ブファリン
Bufalin
基本情報
- CAS
465-21-4- 標準SMILES
C[C@]12CC[C@H](O)C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](c3ccc(=O)oc3)CC[C@]12O- InChIKey
QEEBRPGZBVVINN-BMPKRDENSA-N- 分子式
- C24H34O4
- 平均分子量
- 386.5 g/mol
- 単同位体質量
- 386.24570956
概要
Bufalin is a 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo. It has a role as an antineoplastic agent, a cardiotonic drug, an anti-inflammatory agent and an animal metabolite. It is a 3beta-hydroxy steroid and a 14beta-hydroxy steroid. It is functionally related to a bufanolide.
名称と識別子
- 優先名称
- Bufalin
- IUPAC
- 5-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
- 現地名
- ブファリン
- 英語名
- Bufalin
- 分子式
- C24H34O4
- 分子量
- 386.53
名称と別名
bufalin465-21-43,14-Dihydroxy-bufa-20,22-dienolideCHEBI:5172483-beta,14-Dihydroxy-5-beta-bufa-20,22-dienolideU549S98QLW3beta,14beta-dihydroxy-5beta-bufa-20,22-dienolideDTXSID908735635beta-Bufa-20,22-dienolide, 3beta,14-dihydroxy-NSC-895955-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-oneBufa-20,22-dienolide, 3,14-dihydroxy-, (3beta,5beta)-
名称をさらに表示
ブファリン3β,14-ジヒドロキシ-5β-ブファ-20,22-ジエノリド3β,14-ジヒドロキシ-5β,14β-ブファ-20,22-ジエノリド5-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a,7-ジヒドロキシ-9a,11a-ジメチル-ヘキサデカヒドロ-1H-シクロペンタ[a]フェナントレン-1-イル]-2H-ピラン-2-オンNSC89595NSC 89595Bufalin-RMBufalin std.Bufalin (6CI)Bufalin, >=98%BUFALIN90%,99%Bufalin USP/EP/BP
5-beta-BUFA-20,22-DIENOLIDE, 3-beta,14-DIHYDROXY-Bufa-20,22-dienolide, 3,14-dihydroxy-, (3-beta,5-beta)-5-((3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)pyran-2-oneRefChem:121846DTXCID7014767805-((3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-oneCh'an suUNII-U549S98QLW
物性
構造計算による物性
- XLogP
- 3.2
- 極性表面積
- 66.8 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 1
- 重原子数
- 28
- 形式電荷
- 0
- 複雑度
- 741
実験および物理化学的性質
LipidsLipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Bufanolides and derivatives [ST0113]
LogP3.34
物理化学的性質
- 融点
- 242 · 242-243°
- 比旋光度
- -20 ° · D -20°
- 沸点
- 556.6 · 556.6±50.0 °C(Predicted)
- 比重(密度)
- 1.226 · 1.226±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 36 · DMSO:36.0(Max Conc. mg/mL);93.14(Max Conc. mM)DMF:25.0(Max Conc. mg/mL);64.68(Max Conc. mM)Ethanol:27.5(Max Conc. mg/mL);71.15(Max Conc. mM)Ethanol:PBS (pH 7.2) (1:2):0.3(Max Conc. mg/mL);0.78(Max Conc. mM)
- 酸解離定数(Pka)
- 15.01 · 15.01±0.70(Predicted)
- 外見
- 白からオフホワイトの固体
- 色
- White to off-white
- 主な用途
- 食品および飲料
- InChIKey
- QEEBRPGZBVVINN-ONGIWDLKSA-N
- SMILES
- O[C@]12CC[C@H](C3=COC(C=C3)=O)[C@]1(CC[C@]1([H])[C@]3(CC[C@@H](C[C@@]3([H])CC[C@@]21[H])O)C)C
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 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 2 (100%)
安全データ
- wgk
- 3
- rtecs
- EI2962500
- ridadr
- UN 3462 6.1/PG 2
- hs_code
- 29322090
- risk_code
- 28
- hazard_code
- T+
- safety_code
- 28-36/37-45
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard Classifications
- Acute Tox. 2 Oral
- 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
薬理情報
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
応用分野
使用Bufalin has been used: to test its effect on invasion and activation of nuclear factor kappa- B (NF-κB) cells and tumor necrosis factor-α (TNF-α) stimulated rheumatoid arthritis fibroblast-like synoviocytes (RAFLSs) as a nuclear receptor coactivator 3 (NCOA3) inhibitor in chondrocytesto test its anti-metastasis effect in lung cancer cells (NCI-H460) resistant to gefitinib
一般的な説明Bufalin is a C-24 steroid with an α-pyrone ring positioned at C-17. It is present in the venom glands and skin of toad, Venenum Bufonis. Bufalin is a cardiotonic steroid and is digoxin-like component of Chan Su.
補足説明
定義ChEBI: A 14beta-hydroxy steroid that is bufan-20,22-dienolide having hydroxy substituents at the 5beta- and 14beta-positions. It has been isolated from the skin of the toad Bufo bufo.
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