microbisporicin A2

naturalproductmech:mibig-b546b14194 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	MXXHBKLVTYBKIT-WCMIHIHVSA-N
SMILES	O=C(N[C@H](C(NC(C(N[C@H](C(N[C@H](C(N[C@H]([C@H](C)SC[C@@H](C(N[C@H]([C@H](O)C)C(N[C@@H](C(N1[C@H]2[C@@H](O)CC1)=O)CSC[C@H](NC([C@H](CC(N)=O)NC([C@H](NC(CNC(CNC(CNC2=O)=O)=O)=O)CSC[C@@H](C(N/C=C\SC3)=O)NC4=O)=O)=O)C(N[C@@H]3C(N[C@@H]4CC5=CC=CC=C5)=O)=O)=O)=O)NC6=O)C(N7[C@H](C(NC6)=O)CCC7)=O)=O)CSC8)=O)CC(C)C)=O)=C)=O)CC9=CNC%10=C9C=C(Cl)C=C%10)[C@@H]8NC(/C(NC([C@H](C(C)C)N)=O)=C/C)=O
Stereochemistry	fully defined

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 ribosomal, 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
Microbispora corallina NCBITaxon:83302	BGC_CHARACTERIZED	mibig:BGC0000529	PMID:20628010

Occurrences 0

None cited.

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000529	Microbispora corallina NCBITaxon:83302	CLUSTER_DEMONSTRATED	genbank:HM536998.1

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	MibH tryptophan-5-halogenase with MibS flavin reductase UniProtKB:E2IHC5		ungrounded → naturalproductmech:mibig-b546b14194	DOI:10.1021/acschembio.6b01031

Step 1: MibH catalyzes the terminal FADH2-dependent chlorination of deschloro-microbisporicin A2 to microbisporicin A2; auxiliary MibS supplies reduced flavin to MibH in the reconstituted in vitro reaction.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Partial Microbispora corallina microbisporicin A2 biosynthesis graph for MibH/MibS-catalyzed terminal chlorination of deschloro-microbisporicin A2.

