NaturalProductMech

Browse · Polyketides · patulin

patulin

CHEBI:74926 EXACT SEEDED antimicrobial unspecified

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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 furopyran and lactone that is (2H-pyran-3(6H)-ylidene)acetic acid which is substituted by hydroxy groups at positions 2 and 4 and in which the hydroxy group at position 4 has condensed with the carboxy group to give the corresponding bicyclic lactone. A mycotoxin produced by several species of Aspergillus and Penicillium, it has antibiotic properties but has been shown to be carcinogenic and mutagenic.

Structure

Standard InChIKeyZRWPUFFVAOMMNM-UHFFFAOYSA-N
SMILESC1C=C2C(=CC(=O)O2)C(O1)O
Stereochemistry undefined stereocentres — the InChIKey does not distinguish this compound from its stereoisomers

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.

TaxonBasisClusterEvidence
Penicillium expansum
NCBITaxon:27334		 BGC_CHARACTERIZED mibig:BGC0000120 PMID:25120234

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
Alternaria tenuissima
NCBITaxon:119927		 LOTUS DOI:10.1021/JF00034A040
Talaromyces diversus
NCBITaxon:128434		 LOTUS DOI:10.1021/JF00034A040
Talaromyces funiculosus
NCBITaxon:128442		 LOTUS DOI:10.1021/JF00034A040
Trichoderma virens
NCBITaxon:1331945		 LOTUS DOI:10.1021/JF00034A040
Heterobasidion annosum
NCBITaxon:13563		 LOTUS DOI:10.1021/JF00034A040
Aspergillus petrakii
NCBITaxon:138280		 LOTUS DOI:10.1021/JF00034A040
Thelonectria olida
NCBITaxon:1576542		 LOTUS DOI:10.1021/JF00034A040
Scopulariopsis flava
NCBITaxon:186360		 LOTUS DOI:10.1021/JF00034A040
Aspergillus cejpii
NCBITaxon:1884262		 LOTUS DOI:10.1021/JF00034A040
Corynascus sepedonium
NCBITaxon:190048		 LOTUS DOI:10.1021/JF00034A040
Amesia atrobrunnea
NCBITaxon:1934350		 LOTUS DOI:10.1021/JF00034A040
Cladorrhinum
NCBITaxon:223374		 LOTUS DOI:10.1021/JF00034A040
Calcarisporium arbuscula
NCBITaxon:240499		 LOTUS DOI:10.1021/JF00034A040
Acremonium sclerotigenum
NCBITaxon:261921		 LOTUS DOI:10.1021/JF00034A040
Ageratina calophylla
NCBITaxon:2773065		 LOTUS DOI:10.1016/S0031-9422(00)84545-8
Talaromyces trachyspermus
NCBITaxon:28566		 LOTUS DOI:10.1021/JF00034A040
Penicillium javanicum
NCBITaxon:28578		 LOTUS DOI:10.1021/JF00034A040
Talaromyces duclauxii
NCBITaxon:29842		 LOTUS DOI:10.1021/JF00034A040
Penicillium urticae
NCBITaxon:29844		 LOTUS DOI:10.1128/AEM.45.6.1939-1942.1983
Penicillium urticae
NCBITaxon:29844		 LOTUS DOI:10.1139/M86-051
Cylindrocarpon ianthothele
NCBITaxon:303672		 LOTUS DOI:10.1021/JF00034A040
Drechslera
NCBITaxon:33198		 LOTUS DOI:10.1021/JF00034A040
Purpureocillium lilacinum
NCBITaxon:33203		 LOTUS DOI:10.1021/JF00034A040
Penicillium hirsutum
NCBITaxon:36648		 LOTUS DOI:10.1021/JF00034A040
Penicillium aurantiogriseum
NCBITaxon:36655		 LOTUS DOI:10.1021/JF00034A040

Biosynthetic gene clusters 1

AccessionHostLocus evidenceGenome
mibig:BGC0000120 Penicillium expansum
NCBITaxon:27334 		CLUSTER_DEMONSTRATED genbank:KF899892.1

