Paxilline

Paxilline

IUPAC name (2R,4bS,6aS,12bS,12cR,14aS)-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-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
Identifiers
CAS number	57186-25-1^N
PubChem	105008
ChemSpider	94753^Y
MeSH	Paxilline
ChEMBL	CHEMBL410063^Y
Jmol-3D images	Image 1
SMILES O=C5/C=C6/[C@]4(O)CC[C@H]3Cc2c1ccccc1nc2[C@@]3([C@]4(CC[C@@H]6O[C@@H]5C(O)(C)C)C)C
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^Y Key: ACNHBCIZLNNLRS-UBGQALKQSA-N^Y InChI=1/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 Key: ACNHBCIZLNNLRS-UBGQALKQBX
Properties
Molecular formula	C₂₇H₃₃NO₄
Molar mass	435.56 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Paxilline is a potassium channel blocker. Paxilline is a toxic, tremorgenic indole alkaloid produced by Penicillium paxilli.

Disambiguation:

Paxilline, a mycotoxin of penicillium origin, should not be confused with
Paxillin, a signal transducing adaptor protein involved in cell migration (MESH, NCBI).^[1]

Sources and references

^ Paxilline product page from Fermentek

Channel blocker: potassium channel blockers

Antiarrhythmic III/delayed rectifier	benzofuran (Amiodarone) • quaternary ammonium (Bretylium) • naphthalene (Bunaftine) • phenethylamine (Dofetilide) • sulfonamide (Ibutilide) • pyrimidinone (Nifekalant) • ethanolamine (Sotalol) • cyclopropane (Tedisamil) • E-4031

Other/ungrouped/unknown	aminopyridines (3,4-Diaminopyridine, 4-Aminopyridine) • indole (Linopirdine, Paxilline) • quaternary ammonium (Tetraethylammonium) • peptide (Maurotoxin, Charybdotoxin)