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nystatin A1

CHEBI:473992 EXACT SEEDED antifungal

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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.

A polyene macrolide antibiotic; part of the nystatin complex produced by several Streptomyces species. It is an antifungal antibiotic used for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.

Structure

Standard InChIKeyVQOXZBDYSJBXMA-NQTDYLQESA-N
SMILESC[C@H]1/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H]([C@@H](CC[C@H](C[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O
Stereochemistryfully defined
Cross-referencespubchem:11286230

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, saccharide, 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.

TaxonBasisClusterEvidence
Streptomyces noursei ATCC 11455
NCBITaxon:316284		 BGC_CHARACTERIZED mibig:BGC0000115 PMID:10873841

Occurrences 25

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
Hohenbuehelia grisea
NCBITaxon:104357		 LOTUS DOI:10.1021/ACS.JNATPROD.7B00713
Oscillatoria
NCBITaxon:1158		 LOTUS DOI:10.1021/ACS.JNATPROD.8B00650
Microporus
NCBITaxon:1191098		 LOTUS DOI:10.1021/ACS.JNATPROD.7B00764
Lonchocarpus chiricanus
NCBITaxon:1582177		 LOTUS DOI:10.1021/NP000597W
Sparticola junci
NCBITaxon:1803578		 LOTUS DOI:10.1021/ACS.JNATPROD.9B00604
Streptomyces noursei
NCBITaxon:1971		 CHEBI 10.1016/S0040-4039(01)96531-1
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1007/S002530100613
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1016/J.CHEMBIOL.2008.08.009
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1016/J.FEMSLE.2005.05.052
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1016/S0040-4039(01)96531-1
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1016/S1074-5521(00)00120-4
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1074/JBC.M212611200
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1099/00221287-146-3-611
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1111/J.1574-6968.1999.TB13746.X
Streptomyces noursei
NCBITaxon:1971		 LOTUS DOI:10.1128/JB.186.5.1345-1354.2004
Nocardiopsis
NCBITaxon:2013		 LOTUS DOI:10.1021/ACS.JNATPROD.8B00708
Sporormiella similis
NCBITaxon:269685		 LOTUS DOI:10.1021/ACS.JNATPROD.7B00064
Streptomyces sp. HSG2
NCBITaxon:2797167		 CHEBI PMID:33932153
Amycolatopsis aidingensis
NCBITaxon:2842453		 CHEBI PMID:34938275
Phoma
NCBITaxon:37463		 LOTUS DOI:10.1021/ACS.JNATPROD.8B00685
Streptomyces ahygroscopicus
NCBITaxon:387846		 CHEBI PMID:24231162
Streptomyces ahygroscopicus
NCBITaxon:387850		 LOTUS DOI:10.1007/S10295-015-1660-3
Streptomyces ahygroscopicus
NCBITaxon:387850		 LOTUS DOI:10.1016/J.MICRES.2013.09.017
Hyalangium minutum
NCBITaxon:394096		 LOTUS DOI:10.1021/NP200776V
Armillaria
NCBITaxon:47424		 LOTUS DOI:10.1021/ACS.JNATPROD.8B00685

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0000115 Streptomyces noursei ATCC 11455
NCBITaxon:316284 		CLUSTER_DEMONSTRATED genbank:AF263912.1

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

PRODUCERS & OCCURRENCE 1 producer (1 causal) 25 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 0 curated pathway steps NATURAL PRODUCT nystatin A1 CHEBI:473992 Polyketides TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 2 graphs

Causal graph — biosynthesis 3 nodes, 2 edges

Streptomyces noursei NysL-catalyzed C-10 hydroxylation in the last step of nystatin A1 biosynthesis.

