6-O,7-セコ-5,6-ジデオキシ-6,7-ジデヒドロ-20-O-[(4-ヒドロキシ-3-メトキシフェニル)アセチル]-21-デフェニル-21-ベンジルダフネトキシン

Resiniferatoxin

HCID 5702546CAS 57444-62-9

基本情報

標準SMILES: C=C(C)[C@]12C[C@@H](C)[C@@]34O[C@](Cc5ccccc5)(O[C@@H]1[C@@H]3C=C(COC(=O)Cc1ccc(O)c(OC)c1)C[C@]1(O)C(=O)C(C)=C[C@@H]41)O2
InChIKey: DSDNAKHZNJAGHN-MXTYGGKSSA-N
分子式: C37H40O9
平均分子量: 628.7 g/mol
単同位体質量: 628.26723286

概要

Resiniferatoxin is a heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1). It has a role as a TRPV1 agonist, an analgesic, a neurotoxin and a plant metabolite. It is a tertiary alpha-hydroxy ketone, a diterpenoid, a monomethoxybenzene, a carboxylic ester, a member of phenols, an organic heteropentacyclic compound, an enone and an ortho ester.

名称と識別子

優先名称: Resiniferatoxin
IUPAC: [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
現地名: 6-O,7-セコ-5,6-ジデオキシ-6,7-ジデヒドロ-20-O-[(4-ヒドロキシ-3-メトキシフェニル)アセチル]-21-デフェニル-21-ベンジルダフネトキシン
英語名: RESINIFERATOXIN
分子式: C37H40O9
分子量: 628.71

名称と別名

Resiniferatoxin57444-62-9ReciniferatoxinLopain(+)-resiniferatoxinRTX diterpeneMtx-071NeuroclastinA5O6P1UL4IMTX-71DTXSID00894764CHEBI:8809

名称をさらに表示

(+)-レシニフェラトキシンレシニフェラトキシンレジニフェラトキシン6-O,7-セコ-5,6-ジデオキシ-6,7-ジデヒドロ-20-O-[(4-ヒドロキシ-3-メトキシフェニル)アセチル]-21-デフェニル-21-ベンジルダフネトキシンレシニフィラトキシン4-ヒドロキシ-3-メトキシフェニル酢酸[(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-ベンジル-8,10-ジメチル-2,9b-エポキシ-6a-ヒドロキシ-11a-(1-メチルエテニル)-7-オキソ-3a,3b,6,6a,7,9a,9b,10,11,11a-デカヒドロアズレノ[5,4-e]-1,3-ベンゾジオキソール-5-イル]メチル(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-ベンジル-8,10-ジメチル-2,9b-エポキシ-6a-ヒドロキシ-5-[(4-ヒドロキシ-3-メトキシフェニル)アセトキシメチル]-11a-(1-メチルエテニル)-3a,3b,6,6a,7,9a,9b,10,11,11a-デカヒドロアズレノ[5,4-e]-1,3-ベンゾジオキソール-7-オン[(1R,2R,6R,10S,11R,13S,15R,17R)-13-ベンジル-6-ヒドロキシ-4,17-ジメチル-5-オキソ-15-(プロパ-1-エン-2-イル)-12,14,18-トリオキサペンタシクロ[11.4.1.01,10.02,6.011,15]オクタデカ-3,8-ジエン-8-イル]メチル 2-(4-ヒドロキシ-3-メトキシフェニル)アセタートRTX[3H]resiniferatoxinResiniferatoxin >99%Resiniferatoxin (80%)Resiniferatoxin, 98.5%RESINIFERATOXIN,HIGHPURITYDSDNAKHZNJAGHN-IHCAYWNCSA-NRESINIFERATOXIN, 99%, HIGH PURITYRESINIFERATOXIN,EUPHORBIA POISONII

