Kutzneride 2

naturalproductmech:mibig-c7ae5d3088 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	GOUIVYIRLLTNCF-JJMZTBTASA-N
SMILES	CC1(CC1)[C@@H]2C(=O)O[C@H](C(=O)N3[C@@H](C[C@H](CN3)Cl)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N4[C@@H](C[C@@]5([C@H]4NC6=C5C=CC(=C6Cl)Cl)O)C(=O)N2)[C@H](CC(=O)O)O)COC)C(C)(C)C
Stereochemistry	fully defined
Cross-references	npatlas:NPA015447

Filing pathway

Unclassified — 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
Kutzneria sp. 744 NCBITaxon:345341	SOURCE_ASSERTION	mibig:BGC0000378	DOI:10.1021/np050378g

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
Kutzneria NCBITaxon:43356	LOTUS	DOI:10.1021/NP050378G
Kutzneria NCBITaxon:43356	LOTUS	DOI:10.1021/NP0604331

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000378	Kutzneria sp. 744 NCBITaxon:345341	CLUSTER_UNSTATED	genbank:EU074211.1

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	KtzQ tryptophan 7-halogenase UniProtKB:A8CF75	RHEA:26494	CHEBI:57912 + CHEBI:58307 + CHEBI:17996 + CHEBI:15379 → CHEBI:58713 + CHEBI:57692 + CHEBI:15377	DOI:10.1021/ja806467a
2	KtzR 7-chloro-L-tryptophan 6-halogenase UniProtKB:A8CF74	RHEA:55904	CHEBI:58713 + CHEBI:58307 + CHEBI:17996 + CHEBI:15379 → CHEBI:139336 + CHEBI:57692 + CHEBI:15377	DOI:10.1021/ja806467a

Step 1: KtzQ catalyzes the first tandem halogenase step in the kutzneride pathway, forming 7-chloro-L-tryptophan from free L-tryptophan before KtzR installs the 6-chlorine in a separate downstream step.

Step 2: KtzR catalyzes the second tandem halogenase step in the kutzneride pathway, installing the 6-chlorine on 7-chloro-L-tryptophan to form 6,7-dichloro-L-tryptophan.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 3 nodes, 2 edges

Kutzneria sp. 744 KtzQ-catalyzed 7-chlorination of L-tryptophan in the early kutzneride dichlorotryptophan biosynthetic pathway.