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
30 PatH cytochrome P450 monooxygenase
UniProtKB:A0A075TRL5		 RHEA:62209 CHEBI:17231 → CHEBI:17069 DOI:10.1111/1462-2920.14542
40 PatI cytochrome P450 monooxygenase
UniProtKB:A0A075TMP8		 RHEA:62213 CHEBI:17069 → CHEBI:5325 DOI:10.1111/1462-2920.14542
90 PatD alcohol dehydrogenase
UniProtKB:A0A075TMP0		 RHEA:62225 CHEBI:145111 + CHEBI:57783 + CHEBI:15378 → CHEBI:145112 + CHEBI:58349 DOI:10.1111/1462-2920.14542
100 PatE patulin synthase
UniProtKB:A0A075TRK9		 RHEA:62228 CHEBI:145112 + CHEBI:13193 → CHEBI:74926 + CHEBI:17499 DOI:10.1111/1462-2920.14542

Step 30: PatH hydroxylates m-cresol to 3-hydroxybenzyl alcohol in the Penicillium expansum patulin pathway. This partial pathway step leaves upstream PatG formation of m-cresol uncurated.

Step 40: PatI hydroxylates 3-hydroxybenzyl alcohol to gentisyl alcohol in the Penicillium expansum patulin pathway. This partial pathway step leaves earlier m-cresol formation and the later PatJ/PatO/PatN/PatF steps from gentisyl alcohol to neopatulin uncurated.

Step 90: PatD opens and reduces neopatulin to (E)-ascladiol in the Penicillium expansum patulin pathway. This partial pathway step leaves the PatJ, PatO, PatN, and PatF conversions from gentisyl alcohol to neopatulin uncurated.

Step 100: PatE oxidizes (E)-ascladiol to patulin in the terminal step of P. expansum patulin biosynthesis; RHEA:62228 grounds the generic electron-acceptor reaction.

Mechanism & Biosynthesis Overview

PRODUCERS & OCCURRENCE 1 producer (1 causal) 25 cited occurrences BIOSYNTHETIC LOCUS 1 gene cluster 4 curated pathway steps NATURAL PRODUCT patulin CHEBI:74926 Polyketides TARGETS & BIOACTIVITY 0 molecular targets 0 bioactivities · 6 graphs

Causal graph — biosynthesis 3 nodes, 2 edges

Partial P. expansum patulin biosynthesis graph for PatE-catalyzed terminal oxidation of (E)-ascladiol.

SubjectPredicateObjectNotesEvidence
(E)-ascladiol is oxidized by PatE patulin synthase PatE uses (E)-ascladiol as the terminal biosynthetic precursor of patulin.
DOI:10.1111/1462-2920.14542
DOI:10.1111/febs.16804
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TRK9
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. systematically dissected the Penicillium expansum patulin cluster and connected PatE to the terminal conversion of (E)-ascladiol into patulin.
  • reference
    DOI:10.1111/febs.16804
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Patulin synthase (PatE) from Penicillium expansum is a flavin-dependent enzyme that catalyses the last step
    notes
    Tjallinks et al. expressed P. expansum patE in Aspergillus niger, purified and characterized PatE, and confirmed by HPLC that PatE uses ascladiol as its preferred substrate in patulin biosynthesis.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    MIBiG BGC0000120.5 maps the P. expansum KF899892 patulin biosynthetic gene cluster to CDS AIG62134.1, gene patE, annotated as patulin synthase.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TRK9
    evidence type
    DATABASE_ASSERTION
    snippet
    PatE catalyzes the last step of the pathway which is the conversion of E-ascladiol to patulin
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:A0A075TRK9 is the 628 aa P. expansum Patulin synthase encoded by patE/PEX2_082770, cross-references KF899892 protein AIG62134.1, and annotates RHEA:62228 from PMID:30680886.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TRK9 to RHEA:62228, the generalized oxidation of (E)-ascladiol to patulin.
PatE patulin synthase forms patulin PatE forms patulin from (E)-ascladiol.
DOI:10.1111/1462-2920.14542
DOI:10.1111/febs.16804
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TRK9
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. systematically dissected the Penicillium expansum patulin cluster and connected PatE to the terminal conversion of (E)-ascladiol into patulin.
  • reference
    DOI:10.1111/febs.16804
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    Patulin synthase (PatE) from Penicillium expansum is a flavin-dependent enzyme that catalyses the last step
    notes
    Tjallinks et al. expressed P. expansum patE in Aspergillus niger, purified and characterized PatE, and confirmed by HPLC that PatE uses ascladiol as its preferred substrate in patulin biosynthesis.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    MIBiG BGC0000120.5 maps the P. expansum KF899892 patulin biosynthetic gene cluster to CDS AIG62134.1, gene patE, annotated as patulin synthase.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TRK9
    evidence type
    DATABASE_ASSERTION
    snippet
    PatE catalyzes the last step of the pathway which is the conversion of E-ascladiol to patulin
    retrieved on
    2026-09-30
    notes
    Reviewed UniProtKB:A0A075TRK9 is the 628 aa P. expansum Patulin synthase encoded by patE/PEX2_082770, cross-references KF899892 protein AIG62134.1, and annotates RHEA:62228 from PMID:30680886.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-09-30
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TRK9 to RHEA:62228, the generalized oxidation of (E)-ascladiol to patulin.

