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Paxilline

Paxilline structure

CAS No:
57186-25-1
Formula:
C27H33NO4
Chemical Name:
Paxilline
Synonyms:
2H-1-Benzopyrano[5′,6′:6,7]indeno[1,2-b]indol-3(4bH)-one,5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-,(2R,4bS,6aS,12bS,12cR,14aS)-;2H-1-Benzopyrano[5′,6′:6,7]indeno[1,2-b]indol-3(4bH)-one,5,6,6a,7,12,12b,12c,13,14,14a-decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-,[2R-(2α,4bβ,6aα,12bβ,12cα,14aβ)]-;(2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a,7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-hydroxy-1-methylethyl)-12b,12c-dimethyl-2H-1-benzopyrano[5′,6′:6,7]indeno[1,2-b]indol-3(4bH)-one;Paxilline;(+)-Paxilline;Paxillin;Paxicillin;Paxiline
Categories:
Analytical Chemistry > Standard

Description

Paxilline is an indole alkaloid mycotoxin from Penicillium paxilli, acts as a potent BK channels inhibitor by an almost exclusively closed-channel block mechanism. Paxilline also inhibits the sarco/endoplasmic reticulum Ca2+ ATPase (SERCA) with IC50s between 5μM and 50μM for differing isoforms. Paxilline possesses significant anticonvulsant activity[1][2][3].

Solid

Paxilline is an organic heterotricyclic compound and an organooxygen compound.

Paxilline Basic Attributes

Molecular Weight：

435.56

Exact Mass：

435.56

EC Number：

200-835-2

UNII：

3T9U9Z96L7

HScode：

29419090

Characteristics

PSA：

82.6

XLogP3：

3.77

Appearance：

faint yellow powder

Density：

1.3±0.1 g/cm3

Melting Point：

252 °C

Boiling Point：

648.8±55.0 °C at 760 mmHg

Flash Point：

2℃

Refractive Index：

1.661

Water Solubility：

Soluble in DMSO, acetone or chloroform.

Storage Conditions：

2-8°C

Collision Cross Section：

201 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

23/24/25-36/37/38-41-36-20/21/22-11

safety instructions：

26-36/37/39-45-36/37-16

RTECS Number：

DJ2830000

Marks：

T,Xn,F

Precautionary statement(s)：

P261-P280-P301 + P310-P305 + P351 + P338-P311

Hazard Statements：

H301-H311-H315-H318-H331-H335

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P332+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

A class of drugs that act by inhibition of potassium efflux through cell membranes. Blockade of potassium channels prolongs the duration of ACTION POTENTIALS. They are used as ANTI-ARRHYTHMIA AGENTS and VASODILATOR AGENTS. (See all compounds classified as Potassium Channel Blockers.)

MeSH Entry Terms：

paxilline

Paxilline Use and Manufacturing

Paxilline is a tremorgenic mycotoxin isolated from species of Penicillium, Acremonium and Emericella. Paxilline selectively blocks high-conductance Ca2+-activated potassium channels and inhibits binding to the cerebellar inositol 1,4,5-triphosphate (InsP(3)) receptor.

Computed Properties

Molecular Weight:435.6
XLogP3:3.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:435.24095853
Monoisotopic Mass:435.24095853
Topological Polar Surface Area:82.6
Heavy Atom Count:32
Complexity:868
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes