6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-(3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid

• ChemBase编号: 154390
• 分子式: C32H46O6
• 平均质量: 526.70404
• 单一同位素质量: 526.32943919
• SMILES: CC1C=CC(=O)OC1/C=C/C(=C/C(C)C/C=C/C(=C/C(C)C(=O)C(C)C(C(C)C/C(=C/C(=O)O)/C)O)/C)/C
• Canonical SMILES: C/C(=C\C(C(=O)C(C(C(C/C(=C/C(=O)O)/C)C)O)C)C)/C=C/CC(/C=C(/C=C/C1OC(=O)C=CC1C)\C)C
• InChI: InChI=1S/C32H46O6/c1-20(16-22(3)12-14-28-24(5)13-15-30(35)38-28)10-9-11-21(2)17-25(6)31(36)27(8)32(37)26(7)18-23(4)19-29(33)34/h9,11-17,19-20,24-28,32,37H,10,18H2,1-8H3,(H,33,34)
• InChIKey: QECBVZBMGUAZDL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-(3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• IUPAC传统名: 6-hydroxy-3,5,7,9,11,15,17-heptamethyl-19-(3-methyl-6-oxo-2,3-dihydropyran-2-yl)-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• 别名: Leptomycin A 来源于链霉菌 属; 19-(3,6-Dihydro-3-methyl-6-oxo-2H-pyran-2-yl)-3,5,7,9,11,15,17-heptamethyl-6-hydroxy-8-oxo-2,10,12,16,18-nonadecapentaenoic acid; Jildamycin; Leptomycin A

登记号

• CAS号: 87081-36-5
• MDL号: MFCD01711669
• PubChem SID: 162248529
• PubChem CID: 5384875

理论计算性质

• 极化表面积: 100.9 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false
• Acid pKa: 4.568904
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 6.1527057
• LogD (pH = 7.4): 4.3783813
• Log P: 7.1308365
• 摩尔折射率: 157.877 cm^3
• 极化性: 59.455105 Å^3

分子性质

理化性质

• 外观: methanol solution

安全信息

• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有毒(Toxic) (T)
• 联合国危险货物编号: 1230
• 德国WGK号: 1
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-23/24/25-39/23/24/25
• 安全公开号: 7-16-36/37-45
• RID/ADR: UN 1230 3/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ~95% (HPLC)
• 生物来源: from Streptomyces sp.
• 运输包装: dry ice
• Empirical Formula (Hill Notation): C32H46O6

详细说明

Sigma Aldrich - L6417

Biochem/physiol Actions
Leptomycins are antifungal antibiotics with unique unsaturated, branched-chain fatty acid structures.1, The physiochemical and biological properties of Leptomycins A and B are very similar.2, Both are considered to be specific inhibitors of nuclear export. The suggested inhibition mechanism involves the direct binding of leptomycins to CRM1 (Exportin-1), which is the main nuclear export protein. This blocks the binding of CRM1 to proteins containing a nuclear export signal (NES),3,4 and therefore prevents their export from the nucleus. Although more research on nuclear export inhibition has been performed using Leptomycin B, it has been shown that Leptomycin A has similar effects and can induce, for example, nuclear accumulation of wild-type ERK5.5Leptomycin A is also active against Schizosaccaromyces pombe and Mucor rouxianus.2