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化工社オープンプロジェクト:[email protected]AIアクセス:llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
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(7S,13E,16R,20R)-7β,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-ジエン-1,23-ジオン

(5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-Tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino(2,3-d)isoindole-2,18(3H)-dione

HCID 6438347
ノート反応
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
39156-67-7
標準SMILES
C=C1[C@@H](C)[C@H]2[C@H](Cc3ccccc3)NC(=O)[C@]23OC(=O)CC[C@H](O)CCC[C@@H](C)C/C=C/[C@H]3[C@@H]1O
InChIKey
WIULKAASLBZREV-RXPQEOCGSA-N
分子式
C29H39NO5
平均分子量
481.6 g/mol
単同位体質量
481.28282334

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. Dihydrocytochalasin B is a semi-synthetic derivative of cytochalasin B and is a useful probe for studying cytochalasin binding sites. (A2910, A2911, L1913, L1916)

名称と識別子

優先名称
(5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-Tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino(2,3-d)isoindole-2,18(3H)-dione
IUPAC
(1S,6R,10R,12E,14S,15S,17S,18S,19S)-19-benzyl-6,15-dihydroxy-10,17-dimethyl-16-methylidene-2-oxa-20-azatricyclo[12.7.0.01,18]henicos-12-ene-3,21-dione
現地名
(7S,13E,16R,20R)-7β,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-ジエン-1,23-ジオン
英語名
Dihydrocytochalasin B
分子式
C29H39NO5
分子量
481.62

名称と別名

dihydrocytochalasin B39156-67-721,22-Dihydrophomin21,22-Dihydrochalasin B21,22-Dihydrocytochalasan BL9RT18CY85DTXSID501046323RefChem:404437DTXCID101528151(5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-Tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-2H-oxacyclotetradecino(2,3-d)isoindole-2,18(3H)-dione15-benzyl-4,12-dihydroxy-8,14-dimethyl-13-methylidene-2H,3H,4H,5H,6H,7H,8H,9H,12H,13H,14H,14aH,15H,16H,17H,17bH-oxacyclotrideca(3,2-e)isoindole-2,17-dione254-324-4
名称をさらに表示
21,22-ジヒドロサイトカラシンBジヒドロサイトカラシンB(7S,13E,16R,20R)-7β,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-ジエン-1,23-ジオン(7S,13E,16R,20R)-7,20-ジヒドロキシ-16-メチル-10-フェニル-24-オキサ[14]シトカラサ-6(12),13-ジエン-1,23-ジオン(7S,13E,16R,20R)-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-ジエン-1,23-ジオンDHCBDihidrocytochalasin BCYTOCHALASIN B, DIHYDRO21,22-Dihydrocytochalalsin BCytochalasin B, Dihydro- - CAS 39156-67-7 - Calbiochem7(S),20(R)-dihydroxy-16(R)-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13(E)-diene-1,23-dione(7S,13E,16R,20R)-7,20-Dihydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13-diene-1,23-dione(7S,13E,16R,20R)-7β,20-Dihydroxy-16-methyl-10-phenyl-24-oxa[14]cytochalasa-6(12),13-diene-1,23-dione2H-Oxacyclotetradecino[2,3-d]isoindole-2,18(3H)-dione, 4,5,6,7,8,9,10,12a,13,14,15,15a,16,17-tetradecahydro-5,13-dihydroxy-9,15-dimethyl-14-methylene-16-(phenylmethyl)-, (5R,9R,11E,12aS,13S,15S,15aS,16S,18aS)-
Cytochalasin H2BMFCD12910542C29H39NO5WIULKAASLBZREV-RXPQEOCGSA-NEINECS 254-324-4Cytochalasin H(2)BUNII-L9RT18CY8574409-92-0

データベース識別子

CAS
39156-67-7
PubChem CID
6438347
DTXSID
DTXSID501046323
ChEMBL
CHEMBL2074735
UNII
L9RT18CY85
EC Number
254-324-4
Nikkaji
J261.323I

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
818

物理化学的性質

融点
203 · 203-205 °C
沸点
727.5 · 727.5±60.0 °C(Predicted)
比重(密度)
1.19 · 1.19±0.1 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C
溶解性
30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:20): 0.05 mg/ml; DMSO: 20 mg/ml; Ethanol: 20 mg/ml
酸解離定数(Pka)
13.65 · 13.65±0.70(Predicted)
外見
白い固体
色
white
InChIKey
WIULKAASLBZREV-PEVBMUQXNA-N
SMILES
[C@H]1(C(=C)[C@H]([C@]2([C@]3(OC(CC[C@H](O)CCC[C@@H](C)CC=C2)=O)C(=O)N[C@@H](CC2C=CC=CC=2)[C@]13[H])[H])O)C |t:18,&1:0,3,4,5,10,15,24,32,r|

化学的性質

化学的特性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 · 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)

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

安全データ

wgk
3
rtecs
RO0205000
ridadr
UN 2811 6.1/PG 2
hs_code
29349990
risk_code
26/27/28-40
hazard_code
T+,T
safety_code
22-36/37/39-45
hazard_class
6.1(a)
packing_group
I
Hazard Classifications
Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralCarc. 2
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials

化学と産業

用途と製造

UsesDihydrocytochalasin B is a semi-synthetic derivative of cytochalasin B and is a useful probe for studying cytochalasin binding sites. (L1916)

応用分野

使用Dihydrocytochalasin B is a cell morphology and motility and inducer.

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