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

Causal graph — biosynthesis 3 nodes, 2 edges

Partial P. expansum patulin biosynthesis graph for PatI-catalyzed hydroxylation of 3-hydroxybenzyl alcohol to gentisyl alcohol.

SubjectPredicateObjectNotesEvidence
3-hydroxybenzyl alcohol is hydroxylated by PatI cytochrome P450 monooxygenase PatI hydroxylates 3-hydroxybenzyl alcohol to form gentisyl alcohol in the patulin biosynthetic pathway.
DOI:10.1111/1462-2920.14542
https://mite.lisc.univie.ac.at/repository/MITE0000459
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TMP8
https://www.ncbi.nlm.nih.gov/protein/AIG62145.1
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. systematically dissected the Penicillium expansum patulin cluster; MITE and UniProt both ground PatI hydroxylation to this DOI.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000459
    evidence type
    DATABASE_ASSERTION
    snippet
    Hydroxylation of m-hydroxybenzyl alcohol to gentysil alcohol
    retrieved on
    2026-10-01
    notes
    MITE0000459 is an active PatI cytochrome P450 entry for hydroxylation of m-hydroxybenzyl alcohol to gentisyl alcohol in patulin biosynthesis; it links UniProtKB:A0A075TMP8, GenPept AIG62145.1, MIBiG BGC0000120 and the Li et al. DOI.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    snippet
    protein_id="AIG62145.1"
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000120.5 places AIG62145.1 inside the active Penicillium expansum NRRL 35695 patulin cluster as the patI cytochrome P450 CDS annotated as M-hydroxybenzyl alcohol hydroxylase.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TMP8
    evidence type
    DATABASE_ASSERTION
    snippet
    PatI catalyzes the conversion of m-hydroxybenzyl alcohol into gentisyl alcohol
    retrieved on
    2026-10-01
    notes
    Reviewed UniProtKB:A0A075TMP8 is the 526 aa P. expansum cytochrome P450 monooxygenase patI encoded by patI/PEX2_082860; UniProt annotates RHEA:62213 as its left-to-right physiological 3-hydroxybenzyl alcohol to gentisyl alcohol activity from PMID:30680886.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AIG62145.1
    evidence type
    DATABASE_ASSERTION
    snippet
    M-hydroxybenzyl alcohol hydroxylase [Penicillium expansum]
    retrieved on
    2026-10-01
    notes
    GenPept AIG62145.1 is the 526 aa Penicillium expansum NRRL 35695 CYP619C2 cytochrome P450 encoded by KF899892.1 in the patulin biosynthetic cluster.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TMP8 to the left-to-right RHEA:62213 hydroxylation reaction.
PatI cytochrome P450 monooxygenase forms gentisyl alcohol This graph stops at gentisyl alcohol because the downstream conversion to (E)-ascladiol is not part of this PatI curation.
DOI:10.1111/1462-2920.14542
https://mite.lisc.univie.ac.at/repository/MITE0000459
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TMP8
https://www.ncbi.nlm.nih.gov/protein/AIG62145.1
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. systematically dissected the Penicillium expansum patulin cluster; MITE and UniProt both ground PatI hydroxylation to this DOI.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000459
    evidence type
    DATABASE_ASSERTION
    snippet
    Hydroxylation of m-hydroxybenzyl alcohol to gentysil alcohol
    retrieved on
    2026-10-01
    notes
    MITE0000459 is an active PatI cytochrome P450 entry for hydroxylation of m-hydroxybenzyl alcohol to gentisyl alcohol in patulin biosynthesis; it links UniProtKB:A0A075TMP8, GenPept AIG62145.1, MIBiG BGC0000120 and the Li et al. DOI.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    snippet
    protein_id="AIG62145.1"
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000120.5 places AIG62145.1 inside the active Penicillium expansum NRRL 35695 patulin cluster as the patI cytochrome P450 CDS annotated as M-hydroxybenzyl alcohol hydroxylase.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TMP8
    evidence type
    DATABASE_ASSERTION
    snippet
    PatI catalyzes the conversion of m-hydroxybenzyl alcohol into gentisyl alcohol
    retrieved on
    2026-10-01
    notes
    Reviewed UniProtKB:A0A075TMP8 is the 526 aa P. expansum cytochrome P450 monooxygenase patI encoded by patI/PEX2_082860; UniProt annotates RHEA:62213 as its left-to-right physiological 3-hydroxybenzyl alcohol to gentisyl alcohol activity from PMID:30680886.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AIG62145.1
    evidence type
    DATABASE_ASSERTION
    snippet
    M-hydroxybenzyl alcohol hydroxylase [Penicillium expansum]
    retrieved on
    2026-10-01
    notes
    GenPept AIG62145.1 is the 526 aa Penicillium expansum NRRL 35695 CYP619C2 cytochrome P450 encoded by KF899892.1 in the patulin biosynthetic cluster.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TMP8 to the left-to-right RHEA:62213 hydroxylation reaction.

