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CHEBI:34907 - paxilline

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:
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).
Penicillium metabolite  Any fungal metabolite produced during a metabolic reaction in Penicillium.
mycotoxin  Poisonous substance produced by fungi.
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 .
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.
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