(6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.02,7.011,15]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate hydrate

• ChemBase编号: 154800
• 分子式: C32H48O9
• 平均质量: 576.71812
• 单一同位素质量: 576.32983312
• SMILES: CC(=O)OC(C)(C)/C=C/C(=O)C(C)([C@H]1[C@@H](C[C@@]2([C@@]1(CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@@H](C(=O)C2(C)C)O)C)C)C)O)O.O
• Canonical SMILES: CC(=O)OC(/C=C/C(=O)C([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C[C@H](O)C(=O)C2(C)C)C)C)(O)C)(C)C.O
• InChI: InChI=1S/C32H46O8.H2O/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7;/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3;1H2/t19-,20+,21-,22+,25+,29+,30-,31+,32+;/m1./s1
• InChIKey: YBFJWXSFAMCEAY-BOUKRGDCSA-N

名称和登记号

名称

• IUPAC标准名: (6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate hydrate
• IUPAC传统名: (6R)-6-[(1R,2R,4S,10S,11S,13R,14R,15R)-4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-14-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate hydrate
• 别名: (2β,9β,10α,16α,23E)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-Norlanosta-5,23-diene-3,11,22-trione; Cucurbitacin B hydrate

登记号

• CAS号: 6199-67-3(anhydrous)
• MDL号: MFCD18432707
• PubChem SID: 162248938
• PubChem CID: 71311992

理论计算性质

• Acid pKa: 12.802778
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): 3.133085
• LogD (pH = 7.4): 3.1330833
• Log P: 3.133085
• 摩尔折射率: 151.0433 cm^3
• 极化性: 59.152073 Å^3
• 极化表面积: 138.2 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: ≥20 mg/mL
• 外观: off-white to light brown powder

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C32H46O8 · xH2O

详细说明

Sigma Aldrich - C8499

Biochem/physiol Actions
Cucurbitacin B is a triterpenoid constituent of Cucurbitaceae plant species. Cucurbitacin B inhibits proliferation in a wide variety of tumor cell lines (IC50 15-30 nM) by inducing apoptosis and inducing cell cycle arrest at G2/M phase. Although the mechanism of action is unclear, Cucurbitacin B inhibits STAT 3 phosphorylation and expression levels and has been shown to block JAK2 activity. Curcubitacin B also inhibits the transcriptional activity of HIF1a and Nf-KB. Curcubitacin B is structurally similar to the JAK inhibitor Curcubitacin I.