xantholipin

naturalproductmech:mibig-38bc86114b 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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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	HSVRTPZWHMWONP-JUEDDRGBSA-N
SMILES	[H][C@]12C[C@]3([H])C(=O)C4=C(C(=O)NC(C)=C4)C(=O)[C@]3(O)C3=C(O)C4=C(OC5=C(C=CC(Cl)=C5OC)C4=O)C(OCO1)=C23
Stereochemistry	fully defined
Cross-references	npatlas:NPA03057

Filing pathway

Polyketides — 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 pks, 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
Streptomyces flavogriseus NCBITaxon:67299	SOURCE_ASSERTION	mibig:BGC0000279	DOI:10.1016/s0040-4039(03)01318-2

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
Streptomyces NCBITaxon:1883	LOTUS	DOI:10.1016/S0040-4039(03)01318-2
Streptomyces albus NCBITaxon:1888	LOTUS	DOI:10.1038/JA.2016.60

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000279	Streptomyces flavogriseus NCBITaxon:67299	CLUSTER_UNSTATED	genbank:GQ421798.1

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.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Streptomyces flavogriseus XanH-catalyzed FAD-dependent chlorination in xantholipin biosynthesis.

Subject	Predicate	Object	Notes	Evidence
XanH chlorination substrate	is chlorinated by	XanH FAD-dependent halogenase	MITE represents XanH as the FAD halogenase for an in vitro chlorination of a xantholipin-pathway intermediate; exact local records are absent for the submitted substrate and product structures.	DOI:10.1128/AEM.01225-20 https://mite.bioinformatics.nl/repository/MITE0000024 https://mibig.secondarymetabolites.org/repository/BGC0000279.5/BGC0000279.gbk https://www.uniprot.org/uniprotkb/I1SKW0 https://www.ncbi.nlm.nih.gov/protein/ADE22292.1 reference DOI:10.1128/AEM.01225-20 evidence type PRIMARY_EXPERIMENT snippet a new peak could be detected in the reaction system of XanH notes Kong et al. purified recombinant XanH, assayed in vitro halogenation with FAD, NADH and the compound 5 free-standing xantholipin intermediate, and detected chlorinated product formation. reference https://mite.bioinformatics.nl/repository/MITE0000024 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000024 is active, links XanH to UniProtKB:I1SKW0, GenPept ADE22292.1 and MIBiG BGC0000279, lists FAD as an organic cofactor, and represents an in vitro-supported chlorination reaction in the xantholipin biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000279.5/BGC0000279.gbk evidence type DATABASE_ASSERTION snippet MITE0000024: Halogenation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000279.5 places xanH/ADE22292.1 inside the active Streptomyces flavogriseus xantholipin biosynthetic gene cluster as a biosynthetic-additional flavin-dependent halogenase locus with a 100% identity MITE0000024 halogenation annotation. reference https://www.uniprot.org/uniprotkb/I1SKW0 evidence type DATABASE_ASSERTION snippet GN Name=xanH retrieved on 2026-10-02 notes Current UniProtKB:I1SKW0 resolves as a 471 aa Streptomyces flavogriseus xanH entry and cross-references EMBL GQ421798 protein ADE22292.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE22292.1 evidence type DATABASE_ASSERTION snippet putative non-heme halogenase retrieved on 2026-10-02 notes NCBI Protein ADE22292.1 is the Streptomyces flavogriseus xanH putative non-heme halogenase encoded at GQ421798.1:22057..23472.
FAD	serves as cofactor for	XanH FAD-dependent halogenase	MITE lists FAD as an organic cofactor for XanH, and Kong et al. detected FAD in denatured recombinant XanH.	DOI:10.1128/AEM.01225-20 https://mite.bioinformatics.nl/repository/MITE0000024 https://www.uniprot.org/uniprotkb/I1SKW0 reference DOI:10.1128/AEM.01225-20 evidence type PRIMARY_EXPERIMENT snippet confirmed the prosthetic group as FAD notes Kong et al. heat denatured purified XanH and matched the released cofactor to an FAD standard by LC-MS. reference https://mite.bioinformatics.nl/repository/MITE0000024 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000024 lists FAD as the organic cofactor for XanH. reference https://www.uniprot.org/uniprotkb/I1SKW0 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes UniProtKB:I1SKW0 contains flavin-dependent halogenase family annotations on the current Streptomyces flavogriseus xanH entry.
XanH FAD-dependent halogenase	forms	XanH-chlorinated xantholipin intermediate	The MITE reaction product chlorinates the aromatic system of the submitted xantholipin-pathway substrate structure.	DOI:10.1128/AEM.01225-20 https://mite.bioinformatics.nl/repository/MITE0000024 https://mibig.secondarymetabolites.org/repository/BGC0000279.5/BGC0000279.gbk https://www.uniprot.org/uniprotkb/I1SKW0 https://www.ncbi.nlm.nih.gov/protein/ADE22292.1 reference DOI:10.1128/AEM.01225-20 evidence type PRIMARY_EXPERIMENT snippet a new peak could be detected in the reaction system of XanH notes Kong et al. purified recombinant XanH, assayed in vitro halogenation with FAD, NADH and the compound 5 free-standing xantholipin intermediate, and detected chlorinated product formation. reference https://mite.bioinformatics.nl/repository/MITE0000024 evidence type DATABASE_ASSERTION retrieved on 2026-10-02 notes MITE0000024 is active, links XanH to UniProtKB:I1SKW0, GenPept ADE22292.1 and MIBiG BGC0000279, lists FAD as an organic cofactor, and represents an in vitro-supported chlorination reaction in the xantholipin biosynthetic pathway. reference https://mibig.secondarymetabolites.org/repository/BGC0000279.5/BGC0000279.gbk evidence type DATABASE_ASSERTION snippet MITE0000024: Halogenation (100% identity) retrieved on 2026-10-02 notes MIBiG BGC0000279.5 places xanH/ADE22292.1 inside the active Streptomyces flavogriseus xantholipin biosynthetic gene cluster as a biosynthetic-additional flavin-dependent halogenase locus with a 100% identity MITE0000024 halogenation annotation. reference https://www.uniprot.org/uniprotkb/I1SKW0 evidence type DATABASE_ASSERTION snippet GN Name=xanH retrieved on 2026-10-02 notes Current UniProtKB:I1SKW0 resolves as a 471 aa Streptomyces flavogriseus xanH entry and cross-references EMBL GQ421798 protein ADE22292.1. reference https://www.ncbi.nlm.nih.gov/protein/ADE22292.1 evidence type DATABASE_ASSERTION snippet putative non-heme halogenase retrieved on 2026-10-02 notes NCBI Protein ADE22292.1 is the Streptomyces flavogriseus xanH putative non-heme halogenase encoded at GQ421798.1:22057..23472.

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

Explore across X-Mech

AntibioticMech (xantholipin) ↗ MediaIngredientMech (naturalproductmech:mibig-38bc86114b) ↗ TaxonMech: Streptomyces flavogriseus (NCBITaxon:67299) ↗ PathwayMech (mibig:BGC0000279) ↗

Provenance

Source concept	Source	Version
BGC0000279	MIBIG	5

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