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

Causal graph — biosynthesis 3 nodes, 2 edges

Partial P. expansum patulin biosynthesis graph for PatH-catalyzed hydroxylation of m-cresol to 3-hydroxybenzyl alcohol.

SubjectPredicateObjectNotesEvidence
m-cresol is hydroxylated by PatH cytochrome P450 monooxygenase PatH hydroxylates m-cresol to form 3-hydroxybenzyl alcohol in the patulin biosynthetic pathway.
DOI:10.1111/1462-2920.14542
https://mite.lisc.univie.ac.at/repository/MITE0000335
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TRL5
https://www.ncbi.nlm.nih.gov/protein/AIG62144.1
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. dissected the Penicillium expansum patulin cluster; MITE and UniProt ground PatH m-cresol hydroxylation to this DOI.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000335
    evidence type
    DATABASE_ASSERTION
    snippet
    Hydroxylation of m-cresol in patulin biosynthetic pathway.
    retrieved on
    2026-10-01
    notes
    MITE0000335 is an active PatH cytochrome P450 entry for hydroxylation of m-cresol to 3-hydroxybenzyl alcohol in patulin biosynthesis; it links UniProtKB:A0A075TRL5, GenPept AIG62144.1, MIBiG BGC0000120 and the Li et al. DOI.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    snippet
    protein_id="AIG62144.1"
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000120.5 places AIG62144.1 inside the active Penicillium expansum NRRL 35695 patulin cluster as the patH cytochrome P450 CDS annotated as M-cresol hydroxylase.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TRL5
    evidence type
    DATABASE_ASSERTION
    snippet
    PatH catalyzes the conversion of m-cresol into m-hydroxybenzyl alcohol
    retrieved on
    2026-10-01
    notes
    Reviewed UniProtKB:A0A075TRL5 is the 524 aa P. expansum cytochrome P450 monooxygenase patH encoded by patH/PEX2_082740; UniProt annotates RHEA:62209 as the left-to-right physiological 3-methylphenol to 3-hydroxybenzyl alcohol activity from PMID:30680886.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AIG62144.1
    evidence type
    DATABASE_ASSERTION
    snippet
    M-cresol hydroxylase [Penicillium expansum]
    retrieved on
    2026-10-01
    notes
    GenPept AIG62144.1 is the 524 aa Penicillium expansum NRRL 35695 CYP619C3 cytochrome P450 encoded by KF899892.1 in the patulin biosynthetic cluster.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TRL5 to the left-to-right RHEA:62209 hydroxylation reaction.
PatH cytochrome P450 monooxygenase forms 3-hydroxybenzyl alcohol This graph stops at 3-hydroxybenzyl alcohol because this curation covers the PatH reaction.
DOI:10.1111/1462-2920.14542
https://mite.lisc.univie.ac.at/repository/MITE0000335
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TRL5
https://www.ncbi.nlm.nih.gov/protein/AIG62144.1
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. dissected the Penicillium expansum patulin cluster; MITE and UniProt ground PatH m-cresol hydroxylation to this DOI.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000335
    evidence type
    DATABASE_ASSERTION
    snippet
    Hydroxylation of m-cresol in patulin biosynthetic pathway.
    retrieved on
    2026-10-01
    notes
    MITE0000335 is an active PatH cytochrome P450 entry for hydroxylation of m-cresol to 3-hydroxybenzyl alcohol in patulin biosynthesis; it links UniProtKB:A0A075TRL5, GenPept AIG62144.1, MIBiG BGC0000120 and the Li et al. DOI.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    snippet
    protein_id="AIG62144.1"
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000120.5 places AIG62144.1 inside the active Penicillium expansum NRRL 35695 patulin cluster as the patH cytochrome P450 CDS annotated as M-cresol hydroxylase.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TRL5
    evidence type
    DATABASE_ASSERTION
    snippet
    PatH catalyzes the conversion of m-cresol into m-hydroxybenzyl alcohol
    retrieved on
    2026-10-01
    notes
    Reviewed UniProtKB:A0A075TRL5 is the 524 aa P. expansum cytochrome P450 monooxygenase patH encoded by patH/PEX2_082740; UniProt annotates RHEA:62209 as the left-to-right physiological 3-methylphenol to 3-hydroxybenzyl alcohol activity from PMID:30680886.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AIG62144.1
    evidence type
    DATABASE_ASSERTION
    snippet
    M-cresol hydroxylase [Penicillium expansum]
    retrieved on
    2026-10-01
    notes
    GenPept AIG62144.1 is the 524 aa Penicillium expansum NRRL 35695 CYP619C3 cytochrome P450 encoded by KF899892.1 in the patulin biosynthetic cluster.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TRL5 to the left-to-right RHEA:62209 hydroxylation reaction.