Subject	Predicate	Object	Notes	Evidence
deschloro-microbisporicin A2	is 5-chlorinated by	MibH tryptophan-5-halogenase	MibH chlorinates the tryptophan residue embedded in deschloro-microbisporicin A2 and shows no detectable activity on free tryptophan.	DOI:10.1021/acschembio.6b01031 https://mite.lisc.univie.ac.at/repository/MITE0000054 https://www.ncbi.nlm.nih.gov/nuccore/HM536998.1 https://mibig.secondarymetabolites.org/repository/BGC0000529.5/BGC0000529.gbk https://www.uniprot.org/uniprotkb/E2IHC5 reference DOI:10.1021/acschembio.6b01031 evidence type PRIMARY_EXPERIMENT snippet MibH was only active when Trp was embedded within its cognate peptide substrate deschloro NAI-107 notes Ortega et al. reconstituted Microbispora corallina MibH/MibS in vitro and showed LC/ESI-MS formation of a chlorinated product from deschloromicrobisporicin only when both MibH and MibS were present. reference https://mite.lisc.univie.ac.at/repository/MITE0000054 evidence type DATABASE_ASSERTION snippet Flavin-dependent tryptophan-5-halogenase catalyzed halogenation reaction of deschloro-microbisporicin A2 retrieved on 2026-10-01 notes MITE0000054 is an active entry for Microbispora corallina MibH/E2IHC5, links GenPept ADK32563.1, MIBiG BGC0000529 and auxiliary MibS/E2IHC6, and records chlorination of deschloro-microbisporicin A2 to the mature product. reference https://www.ncbi.nlm.nih.gov/nuccore/HM536998.1 evidence type DATABASE_ASSERTION snippet protein_id="ADK32563.1" retrieved on 2026-10-01 notes GenBank HM536998.1 is the Microbispora corallina microbisporicin cluster sequence and maps mibH to ADK32563.1. reference https://mibig.secondarymetabolites.org/repository/BGC0000529.5/BGC0000529.gbk evidence type DATABASE_ASSERTION snippet MITE0000054: Halogenation (100% identity) retrieved on 2026-10-01 notes MIBiG BGC0000529.5 places mibH/ADK32563.1 inside the active microbisporicin A2 cluster and annotates the mibH CDS with MITE0000054. reference https://www.uniprot.org/uniprotkb/E2IHC5 evidence type DATABASE_ASSERTION snippet GN=mibH retrieved on 2026-10-01 notes Current unreviewed UniProtKB:E2IHC5 resolves as Microbispora corallina MibH tryptophan-5-halogenase, cross-references EMBL HM536998 protein ADK32563.1, and is sequence-identical to GenPept ADK32563.1.
MibS flavin reductase	provides reduced flavin to	MibH tryptophan-5-halogenase	MibS functions as the flavin reductase partner for the MibH-dependent chlorination of deschloro-microbisporicin A2.	DOI:10.1021/acschembio.6b01031 https://mite.lisc.univie.ac.at/repository/MITE0000054 https://www.ncbi.nlm.nih.gov/nuccore/HM536998.1 https://mibig.secondarymetabolites.org/repository/BGC0000529.5/BGC0000529.gbk https://www.uniprot.org/uniprotkb/E2IHC6 reference DOI:10.1021/acschembio.6b01031 evidence type PRIMARY_EXPERIMENT snippet MibH and MibS form an FAD-dependent halogenase system notes Ortega et al. reconstituted chlorination of deschloromicrobisporicin with MibH, MibS, FAD, NADH and NaCl, and did not observe the chlorinated product when MibS or MibH was omitted. reference https://mite.lisc.univie.ac.at/repository/MITE0000054 evidence type DATABASE_ASSERTION snippet Flavin-dependent tryptophan-5-halogenase catalyzed halogenation reaction of deschloro-microbisporicin A2 retrieved on 2026-10-01 notes MITE0000054 is an active entry for Microbispora corallina MibH/E2IHC5, links GenPept ADK32563.1, MIBiG BGC0000529 and auxiliary MibS/E2IHC6, and records chlorination of deschloro-microbisporicin A2 to the mature product. reference https://www.ncbi.nlm.nih.gov/nuccore/HM536998.1 evidence type DATABASE_ASSERTION snippet protein_id="ADK32564.1" retrieved on 2026-10-01 notes GenBank HM536998.1 is the Microbispora corallina microbisporicin cluster sequence and maps mibS to ADK32564.1. reference https://mibig.secondarymetabolites.org/repository/BGC0000529.5/BGC0000529.gbk evidence type DATABASE_ASSERTION snippet protein_id="ADK32564.1" retrieved on 2026-10-01 notes MIBiG BGC0000529.5 places mibS/ADK32564.1 inside the active microbisporicin A2 cluster as the MibS flavin reductase CDS. reference https://www.uniprot.org/uniprotkb/E2IHC6 evidence type DATABASE_ASSERTION snippet GN=mibS retrieved on 2026-10-01 notes Current unreviewed UniProtKB:E2IHC6 resolves as Microbispora corallina MibS flavin reductase, cross-references EMBL HM536998 protein ADK32564.1, and is sequence-identical to GenPept ADK32564.1.
MibH tryptophan-5-halogenase	forms	microbisporicin A2	MITE records MibH chlorination of deschloro-microbisporicin A2 as producing the mature microbisporicin A2 product.	DOI:10.1021/acschembio.6b01031 https://mite.lisc.univie.ac.at/repository/MITE0000054 https://www.ncbi.nlm.nih.gov/nuccore/HM536998.1 https://mibig.secondarymetabolites.org/repository/BGC0000529.5/BGC0000529.gbk https://www.uniprot.org/uniprotkb/E2IHC5 reference DOI:10.1021/acschembio.6b01031 evidence type PRIMARY_EXPERIMENT snippet MibH was only active when Trp was embedded within its cognate peptide substrate deschloro NAI-107 notes Ortega et al. reconstituted Microbispora corallina MibH/MibS in vitro and showed LC/ESI-MS formation of a chlorinated product from deschloromicrobisporicin only when both MibH and MibS were present. reference https://mite.lisc.univie.ac.at/repository/MITE0000054 evidence type DATABASE_ASSERTION snippet Flavin-dependent tryptophan-5-halogenase catalyzed halogenation reaction of deschloro-microbisporicin A2 retrieved on 2026-10-01 notes MITE0000054 is an active entry for Microbispora corallina MibH/E2IHC5, links GenPept ADK32563.1, MIBiG BGC0000529 and auxiliary MibS/E2IHC6, and records chlorination of deschloro-microbisporicin A2 to the mature product. reference https://www.ncbi.nlm.nih.gov/nuccore/HM536998.1 evidence type DATABASE_ASSERTION snippet protein_id="ADK32563.1" retrieved on 2026-10-01 notes GenBank HM536998.1 is the Microbispora corallina microbisporicin cluster sequence and maps mibH to ADK32563.1. reference https://mibig.secondarymetabolites.org/repository/BGC0000529.5/BGC0000529.gbk evidence type DATABASE_ASSERTION snippet MITE0000054: Halogenation (100% identity) retrieved on 2026-10-01 notes MIBiG BGC0000529.5 places mibH/ADK32563.1 inside the active microbisporicin A2 cluster and annotates the mibH CDS with MITE0000054. reference https://www.uniprot.org/uniprotkb/E2IHC5 evidence type DATABASE_ASSERTION snippet GN=mibH retrieved on 2026-10-01 notes Current unreviewed UniProtKB:E2IHC5 resolves as Microbispora corallina MibH tryptophan-5-halogenase, cross-references EMBL HM536998 protein ADK32563.1, and is sequence-identical to GenPept ADK32563.1.

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

Explore across X-Mech

AntibioticMech (microbisporicin A2) ↗ MediaIngredientMech (naturalproductmech:mibig-b546b14194) ↗ TaxonMech: Microbispora corallina (NCBITaxon:83302) ↗ PathwayMech (mibig:BGC0000529) ↗

Provenance

Source concept	Source	Version
BGC0000529	MIBIG	5

This page is generated from data/natural_products/amino_acids_and_peptides/microbisporicin-a2.yaml, which is generated from the committed inventories. Neither is edited by hand.