(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate

• ChemBase编号: 5687
• 分子式: C23H24O8
• 平均质量: 428.43186
• 单一同位素质量: 428.14711773
• SMILES: [C@@H]1(OC(=O)c2c3[C@]1(C1=C(C(=O)c3oc2)[C@H]2[C@@](C[C@H]1OC(=O)C)(C)C(=O)CC2)C)COC
• Canonical SMILES: COC[C@H]1OC(=O)c2c3[C@@]1(C)C1=C(C(=O)c3oc2)[C@H]2[C@@](C[C@H]1OC(=O)C)(C)C(=O)CC2
• InChI: InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1
• InChIKey: QDLHCMPXEPAAMD-QAIWCSMKSA-N

名称和登记号

名称

• IUPAC标准名: (1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate; (1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^2,^1^0.0^5,^9.0^1^5,^1^9]nonadeca-2(10),12(19),14-trien-3-yl acetate
• IUPAC传统名: wortmannin
• 别名: (1S,6BR,9AS,11R,11BR)-9A,11B-DIMETHYL-1-[(METHYLOXY)METHYL]-3,6,9-TRIOXO-1,6,6B,7,8,9,9A,10,11,11B-DECAHYDRO-3H-FURO[4,3,2-DE]INDENO[4,5-H][2]BENZOPYRAN-11-YL ACETATE; Wortmannin; KY 12420; Wortmannin

登记号

• CAS号: 19545-26-7
• MDL号: MFCD00133927
• Beilstein号: 67676
• PubChem SID: 160969114; 24278777; 99444530
• PubChem CID: 312145
• CHEMBL: 428496
• Chemspider ID: 276037
• 维基百科标题: Wortmannin

理论计算性质

JChem

• Acid pKa: 19.667614
• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): 1.4426177
• LogD (pH = 7.4): 1.4426177
• Log P: 1.4426177
• 摩尔折射率: 106.8572 cm^3
• 极化性: 41.506565 Å^3
• 极化表面积: 109.11 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.31
• LOG S: -3.55
• 溶解度: 1.21e-01 g/l

分子性质

理化性质

• 溶解度: DMSO: soluble; H2O: unstable
• 外观: off-white powder
• 熔点: 238-242 °C

安全信息

• RTECS编号: CB9641000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1
• 危险公开号: 26/27/28
• 安全公开号: 28-36/37-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330
• GHS警示性声明: P260-P264-P280-P284-P302 + P350-P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• 保存温度: 2-8°C

药理学性质

• 作用靶点: PI3K
• 相关基因信息: human ... PIK3CD(5293), PIK3CG(5294), PIK3R1(5295)

产品相关信息

• 纯度: ≥98% (HPLC and TLC); ≥98.0% (TLC)
• 成盐信息: Free Base
• 生物来源: from Penicillium funiculosum
• 产品质量级别: PREMIUM
• Empirical Formula (Hill Notation): C23H24O8

详细说明

DrugBank - DB08059

Drug information: experimental

Sigma Aldrich - W1628

Biochem/physiol Actions
Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM. Inhibition of PI3-K/Akt signal transduction cascade enhances the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. Inhibition of PI3-K by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation.

Sigma Aldrich - 95455

Biochem/physiol Actions
Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM. Inhibition of PI3-K/Akt signal transduction cascade enhances the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. Inhibition of PI3-K by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation.