NaturalProductMech

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dixiamycin A

naturalproductmech:mibig-abcb3d7c73 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 InChIKeyCPQSJHUUXUXWOT-IPPPMHIGSA-N
SMILESC[C@]12CC[C@@H]([C@@]([C@@H]1CCC3=CC4=C(C=C23)C5=CC=CC=C5N4N6C7=CC=CC=C7C8=C6C=C9CC[C@@H]1[C@@](C9=C8)(CC[C@@H]([C@@]1(C)C(=O)O)O)C)(C)C(=O)O)O
Stereochemistryfully defined

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 terpene, other, 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.

TaxonBasisClusterEvidence
Streptomyces sp. HKI0576
NCBITaxon:995841		 BGC_CHARACTERIZED mibig:BGC0000665 DOI:10.1002/anie.201204087
Streptomyces sp. HKI0576
NCBITaxon:995841		 BGC_CHARACTERIZED mibig:BGC0000665 DOI:10.1002/anie.201204087

Occurrences 3

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.

TaxonSourceReference
Streptomyces xinghaiensis
NCBITaxon:1038928		 LOTUS DOI:10.1007/S00253-018-9337-2
Streptomyces
NCBITaxon:1883		 LOTUS DOI:10.1002/ANIE.201204087
Streptomyces
NCBITaxon:1883		 LOTUS DOI:10.1002/EJOC.201200599

Biosynthetic gene clusters 2

AccessionHostLocus evidenceGenome
mibig:BGC0000665 Streptomyces sp. HKI0576
NCBITaxon:995841 		CLUSTER_DEMONSTRATED genbank:HE815466.1
mibig:BGC0000665 Streptomyces sp. HKI0576
NCBITaxon:995841 		CLUSTER_DEMONSTRATED genbank:HE815466.1

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.

StepEnzymeReactionSubstrate → productEvidence
1 XiaH aryl-coupling flavoprotein
NCBIProtein:CCH63734.1		 ungrounded → ungrounded DOI:10.1002/anie.201303733

Step 1: This proposed pathway entry captures Streptomyces sp. HKI0576 xiaH/CCH63734.1 as the BGC0000665 aryl-coupling flavoprotein that forms the N-N-linked dixiamycin scaffold. The immediate xiamycin monomer and the atropodiastereomer branch between dixiamycin A and B are left unexpanded. XiaH is grounded on enzyme_id and in the causal graph to the native GenPept accession NCBIProtein:CCH63734.1 because UniParc UPI0002777695 maps only to retired/obsolete UniProtKB/TrEMBL entries I7JVY9.1 and A0A0P0HXR3.1 with no active UniProtKB accession.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 2 producers (2 causal) 3 cited occurrences BIOSYNTHETIC LOCUS 2 gene clusters 1 curated pathway step NATURAL PRODUCT dixiamycin A naturalproductmech:mibig-abcb3d7c73 Alkaloids TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 1 graph

Causal graph — biosynthesis 3 nodes, 2 edges

Partial Streptomyces sp. HKI0576 dixiamycin A biosynthesis graph for XiaH-mediated aryl coupling of xiamycin-type indoloterpenes.

