35287-69-5

• 常用中文名：黑麦酮酸D,SECALONIC ACID D
• 常用英文名：[7,7'-Bi-4aH-xanthene]-4a,4'a-dicarboxylicacid,2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-,4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4aR,4'aR)
• CAS号：35287-69-5
• 分子式：C₃₂H₃₀O₁₄
• 分子量：638.57200
• 相关类别： 信号通路 细胞凋亡 细胞凋亡
• 发布时间：2016-10-07 17:25:23
• 更新时间：2026-07-16 22:36:53
• Secalonic acid D是一种对肿瘤细胞具有毒性的化合物。Secalonic acid D可以从刺曲霉的代谢产物中分离出来。Secalonic acid D激活GSK3-β,并降解β-连环蛋白。因此,Secalonic acid D下调c-Myc的表达,将细胞周期阻滞在G1期,诱导细胞凋亡[1][2]。

名称

• 中文名: 黑麦酮酸D,SECALONIC ACID D
• 英文名: (7,7'-Bi-4aH-xanthene)-4a,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, [3S-[3.α.,4.β.,4a.β.,7(3'r*,4's*,4'as*)]]
• 中文别名: 黑麦酮酸D
• 英文别名: lpha,4-beta,4a-beta,7(3’r,4’s,4’as))); [7,7'-Bi-4aH-xanthene]-4a,4'a-dicboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8,8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, 4a,4'a-dimethyl ester, (3S,3'S,4R,4'R,4,4'); sad; SECALONIC ACID D FROM PENICILLIUM*OXALICUM; secalonicacidd; ergochrome EE; ergochromeaa(2,2’)-5-beta,6-alpha,10-beta-5’,6’-alpha,10’-beta; secalonic acid D1; 7’-bi-4ah-xanthene)-4a,4’a-dicboxylicacid,2,2’,3,3’,4,4’,9,9’-octahydro-(; Secalonsaeure D; 1,1’,4,4’,8,8’-hexahydroxy-3,3’-dimethyl-9,9’-dioxo-,dimethylester,(3s-(3-a

物化性质

• 密度: 1.67g/cm3
• 沸点: 846ºC at 760 mmHg
• 分子式: C₃₂H₃₀O₁₄
• 分子量: 638.57200
• 闪点: 273.7ºC
• 精确质量: 638.16400
• PSA: 226.58000
• LogP: 2.16420
• 折射率: 1.725

生物活性

• 描述: Secalonic acid D是一种对肿瘤细胞具有毒性的化合物。Secalonic acid D可以从刺曲霉的代谢产物中分离出来。Secalonic acid D激活GSK3-β,并降解β-连环蛋白。因此,Secalonic acid D下调c-Myc的表达,将细胞周期阻滞在G1期,诱导细胞凋亡[1][2]。
• 相关类别:
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  信号通路 >> 干细胞及 Wnt 通路 >> GSK-3
  研究领域 >> 癌症
  信号通路 >> 细胞凋亡 >> c-Myc的
  信号通路 >> PI3K/Akt/mTOR 信号通路 >> GSK-3
• 体外研究: 司卡隆酸D(0.1-1μM；72小时)在 HL60型和 K562细胞中以浓度依赖性方式抑制细胞增殖,IC50型分别为 0.38微米和 0.43微米[1]癸酸D(0.3μM；12小时,24小时)导致细胞周期停滞在 G1期,(1.2μM；0-72小时)并诱导 HL60型和 K562细胞细胞凋亡[1]。 细胞凋亡分析[1]细胞系：HL60和K562细胞浓度：1.2μM培养时间：0、24、48和72小时结果：通过将细胞周期阻滞在G1期诱导细胞凋亡。以及下调c-Myc的表达水平。Western印迹分析[1]细胞系：HL60和K562细胞浓度：1.2μM孵育时间：0、24、48和72小时结果：Caspase-1水平呈剂量依赖性降低。
• 参考文献:

  [1]. Andersen R, et al. Secalonic acids D and F are toxic metabolites of Aspergillus aculeatus. J Org Chem. 1977 Jan 21;42(2):352-3.

  [2]. Zhang JY, et al. Secalonic acid D induced leukemia cell apoptosis and cell cycle arrest of G(1) with involvement of GSK-3beta/beta-catenin/c-Myc pathway. Cell Cycle. 2009 Aug;8(15):2444-50.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : EC2460000 CHEMICAL NAME : (7,7'-Bi-4aH-xanthene)-4a,4'a-dicarboxylic acid, 2,2',3,3',4,4',9,9'-octahydro-1,1',4,4',8, 8'-hexahydroxy-3,3'-dimethyl-9,9'-dioxo-, dimethyl ester, (3S-(3-alpha,4-beta,4a-beta, 7(3'R,4'S,4'aS))) CAS REGISTRY NUMBER : 35287-69-5 LAST UPDATED : 199609 DATA ITEMS CITED : 17 MOLECULAR FORMULA : C32-H30-O14 MOLECULAR WEIGHT : 638.62 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 22 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Liver - hepatitis (hepatocellular necrosis), zonal Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 30 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Liver - hepatitis (hepatocellular necrosis), zonal Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 26500 ug/kg TOXIC EFFECTS : Vascular - regional or general arteriolar or venous dilation Lungs, Thorax, or Respiration - changes in pulmonary vascular resistance Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 25 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Behavioral - food intake (animal) Skin and Appendages - hair TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 50 mg/kg/5D-I TOXIC EFFECTS : Lungs, Thorax, or Respiration - chronic pulmonary edema Related to Chronic Data - death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 25 mg/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - respiratory system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 15 mg/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Specific Developmental Abnormalities - musculoskeletal system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 15 mg/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - gastrointestinal system Reproductive - Specific Developmental Abnormalities - urogenital system TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 25 mg/kg SEX/DURATION : female 9 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 15 mg/kg SEX/DURATION : female 13 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - physical Reproductive - Effects on Newborn - delayed effects TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 150 mg/kg SEX/DURATION : lactating female 10 day(s) post-birth TOXIC EFFECTS : Reproductive - Effects on Newborn - behavioral TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 45 mg/kg SEX/DURATION : female 7-15 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 25 mg/kg SEX/DURATION : female 10 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 25 mg/kg SEX/DURATION : female 11 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 25 mg/kg SEX/DURATION : female 11 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) MUTATION DATA TEST SYSTEM : Rodent - mouse DOSE/DURATION : 30 mg/kg REFERENCE : JEPTDQ Journal of Environmental Pathology and Toxicology. (Park Forest South, IL) V.1-5(3), 1977-81(?). For publisher information, see JEPOEC. Volume(issue)/page/year: 4(5-6),31,1980

安全

• 危害码 (欧洲): T+
• 风险声明 (欧洲): 28
• 危险品运输编码: UN 2811 6.1/PG 2