CHEBI:34907 - paxilline

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ChEBI Name paxilline
ChEBI ID CHEBI:34907
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H33NO4
Net Charge 0
Average Mass 435.564
Monoisotopic Mass 435.24096
InChI InChI=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
InChIKey ACNHBCIZLNNLRS-UBGQALKQSA-N
SMILES [H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]1(C)CC[C@]3([H])O[C@@H](C(=O)C=C3[C@]1(O)CC2)C(C)(C)O
Metabolite of Species Details
Aspergillus oryzae (NCBI:txid5062) See: PubMed
Penicillium paxilli (NCBI:txid70109) See: PubMed
Penicillium shearii (NCBI:txid904690) Species also known as Eupenicillium shearii. See: PubMed
Roles Classification
Biological Role(s): Aspergillus metabolite
Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
potassium channel blocker
An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.
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.
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).
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.
(via alkaloid )
Application(s): anticonvulsant
A drug used to prevent seizures or reduce their severity.
geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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ChEBI Ontology
Outgoing 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 Sources
(+)-paxilline ChEBI
(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)-one IUPAC
paxiline ChEBI
paxillin ChEBI
paxilline UniProt
Manual Xrefs Databases
C00023582 KNApSAcK
C13782 KEGG COMPOUND
CPD-16744 MetaCyc
FDB002165 FooDB
HMDB0030323 HMDB
Paxilline Wikipedia
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Registry Numbers Types Sources
5317894 Reaxys Registry Number Reaxys
57186-25-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
12 July 2022