Subject	Predicate	Object	Notes	Evidence
L-tryptophan	is 7-chlorinated by	KtzQ tryptophan 7-halogenase	KtzQ accepts free L-tryptophan as its first substrate in the tandem KtzQ/KtzR halogenation sequence. KtzS supplies reduced flavin for catalysis; that partner is outside this KtzQ-specific graph.	DOI:10.1021/ja806467a https://mite.bioinformatics.nl/repository/MITE0000029 https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk https://www.uniprot.org/uniprotkb/A8CF75 https://www.ncbi.nlm.nih.gov/protein/ABV56597.1 reference DOI:10.1021/ja806467a evidence type PRIMARY_EXPERIMENT snippet KtzQ (along with the flavin reductase KtzS) acts first to chlorinate at the 7-position of L-tryptophan notes Heemstra and Walsh identified KtzQ as the first tryptophan halogenase in kutzneride biosynthesis, assayed the purified enzyme with KtzS, and showed that it forms 7-chloro-L-tryptophan from free L-tryptophan. reference https://mite.bioinformatics.nl/repository/MITE0000029 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000029 is active, assigns KtzQ to the in vitro-supported C7 chlorination of L-tryptophan to 7-chlorotryptophan, records RHEA:26494 and EC:1.14.19.9 for the reaction, and links KtzQ to UniProtKB:A8CF75, GenPept ABV56597.1 and MIBiG BGC0000378. reference https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk evidence type DATABASE_ASSERTION snippet MITE0000029: Halogenation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000378.5 places ktzQ/ABV56597.1 inside the active Kutzneria sp. 744 kutzneride biosynthetic gene cluster as a Trp_halogenase locus with a MITE0000029 halogenation annotation. reference https://www.uniprot.org/uniprotkb/A8CF75 evidence type DATABASE_ASSERTION snippet GN Name=ktzQ retrieved on 2026-10-02 notes Current reviewed UniProtKB:A8CF75 resolves as the Kutzneria sp. strain 744 Tryptophan 7-halogenase KtzQ entry, cross-references EMBL EU074211 protein ABV56597.1, and annotates the RHEA:26494 / EC:1.14.19.9 L-tryptophan 7-halogenase catalytic activity. reference https://www.ncbi.nlm.nih.gov/protein/ABV56597.1 evidence type DATABASE_ASSERTION snippet KtzQ [Kutzneria sp. 744] retrieved on 2026-10-02 notes NCBI Protein ABV56597.1 is the 533 aa Kutzneria sp. 744 KtzQ protein encoded by ktzQ at EU074211.1:11603..13204.
KtzQ tryptophan 7-halogenase	forms	7-chloro-L-tryptophan	KtzQ produces 7-chloro-L-tryptophan for the downstream KtzR 6-chlorination step toward 6,7-dichloro-L-tryptophan.	DOI:10.1021/ja806467a https://mite.bioinformatics.nl/repository/MITE0000029 https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk https://www.uniprot.org/uniprotkb/A8CF75 https://www.ncbi.nlm.nih.gov/protein/ABV56597.1 reference DOI:10.1021/ja806467a evidence type PRIMARY_EXPERIMENT snippet KtzQ (along with the flavin reductase KtzS) acts first to chlorinate at the 7-position of L-tryptophan notes Heemstra and Walsh identified KtzQ as the first tryptophan halogenase in kutzneride biosynthesis, assayed the purified enzyme with KtzS, and showed that it forms 7-chloro-L-tryptophan from free L-tryptophan. reference https://mite.bioinformatics.nl/repository/MITE0000029 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000029 is active, assigns KtzQ to the in vitro-supported C7 chlorination of L-tryptophan to 7-chlorotryptophan, records RHEA:26494 and EC:1.14.19.9 for the reaction, and links KtzQ to UniProtKB:A8CF75, GenPept ABV56597.1 and MIBiG BGC0000378. reference https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk evidence type DATABASE_ASSERTION snippet MITE0000029: Halogenation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000378.5 places ktzQ/ABV56597.1 inside the active Kutzneria sp. 744 kutzneride biosynthetic gene cluster as a Trp_halogenase locus with a MITE0000029 halogenation annotation. reference https://www.uniprot.org/uniprotkb/A8CF75 evidence type DATABASE_ASSERTION snippet GN Name=ktzQ retrieved on 2026-10-02 notes Current reviewed UniProtKB:A8CF75 resolves as the Kutzneria sp. strain 744 Tryptophan 7-halogenase KtzQ entry, cross-references EMBL EU074211 protein ABV56597.1, and annotates the RHEA:26494 / EC:1.14.19.9 L-tryptophan 7-halogenase catalytic activity. reference https://www.ncbi.nlm.nih.gov/protein/ABV56597.1 evidence type DATABASE_ASSERTION snippet KtzQ [Kutzneria sp. 744] retrieved on 2026-10-02 notes NCBI Protein ABV56597.1 is the 533 aa Kutzneria sp. 744 KtzQ protein encoded by ktzQ at EU074211.1:11603..13204.

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

Causal graph — biosynthesis 3 nodes, 2 edges

Kutzneria sp. 744 KtzR-catalyzed 6-chlorination of 7-chloro-L-tryptophan in the early kutzneride dichlorotryptophan biosynthetic pathway.

