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CHEBI:34907 - paxilline

Default Structure
ChEBI IDCHEBI:34907
ChEBI Namepaxilline
Stars
DefinitionAn 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.
Last Modified12 July 2022
DownloadsMolfile
FormulaC27H33NO4
Net Charge0
Average Mass435.564
Monoisotopic Mass435.24096
SMILES[H][C@@]12CC[C@@]3(O)C4=CC(=O)[C@@H](C(C)(C)O)O[C@@]4([H])CC[C@]3(C)[C@@]1(C)c1nc3ccccc3c1C2
InChIInChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1
InChIKeyACNHBCIZLNNLRS-UBGQALKQSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Aspergillus oryzae (ncbitaxon:5062) - PubMed (23311903)
Penicillium paxilli (ncbitaxon:70109) - PubMed (17428785)
Penicillium shearii (ncbitaxon:904690) - PubMed (24894186) Species also known as Eupenicillium shearii.
Roles Classification
Biological Roles:
potassium channel blocker  An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor  An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Ca2+-transporting ATPase (EC 3.6.3.8).
genotoxin  A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
mycotoxin  Poisonous substance produced by fungi.
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
anticonvulsant  A drug used to prevent seizures or reduce their severity.
ChEBI Ontology
Outgoing Relation(s)
paxilline (CHEBI:34907) has role Aspergillus metabolite (CHEBI:76956)
paxilline (CHEBI:34907) has role Penicillium metabolite (CHEBI:76964)
paxilline (CHEBI:34907) has role anticonvulsant (CHEBI:35623)
paxilline (CHEBI:34907) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186)
paxilline (CHEBI:34907) has role genotoxin (CHEBI:50902)
paxilline (CHEBI:34907) has role geroprotector (CHEBI:176497)
paxilline (CHEBI:34907) has role mycotoxin (CHEBI:25442)
paxilline (CHEBI:34907) has role potassium channel blocker (CHEBI:50509)
paxilline (CHEBI:34907) is a diterpene alkaloid (CHEBI:23847)
paxilline (CHEBI:34907) is a enone (CHEBI:51689)
paxilline (CHEBI:34907) is a organic heterohexacyclic compound (CHEBI:51914)
paxilline (CHEBI:34907) is a terpenoid indole alkaloid (CHEBI:65321)
paxilline (CHEBI:34907) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-chromeno[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
Synonyms  Source
(2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(2-hydroxypropan-2-yl)-12b,12c-dimethyl-5,6,6a,7,12,12b,12c,13,14,14a-decahydro-2H-[1]benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-oneIUPAC
paxilineChEBI
paxillinChEBI
(+)-paxillineChEBI
UniProt Name  Source
paxillineUniProt
Manual XrefsDatabases
C00023582KNApSAcK
C13782KEGG COMPOUND
CPD-16744MetaCyc
FDB002165FooDB
HMDB0030323HMDB
PaxillineWikipedia
Registry NumbersSources
Reaxys:5317894Reaxys
CAS:57186-25-1ChemIDplus
Citations