2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン
Staurosporine
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基本情報
- CAS
62996-74-1- 標準SMILES
CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4- InChIKey
HKSZLNNOFSGOKW-FYTWVXJKSA-N- 分子式
- C28H26N4O3
- 平均分子量
- 466.5 g/mol
- 単同位体質量
- 466.20049069
概要
Staurosporine is an indolocarbazole alkaloid and an organic heterooctacyclic compound. It has a role as a geroprotector, an EC 2.7.11.13 (protein kinase C) inhibitor, an apoptosis inducer and a bacterial metabolite. It is a conjugate base of a staurosporinium.
名称と識別子
- 優先名称
- Staurosporine
- IUPAC
- (2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one
- 現地名
- 2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン
- 英語名
- STAUROSPORINE
- 分子式
- C28H26N4O3
- 分子量
- 466.54
名称と別名
staurosporineStaurosporin62996-74-1Antibiotic 230Antibiotic AM 2282AM-2282H88EPA0A3NDTXSID6041131CHEBI:15738CGP-393608,12-Epoxy-1H,8H-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)trinden-1-one, 2,3,9,10,11,12-hexahydro-9-methoxy-8-methyl-10-(methylamino)-, (8alpha,9beta,10beta,12alpha)-(+)-(2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one
名称をさらに表示
スタウロスポリン(9S,10α,11α,13β)-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン[9S,10α,11α,13β,(+)]-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オンスタウロスポリン 放線菌由来(2S,3S,4S,6R)-3-メトキシ-2-メチル-4-(メチルアミノ)-29-オキサ-1,7,17-トリアザオクタシクロ[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]ノナコサ-8,10,12,14(28),15(19),20(27),21(26),22,24-ノナエン-16-オン(9S,10α,11α,13β)-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3′,2′,1′-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン(9S,10R,11R,13R)-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3′,2′,1′-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン[9S,10α,11α,13β,(+)]-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3′,2′,1′-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3′,2′,1′-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン(2S,3R,4R,6R)-3-メトキシ-2-メチル-4-(メチルアミノ)-29-オキサ-1,7,17-トリアザオクタシクロ[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]ノナコサ-8,10,12,14(28),15(19),20(27),21(26),22,24-ノナエン-16-オン2,3,10,11,12,13-ヘキサヒドロ-10β-メトキシ-9-メチル-11β-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3′,2′,1′-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オンSTSPStauroporineStaurosporine,98%2,3,10,11,12,13-HEXAHYDRO-10R-METHOXY-9S-METHYL-11R-METHYLAMINO-9S,13R-EPOXY-1H,9H-DIINDOLO[1,2,3-GH:3',2',1'-LM]PYRROLO[3,4-J][1,7]BENZODIAZONIN-1 ONECBR113CS-2206SporosinCGP 39360
NSC618487(2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo(12.12.2.1^(2,6).0^(7,28).0^(8,13).0^(15,19).0^(20,27).0^(21,26))nonacosa-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-16-one(2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo(12.12.2.12,6.07,28.08,13.015,19.020,27.021,26)nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one(2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-16-oneRefChem:889116DTXCID201340061(9alpha,10beta,11beta,13alpha)-(+)-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H-9H-diindolo(1,2,3-gh:3',2',1'-lm)pyrrolo(3,4-j)(1,7)benzodiazonin-1-one1-((2R,3S,4S,6S)-3-methoxy-2-methyl-16-oxo-29-oxa-1,7,17-triazaoctacyclo(12.12.2.12,6.07,28.08,13.015,19.020,27.021,26)nonacosa-8,10,12,14,19,21,23,25,27-nonaen-4-yl)-1-methylurea
データベース識別子
- CAS