[(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate6,7-Deepoxy-6,7-didehydro-5-deoxy-21-dephenyl-21-(phenylmethyl)daphnetoxin 20-(3-hydroxy-5-methoxybenzeneacetate)Benzeneacetic acid, 4-hydroxy-3-methoxy-, ((2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-3a,3b,6,6a,9a,10,11,11a-octahydro-6a-hydroxy-8,10-dimethyl-11a-(1-methylethenyl)-7-oxo-2-(phenylmethyl)-7H-2,9b-epoxyazuleno(5,4-e)-1,3-benzodioxol-5-yl)methyl ester((1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo(11.4.1.01,10.02,6.011,15)octadeca-3,8-dien-8-yl)methyl 2-(4-hydroxy-3-methoxyphenyl)acetateRefChem:879415DTXCID501324327((1R,2R,6R,10S,11R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo(11.4.1.01,10.02,6.011,15)octadeca-3,8-dien-8-yl)methyl 2-(4-hydroxy-3-methoxyphenyl)acetate((1R,2R,6R,10S,11R,15S,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo(11.4.1.01,10.02,6.011,15)octadeca-3,8-dien-8-yl)methyl 2-(4-hydroxy-3-methoxyphenyl)acetate

データベース識別子

CAS: 57444-62-9
PubChem CID: 5702546
DTXSID: DTXSID00894764
ChEMBL: CHEMBL17976
ChEBI: CHEBI:8809
UNII: A5O6P1UL4I
EC Number: 637-354-6
Nikkaji: J282.917G

物性

構造計算による物性

XLogP: 4.5
極性表面積: 121 Å²
水素結合供与体数: 2
水素結合受容体数: 9
回転可能結合数: 9
重原子数: 46
形式電荷: 0
複雑度: 1,330

物理化学的性質

沸点: 768.7 · 768.7±60.0 °C(Predicted)
比重(密度): 1.35 · 1.35±0.1 g/cm3(Predicted)
貯蔵温度: -20 °C · -20°C
溶解性: 100 mMまで、エタノールで50mMまで可溶 · DMSOで100mMまで、エタノールで50mMまで可溶
外見: 個体
酸解離定数(Pka): 9.85 · 9.85±0.20(Predicted)
色: ホワイトからオフホワイト
由来生物: Euphorbia poisonii
BRN: 5371150 · 5371150
安定性: -20 °Cで最大1か月保存できます。 · DMSO溶液またはエタノール溶液で-20°Cで最大1か月保存できます。
InChIKey: DSDNAKHZNJAGHN-MXTYGGKSSA-N
SMILES: C1(CC(OCC2C[C@@]3(O)[C@]([H])([C@]45O[C@]6(CC7=CC=CC=C7)O[C@]([H])([C@]4([H])C=2)[C@](C(C)=C)(C[C@H]5C)O6)C=C(C)C3=O)=O)=CC=C(O)C(OC)=C1

化学的性質

化学的特性white to off-white solid

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 6 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

Health EffectsResiniferatoxin is a neurotoxin that targets afferent sensory neurons involved in nociception. It evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)

Toxicity Summary · 1 件

Resiniferatoxin activates the vanilloid receptor in a subpopulation of primary afferent sensory neurons involved in nociception (the transmission of physiological pain). RTX causes a novel ion channel in the plasma membrane of sensory neurons, the transient receptor potential vanilloid 1, to become permeable to cations, most particularly the calcium cation. This evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

Signs and SymptomsResiniferatoxin evokes a powerful irritant effect followed by desensitization and analgesia. (L1244)

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

安全データ

F: 10-23
wgk: 3
rtecs: CY1633700
ridadr: UN 2928 6.1/PG 2
hs_code: 29329990
risk_code: 25-35
hazard_code: T
safety_code: 26-36/37/39-45
hazard_class: 6.1(a)
packing_group: II
Hazard Classifications: Acute Tox. 3 OralSkin Corr. 1A
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

用途と製造

Uses · 1 件

Resiniferatoxin (RTX) is a plant toxin and ultrapotent capsaicin analog that occurs in various species of plants, such as resin spurge (Euphorbia resinifera). (L1244) Investigated for use/treatment in interstitial cystitis and urinary incontinence.

応用分野 · 1 件

使用Resiniferatoxin has been used as an agonist to transient receptor potential vanilloid 2 (TRPV2): for complex preparation for cryo-electron microscopy structural studies to test its effect towards immune responses toP.aeruginosa in sensory neurons associated with the cornea to study its effects in the denervation of the peripheral sensory nerves in psoriatic mice

上流・下流製品情報

上流原料

Benzeneacetic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-4-ヒドロキシ-3-メトキシフェニル酢酸

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