Sc-IndB catalytic reaction, a demonstrated physical complex, or native essentiality. | DOI:10.1007/s10295-012-1207-9 |
| GlnA (BL21(DE3), sequence unresolved) | increases yield of when coexpressed with Sc-IndC | indigoidine | Reported additional GlnA expression in E. coli BAP1 carrying Sc-IndC, with or without Sc-IndB. This is a host-engineering yield effect, not native cluster membership, an isolated catalytic reaction or direct glutamine-flux measurement. The exact expressed sequence is unresolved; no protein accession is assigned. | DOI:10.1007/s10295-015-1642-5 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — biosynthesis 3 nodes, 2 edges
S. lavendulae ATCC11924 BpsA indigoidine biosynthesis, represented by its exact native reference. Catalytic activity requires the phosphopantetheinylated enzyme. This is an independent organism-specific mechanism, not a downstream step of the existing Sc-IndC pathway.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| L-glutamine zwitterion | is_substrate_for | BpsA (S. lavendulae native reference) | Substrate use by the phosphopantetheinylated enzyme; no activity claim for apo-BpsA. | DOI:10.1074/jbc.M611319200 |
| BpsA (S. lavendulae native reference) | catalyzes_overall_formation_of | indigoidine | Overall pigment formation in the reported activated-enzyme context. No direct assignment of spontaneous dimerization, reaction intermediates, native essentiality or membership in BGC0000375/BGC0002295 is made. | DOI:10.1074/jbc.M611319200 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — biosynthesis 5 nodes, 5 edges
PPTase deletion/rescue in engineered J1074 carrying a heterologous BpsA indigoidine reporter. AGI92022.1 denotes the native PPTase reference, not a verified engineered allele. The reporter sequence is unresolved; this graph does not extend the canonical BpsA or native IndC mechanism.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| XNR_5716 PPTase (J1074 native reference) | has its encoding locus targeted by | PPTase deletion in J1074 BpsA reporter | Reference-to-intervention correspondence, not a direct catalytic edge. | DOI:10.1093/femsle/fnx155 |
| PPTase deletion in J1074 BpsA reporter | abolishes detectable reporter production of | indigoidine | Restricted to the tested engineered reporter context; not universal essentiality or native IndC dependence. | DOI:10.1093/femsle/fnx155 |
| XNR_5716 PPTase (J1074 native reference) | is native reference for protein supplied in | PPTase reintroduction in deletion reporter | Reference-to-intervention correspondence; complete rescue-construct sequence remains unverified. | DOI:10.1093/femsle/fnx155 |
| PPTase reintroduction in deletion reporter | restores reporter production of | indigoidine | Genetic complementation readout, not purified phosphopantetheinyl-transfer activity, a physical complex, or membership in BGC0000375/BGC0002295. | DOI:10.1093/femsle/fnx155
|
| XNR_5716 PPTase (J1074 native reference) | has a sequence-identical UniProtKB example | XNR_5716 PPTase (S. wadayamensis DC60_07595 UniProtKB example) | UniProtKB:A0ABR4SFP3 (Streptomyces wadayamensis DC60_07595) shares 100% amino-acid sequence identity (UPI0001AEDEA9) with Streptomyces albus J1074 XNR_5716 PPTase (AGI92022.1). | https://www.uniprot.org/uniprotkb/A0ABR4SFP3 |
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — biosynthesis 4 nodes, 3 edges
FRI-5 LbpA heterologous-expression evidence in S. avermitilis SUKA22. The protein node is the exact native reference, not a verified engineered construct. This independent graph does not extend the Sc-IndC, ATCC11924 BpsA or J1074 reporter mechanisms.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| LbpA (S. lavendulae FRI-5 native reference) | is native reference for protein encoded in | Heterologous lbpA expression in SUKA22 | Reference-to-expression correspondence; not an isolated catalytic reaction or proof of construct identity. | DOI:10.1016/j.jbiosc.2017.04.020 |
| Heterologous lbpA expression in SUKA22 | enables reported production of | indigoidine | Host-level expression result, not purified-enzyme catalysis, native essentiality, a physical complex or membership in BGC0000375/BGC0002295. | DOI:10.1016/j.jbiosc.2017.04.020 |
| L-glutamine feeding of SUKA22 expressing lbpA | enhances reported production of | indigoidine | Conditional feeding effect in the lbpA-expressing heterologous host; not direct substrate specificity, isotope incorporation or measured precursor flux. | DOI:10.1016/j.jbiosc.2017.04.020
|
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Causal graph — biosynthesis 5 nodes, 4 edges
CCM3239 bpsA deletion and upstream-promoter interventions. Historical and current native protein references differ at residue 385 and are separate nodes, not verified experimental alleles. The readouts support genetic involvement, not isolated catalysis or a mechanism shared with the other indigoidine graphs.
| Subject | Predicate | Object | Notes | Evidence |
|---|---|---|---|---|
| BpsA (CCM3239 historical reference, Ala385) | is historical reference for the gene product targeted by | Reported bpsA deletion in CCM3239 | Reference-to-locus correspondence, not proof of the tested parental allele. | DOI:10.1007/s12223-010-0018-5 |
| Reported bpsA deletion in CCM3239 | abolishes reported blue-pigment production of | indigoidine | Abstract-level deletion phenotype in the tested strain. No rescue, isolated catalytic step, universal essentiality or BGC membership is asserted. | DOI:10.1007/s12223-010-0018-5 |
| BpsA (CCM3239 current reference, Thr385) | has its encoding locus preceded by | AprR-kasOp* insertion upstream of CCM3239 bpsA | Reference-to-intervention correspondence only; the complete engineered bpsA allele and residue 385 genotype are unresolved. | DOI:10.1007/s00253-026-13908-9 |
| AprR-kasOp* insertion upstream of CCM3239 bpsA | increases the reported pigment readout for | indigoidine | Intervention-level result; neighboring transcriptional effects remain possible. Not proof that BpsA alone accounts for the increase. | DOI:10.1007/s00253-026-13908-9
|
Every edge carries its own citation; an uncited edge is refused by the corpus tests.
Explore across X-Mech
Open questions 3
curator-indigoidine-glna-construct-identity — Which complete GlnA protein sequence was expressed in pFC6/pFC7, and how should the reported 1284-bp fragment be reconciled with the 1410-bp BL21(DE3) references?
curator-indigoidine-bpsa-reporter-construct — What is the complete sequence of the BpsA reporter used in the J1074 PPTase experiment?
curator-indigoidine-ccm3239-bpsa-alleles — Which complete bpsA alleles occur in the parental stocks and engineered strains used for the 2010 deletion and 2026 upstream-promoter experiments?
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000375 | MIBIG | 5 |
| CHEBI:79296 | CHEBI | 3-star |
This page is generated from data/natural_products/alkaloids/indigoidine.yaml, which is generated from the committed inventories. Neither is edited by hand.