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サイトカラシンC

Cytochalasin C

HCID 6440868
ノートを作成反応を作成見積依頼を出す印刷プレビュー
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
部分構造検索類似構造を探す

基本情報

CAS
22144-76-9
標準SMILES
CC(=O)O[C@@H]1/C=C\[C@@](C)(O)C(=O)[C@@H](C)C/C=C\[C@H]2[C@H](O)C(C)=C(C)[C@H]3C(Cc4ccccc4)NC(=O)[C@]132
InChIKey
NAIODHJWOHMDJX-NGFXLRBHSA-N
分子式
C30H37NO6
平均分子量
507.6 g/mol
単同位体質量
507.2620879

概要

Cytochalasins are mycotoxins that have the ability to bind to actin filaments and block polymerization and the elongation of actin. As a result, they can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. Cytochalasins also have the ability to permeate cell membranes, prevent cellular translocation, cause cells to enucleate, and affect other aspects of biological processes unrelated to actin polymerization. Cytochalasin C was first isolated in the fungus Metarrhizium anisopliae. (A2910, A2911, L1913, A2912)

名称と識別子

優先名称
Cytochalasin C
IUPAC
[(1R,2R,3Z,5R,7S,9Z,11R,12S,15R)-16-benzyl-5,12-dihydroxy-5,7,13,14-tetramethyl-6,18-dioxo-17-azatricyclo[9.7.0.01,15]octadeca-3,9,13-trien-2-yl] acetate
現地名
サイトカラシンC
英語名
CYTOCHALASIN C
分子式
C30H37NO6
分子量
507.62

名称と別名

Cytochalasin C22144-76-9DTXSID101017588RefChem:581434DTXCID101475772244-803-63-benzyl-6,12-dihydroxy-4,5,10,12-tetramethyl-1,11-dioxo-1H,2H,3H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca(e)isoindol-15-yl acetateEINECS 244-803-6(3S-(3R*,3aS*,6R*,6aS*,7E,10R*,12S*,13E,15S*,15aS*))-15-(Acetyloxy)-3,3a,6,6a,9,10,12,15-octahydro-6,12-dihydroxy-4,5,10,12-tetramethyl-3-(phenylmethyl)-1H-cycloundec(d)isoindole-1,11(2H)-dione1H-cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3a,6,6a,9,10,12,15-octahydro-6,12,15-trihydroxy-4,5,10,12-tetramehtyl-, 15-acetate(11)Cytochalasa-5,13,19-triene-1,17-dione, 21-(acetoxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E,21R)-(11)Cytochalasa-5,13,19-triene-1,17-dione, 21-(acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E,21R)-
名称をさらに表示
サイトカラシンCサイトカラシンC METARHIZIUM ANISOPLIAE由来シトカラシンC(3S,3aR,6S,6aR,10S,12R,15R,15aR)-3-ベンジル-6,12-ジヒドロキシ-4,5,10,12-テトラメチル-1,11-ジオキソ-1H,2H,3H,3aH,6H,6aH,9H,10H,11H,12H,15H-シクロウンデカ[e]イソインドール-15-イル アセタート

物性

構造計算による物性

XLogP
2.2
極性表面積
113 Ų
水素結合供与体数
3
水素結合受容体数
6
回転可能結合数
4
重原子数
37
形式電荷
0
複雑度
1,020

物理化学的性質

融点
260 · 260-264°C
沸点
595.84 °C · 595.84°C (rough estimate)
比重(密度)
1.1764 · 1.1764 (rough estimate)
屈折率
1.631 · 1.6310 (estimate)
貯蔵温度
20 °C · −20°C
溶解性
5 mg/mL · 塩化メチレン:5 mg/mL 無色透明
外見
白色からオフホワイトの粉末。
酸解離定数(Pka)
11.95 · 11.95±0.70(Predicted)
色
White to off-white
BRN
1613194 · 1613194
LogP
3.25 · 3.250 (est)

化学的性質

化学的特性White solid

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

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 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. 2 (100%)

