基本情報
- CAS
14930-96-2- 標準SMILES
C=C1C(C)C2C(Cc3ccccc3)NC(=O)C23OC(=O)/C=C\C(O)CCCC(C)C/C=C\C3C1O- InChIKey
GBOGMAARMMDZGR-NBOXQWGESA-N- 分子式
- C29H37NO5
- 平均分子量
- 479.6 g/mol
- 単同位体質量
- 479.26717328
名称と識別子
- 優先名称
- 7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione
- IUPAC
- (4Z,12Z)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicosa-4,12-diene-3,21-dione
- 現地名
- サイトカラシンB
- 英語名
- CYTOCHALASIN B
- 分子式
- C29H37NO5
- 分子量
- 479.61
名称と別名
7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E),21(E)-triene-1,23-dione7(S),20(R)-Dihydroxy-16(R)-methyl-10-phenyl-24-oxa(14)cytochalasa-6(12),13(E),21(E)-triene-1,23-dioneRefChem:544687ホミンシトカラシンB(7S,13E,16R,20R,21E)-7,20-ジヒドロキシ-16-メチル-10-フェニル-24-オキサ[14]サイトカラサ-6(12),13,21-トリエン-1,23-ジオンサイトカラシンB DRECHSLERA DEMATIOIDEA由来サイトカラシンB(5R,9R,12aS,13S,15S,15aS,16S,18aS)-16-ベンジル-5,13-ジヒドロキシ-9,15-ジメチル-14-メチリデン-2H,5H,6H,7H,8H,9H,10H,12aH,13H,14H,15H,15aH,16H,17H,18H-オキサシクロテトラデカ[3,2-e]イソインドール-2,18-ジオンシトカラシンcytochalasinPHOMIN
名称をさらに表示
(E,E)-16-BENZYL-6,7,8,9,10,12A,13,14,15,15A,16,17-DODECAHYDRO-5,13-DIHYDROXY-9,15-DIMETHYL-14-METHYLENE-2H-OXACYCLOTETRADE[2,3-D]ISOINDOLE-2,18(5H)-DIONE-23-oneCYTOCHALACINBCYTOCHALICINBCYTOCHALASIN BCYTOCHALASIN B(RG)Cytochalasin B (Phomin)CYTOCHALASIN B USP/EP/BP
物性
構造計算による物性
- XLogP
- 3.4
- 極性表面積
- 95.9 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 5
- 回転可能結合数
- 2
- 重原子数
- 35
- 形式電荷
- 0
- 複雑度
- 859
物理化学的性質
- 融点
- 218 · 218-223 °C
- 沸点
- 577.96 °C · 577.96°C (rough estimate)
- 比重(密度)
- 1.149 · 1.1490 (rough estimate)
- 屈折率
- 1.629 · 1.6290 (estimate)
- 闪点
- 85 ℃ · 85℃
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 20 mg/mL · エタノール: 20 mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 13.6 · 13.60±0.70(Predicted)
- 色
- 白い
- Merck
- 13 · 13,2819
- BRN
- 1096207 · 1096207
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 1 か月間保存できます。
- InChIKey
- UXVDBQLLXVKPRS-UZBFCAAUSA-N
- SMILES
- C[C@@H]1CCC[C@@H](O)\C=C\C(=O)O[C@]23[C@@H](\C=C\C1)[C@H](O)C(=C)[C@@H](C)[C@H]2[C@H](Cc4ccccc4)NC3=O
- LogP
- 3.37 · 3.370
- EPAの化学物質情報
- Cytochalasin B (14930-96-2)
化学的性質
white to off-white powder
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
Danger
H300+H310+H330 (38.7%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
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 75 reports by companies from 5 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%)
安全データ
- F
- 10
- wgk
- 3
- rtecs
- RO0205000
- ridadr
- UN 1544 6.1/PG 2
- 毒性
- LD50 intraperitoneal in mouse: 30mg/kg
- hs_code
- 29349990
- risk_code
- 26/27/28-63-23/24/25
- hazard_code
- T+,T
- safety_code
- 28-36/37-45
- hazard_class
- 6.1(a)
- packing_group
- I
- Hazard Classifications
- Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 OralRepr. 2
- ストレージクラス
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- 有毒物質データの
- 14930-96-2(Hazardous Substances Data)
化学と産業
応用分野
解説細胞骨格の形成を阻害する化合物．サイトカラシンというのがふつう．菌類Helminthosporium dematiodeumから分離された．
用途アクチン重合阻害剤。
用途抗ウイルス薬, ノイラミニダーゼ阻害薬。
使用Cytochalasin B is one of the most extensively studied members of a family of potent mycotoxins produced by several species of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, giving rise to pronounced morphogenic activity in animals and plants. Like most cytochalsins, cytochalasin B exhibits potent inhibition of actin filament function leading to cell death by apoptosis, and displays a broad range of resultant cellular actions. Despite the common mode of action, there is evidence that individual members of this class display diverse selectivity. However, lack of comparative co-metabolite analysis has restricted a more complete understanding of their individual selectivity.
一般的な説明Cytochalasin B is a cell-permeable fungal toxin / mycotoxin that binds to the ′barbed′ end of actin / actin filaments. This binding leads to:Disruption of actin filaments and of interaction of actin filaments in solutionInhibition of actin polymerizationInhibition of subunit association and dissociationCytochalasin B is widely used in studies of glucose transporters (GLUT). Cytochalasin B is also used as an integral part of various in vitro micronucleus assay protocols.
調製方法
純化方法Purify it by MeOH extraction, reverse phase C18 silica gel batch extraction by selective elution with 1:1 v/v hexane/tetrahydrofuran, crystallisation, subjected to TLC and recrystallisation [Lipski et al. Anal Biochem 161 332 1987]. It is soluble in EtOH (3.6%), Me2CO (1%), Me2SO (37%) and Me2NCHO (49%) at 24o, and can be crystallised from the first two solvents. It interferes with cellular movement [Korm Physiol Reviews 62 672 1982].
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