SubjectPredicateObjectNotesEvidence
xiamycin-type indoloterpene monomers are aryl-coupled by XiaH This edge captures only the XiaH aryl-coupling branch toward dixiamycins; upstream xiamycin biosynthesis by the same cluster is left unexpanded.
DOI:10.1002/anie.201303733
https://mibig.secondarymetabolites.org/repository/BGC0000665.5/index.html
https://mibig.secondarymetabolites.org/repository/BGC0000665.5/BGC0000665.gbk
https://www.ncbi.nlm.nih.gov/protein/CCH63734.1
https://www.uniprot.org/uniparc/UPI0002777695
  • reference
    DOI:10.1002/anie.201303733
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Regiodivergent N-C and N-N Aryl Coupling Reactions of Indoloterpenes
    notes
    Baunach et al. assigned the HKI0576 xiamycin flavoenzyme XiaH as an aryl-coupling enzyme for N-N-linked dixiamycin formation.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000665.5/index.html
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    MIBiG BGC0000665.5 lists dixiamycin A and dixiamycin B as products of the HE815466.1 Streptomyces sp. HKI0576 xiamycin cluster.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000665.5/BGC0000665.gbk
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    The official MIBiG BGC0000665.5 GenBank summary annotates xiaH as HE815466.1:7534..9327 on the reverse strand with GenPept product CCH63734.1.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/CCH63734.1
    evidence type
    DATABASE_ASSERTION
    snippet
    XiaH protein
    retrieved on
    2026-09-27
    notes
    NCBI GenPept CCH63734.1 is the 597 aa xiaH coding sequence from the Streptomyces sp. HKI0576 HE815466.1 indolosesquiterpenoid cluster. UniProtKB currently has no exact entry for this GenPept or EMBL accession.
  • reference
    https://www.uniprot.org/uniparc/UPI0002777695
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-23
    snippet
    CCH63734.1
    notes
    UniParc UPI0002777695 archives the exact 597 aa Streptomyces sp. HKI0576 xiaH sequence (EMBL HE815466.1:7534..9327 reverse strand, protein CCH63734.1) and records that UniProtKB/TrEMBL entries I7JVY9.1 and A0A0P0HXR3.1 are inactive/obsolete, confirming no active UniProtKB accession resolves for CCH63734.1.
XiaH forms N-N-linked dixiamycin A The record represents the Standard InChIKey shared by the MIBiG dixiamycin A and dixiamycin B rows from BGC0000665.
DOI:10.1002/anie.201303733
https://mibig.secondarymetabolites.org/repository/BGC0000665.5/index.html
https://mibig.secondarymetabolites.org/repository/BGC0000665.5/BGC0000665.gbk
https://www.ncbi.nlm.nih.gov/protein/CCH63734.1
https://www.uniprot.org/uniparc/UPI0002777695
  • reference
    DOI:10.1002/anie.201303733
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Regiodivergent N-C and N-N Aryl Coupling Reactions of Indoloterpenes
    notes
    Baunach et al. assigned the HKI0576 xiamycin flavoenzyme XiaH as an aryl-coupling enzyme for N-N-linked dixiamycin formation.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000665.5/index.html
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    MIBiG BGC0000665.5 lists dixiamycin A and dixiamycin B as products of the HE815466.1 Streptomyces sp. HKI0576 xiamycin cluster.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000665.5/BGC0000665.gbk
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-27
    notes
    The official MIBiG BGC0000665.5 GenBank summary annotates xiaH as HE815466.1:7534..9327 on the reverse strand with GenPept product CCH63734.1.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/CCH63734.1
    evidence type
    DATABASE_ASSERTION
    snippet
    XiaH protein
    retrieved on
    2026-09-27
    notes
    NCBI GenPept CCH63734.1 is the 597 aa xiaH coding sequence from the Streptomyces sp. HKI0576 HE815466.1 indolosesquiterpenoid cluster. UniProtKB currently has no exact entry for this GenPept or EMBL accession.
  • reference
    https://www.uniprot.org/uniparc/UPI0002777695
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-23
    snippet
    CCH63734.1
    notes
    UniParc UPI0002777695 archives the exact 597 aa Streptomyces sp. HKI0576 xiaH sequence (EMBL HE815466.1:7534..9327 reverse strand, protein CCH63734.1) and records that UniProtKB/TrEMBL entries I7JVY9.1 and A0A0P0HXR3.1 are inactive/obsolete, confirming no active UniProtKB accession resolves for CCH63734.1.

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

Explore across X-Mech

AntibioticMech (dixiamycin A) ↗ MediaIngredientMech (naturalproductmech:mibig-abcb3d7c73) ↗ TaxonMech: Streptomyces sp. HKI0576 (NCBITaxon:995841) ↗ TaxonMech: Streptomyces sp. HKI0576 (NCBITaxon:995841) ↗ PathwayMech (mibig:BGC0000665) ↗ PathwayMech (mibig:BGC0000665) ↗

Provenance

Source conceptSourceVersion
BGC0000665MIBIG5
BGC0000665MIBIG5

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