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Paxilline

HCID 105008
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
1233509-81-3
標準SMILES
CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O
InChIKey
ACNHBCIZLNNLRS-UBGQALKQSA-N
分子式
C27H33NO4
平均分子量
435.6 g/mol
単同位体質量
435.24095853

概要

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 geroprotector, a mycotoxin, an anticonvulsant, a potassium channel blocker, a genotoxin, an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor, an Aspergillus metabolite and a Penicillium metabolite. It is a diterpene alkaloid, a tertiary alcohol, an enone, an organic heterohexacyclic compound and a terpenoid indole alkaloid.

名称と識別子

優先名称
Paxilline
IUPAC
(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one

名称と別名

paxilline57186-25-1DTXSID109726433T9U9Z96L7(1s,2r,5s,7r,11s,14s)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-oneNSC-658707(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo(12.10.0.02,11.05,10.016,24.017,22)tetracosa-9,16(24),17,19,21-pentaen-8-oneRefChem:858745DTXCID80153012311-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo(12.10.0.0^(2,11).0^(5,10).0^(16,24).0^(17,22))tetracosa-9,16(24),17,19,21-pentaen-8-one637-206-011-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo(12.10.0.02,11.05,10.016,24.017,22)tetracosa-9,16(24),17,19,21-pentaen-8-one
名称をさらに表示
NSC 658707BRN 5317894MLS000028812(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)-oneSMR000058863A1C9G(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(2R,4bS,6aS,12bS,12cR,14aS)-5,6,6a, 7,12,12b,12c,13,14,14a-Decahydro-4b-hydroxy-2-(1-h ydroxy-1-methylethyl)-12b,12c-dimethyl-2H-pyrano[2 '',3'':5',6']benz[1',2':6,7]indeno[1,2-b]indol-3(4bH)-one

データベース識別子

CAS
1233509-81-3、57186-25-1
PubChem CID
105008
DTXSID
DTXSID10972643
ChEMBL
CHEMBL410063
ChEBI
CHEBI:34907
UNII
3T9U9Z96L7
EC Number
637-206-0
Nikkaji
J31.896E

物性

構造計算による物性

XLogP
3.5
極性表面積
82.6 Ų
水素結合供与体数
3
水素結合受容体数
4
回転可能結合数
1
重原子数
32
形式電荷
0
複雑度
868

実験および物理化学的性質

Melting Point252 °C
Physical DescriptionSolid
Collision Cross Section201 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H301+H311+H331 (42.6%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 68 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

毒性情報

Treatment · 1 件

To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (A744)

Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (A2976)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 件

Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. In addition, paxilline inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. Paxilline is also genotoxic and causes DNA damage. (A2976, A2993, A3026)

Signs and Symptoms · 1 件

Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors, hyperexcitability, convulsions and ataxia. (A2976)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

MeSH Pharmacological ClassificationA 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.
Cellular LocationsExtracellular

用途と製造

UsesPaxilline is a tremorgenic mycotoxin that has been found in fungus Penicillium paxilli. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (A2976, A3082)

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