endophenazine A

naturalproductmech:mibig-383a92387c MINTED SEEDED

Grounding review: No 3-star ChEBI entry shares this structure, so the record keeps a content-hashed identifier.

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

Structure

Standard InChIKey	WLQXISHGKXGNFV-UHFFFAOYSA-N
SMILES	CC(C)=CCC1=CC=CC2=NC3=CC=CC(C(O)=O)=C3N=C12
Stereochemistry	fully defined
Cross-references	npatlas:NPA015622, pubchem:10039975

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 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
Streptomyces anulatus NCBITaxon:1892	BGC_CHARACTERIZED	mibig:BGC0001080	PMID:22509222

Occurrences 4

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 cinnamonensis NCBITaxon:1961	LOTUS	DOI:10.1021/JO0703404
Streptomyces anulatus NCBITaxon:1892	LOTUS	DOI:10.3762/BJOC.8.57
Streptomyces anulatus NCBITaxon:1892	LOTUS	DOI:10.7164/ANTIBIOTICS.55.794
Streptomyces anulatus NCBITaxon:1892	LOTUS	DOI:10.7164/ANTIBIOTICS.55.801

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0001080	Streptomyces anulatus NCBITaxon:1892	CLUSTER_DEMONSTRATED	genbank:FN178498.1

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	PpzP 5,10-dihydrophenazine-1-carboxylate 9-dimethylallyltransferase UniProtKB:C4PWA1	RHEA:41580	CHEBI:78312 → CHEBI:78313	DOI:10.1074/jbc.M901312200

Step 1: This partial endophenazine A pathway captures the assayed Streptomyces anulatus PpzP dimethylallylation of 5,10-dihydrophenazine-1-carboxylate. Upstream PCA reduction and downstream oxidation to endophenazine A are left unexpanded because they were not assigned to exact assayed enzymes in the inspected sources.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Partial Streptomyces anulatus 9663 endophenazine A biosynthesis graph for the assayed PpzP dimethylallyltransferase reaction.

Subject	Predicate	Object	Notes	Evidence
5,10-dihydrophenazine-1-carboxylate	is dimethylallylated by	PpzP	This edge is the assayed Rhea reaction substrate rather than oxidized phenazine-1-carboxylic acid.	DOI:10.1074/jbc.M901312200 https://www.uniprot.org/uniprotkb/C4PWA1 RHEA:41580 reference DOI:10.1074/jbc.M901312200 evidence type PRIMARY_EXPERIMENT snippet identified as a 5,10-dihydrophenazine 1-carboxylate dimethylallyltransferase notes Saleh et al. identified Streptomyces anulatus 9663 ppzP in the endophenazine cluster, showed that ppzP inactivation abolished prenylated phenazine formation, and biochemically assigned purified PpzP to dimethylallyl transfer from 5,10-dihydrophenazine 1-carboxylate. reference https://www.uniprot.org/uniprotkb/C4PWA1 evidence type DATABASE_ASSERTION snippet DR EMBL; FN178498; CAX48655.1; -; Genomic_DNA. retrieved on 2026-09-28 notes Reviewed UniProtKB:C4PWA1 is Streptomyces anulatus PpzP, length 299 aa, names ppzP, assigns EC 2.5.1.121, and cross-references EMBL FN178498 protein CAX48655.1. reference RHEA:41580 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes Rhea grounds EC 2.5.1.121 as transfer of dimethylallyl diphosphate to 5,10-dihydrophenazine 1-carboxylate, forming 5,10-dihydro-9-dimethylallylphenazine 1-carboxylate and diphosphate.
PpzP	forms	5,10-dihydro-9-dimethylallylphenazine 1-carboxylate	PpzP forms the reduced 9-dimethylallyl intermediate on the route to endophenazine A.	DOI:10.1074/jbc.M901312200 https://www.uniprot.org/uniprotkb/C4PWA1 RHEA:41580 reference DOI:10.1074/jbc.M901312200 evidence type PRIMARY_EXPERIMENT snippet identified as a 5,10-dihydrophenazine 1-carboxylate dimethylallyltransferase notes Saleh et al. identified Streptomyces anulatus 9663 ppzP in the endophenazine cluster, showed that ppzP inactivation abolished prenylated phenazine formation, and biochemically assigned purified PpzP to dimethylallyl transfer from 5,10-dihydrophenazine 1-carboxylate. reference https://www.uniprot.org/uniprotkb/C4PWA1 evidence type DATABASE_ASSERTION snippet DR EMBL; FN178498; CAX48655.1; -; Genomic_DNA. retrieved on 2026-09-28 notes Reviewed UniProtKB:C4PWA1 is Streptomyces anulatus PpzP, length 299 aa, names ppzP, assigns EC 2.5.1.121, and cross-references EMBL FN178498 protein CAX48655.1. reference RHEA:41580 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes Rhea grounds EC 2.5.1.121 as transfer of dimethylallyl diphosphate to 5,10-dihydrophenazine 1-carboxylate, forming 5,10-dihydro-9-dimethylallylphenazine 1-carboxylate and diphosphate.
5,10-dihydro-9-dimethylallylphenazine 1-carboxylate	is an immediate reduced precursor of	endophenazine A	Saleh et al. assigned the PpzP assay product after sodium-persulfate oxidation to endophenazine A; this graph keeps the reduced Rhea product as the enzymatic product and stops short of asserting the final oxidation as an assigned enzymatic step.	DOI:10.1074/jbc.M901312200 reference DOI:10.1074/jbc.M901312200 evidence type PRIMARY_EXPERIMENT snippet identified as endophenazine A by LC-MS analysis notes Saleh et al. incubated chemically generated 5,10-dihydrophenazine 1-carboxylate with purified PpzP and DMAPP; because the reduced phenazine products oxidized rapidly, the reaction mix was oxidized with sodium persulfate before LC-MS identified oxidized endophenazine A against an authentic standard.

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

Explore across X-Mech

AntibioticMech (endophenazine A) ↗ MediaIngredientMech (naturalproductmech:mibig-383a92387c) ↗ TaxonMech: Streptomyces anulatus (NCBITaxon:1892) ↗ PathwayMech (mibig:BGC0001080) ↗

Provenance

Source concept	Source	Version
BGC0001080	MIBIG	5

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