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

Causal graph — biosynthesis 3 nodes, 2 edges

Partial P. expansum patulin biosynthesis graph for PatD-catalyzed ring opening and reduction of neopatulin to (E)-ascladiol.

SubjectPredicateObjectNotesEvidence
neopatulin is reduced by PatD alcohol dehydrogenase PatD opens and reduces neopatulin in the NADPH-dependent RHEA:62225 reaction.
DOI:10.1111/1462-2920.14542
https://mite.lisc.univie.ac.at/repository/MITE0000365
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TMP0
https://www.ncbi.nlm.nih.gov/protein/AIG62135.1
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. dissected the Penicillium expansum patulin cluster; MITE and UniProt ground PatD neopatulin reduction to this DOI.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000365
    evidence type
    DATABASE_ASSERTION
    snippet
    ring opening and reduction of neopatulin to E-ascladiol
    retrieved on
    2026-10-01
    notes
    MITE0000365 is an active PatD alcohol dehydrogenase entry for neopatulin ring opening and reduction to (E)-ascladiol in patulin biosynthesis; it links UniProtKB:A0A075TMP0, GenPept AIG62135.1 and the Li et al. DOI.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    snippet
    protein_id="AIG62135.1"
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000120.5 places AIG62135.1 inside the active Penicillium expansum NRRL 35695 patulin cluster as the patD CDS with medium-chain reductase/dehydrogenase domains.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TMP0
    evidence type
    DATABASE_ASSERTION
    snippet
    PatD catalyzes the conversion of neopatulin into E-ascladiol
    retrieved on
    2026-10-01
    notes
    Reviewed UniProtKB:A0A075TMP0 is the 340 aa P. expansum alcohol dehydrogenase patD encoded by patD/PEX2_082780; UniProt annotates RHEA:62225 as the left-to-right physiological neopatulin to (E)-ascladiol reduction from PMID:30680886.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AIG62135.1
    evidence type
    DATABASE_ASSERTION
    snippet
    <GBQualifier_value>patD</GBQualifier_value>
    retrieved on
    2026-10-01
    notes
    GenPept AIG62135.1 is the 340 aa Penicillium expansum NRRL 35695 KF899892.1 coding sequence annotated with gene patD in the patulin biosynthetic cluster.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TMP0 to the left-to-right RHEA:62225 neopatulin reduction reaction.
PatD alcohol dehydrogenase forms (E)-ascladiol PatD forms (E)-ascladiol, the substrate of the terminal PatE patulin synthase reaction.
DOI:10.1111/1462-2920.14542
https://mite.lisc.univie.ac.at/repository/MITE0000365
https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
https://www.uniprot.org/uniprotkb/A0A075TMP0
https://www.ncbi.nlm.nih.gov/protein/AIG62135.1
