alazopeptin

naturalproductmech:mibig-7a2a294289 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	LYUGICBKRYXVHJ-UHFFFAOYSA-N
SMILES	C=CCNC(CCC(=O)C=[N+]=[N-])C(=O)NC(CCC(=O)C=[N+]=[N-])C(=O)O
Stereochemistry	undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers
Cross-references	npatlas:NPA033438

Filing pathway

Amino acids and peptides — 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 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
Streptacidiphilus griseoplanus NCBITaxon:66896	SOURCE_ASSERTION	mibig:BGC0002458	PMID:33624374
Kitasatospora azatica KCTC 9699 NCBITaxon:1449346	SOURCE_ASSERTION	mibig:BGC0002536	DOI:10.1038/ja.2008.83

Occurrences 0

None cited.

Biosynthetic gene clusters 2

Accession	Host	Locus evidence	Genome
mibig:BGC0002458	Streptacidiphilus griseoplanus NCBITaxon:66896	CLUSTER_DEMONSTRATED	genbank:LC593326.1
mibig:BGC0002536	Kitasatospora azatica KCTC 9699 NCBITaxon:1449346	CLUSTER_DEMONSTRATED	genbank:NZ_JQMO01000003.1

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	AzpE EC:1.14.13.248	RHEA:69008	CHEBI:29991 → CHEBI:180682	DOI:10.1002/anie.202100462
2	AzpD EC:4.3.99.5	RHEA:69044	CHEBI:180682 → CHEBI:16301	DOI:10.1002/anie.202100462

Step 1: AzpE is annotated as the Streptacidiphilus griseoplanus JCM 4300 BGC0002458 aspartate monooxygenase. The exact BCN13467.1 protein does not currently resolve as a UniProtKB entry, so this partial alazopeptin nitrite-supply step grounds the reaction class by EC and Rhea while grounding the AzpE causal-graph enzyme node to the native GenPept accession NCBIProtein:BCN13467.1 (not indexed in UniProtKB or UniParc).

Step 2: AzpD is annotated as the Streptacidiphilus griseoplanus JCM 4300 BGC0002458 nitrosuccinate lyase. The exact BCN13466.1 protein does not currently resolve as a UniProtKB entry, so this partial alazopeptin nitrite-supply step grounds the reaction class by EC and Rhea while grounding the AzpD causal-graph enzyme node to the native GenPept accession NCBIProtein:BCN13466.1 (not indexed in UniProtKB or UniParc).

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 5 nodes, 4 edges

Partial Streptacidiphilus griseoplanus alazopeptin biosynthesis graph for the BGC0002458 AzpE/AzpD ANS-module reactions that convert L-aspartate to nitrite for downstream diazotization.

