paxilline

CHEBI:34907 EXACT SEEDED

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REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record.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

An indole diterpene alkaloid with formula C27H33NO4 isolated from Penicillium paxilli. It is a potent inhibitor of large conductance Ca2+- and voltage-activated K+ (BK)-type channels.

Structure

Standard InChIKey	ACNHBCIZLNNLRS-UBGQALKQSA-N
SMILES	CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4CC5=C([NH]C6=CC=CC=C56)[C@@]43C)C2=CC1=O
Stereochemistry	fully defined
Cross-references	npatlas:NPA028977

Filing pathway

Unclassified — 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, 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
Penicillium paxilli NCBITaxon:70109	BGC_CHARACTERIZED	mibig:BGC0001082	DOI:10.1021/ja3116636

Occurrences 24

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
Penicillium thiersii NCBITaxon:116978	LOTUS	DOI:10.1021/OL026424A
Emericella desertorum NCBITaxon:1810909	LOTUS	DOI:10.1016/B978-0-12-179760-7.50023-1
Emericella desertorum NCBITaxon:1810909	LOTUS	DOI:10.1039/P19870001735
Emericella desertorum NCBITaxon:1810909	LOTUS	DOI:10.1039/P19880001689
Emericella desertorum NCBITaxon:1810909	LOTUS	DOI:10.1248/CPB.37.1387
Aspergillus foveolatus NCBITaxon:210207	LOTUS	DOI:10.1248/CPB.37.1387
Penicillium miczynskii NCBITaxon:36645	LOTUS	DOI:10.1016/0040-4020(95)00138-X
Claviceps paspali NCBITaxon:40601	LOTUS	DOI:10.1021/JF902208W
Lolium perenne NCBITaxon:4522	LOTUS	DOI:10.1016/S0031-9422(00)82327-4
Aspergillus striatus NCBITaxon:469280	LOTUS	DOI:10.1248/CPB.34.2411
Aspergillus striatus NCBITaxon:469280	LOTUS	DOI:10.1248/CPB.37.1387
Aspergillus oryzae NCBITaxon:5062	CHEBI	PMID:23311903
Penicillium camemberti NCBITaxon:5075	LOTUS	DOI:10.1021/NP400304Q
Penicillium shearii NCBITaxon:904690	CHEBI	PMID:24894186
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1016/B978-0-12-179760-7.50024-3
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1016/S0003-2670(00)82471-X
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1016/S0031-9422(00)82327-4
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1016/S0031-9422(00)89639-9
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1016/S0040-4039(00)75170-7
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1021/JO00124A016
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1021/NP50005A017
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1046/J.1365-2958.2001.02265.X
Penicillium paxilli NCBITaxon:70109	LOTUS	DOI:10.1248/CPB.55.1383
Penicillium paxilli NCBITaxon:70109	CHEBI	PMID:17428785

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0001082	Penicillium paxilli NCBITaxon:70109	CLUSTER_DEMONSTRATED	genbank:HM171111.1

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	PaxD UniProtKB:Q9C451		CHEBI:34907 → naturalproductmech:mibig-8e09316737	DOI:10.1007/s00253-013-4834-9

Step 1: PaxD is represented as the terminal P. paxilli prenyltransferase that accepts paxilline and dimethylallyl diphosphate and catalyzes successive prenylations to the exact 21,22-diprenylated paxilline product.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Penicillium paxilli BGC0001082 aromatic prenyltransferase PaxD catalyzes diprenylation of paxilline to 21,22-diprenylated paxilline.

Subject	Predicate	Object	Evidence
paxilline	is prenylated by	PaxD successive prenylation	DOI:10.1007/s00253-013-4834-9 reference DOI:10.1007/s00253-013-4834-9 evidence type PRIMARY_EXPERIMENT snippet PaxD catalyzed the successive di-prenylation notes Liu et al. overexpressed Penicillium paxilli PaxD in Escherichia coli, purified the enzyme, and showed that paxilline plus dimethylallyl diphosphate produced mono- and di-prenyl paxilline, with the major di-prenyl product assigned as 21,22-diprenylated paxilline.
PaxD	catalyzes	PaxD successive prenylation	DOI:10.1007/s00253-013-4834-9 https://www.uniprot.org/uniprotkb/Q9C451 https://www.ncbi.nlm.nih.gov/nuccore/HM171111.1 https://www.ncbi.nlm.nih.gov/protein/AAK11526.2 reference DOI:10.1007/s00253-013-4834-9 evidence type PRIMARY_EXPERIMENT snippet PaxD catalyzed the successive di-prenylation notes Liu et al. overexpressed Penicillium paxilli PaxD in Escherichia coli, purified the enzyme, and showed that paxilline plus dimethylallyl diphosphate produced mono- and di-prenyl paxilline, with the major di-prenyl product assigned as 21,22-diprenylated paxilline. reference https://www.uniprot.org/uniprotkb/Q9C451 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes Reviewed UniProtKB:Q9C451 resolves Penicillium paxilli PaxD, cites PMID:23525886 for catalytic activity and pathway placement, and cross-references EMBL HM171111 / GenPept AAK11526.2. reference https://www.ncbi.nlm.nih.gov/nuccore/HM171111.1 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes GenBank HM171111.1 is the Penicillium paxilli paxilline biosynthetic locus; its paxD coding sequence maps to protein AAK11526.2. reference https://www.ncbi.nlm.nih.gov/protein/AAK11526.2 evidence type DATABASE_ASSERTION retrieved on 2026-09-27 notes NCBI GenPept AAK11526.2 is the HM171111.1 paxD coding sequence cross-referenced by UniProtKB:Q9C451.
PaxD successive prenylation	produces	21,22-diprenylated paxilline	DOI:10.1007/s00253-013-4834-9 reference DOI:10.1007/s00253-013-4834-9 evidence type PRIMARY_EXPERIMENT snippet PaxD catalyzed the successive di-prenylation notes Liu et al. overexpressed Penicillium paxilli PaxD in Escherichia coli, purified the enzyme, and showed that paxilline plus dimethylallyl diphosphate produced mono- and di-prenyl paxilline, with the major di-prenyl product assigned as 21,22-diprenylated paxilline.

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

Explore across X-Mech

AntibioticMech (paxilline) ↗ MediaIngredientMech (CHEBI:34907) ↗ TaxonMech: Penicillium paxilli (NCBITaxon:70109) ↗ PathwayMech (mibig:BGC0001082) ↗

Provenance

Source concept	Source	Version
BGC0001082	MIBIG	4
CHEBI:34907	CHEBI	3-star

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