https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
  • reference
    DOI:10.1111/1462-2920.14542
    evidence type
    PRIMARY_EXPERIMENT
    snippet
    functions of eight enzymes in the 10-step patulin biosynthetic pathway were verified in P. expansum
    notes
    Li et al. dissected the Penicillium expansum patulin cluster; MITE and UniProt ground PatD neopatulin reduction to this DOI.
  • reference
    https://mite.lisc.univie.ac.at/repository/MITE0000365
    evidence type
    DATABASE_ASSERTION
    snippet
    ring opening and reduction of neopatulin to E-ascladiol
    retrieved on
    2026-10-01
    notes
    MITE0000365 is an active PatD alcohol dehydrogenase entry for neopatulin ring opening and reduction to (E)-ascladiol in patulin biosynthesis; it links UniProtKB:A0A075TMP0, GenPept AIG62135.1 and the Li et al. DOI.
  • reference
    https://mibig.secondarymetabolites.org/repository/BGC0000120.5/BGC0000120.gbk
    evidence type
    DATABASE_ASSERTION
    snippet
    protein_id="AIG62135.1"
    retrieved on
    2026-10-01
    notes
    MIBiG BGC0000120.5 places AIG62135.1 inside the active Penicillium expansum NRRL 35695 patulin cluster as the patD CDS with medium-chain reductase/dehydrogenase domains.
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TMP0
    evidence type
    DATABASE_ASSERTION
    snippet
    PatD catalyzes the conversion of neopatulin into E-ascladiol
    retrieved on
    2026-10-01
    notes
    Reviewed UniProtKB:A0A075TMP0 is the 340 aa P. expansum alcohol dehydrogenase patD encoded by patD/PEX2_082780; UniProt annotates RHEA:62225 as the left-to-right physiological neopatulin to (E)-ascladiol reduction from PMID:30680886.
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AIG62135.1
    evidence type
    DATABASE_ASSERTION
    snippet
    <GBQualifier_value>patD</GBQualifier_value>
    retrieved on
    2026-10-01
    notes
    GenPept AIG62135.1 is the 340 aa Penicillium expansum NRRL 35695 KF899892.1 coding sequence annotated with gene patD in the patulin biosynthetic cluster.
  • reference
    https://ftp.expasy.org/databases/rhea/tsv/rhea2uniprot_sprot.tsv
    evidence type
    DATABASE_ASSERTION
    retrieved on
    2026-10-01
    notes
    The Rhea Swiss-Prot mapping links UniProtKB:A0A075TMP0 to the left-to-right RHEA:62225 neopatulin reduction reaction.

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

Causal graph — biosynthesis 8 nodes, 7 edges

PatL-associated production genetics, not a direct DNA-binding or catalytic assay. Native sequence, deletion allele and study cultures remain distinct. No pathogenicity, toxin-target or antimicrobial mechanism; source grades and stereochemical limits unchanged. Main/figures/SI unread; not full-record sign-off.

