Structure via PubChem · Public domain (PubChem)
paxilline
Sign in to savePaxilline is a toxic, tremorgenic diterpene indole polycyclic alkaloid molecule produced by Penicillium paxilli which was first characterized in 1975. Paxilline is one of a class of tremorigenic mycotoxins, is a potassium channel blocker, and is potentially genotoxic.
Chemical data
- Formula
- C27H33NO4
- Molecular weight
- 435.6 g/mol
- IUPAC name
- (1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
584 papers- Synthesis of rearranged indole diterpenes of the paxilline type.Natural product reports · 2022
- Paxilline derived from an endophytic fungus of Baphicacanthus cusia alleviates hepatocellular carcinoma through autophagy-mediated apoptosis.Scientific reports · 2025
- Flavonoid quercetin abolish paxilline inhibition of the mitochondrial BK(Ca) channel.Mitochondrion · 2022
- The Bi-Functional Paxilline Enriched in Skin Secretion of Tree Frogs (Hyla japonica) Targets the KCNK18 and BK(Ca) Channels.Toxins · 2023
- Paxilline inhibits BK channels by an almost exclusively closed-channel block mechanism.The Journal of general physiology · 2014
via PubMed
Wikidata facts
- Mass
- 435.241
Show 4 more facts
- chemical formula
- C₂₇H₃₃NO₄
- canonical SMILES
- CC12CCC3C(=CC(=O)C(O3)C(C)(C)O)C1(CCC4C2(C5=C(C4)C6=CC=CC=C6N5)C)O
- isomeric SMILES
- C[C@]12CC[C@H]3C(=CC(=O)[C@H](O3)C(C)(C)O)[C@@]1(CC[C@@H]4[C@@]2(C5=C(C4)C6=CC=CC=C6N5)C)O
- found in taxon
- Aspergillus foveolatus
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Biosynthesis
- Sources and references
Paxilline is a toxic, tremorgenic diterpene indole polycyclic alkaloid molecule produced by Penicillium paxilli which was first characterized in 1975. Paxilline is one of a class of tremorigenic mycotoxins, is a potassium channel blocker, and is potentially genotoxic.
Paxilline was found to significantly extend the lifespan, healthspan, and mobility of aged C. elegans worms, but had no such effect on young worms. Paxilline was not found to induce seizures when injected intracerebroventricularly in mice but paradoxically had anticonvulsant activity against picrotoxin and pentylenetetrazol seizures in mice. It has also been used in mice to induce autism-like behaviors through inhibition of the BK channel.
Excerpted from Wikipedia’s “paxilline” article, available under the CC BY-SA 4.0 licence.