endophenazine B

naturalproductmech:mibig-4acf6c9688 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	CIWWONHFDUMHHK-UHFFFAOYSA-N
SMILES	CN1C2=CC=CC(C(O)=O)=C2N=C2C(CC=C(C)C)=CC(=O)C=C12
Stereochemistry	fully defined
Cross-references	npatlas:NPA07331, pubchem:90657423

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 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 NCBITaxon:1883	LOTUS	DOI:10.1021/NP100818D
Streptomyces anulatus NCBITaxon:1892	LOTUS	DOI:10.7164/ANTIBIOTICS.55.794

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	PpzM phenazine N-methyltransferase NCBIProtein:CAX48665.1		ungrounded → naturalproductmech:mibig-4acf6c9688	DOI:10.3762/BJOC.8.57

Step 1: This partial endophenazine B pathway captures the genetically implicated Streptomyces anulatus 9663 PpzM N-methyltransferase. ppzM deletion abolished endophenazine B production, but purified PpzM did not methylate PCA or dihydro-PCA with S-adenosylmethionine in the inspected in vitro assay; the exact methyl acceptor and any partner protein are unresolved. PpzM enzyme_id is grounded to the native GenPept accession NCBIProtein:CAX48665.1 (UniParc UPI0001A648F5 maps only to retired/obsolete UniProtKB/TrEMBL entry C4PWB1.1).

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 2 nodes, 1 edge

Partial Streptomyces anulatus 9663 endophenazine B biosynthesis graph for the ppzM-dependent N-methylation branch.

Subject	Predicate	Object	Notes	Evidence
PpzM	is required for formation of	endophenazine B	The genetic deletion identifies ppzM as required for formation of the N-methylated product. Because the exact methyl acceptor and in vitro coupling partner were not identified, this graph does not assert a direct isolated-substrate reaction or a Rhea ID.	DOI:10.3762/BJOC.8.57 https://www.ncbi.nlm.nih.gov/nuccore/FN178498.1 https://www.ncbi.nlm.nih.gov/protein/CAX48665.1 https://www.uniprot.org/uniparc/UPI0001A648F5 https://mibig.secondarymetabolites.org/repository/BGC0001080.5/BGC0001080.gbk reference DOI:10.3762/BJOC.8.57 evidence type PRIMARY_EXPERIMENT snippet production of endophenazine B had been abolished by the ppzM deletion notes Saleh et al. deleted ppzM from the Streptomyces anulatus 9663 endophenazine cluster in the heterologous S. coelicolor M512 ppzOS04 production system and used HPLC-ESI-MS to show that the resulting ppzOS26 strain no longer produced endophenazine B. reference https://www.ncbi.nlm.nih.gov/nuccore/FN178498.1 evidence type DATABASE_ASSERTION snippet gene="ppzM" retrieved on 2026-10-01 notes GenBank FN178498.1 maps Streptomyces anulatus 9663 ppzM to the reverse-strand 10210..11232 CDS, assigns protein_id CAX48665.1, and carries the historical UniProtKB/TrEMBL cross-reference C4PWB1. reference https://www.ncbi.nlm.nih.gov/protein/CAX48665.1 evidence type DATABASE_ASSERTION snippet putative phenazine N-methyltransferase retrieved on 2026-10-01 notes NCBI GenPept CAX48665.1 is the 340 aa Streptomyces anulatus 9663 ppzM coding sequence from FN178498.1 and is not represented by a live current UniProtKB accession. reference https://www.uniprot.org/uniparc/UPI0001A648F5 evidence type DATABASE_ASSERTION retrieved on 2026-10-23 snippet CAX48665.1 notes UniParc UPI0001A648F5 archives the exact 340 aa Streptomyces anulatus 9663 ppzM sequence (EMBL FN178498.1 reverse-strand 10210..11232, protein CAX48665.1) and records that UniProtKB/TrEMBL entry C4PWB1.1 is inactive/obsolete, confirming no active UniProtKB accession resolves for CAX48665.1. reference https://mibig.secondarymetabolites.org/repository/BGC0001080.5/BGC0001080.gbk evidence type DATABASE_ASSERTION snippet protein_id="CAX48665.1" retrieved on 2026-10-01 notes MIBiG BGC0001080.5 places ppzM at 10210..11232 on the Streptomyces anulatus endophenazine cluster and annotates the CDS as CAX48665.1 phenazine N-methyltransferase.

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

Explore across X-Mech

AntibioticMech (endophenazine B) ↗ MediaIngredientMech (naturalproductmech:mibig-4acf6c9688) ↗ 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-b.yaml, which is generated from the committed inventories. Neither is edited by hand.