基本情報
- CAS
22862-76-6- 標準SMILES
COc1ccc(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)cc1- InChIKey
YKJYKKNCCRKFSL-RDBSUJKOSA-N- 分子式
- C14H19NO4
- 平均分子量
- 265.3 g/mol
- 単同位体質量
- 265.13140809
概要
(-)-anisomycin is an antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system. It has a role as an anticoronaviral agent, an antimicrobial agent, an antiparasitic agent, an antineoplastic agent, a protein synthesis inhibitor, a DNA synthesis inhibitor and a bacterial metabolite. It is an organonitrogen heterocyclic antibiotic and a monohydroxypyrrolidine.
名称と識別子
- 優先名称
- Anisomycin
- IUPAC
- [(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate
- 現地名
- 酢酸(2R)-4β-ヒドロキシ-2-(4-メトキシベンジル)ピロリジン-3α-イル
- 英語名
- ANISOMYCIN
- 分子式
- C14H19NO4
- 分子量
- 265.3
名称と別名
anisomycin22862-76-6Flagecidin(-)-Anisomycin(2R,3S,4S)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetateNSC-76712(2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetateNSC767126C74YM2NGI[(2R,3S,4S)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetateDTXSID5040966
名称をさらに表示
アニソマイシン(2R)-2α-(4-メトキシベンジル)ピロリジン-3α,4β-ジオール3-アセタート1,4-イミノ-5-(4-メトキシフェニル)1,4,5-トリデオキシ-D-xylo-ペンチトール3-アセタートフラゲシジン酢酸(2R)-4β-ヒドロキシ-2-(4-メトキシベンジル)ピロリジン-3α-イル(-)-アニソマイシン(2R,3S,4S)-2-(4-メトキシベンジル)-3,4-ピロリジンジオール3-アセタートアニソマイシン, STREPTOMYCES GRISEOLUS由来アニソマイシン FROM STREPTOMYCES GRISEOLUS(2R,3S,4S)-4-ヒドロキシ-2-[(4-メトキシフェニル)メチル]ピロリジン-3-イル アセタートNsc147340Aids031977Aids-031977Wuningmeisu C4-beta))-alphAnisomycin>(-)-anisomycin
物性
構造計算による物性
- XLogP
- 0.9
- 極性表面積
- 67.8 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 5
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 302
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section165.8 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 140 · 140-141 C
- 比旋光度
- 23 · D23 -30° (methanol)
- 沸点
- 408.52 °C · 408.52°C (rough estimate)
- 比重(密度)
- 1.1356 · 1.1356 (rough estimate)
- 屈折率
- 1.523 · 1.5230 (estimate)
- 闪点
- 87 ℃ · 87℃
- 貯蔵温度
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- 20 mg/mL · メタノール: 20 mg/mL 無色透明～微黄色
- 外見
- 個体
- 酸解離定数(Pka)
- 7.9 · 7.9(at 25℃)
- 色
- 白い
- 水溶解度
- 2 mg/ml）、DMSOに溶解 · 水に溶解（2mg/ml）、DMSOに溶解（20mg/ml）、メタノールに溶解（20mg/ml）
- Merck
- 14 · 14,670
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
H301 (98.5%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 65 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
Regulatory InformationStreptomyces griseolus: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - D-xylo-Pentitol, 1,4,5-trideoxy-1,4-imino-5-(4-methoxyphenyl)-, 3-acetate: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 2 (98.5%)
安全データ
- F
- 3-10
- wgk
- 3
- rtecs
- BZ9800000
- ridadr
- UN 3462 6.1/PG 3
- 毒性
- LD50 orl-rat: 72 mg/kg ANTCAO 5,490,55
- hs_code
- 29419090
- risk_code
- 25-36/37/38-20/21/22
- hazard_code
- T,Xn
- safety_code
- 45-36-26
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 3 Oral
化学と産業
薬理情報
MeSH Pharmacological Classification
Substances that are destructive to protozoans.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Compounds that inhibit cell production of DNA or RNA.
Substances that inhibit the growth or reproduction of BACTERIA.
応用分野
使用Anisomycin is a phenylmethylenepyrrolidine first isolated from Streptomyces griseolus in 1954 as an antiprotozoan with antifungal activity. Anisomycin is an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. Interestingly, anisomycin has found use for the induction of amnesia in animal models. More recently, anisomycin has been demonstrated to induce apoptosis, to be a selective signalling agonist, to activate mitogen-activated protein (MAP) kinases and to be immunomodulatory via its action on T cells.
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関連反応
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