毒性情報

Treatment · 1 件

Consider activated charcoal after gastrointestinal absportion. Nitroprusside is recommended to reverse peripheral ischemia secondary to vasoconstriction and for the treatment of hypertension. Anticoagulant therapy with intravenous heparin is also recommended. (A704)

Health Effects · 1 件

Major biological effects of cytochalasins include inhibition of the division of cytoplasm, reversible inhibition of cell movement, induction of nuclear extrusion, inhibition of such processes as phagocytosis, platelet aggregation and clot retraction, glucose transport, thyroid secretion, and release of growth hormone. Some cytochalasins have been shown to have developmental effects. (L1916)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 件

Cytochalasins are known to bind to the barbed, fast growing plus ends of microfilaments, which then blocks both the assembly and disassembly of individual actin monomers from the bound end. Once bound, cytochalasin essentially caps the end of the new actin filament. One cytochalasin will bind to one actin filament. By blocking the polymerization and elongation of actin, cytochalasins can change cellular morphology, inhibit cellular processes such as cell division, and cause cells to undergo apoptosis. (A2910, A2911, L1913, L1914)

化学と産業

用途と製造

UsesCytochalasin C was first isolated in the fungus Metarrhizium anisopliae. (A2912)
応用分野 · 2 件

用途試験研究用。

使用Cytochalasin C is one of a family of potent mycotoxins produced by a range of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, resulting in pronounced morphogenic changes in animals and plants. The cytochalasins act by disrupting actin microfilaments and these effects are most noticeable by the inhibition of cell division.

サプライヤー

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化合物ノート

読み込み中…

このページの内容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
(7S,13E,16S,18R,19E,21R)-21-アセトキシ-7,18-ジヒドロキシ-16,18-ジメチル-10-フェニル[11]シトカラサ-5,13,19-トリエン-1,17-ジオン
(7S,13E,16S,18R,19E,21R)-21-アセチルオキシ-7,18-ジヒドロキシ-16,18-ジメチル-10-フェニル[11]シトカラサ-5,13,19-トリエン-1,17-ジオン
CYTOCHALASIN C(RG)
NAIODHJWOHMDJX-VBWDGLFXSA-N
(7s,13e,16s,18r,19e,21r)-methyl-10-phenyl
cytochalasin-C from metarrhizium*anisopliae
cytochalasin C from metarrhizium anisopliae
CYTOCHALASIN C FROM METARRHIRIUM ANISOPL IAE
Cytochalasin C, 97%, from Metarrhizium anisopliae
(11)cytochalasa-5,13,19-triene-1,17-dione,21-(acetoxy)-7,18-dihydroxy-16,18-di
7(S),18-dihydroxy-16(S),18(R)-dimethyl-10-phenyl[11]cytochalasa-5,13(E),19(E)-triene-1,17-dione 21(R)-acetate
1H-Cycloundec(d)isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,6,6a,9,10,12,15-octahydro-6,12-dihydroxy-4,5,10,12-tetramethyl-3-(phenylmethyl)-, (3S-(3R*,3aS*,6R*,6aS*,7E,10R*,12S*,13E,15S*,15aS*))-7(S),18-Dihydroxy-16(S),18(R)-dimethyl-10-phenyl(11)cytochalasa-5,13(E),19(E)-triene-1,17-dione 21(R)-acetateC9880(3aR,6S,6aR,7Z,10S,12R,13Z,15R,15aR)-3-Benzyl-6,12-dihydroxy-4,5,10,12-tetramethyl-1,11-dioxo-2,3,3a,6,6a,9,10,11,12,15-decahydro-1H-cycloundeca[d]isoindol-15-yl acetate

データベース識別子

CAS
22144-76-9
PubChem CID
6440868
DTXSID
DTXSID101017588
EC Number
244-803-6
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

F
10
wgk
3
rtecs
HA5300500
ridadr
UN 1544 6.1/PG 2
毒性
mouse,LD,intraperitoneal,> 100mg/kg (100mg/kg),Chemical and Pharmaceutical Bulletin. Vol. 21, Pg. 2268, 1973.
hs_code
29337900
risk_code
26/27/28-63
hazard_code
T+,T
safety_code
28-36/37-45
hazard_class
6.1(a)
packing_group
I