pyocyanine

CHEBI:8653 EXACT SEEDED antibacterialcytotoxic

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 iminium betaine that is 5-methylphenazin-5-ium which is substituted at position 1 by an oxidanidyl group. An antibiotic pigment produced by Pseudomonas aeruginosa.

Structure

Standard InChIKey	YNCMLFHHXWETLD-UHFFFAOYSA-N
SMILES	CN1C2=CC=CC=C2N=C2C(=O)C=CC=C12
Stereochemistry	fully defined
Cross-references	npatlas:NPA0489, pubchem:6817

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
Pseudomonas aeruginosa PAO1 NCBITaxon:208964	SOURCE_ASSERTION	mibig:BGC0000936	PMID:11591691

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
Pseudomonas aeruginosa NCBITaxon:287	LOTUS	DOI:10.1084/JEM.4.5-6.627
Pseudomonas aeruginosa NCBITaxon:287	LOTUS	DOI:10.1128/JB.183.21.6454-6465.2001
Pseudomonas aeruginosa NCBITaxon:287	LOTUS	DOI:10.7164/ANTIBIOTICS.46.1232
Pseudomonas aeruginosa NCBITaxon:287	CHEBI	Z. Physiol. Chem., 1924, v140, 1

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000936	Pseudomonas aeruginosa PAO1 NCBITaxon:208964	CLUSTER_UNSTATED	genbank:AF005404.2

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	PhzM UniProtKB:Q9HWH2	RHEA:49112	CHEBI:62248 → CHEBI:62221	DOI:10.1128/JB.183.21.6454-6465.2001
2	PhzS UniProtKB:Q9HWG9	RHEA:48976	CHEBI:62221 → CHEBI:8653	DOI:10.1128/JB.183.21.6454-6465.2001

Step 1: Pseudomonas aeruginosa PAO1 PA4209/PhzM is outside the seeded BGC0000936 phzA-G phenazine-1-carboxylate core locus. RHEA:49112 captures the first tailoring step: SAM-dependent N-methylation of phenazine-1-carboxylate to 5-methyl-phenazine-1-carboxylate.

Step 2: Pseudomonas aeruginosa PAO1 PA4217/PhzS is outside the seeded BGC0000936 phzA-G phenazine-1-carboxylate core locus. RHEA:48976 captures the second tailoring step and forms CHEBI:62220 pyocyanine(1+), the conjugate acid of the seeded CHEBI:8653 pyocyanine structure.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 5 nodes, 4 edges

Partial PAO1 tailoring route from phenazine-1-carboxylate to pyocyanine through PhzM and PhzS after the BGC0000936 phzA-G core locus forms the phenazine-1-carboxylate precursor.

