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ChemicalBook--->CAS DataBase List--->57186-25-1

57186-25-1

57186-25-1 Structure

57186-25-1 Structure
IdentificationBack Directory
[Name]

PAXILLINE
[CAS]

57186-25-1
[Synonyms]

PAXILINE
PAXILLINE
Paxicillin
Paxilline solution
PAXILLINE, PENICILLIUM PAXILLI
paxilline from penicillium paxilli
4b-beta,6a-alpha,12b-beta,12c-alpha,14a-beta)-2-alph
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,5,6,6a,7,12,12b,12c,1
(2R)-5,6,6aα,7,12,12b,12c,13,14,14aβ-Decahydro-4bβ-hydroxy-2-(1-hydroxy-1-methylethyl)-12bβ,12cα-dimethyl-2H-1-benzopyrano[5',6':6,7]indeno[1,2-b]indol-3(4bH)-one
(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 solution
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)-
(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-PYRANO[2'',3'':5',6']BENZ[1',2':6,7]INDENO[1,2-B]INDOL-3(4BH)-ONE
Paxilline,(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-pyrano[2'',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one
[EINECS(EC#)]

637-206-0
[Molecular Formula]

C27H33NO4
[MDL Number]

MFCD00083464
[MOL File]

57186-25-1.mol
[Molecular Weight]

435.56
Chemical PropertiesBack Directory
[Fp ]

2℃
[storage temp. ]

2-8°C
[solubility ]

Soluble in DMSO, acetone or chloroform.
[form ]

powder
[color ]

faint yellow
Safety DataBack Directory
[Hazard Codes ]

T,Xn,F
[Risk Statements ]

23/24/25-36/37/38-41-36-20/21/22-11
[Safety Statements ]

26-36/37/39-45-36/37-16
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

DJ2830000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29419090
Hazard InformationBack Directory
[Description]

A complex alkaloid, paxilline occurs in the mycelium of the mold Penicillium paxilli. The structure has been confirmed by X-ray crystallography. The crystals are orthorhombic with space group P2 12 121 and a = 31.009, b = 11.522 and c = 7.70 A.
[Description]

Paxilline is an indole diterpene from fungi which potently and reversibly inhibits large conductance Ca2+-activated K+ (BKCa) channels, as shown in patch clamp (Ki = 1.9 nM) and whole smooth muscle cell studies (Ki = 35.7 nM). It also enhances the binding of charybdotoxin , a peptidyl neurotoxin, to BKCa channels. Paxilline is currently used to evaluate the role of BKCa channels in various cell processes and responses.
[Chemical Properties]

Powder
[Uses]

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.
[Definition]

ChEBI: Paxilline is 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. It has a role as a mycotoxin, a Penicillium metabolite, an anticonvulsant, an Aspergillus metabolite, a potassium channel blocker, a genotoxin, a geroprotector and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is an organic heterohexacyclic compound, a tertiary alcohol, a terpenoid indole alkaloid, an enone and a diterpene alkaloid.
[Biological Activity]

Potent blocker of high-conductance Ca 2+ -activated K + (BK Ca ) channels. Binds to the α -subunit of BK Ca (K i = 1.9 nM for block of currents in α -subunit-expressing oocytes) and enhances binding of charybdotoxin to BK Ca channels in vascular smooth muscle. Also inhibits sarco/endoplasmic reticulum Ca 2+ -ATPase (IC 50 = 5-50 μ M).
[Enzyme inhibitor]

This BKCa/KCa1.1) channel blocker (FW = 435.56 g/mol; CAS 57186-25-1; Solubility: 100 mM in DMSO), also named (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-pyrano[2'',3'': 5',6']benz[1',2':6,7]indeno [1,2-b]indol-3(4bH)-one, binds to the α-subunit of BKCa, exhibiting a Ki value of 1.9 nM in blocking currents in α-subunit-expressing oocytes and enhancing binding of to BKCa channels in vascular smooth muscle. (See Charybdotoxin) Paxilline also inhibits sarco/endoplasmic reticulum Ca2+-ATPase, IC50 = 5 - 50 μM.
[storage]

Desiccate at -20°C
[References]

Springer et ai., Tetrahedron Lett., 2531 (1975)
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