SubjectPredicateObjectNotesEvidence
10-deoxynystatin is C-10 hydroxylated by NysL cytochrome P450 monooxygenase Genetic replacement of nysL caused Streptomyces noursei to accumulate 10-deoxynystatin, and purified recombinant NysL used 10-deoxynystatin as an in vitro substrate.
DOI:10.1128/AEM.72.4.2514-2519.2006
https://mite.lisc.univie.ac.at/repository/MITE0000322
https://mibig.secondarymetabolites.org/repository/BGC0000115.5/BGC0000115.gbk
https://www.uniprot.org/uniprotkb/Q9L4X0
https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
  • reference
    DOI:10.1128/AEM.72.4.2514-2519.2006
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    NysL is a hydroxylase responsible for the post-polyketide synthase modification of 10-deoxynystatin at position C-10.
    notes
    Volokhan et al. replaced nysL in Streptomyces noursei, observed 10-deoxynystatin accumulation, heterologously expressed His-tagged NysL in Escherichia coli and assayed the purified enzyme with 10-deoxynystatin as substrate.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000322
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    MITE0000322 is active and links NysL to UniProtKB:Q9L4X0, GenPept AAF71769.1, MIBiG BGC0000115 and an in vitro C10-hydroxylation reaction in nystatin A1 biosynthesis.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000115.5/BGC0000115.gbk
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000115.5 places AAF71769.1 in the active Streptomyces noursei ATCC 11455 nystatin biosynthetic gene cluster as nysL/NysL.
  • reference
    https://www.uniprot.org/uniprotkb/Q9L4X0
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    UniProtKB:Q9L4X0 is the unreviewed 394 aa Streptomyces noursei NysL entry and cross-references GenBank AF263912 protein AAF71769.1.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    GenBank AF263912.1 is the Streptomyces noursei ATCC 11455 nystatin biosynthetic gene cluster sequence and maps nysL to the NysL protein accession AAF71769.1.
NysL cytochrome P450 monooxygenase forms nystatin A1 NysL installs the C-10 hydroxyl group during the last tailoring step from 10-deoxynystatin toward the final BGC0000115 nystatin A1 product.
DOI:10.1128/AEM.72.4.2514-2519.2006
https://mite.lisc.univie.ac.at/repository/MITE0000322
https://mibig.secondarymetabolites.org/repository/BGC0000115.5/BGC0000115.gbk
https://www.uniprot.org/uniprotkb/Q9L4X0
https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
  • reference
    DOI:10.1128/AEM.72.4.2514-2519.2006
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    NysL is a hydroxylase responsible for the post-polyketide synthase modification of 10-deoxynystatin at position C-10.
    notes
    Volokhan et al. replaced nysL in Streptomyces noursei, observed 10-deoxynystatin accumulation, heterologously expressed His-tagged NysL in Escherichia coli and assayed the purified enzyme with 10-deoxynystatin as substrate.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000322
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    MITE0000322 is active and links NysL to UniProtKB:Q9L4X0, GenPept AAF71769.1, MIBiG BGC0000115 and an in vitro C10-hydroxylation reaction in nystatin A1 biosynthesis.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000115.5/BGC0000115.gbk
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000115.5 places AAF71769.1 in the active Streptomyces noursei ATCC 11455 nystatin biosynthetic gene cluster as nysL/NysL.
  • reference
    https://www.uniprot.org/uniprotkb/Q9L4X0
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    UniProtKB:Q9L4X0 is the unreviewed 394 aa Streptomyces noursei NysL entry and cross-references GenBank AF263912 protein AAF71769.1.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    GenBank AF263912.1 is the Streptomyces noursei ATCC 11455 nystatin biosynthetic gene cluster sequence and maps nysL to the NysL protein accession AAF71769.1.

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

Causal graph — biosynthesis 3 nodes, 2 edges

Gene-level MIBiG database assignments of NysDI and NysN as tailoring participants in nystatin A1 biosynthesis, with independently verified native ATCC11455 protein references. This graph does not specify an exact chemical reaction or a sequence of steps. MITE's incompatible product stereochemistry is not transferred to the fully stereospecified owner. The existing NysL mechanism remains unchanged; no new primary assay or full-record sign-off is claimed.

SubjectPredicateObjectNotesEvidence
NysDI, native ATCC 11455 reference is_database_reported_tailoring_participant_in_biosynthesis_of nystatin A1 MIBiG assigns this specific gene a tailoring role in the exact nystatin A1 cluster; the database knock-out code is not an independently inspected mutant experiment. This is pathway participation, not a claim that the protein alone directly forms the mature compound. No substrate, donor, site-specific reaction, kinetic result, cofactor occupancy, physical complex or order relative to NysL or the other enzyme is asserted. The conflicting MITE reaction models are not adopted; issue658 remains open.
https://dl.secondarymetabolites.org/mibig/mibig_json_4.0.tar.gz
https://www.ncbi.nlm.nih.gov/protein/AAF71773.1
https://www.uniprot.org/uniprotkb/Q9L4W6
https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
  • reference
    https://dl.secondarymetabolites.org/mibig/mibig_json_4.0.tar.gz
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-06
    notes
    Adopted MIBiG4.0 archive SHA256 986f1a69fb5eeb84fd7c0175ae921304c22fd5f8ed04c96d8c1c0c95a145837b, member mibig_json_4.0/BGC0000115.json inspected2026-10-07. Active entry version5 has one exact owner-matching nystatin A1 SMILES, native locus AF263912.1 and taxon316284. Gene AAF71773.1/nysDI has function Tailoring with database evidence method Knock-out. This does not convert its cited PMID10873841 into an inspected primary assay or assign a precise reaction.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AAF71773.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-07
    snippet
    presumably responsible for attachment
    notes
    Independent complete 506-aa NysDI conceptual translation from Streptomyces noursei ATCC11455/taxon316284. Original function qualifier is explicitly tentative. CDD domain and binding-site annotations are predictions, not measurements. No exact historical assay stock or construct is established.
  • reference
    https://www.uniprot.org/uniprotkb/Q9L4W6
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-07
    notes
    Current unreviewed 506-aa NysDI reference matches native CDS and GenPeptAAF71773.1 exactly. UniProt species tax1971 and reference strain ATCC11455 are consistent with the strain-level native record. This entry has no FUNCTION annotation; predicted or homology-level protein existence is not an independently measured assay.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
    evidence type
    CURATOR_INFERENCE
    retrieved on
    2026-10-07
    notes
    Complete native CDS translation, annotation, independent GenPept and UniProt agree; coded_by strand/coordinates/DNA and ATCC11455 qualifiers verified. NysDI uses reverse60909..62429,1521nt,table11/codon1,506aa. AF263912.1 is the complete123580bp cluster, not a complete genome. No claim about every unrelated feature, experimental folding or expression is made.
NysN, native ATCC 11455 reference is_database_reported_tailoring_participant_in_biosynthesis_of nystatin A1 MIBiG assigns this specific gene a tailoring role in the exact nystatin A1 cluster; the database knock-out code is not an independently inspected mutant experiment. This is pathway participation, not a claim that the protein alone directly forms the mature compound. No substrate, donor, site-specific reaction, kinetic result, cofactor occupancy, physical complex or order relative to NysL or the other enzyme is asserted. The conflicting MITE reaction models are not adopted; issue658 remains open.
https://dl.secondarymetabolites.org/mibig/mibig_json_4.0.tar.gz
https://www.ncbi.nlm.nih.gov/protein/AAF71771.1
https://www.uniprot.org/uniprotkb/Q9L4W8
https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
  • reference
    https://dl.secondarymetabolites.org/mibig/mibig_json_4.0.tar.gz
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-06
    notes
    Adopted MIBiG4.0 archive SHA256 986f1a69fb5eeb84fd7c0175ae921304c22fd5f8ed04c96d8c1c0c95a145837b, member mibig_json_4.0/BGC0000115.json inspected2026-10-07. Active entry version5 has one exact owner-matching nystatin A1 SMILES, native locus AF263912.1 and taxon316284. Gene AAF71771.1/nysN has function Tailoring with database evidence method Knock-out. This does not convert its cited PMID10873841 into an inspected primary assay or assign a precise reaction.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AAF71771.1
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-07
    snippet
    presumably involved in modification of the nystatin macrolactone ring
    notes
    Independent complete 398-aa NysN conceptual translation from Streptomyces noursei ATCC11455/taxon316284. Original function qualifier is explicitly tentative. CDD domain and binding-site annotations are predictions, not measurements. No exact historical assay stock or construct is established.
  • reference
    https://www.uniprot.org/uniprotkb/Q9L4W8
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-07
    notes
    Current unreviewed 398-aa NysN reference matches native CDS and GenPeptAAF71771.1 exactly. UniProt species tax1971 and reference strain ATCC11455 are consistent with the strain-level native record. This entry has no FUNCTION annotation; predicted or homology-level protein existence is not an independently measured assay.
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/AF263912.1
    evidence type
    CURATOR_INFERENCE
    retrieved on
    2026-10-07
    notes
    Complete native CDS translation, annotation, independent GenPept and UniProt agree; coded_by strand/coordinates/DNA and ATCC11455 qualifiers verified. NysN uses reverse58637..59833,1197nt,table11/codon1,398aa. AF263912.1 is the complete123580bp cluster, not a complete genome. No claim about every unrelated feature, experimental folding or expression is made.

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

Elsewhere in the fleet

Explore across X-Mech

AntibioticMech (nystatin A1) ↗ MediaIngredientMech (CHEBI:473992) ↗ TaxonMech: Streptomyces noursei ATCC 11455 (NCBITaxon:316284) ↗ PathwayMech (mibig:BGC0000115) ↗

Provenance

Source conceptSourceVersion
BGC0000115MIBIG5
CHEBI:473992CHEBI3-star

This page is generated from data/natural_products/polyketides/nystatin-a1.yaml, which is generated from the committed inventories. Neither is edited by hand.