Subject	Predicate	Object	Notes	Evidence
phenazine-1-carboxylate	is N-methylated by	PhzM	PhzM methylates phenazine-1-carboxylate in the first step of the PhzM/PhzS coupled tailoring route to pyocyanine.	DOI:10.1128/JB.183.21.6454-6465.2001 https://www.uniprot.org/uniprotkb/Q9HWH2 https://www.rhea-db.org/rhea/49112 reference DOI:10.1128/JB.183.21.6454-6465.2001 evidence type PRIMARY_EXPERIMENT snippet SAM-dependent methyltransferase PhzM, PCA is converted to 5-methylphenazine-1-carboxylic acid betaine. notes Mavrodi et al. identified PA4209/phzM in Pseudomonas aeruginosa PAO1, inactivated phzM, restored pyocyanin production by complementation, reconstituted PCA to pyocyanin conversion with PAO1 phzM plus phzS, and ordered PhzM before PhzS by cross-feeding. reference https://www.uniprot.org/uniprotkb/Q9HWH2 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:Q9HWH2 is the Pseudomonas aeruginosa PAO1 PA4209/phzM phenazine-1-carboxylate N-methyltransferase and annotates catalytic activity RHEA:49112. reference https://www.rhea-db.org/rhea/49112 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:49112 is the phenazine-1-carboxylate plus S-adenosyl-L-methionine to 5-methyl-phenazine-1-carboxylate plus S-adenosyl-L-homocysteine reaction.
PhzM	forms	5-methyl-phenazine-1-carboxylate	5-methyl-phenazine-1-carboxylate is the unstable common intermediate produced by PhzM before PhzS decarboxylation.	DOI:10.1128/JB.183.21.6454-6465.2001 https://www.uniprot.org/uniprotkb/Q9HWH2 https://www.rhea-db.org/rhea/49112 reference DOI:10.1128/JB.183.21.6454-6465.2001 evidence type PRIMARY_EXPERIMENT snippet SAM-dependent methyltransferase PhzM, PCA is converted to 5-methylphenazine-1-carboxylic acid betaine. notes Mavrodi et al. identified PA4209/phzM in Pseudomonas aeruginosa PAO1, inactivated phzM, restored pyocyanin production by complementation, reconstituted PCA to pyocyanin conversion with PAO1 phzM plus phzS, and ordered PhzM before PhzS by cross-feeding. reference https://www.uniprot.org/uniprotkb/Q9HWH2 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:Q9HWH2 is the Pseudomonas aeruginosa PAO1 PA4209/phzM phenazine-1-carboxylate N-methyltransferase and annotates catalytic activity RHEA:49112. reference https://www.rhea-db.org/rhea/49112 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:49112 is the phenazine-1-carboxylate plus S-adenosyl-L-methionine to 5-methyl-phenazine-1-carboxylate plus S-adenosyl-L-homocysteine reaction.
5-methyl-phenazine-1-carboxylate	is hydroxylatively decarboxylated by	PhzS	PhzS consumes NADH and oxygen while decarboxylating 5-methyl-phenazine-1-carboxylate.	DOI:10.1128/JB.183.21.6454-6465.2001 https://www.uniprot.org/uniprotkb/Q9HWG9 https://www.rhea-db.org/rhea/48976 reference DOI:10.1128/JB.183.21.6454-6465.2001 evidence type PRIMARY_EXPERIMENT snippet catalyzed by the NADH (or NADPH)-dependent flavoprotein monooxygenase PhzS notes Mavrodi et al. identified PA4217/phzS in Pseudomonas aeruginosa PAO1, inactivated phzS, restored pyocyanin production by complementation, and reconstituted PCA to pyocyanin conversion with PAO1 phzM plus phzS. reference https://www.uniprot.org/uniprotkb/Q9HWG9 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:Q9HWG9 is the Pseudomonas aeruginosa PAO1 PA4217/phzS 5-methylphenazine-1-carboxylate 1-monooxygenase and annotates catalytic activity RHEA:48976. reference https://www.rhea-db.org/rhea/48976 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:48976 is the 5-methyl-phenazine-1-carboxylate plus NADH plus O2 to pyocyanin, CO2, NAD(+), and H2O reaction; its CHEBI:62220 pyocyanine(1+) product is the conjugate acid of this record's CHEBI:8653 pyocyanine.
PhzS	forms	pyocyanine	RHEA:48976 represents the immediate product as the CHEBI:62220 protonation state; CHEBI:62220 is the conjugate acid of CHEBI:8653.	DOI:10.1128/JB.183.21.6454-6465.2001 https://www.uniprot.org/uniprotkb/Q9HWG9 https://www.rhea-db.org/rhea/48976 reference DOI:10.1128/JB.183.21.6454-6465.2001 evidence type PRIMARY_EXPERIMENT snippet catalyzed by the NADH (or NADPH)-dependent flavoprotein monooxygenase PhzS notes Mavrodi et al. identified PA4217/phzS in Pseudomonas aeruginosa PAO1, inactivated phzS, restored pyocyanin production by complementation, and reconstituted PCA to pyocyanin conversion with PAO1 phzM plus phzS. reference https://www.uniprot.org/uniprotkb/Q9HWG9 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes Reviewed UniProtKB:Q9HWG9 is the Pseudomonas aeruginosa PAO1 PA4217/phzS 5-methylphenazine-1-carboxylate 1-monooxygenase and annotates catalytic activity RHEA:48976. reference https://www.rhea-db.org/rhea/48976 evidence type DATABASE_ASSERTION retrieved on 2026-10-01 notes RHEA:48976 is the 5-methyl-phenazine-1-carboxylate plus NADH plus O2 to pyocyanin, CO2, NAD(+), and H2O reaction; its CHEBI:62220 pyocyanine(1+) product is the conjugate acid of this record's CHEBI:8653 pyocyanine.

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

Bioactivities 2

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
NCI Yeast Anticancer Drug Screen. Data for the mlh1 rad18 strain	ACTIVE	Not recorded	pubchem.aid:175 assay NCI Yeast Anticancer Drug Screen. Data for the mlh1 rad18 strain evidence reference pubchem.aid:175 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 175, deposited by DTP/NCI; assay type Other. call ACTIVE activity class CYTOTOXIC
NCI Yeast Anticancer Drug Screen. Data for the rad50 strain	ACTIVE	Not recorded	pubchem.aid:155 assay NCI Yeast Anticancer Drug Screen. Data for the rad50 strain evidence reference pubchem.aid:155 evidence type DATABASE_ASSERTION notes PubChem BioAssay AID 155, deposited by DTP/NCI; assay type Other. call ACTIVE activity class CYTOTOXIC

Elsewhere in the fleet

AntibioticMech — CHEBI:8653 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (pyocyanine) ↗ MediaIngredientMech (CHEBI:8653) ↗ TaxonMech: Pseudomonas aeruginosa PAO1 (NCBITaxon:208964) ↗ PathwayMech (mibig:BGC0000936) ↗

Provenance

Source concept	Source	Version
BGC0000936	MIBIG	5
CHEBI:8653	CHEBI	3-star

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