Subject	Predicate	Object	Notes	Evidence
L-aspartate	is oxidized by	AzpE	RHEA:69008 also consumes NADPH, O2, and protons and releases NADP(+) and water.	DOI:10.1002/anie.202100462 https://www.ncbi.nlm.nih.gov/protein/BCN13467.1 RHEA:69008 reference DOI:10.1002/anie.202100462 evidence type PRIMARY_EXPERIMENT snippet gene inactivation and in vitro analysis of recombinant enzymes notes Kawai et al. reported the complete Streptacidiphilus griseoplanus alazopeptin pathway; this curation uses the BGC0002458 ANS module that supplies nitrite for diazotization but leaves downstream AzpL and NRPS steps uncurated. reference https://www.ncbi.nlm.nih.gov/protein/BCN13467.1 evidence type DATABASE_ASSERTION snippet aspartate monooxygenase retrieved on 2026-09-28 notes NCBI GenPept BCN13467.1 is the LC593326.1 azpE coding sequence; exact UniProtKB searches for BCN13467 returned no matching entry; exact UniParc queries for BCN13467.1 and LC593326 on 2026-10-23 also returned no indexed entry, grounding the AzpE enzyme node as NCBIProtein:BCN13467.1. reference RHEA:69008 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes Rhea maps EC:1.14.13.248 to L-aspartate conversion to 2-nitrobutanedioate and annotates ChEBI participants CHEBI:29991 and CHEBI:180682.
AzpE	forms	2-nitrobutanedioate	The EC/Rhea-grounded product of the annotated AzpE aspartate monooxygenase reaction is 2-nitrobutanedioate.	DOI:10.1002/anie.202100462 https://www.ncbi.nlm.nih.gov/protein/BCN13467.1 RHEA:69008 reference DOI:10.1002/anie.202100462 evidence type PRIMARY_EXPERIMENT snippet gene inactivation and in vitro analysis of recombinant enzymes notes Kawai et al. reported the complete Streptacidiphilus griseoplanus alazopeptin pathway; this curation uses the BGC0002458 ANS module that supplies nitrite for diazotization but leaves downstream AzpL and NRPS steps uncurated. reference https://www.ncbi.nlm.nih.gov/protein/BCN13467.1 evidence type DATABASE_ASSERTION snippet aspartate monooxygenase retrieved on 2026-09-28 notes NCBI GenPept BCN13467.1 is the LC593326.1 azpE coding sequence; exact UniProtKB searches for BCN13467 returned no matching entry; exact UniParc queries for BCN13467.1 and LC593326 on 2026-10-23 also returned no indexed entry, grounding the AzpE enzyme node as NCBIProtein:BCN13467.1. reference RHEA:69008 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes Rhea maps EC:1.14.13.248 to L-aspartate conversion to 2-nitrobutanedioate and annotates ChEBI participants CHEBI:29991 and CHEBI:180682.
2-nitrobutanedioate	is cleaved by	AzpD	RHEA:69044 places 2-nitrobutanedioate upstream of nitrite in the EC:4.3.99.5 reaction.	DOI:10.1002/anie.202100462 https://www.ncbi.nlm.nih.gov/protein/BCN13466.1 RHEA:69044 reference DOI:10.1002/anie.202100462 evidence type PRIMARY_EXPERIMENT snippet Complete Biosynthetic Pathway of Alazopeptin notes Kawai et al. reported the complete Streptacidiphilus griseoplanus alazopeptin pathway; this curation uses the BGC0002458 ANS module that supplies nitrite for diazotization but leaves downstream AzpL and NRPS steps uncurated. reference https://www.ncbi.nlm.nih.gov/protein/BCN13466.1 evidence type DATABASE_ASSERTION snippet nitrosuccinate lyase retrieved on 2026-09-28 notes NCBI GenPept BCN13466.1 is the LC593326.1 azpD coding sequence; exact UniProtKB searches for BCN13466 returned no matching entry; exact UniParc queries for BCN13466.1 and LC593326 on 2026-10-23 also returned no indexed entry, grounding the AzpD enzyme node as NCBIProtein:BCN13466.1. reference RHEA:69044 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes Rhea maps EC:4.3.99.5 to 2-nitrobutanedioate cleavage to fumarate, nitrite, and a proton and annotates ChEBI participants CHEBI:180682, CHEBI:29806, CHEBI:16301, and CHEBI:15378.
AzpD	forms	nitrite	The AzpD-associated Rhea reaction also releases fumarate and a proton.	DOI:10.1002/anie.202100462 https://www.ncbi.nlm.nih.gov/protein/BCN13466.1 RHEA:69044 reference DOI:10.1002/anie.202100462 evidence type PRIMARY_EXPERIMENT snippet Complete Biosynthetic Pathway of Alazopeptin notes Kawai et al. reported the complete Streptacidiphilus griseoplanus alazopeptin pathway; this curation uses the BGC0002458 ANS module that supplies nitrite for diazotization but leaves downstream AzpL and NRPS steps uncurated. reference https://www.ncbi.nlm.nih.gov/protein/BCN13466.1 evidence type DATABASE_ASSERTION snippet nitrosuccinate lyase retrieved on 2026-09-28 notes NCBI GenPept BCN13466.1 is the LC593326.1 azpD coding sequence; exact UniProtKB searches for BCN13466 returned no matching entry; exact UniParc queries for BCN13466.1 and LC593326 on 2026-10-23 also returned no indexed entry, grounding the AzpD enzyme node as NCBIProtein:BCN13466.1. reference RHEA:69044 evidence type DATABASE_ASSERTION retrieved on 2026-09-28 notes Rhea maps EC:4.3.99.5 to 2-nitrobutanedioate cleavage to fumarate, nitrite, and a proton and annotates ChEBI participants CHEBI:180682, CHEBI:29806, CHEBI:16301, and CHEBI:15378.

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

Explore across X-Mech

AntibioticMech (alazopeptin) ↗ MediaIngredientMech (naturalproductmech:mibig-7a2a294289) ↗ TaxonMech: Streptacidiphilus griseoplanus (NCBITaxon:66896) ↗ TaxonMech: Kitasatospora azatica KCTC 9699 (NCBITaxon:1449346) ↗ PathwayMech (mibig:BGC0002458) ↗ PathwayMech (mibig:BGC0002536) ↗

Open questions 1

shared-structure — This structure is reported by more than one MIBiG entry: BGC0002458, BGC0002536. Confirm they describe the same compound rather than an upstream cross-reference error.

Provenance

Source concept	Source	Version
BGC0002458	MIBIG	3
BGC0002536	MIBIG	3

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