SubjectPredicateObjectNotesEvidence
Native Penicillium expansum NRRL 35695 source encodes_native_reference PatL NRRL 35695 native sequence reference KF899892.1 complement(join(26056..28216,28273..28511)), 1-based inclusive; table-1 spliced CDS translation equals AIG62143.1 and A0A075TXZ8, 799 aa. GenBank, GenPept and UniProt reference metadata identify NRRL 35695; taxon 27334 is species-level. Reviewed UniProt entry 48, sequence 1. Primary accession selected instead of secondary A0A0A2J7W4. Alternative KGO52638.1 carries an erroneous-initiation/truncated-N-terminus caution; it is not substituted for the inspected reference.
https://www.ncbi.nlm.nih.gov/nuccore/KF899892.1
https://www.ncbi.nlm.nih.gov/protein/AIG62143.1
https://www.uniprot.org/uniprotkb/A0A075TXZ8
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/KF899892.1
    evidence type
    DATABASE_ASSERTION
    notes
    Native source and spliced CDS inspected.
    retrieved on
    2026-10-06
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AIG62143.1
    evidence type
    DATABASE_ASSERTION
    notes
    Independent versioned translation and strain inspected.
    retrieved on
    2026-10-06
  • reference
    https://www.uniprot.org/uniprotkb/A0A075TXZ8
    evidence type
    CURATOR_INFERENCE
    notes
    Exact native sequence, cross-reference and strain correspondence; not complete study-stock identity.
    retrieved on
    2026-10-06
Study patL deletion allele (lesion unresolved) affects_coding_locus_of PatL NRRL 35695 native sequence reference Gene/strain correspondence, not resolved mutation boundaries, an intact mutant protein or proof excluding polar effects.
DOI:10.1111/mpp.12338
  • reference
    DOI:10.1111/mpp.12338
    evidence type
    CURATOR_INFERENCE
    notes
    Abstract and figure captions inspected before PMC CAPTCHA STOP; main, images and SI unread.
    retrieved on
    2026-10-06
Study patL deletion allele (lesion unresolved) was_present_in Study patL-deletion culture Reported deletion background; complete historical genotype unverified.
DOI:10.1111/mpp.12338
  • reference
    DOI:10.1111/mpp.12338
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract and figure captions inspected before PMC CAPTCHA STOP; main, images and SI unread.
    retrieved on
    2026-10-06
Study NRRL 35695 reference culture is_reference_background_for Reported patL deletion and complementation comparison Named parental comparator, not proof of a complete historical stock sequence.
DOI:10.1111/mpp.12338
  • reference
    DOI:10.1111/mpp.12338
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract and figure captions inspected before PMC CAPTCHA STOP; main, images and SI unread.
    retrieved on
    2026-10-06
Study patL-deletion culture had_undetected_reported_product_in Reported patL deletion and complementation comparison No detected patulin in the reported comparison, not universal absence across conditions or a reconstructed detection limit.
DOI:10.1111/mpp.12338
  • reference
    DOI:10.1111/mpp.12338
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract and figure captions inspected before PMC CAPTCHA STOP; main, images and SI unread.
    retrieved on
    2026-10-06
Study complemented patL-deletion culture showed_restored_reported_production_in Reported patL deletion and complementation comparison Reported complementation outcome; exact vector, insertion site, copy number and complete protein sequence unresolved.
DOI:10.1111/mpp.12338
  • reference
    DOI:10.1111/mpp.12338
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract and figure captions inspected before PMC CAPTCHA STOP; main, images and SI unread.
    retrieved on
    2026-10-06
Reported patL deletion and complementation comparison measured_reported_product patulin Captions identify HPLC-DAD product measurements. No titer, normalized flux, purified-enzyme activity or direct promoter binding adopted.
DOI:10.1111/mpp.12338
  • reference
    DOI:10.1111/mpp.12338
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract and figure captions inspected before PMC CAPTCHA STOP; main, images and SI unread.
    retrieved on
    2026-10-06

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

Causal graph — biosynthesis 7 nodes, 6 edges

Patulin-pathway-associated PatG bioconversion, bounded to the primary abstract. Paper-linked NRRL1980 sequence and NRRL1 locus reference differ; the study preparation remains REVIEW_NEEDED. No P.expansum enzyme substitution, kinetic mechanism, producer upgrade or antimicrobial target. Main/figures/SI unread; not full-record sign-off.