62996-74-1- PubChem CID
- 44259
- DTXSID
DTXSID6041131- ChEMBL
CHEMBL388978- ChEBI
CHEBI:15738- UNII
- H88EPA0A3N
- EC Number
- 613-127-7
- Nikkaji
- J445.409J
物性
構造計算による物性補完中
- XLogP
- 3.2
- 極性表面積
- 69.5 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
- 2
- 重原子数
- 35
- 形式電荷
- 0
- 複雑度
- 901
実験および物理化学的性質
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
物理化学的性質
- 融点
- 270 °C · 270°C
- 比旋光度
- 25 · D25 +35.0° (c = 1 in methanol); D22 +56.1° (c = 0.14 in methanol)
- 沸点
- 677.5 · 677.5±55.0 °C(Predicted)
- 比重(密度)
- 1.56 · 1.56±0.1 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMSO：可溶
- 外見
- 白色～淡黄色の固体
- 酸解離定数(Pka)
- 14.25 · 14.25±0.70(Predicted)
- 色
- オフホワイトから淡黄色
- 水溶解度
- DMSOまたはエタノールに可溶。ジメチルスルホキシド、ジメチルホルムアミド、酢酸エチル、熱アセトン、エタノールに可溶。クロロホルム、メタノールに溶けにくい。水に溶けません。
- BRN
- 1060573 · 1060573
- 安定性
- -20 °C · -20°C の DMSO 溶液で最大 4 か月間保存できます。
- InChIKey
- HKSZLNNOFSGOKW-WIFUGMKFSA-N
- SMILES
- CN[C@@H]1C[C@@H]2O[C@@](C)([C@@H]1OC)n3c4ccccc4c5c6CNC(=O)c6c7c8ccccc8n2c7c35
- CAS データベース
- 62996 · 62996-74-1
化学的性質
化学的特性Light Yellow 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
Danger
H302 (10%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 10 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
9,13-Epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, (9S,10R,11R,13R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (10%)
安全データ
- F
- 8-10
- wgk
- 2
- ridadr
- UN 2811 6.1 / PGII
- hs_code
- 29419090
- risk_code
- 40-45-36/37/38-46
- hazard_code
- Xn,T,Xi
- safety_code
- 36/37-53-36-26-45
- hazard_class
- 3
- Hazard Classifications
- Aquatic Chronic 4Carc. 1BMuta. 1BRepr. 2
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
化学と産業
薬理情報
MeSH Pharmacological ClassificationCompounds 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
用途プロテインキナーゼC阻害剤。
説明Staurosporine (Stsp) is potent inhibitor of protein kinase C (PKC) from rat brain, exhibiting an IC50 value of 2.7 nM. It inhibits rat recombinant PKC-α approximately 100- and 1,000-fold better than PKC-δ and PKC-ζ, respectively. However, Stsp is non-selective in that it also inhibits the activity of a variety of other protein kinases, not only PKC isoforms. The biological effects of Stsp include cytotoxicity, relaxation of smooth muscle, and regulation of eNOS gene expression.
天然物の起源A complex alkaloid. staurosporine has been isolated from a strain of Streptomyces.
使用Staurosporine is an unusual indolocarbazole alkaloid produced by a range of actinomycete species. It is a potent antitumour active, inducing apoptosis in a variety of cell lines. Staurosporine is a potent inhibitor of many kinases including protein kinase C, tyrosine kinase, CDK2/cyclin A and CDK4/cyclin D. At submicromolar concentrations, staurosporine inhibits both IKKalpha and IKKbeta.
一般的な説明A potent, cell-permeable, reversible, ATP-competitive and broad spectrum inhibitor of protein kinases. Inhibits CaM kinase (IC50 = 20 nM), myosin light chain kinase (IC50 = 1.3 nM), protein kinase A (IC50 = 7 nM), protein kinase C (IC50 = 0.7 nM), and protein kinase G (IC50 = 8.5 nM). Also inhibits platelet aggregation induced by collagen or ADP but has no effect on thrombin-induced platelet aggregation. Induces apoptosis in human malignant glioma cell lines. Arrests normal cells at the G1 checkpoint.
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