Subject	Predicate	Object	Notes	Evidence
7-chloro-L-tryptophan	is 6-chlorinated by	KtzR 7-chloro-L-tryptophan 6-halogenase	KtzR uses the KtzQ product 7-chloro-L-tryptophan as its preferred substrate in the tandem KtzQ/KtzR halogenation sequence.	DOI:10.1021/ja806467a https://mite.bioinformatics.nl/repository/MITE0000030 https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk https://www.uniprot.org/uniprotkb/A8CF74 https://www.ncbi.nlm.nih.gov/protein/ABV56598.1 reference DOI:10.1021/ja806467a evidence type PRIMARY_EXPERIMENT snippet KtzR, with a 120 fold preference for 7-chloro-L-tryptophan over L-tryptophan, then installs the second chlorine at the 6-position notes Heemstra and Walsh identified KtzR as the second tandem tryptophan halogenase in kutzneride biosynthesis, assayed the purified enzyme with KtzS, and showed that the enzyme 6-chlorinates 7-chloro-L-tryptophan. reference https://mite.bioinformatics.nl/repository/MITE0000030 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000030 is active, assigns KtzR to the in vitro-supported C6 chlorination of 7-Cl-L-tryptophan to 6,7-diCl-L-Trp, records RHEA:55904 and EC:1.14.19.60 for the reaction, and links KtzR to UniProtKB:A8CF74, GenPept ABV56598.1 and MIBiG BGC0000378. reference https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk evidence type DATABASE_ASSERTION snippet MITE0000030: Halogenation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000378.5 places ktzR/ABV56598.1 inside the active Kutzneria sp. 744 kutzneride biosynthetic gene cluster as a Trp_halogenase locus with a MITE0000030 halogenation annotation. reference https://www.uniprot.org/uniprotkb/A8CF74 evidence type DATABASE_ASSERTION snippet GN Name=ktzR retrieved on 2026-10-02 notes Current reviewed UniProtKB:A8CF74 resolves as the Kutzneria sp. strain 744 7-chloro-L-tryptophan 6-halogenase KtzR entry, cross-references EMBL EU074211 protein ABV56598.1, and annotates the RHEA:55904 / EC:1.14.19.60 7-chloro-L-tryptophan 6-halogenase catalytic activity. reference https://www.ncbi.nlm.nih.gov/protein/ABV56598.1 evidence type DATABASE_ASSERTION snippet KtzR [Kutzneria sp. 744] retrieved on 2026-10-02 notes NCBI Protein ABV56598.1 is the Kutzneria sp. 744 KtzR protein encoded by ktzR at EU074211.1:9791..11308.
KtzR 7-chloro-L-tryptophan 6-halogenase	forms	6,7-dichloro-L-tryptophan	KtzR installs the second chlorine at the 6-position, forming the dichlorinated tryptophan precursor for kutzneride assembly.	DOI:10.1021/ja806467a https://mite.bioinformatics.nl/repository/MITE0000030 https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk https://www.uniprot.org/uniprotkb/A8CF74 https://www.ncbi.nlm.nih.gov/protein/ABV56598.1 reference DOI:10.1021/ja806467a evidence type PRIMARY_EXPERIMENT snippet KtzR, with a 120 fold preference for 7-chloro-L-tryptophan over L-tryptophan, then installs the second chlorine at the 6-position notes Heemstra and Walsh identified KtzR as the second tandem tryptophan halogenase in kutzneride biosynthesis, assayed the purified enzyme with KtzS, and showed that the enzyme 6-chlorinates 7-chloro-L-tryptophan. reference https://mite.bioinformatics.nl/repository/MITE0000030 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000030 is active, assigns KtzR to the in vitro-supported C6 chlorination of 7-Cl-L-tryptophan to 6,7-diCl-L-Trp, records RHEA:55904 and EC:1.14.19.60 for the reaction, and links KtzR to UniProtKB:A8CF74, GenPept ABV56598.1 and MIBiG BGC0000378. reference https://mibig.secondarymetabolites.org/repository/BGC0000378.5/BGC0000378.gbk evidence type DATABASE_ASSERTION snippet MITE0000030: Halogenation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000378.5 places ktzR/ABV56598.1 inside the active Kutzneria sp. 744 kutzneride biosynthetic gene cluster as a Trp_halogenase locus with a MITE0000030 halogenation annotation. reference https://www.uniprot.org/uniprotkb/A8CF74 evidence type DATABASE_ASSERTION snippet GN Name=ktzR retrieved on 2026-10-02 notes Current reviewed UniProtKB:A8CF74 resolves as the Kutzneria sp. strain 744 7-chloro-L-tryptophan 6-halogenase KtzR entry, cross-references EMBL EU074211 protein ABV56598.1, and annotates the RHEA:55904 / EC:1.14.19.60 7-chloro-L-tryptophan 6-halogenase catalytic activity. reference https://www.ncbi.nlm.nih.gov/protein/ABV56598.1 evidence type DATABASE_ASSERTION snippet KtzR [Kutzneria sp. 744] retrieved on 2026-10-02 notes NCBI Protein ABV56598.1 is the Kutzneria sp. 744 KtzR protein encoded by ktzR at EU074211.1:9791..11308.

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

Explore across X-Mech

AntibioticMech (Kutzneride 2) ↗ MediaIngredientMech (naturalproductmech:mibig-c7ae5d3088) ↗ TaxonMech: Kutzneria sp. 744 (NCBITaxon:345341) ↗ PathwayMech (mibig:BGC0000378) ↗

Provenance

Source concept	Source	Version
BGC0000378	MIBIG	5

This page is generated from data/natural_products/unclassified/kutzneride-2.yaml, which is generated from the committed inventories. Neither is edited by hand.