SubjectPredicateObjectNotesEvidence
Native Aspergillus clavatus NRRL1980 source encodes_native_reference PatG NRRL1980 native sequence reference JN698985.1 join(42..93,175..1100),plus strand,1-based inclusive; table1 CDS translation equals AFQ22736.1 and T1PRE6,325aa. GenBank/GenPept and UniProt reference metadata identify NRRL1980; taxon5057 is species-level. UniProt unreviewed entry30/sequence1. NRRL1 A1CFL4/ACLA_093620 is a distinct325aa comparator: NRRL1980 V143/L244 versus NRRL1 I143/F244. A Swiss-Prot label does not make the comparator an exact sequence match.
https://www.ncbi.nlm.nih.gov/nuccore/JN698985.1
https://www.ncbi.nlm.nih.gov/protein/AFQ22736.1
https://www.uniprot.org/uniprotkb/T1PRE6
https://www.uniprot.org/uniprotkb/A1CFL4
  • reference
    https://www.ncbi.nlm.nih.gov/nuccore/JN698985.1
    evidence type
    DATABASE_ASSERTION
    notes
    Native source and spliced CDS inspected.
    retrieved on
    2026-10-06
  • reference
    https://www.ncbi.nlm.nih.gov/protein/AFQ22736.1
    evidence type
    DATABASE_ASSERTION
    notes
    Independent versioned protein/source inspected.
    retrieved on
    2026-10-06
  • reference
    https://www.uniprot.org/uniprotkb/T1PRE6
    evidence type
    CURATOR_INFERENCE
    notes
    Exact native source/CDS/GenPept/UniProt correspondence.
    retrieved on
    2026-10-06
  • reference
    https://www.uniprot.org/uniprotkb/A1CFL4
    evidence type
    CURATOR_INFERENCE
    notes
    Different-strain comparator,not chosen as exact NRRL1980 reference.
    retrieved on
    2026-10-06
Study expressed PatG preparation (sequence unresolved) has_candidate_native_reference PatG NRRL1980 native sequence reference JN698985 is paper-linked, but the abstract names ACLA_093620. The two native references differ. Historical construct/strain identity remains unresolved.
DOI:10.1016/j.ijfoodmicro.2013.11.020
https://www.uniprot.org/uniprotkb/T1PRE6
  • reference
    DOI:10.1016/j.ijfoodmicro.2013.11.020
    evidence type
    CURATOR_INFERENCE
    notes
    Abstract only; publisher403 STOP. Main, images and SI unread.
    retrieved on
    2026-10-06
  • reference
    https://www.uniprot.org/uniprotkb/T1PRE6
    evidence type
    DATABASE_ASSERTION
    notes
    Paper cross-reference and NRRL1980 reference metadata inspected; not complete stock identity.
    retrieved on
    2026-10-06
Study Saccharomyces cerevisiae expression context was_expression_context_for Study expressed PatG preparation (sequence unresolved) Host species reported; strain, vector and complete construct not adopted.
DOI:10.1016/j.ijfoodmicro.2013.11.020
  • reference
    DOI:10.1016/j.ijfoodmicro.2013.11.020
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract only; publisher403 STOP. Main, images and SI unread.
    retrieved on
    2026-10-06
Study expressed PatG preparation (sequence unresolved) was_tested_in Reported PatG-associated bioconversion Reported bioconversion,not a reconstructed purified-enzyme assay or native flux.
DOI:10.1016/j.ijfoodmicro.2013.11.020
  • reference
    DOI:10.1016/j.ijfoodmicro.2013.11.020
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract only; publisher403 STOP. Main, images and SI unread.
    retrieved on
    2026-10-06
Source-assigned 6-methylsalicylic acid is_reported_substrate_of Reported PatG-associated bioconversion Named source substrate; no quantitative kinetics or general specificity.
DOI:10.1016/j.ijfoodmicro.2013.11.020
  • reference
    DOI:10.1016/j.ijfoodmicro.2013.11.020
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract only; publisher403 STOP. Main, images and SI unread.
    retrieved on
    2026-10-06
Reported PatG-associated bioconversion yielded_reported_product Source-assigned m-cresol Reported product only,not complete patulin synthesis or producer-grade evidence.
DOI:10.1016/j.ijfoodmicro.2013.11.020
  • reference
    DOI:10.1016/j.ijfoodmicro.2013.11.020
    evidence type
    PRIMARY_EXPERIMENT
    notes
    Abstract only; publisher403 STOP. Main, images and SI unread.
    retrieved on
    2026-10-06
    snippet
    decarboxylation of 6-methylsalicylic acid into m-cresol

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

Elsewhere in the fleet

Explore across X-Mech

AntibioticMech (patulin) ↗ MediaIngredientMech (CHEBI:74926) ↗ TaxonMech: Penicillium expansum (NCBITaxon:27334) ↗ PathwayMech (mibig:BGC0000120) ↗

Provenance

Source conceptSourceVersion
BGC0000120MIBIG5
CHEBI:74926CHEBI3-star

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