(2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid

• ChemBase编号: 132825
• 分子式: C33H48O6
• 平均质量: 540.73062
• 单一同位素质量: 540.34508926
• SMILES: CC/C(=C/[C@H](C)C/C=C/C(=C/[C@@H](C)C(=O)[C@@H](C)[C@@H]([C@@H](C)C/C(=C/C(=O)O)/C)O)/C)/C=C/[C@H]1[C@H](C=CC(=O)O1)C
• Canonical SMILES: CC/C(=C/[C@@H](C/C=C/C(=C/[C@H](C(=O)[C@H]([C@@H]([C@H](C/C(=C/C(=O)O)/C)C)O)C)C)/C)C)/C=C/[C@@H]1OC(=O)C=C[C@@H]1C
• InChI: InChI=1S/C33H48O6/c1-9-28(14-15-29-24(5)13-16-31(36)39-29)19-22(3)12-10-11-21(2)17-25(6)32(37)27(8)33(38)26(7)18-23(4)20-30(34)35/h10-11,13-17,19-20,22,24-27,29,33,38H,9,12,18H2,1-8H3,(H,34,35)/b11-10+,15-14+,21-17+,23-20+,28-19-/t22-,24+,25-,26+,27-,29+,33-/m1/s1
• InChIKey: YACHGFWEQXFSBS-XYERBDPFSA-N

名称和登记号

名称

• IUPAC标准名: (2E,5S,6R,7S,9R,10E,12E,15R,16Z,18E)-17-ethyl-6-hydroxy-3,5,7,9,11,15-hexamethyl-19-[(2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-8-oxononadeca-2,10,12,16,18-pentaenoic acid
• IUPAC传统名: leptomycin B
• 别名: Leptomycin B solution from Streptomyces sp.

登记号

• CAS号: 87081-35-4
• MDL号: MFCD06795848
• PubChem SID: 162227102; 24896330
• PubChem CID: 6917907

理论计算性质

• Acid pKa: 4.568904
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 6.5972743
• LogD (pH = 7.4): 4.82295
• Log P: 7.575405
• 摩尔折射率: 162.478 cm^3
• 极化性: 61.297455 Å^3
• 极化表面积: 100.9 Å^2
• 可自由旋转的化学键: 15
• 里宾斯基五规则: false

分子性质

理化性质

• 闪点: 18 °C; 64.4 °F

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: 16-36/37-45
• GHS危险品标识: GHS02; GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H225-H301-H311-H331-H370
• GHS警示性声明: P210-P260-P280-P301 + P310-P311
• RID/ADR: UN 1230 3/PG 2
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95% (HPLC)
• 产品质量级别: PREMIUM
• 运输包装: dry ice

详细说明

Sigma Aldrich - L2913

Biochem/physiol Actions
Leptomycin B is an unsaturated, branched-chain fatty acid, and is an important tool in the study of nuclear export. It is a specific inhibitor of proteins containing nuclear export signal. It inhibits nucleo-cytoplasmic translocation of molecules such as the HIV-1 Rev protein and Rev-dependent export of mRNA. The addition of very small amounts to fibroblasts causes accumulation of MEK in the nucleus. Other proteins that are influenced by leptomycin B are actin, c-Abl, cyclin B1, MDM2/p53, IκB, MPF, and PKA. The suggested inhibition mechanism involves the direct binding of leptomycin B to CRM1, which blocks the binding of CRM1 to proteins containing the nuclear export signal, via the interaction with cysteine residue in CRM1 control conserved region.
General description
Leptomycin B is an anti-fungal antibiotic, anti-tumor cytotoxin that inhibits CRM1-dependent, NES-dependent nucleo-cytoplasmic translocation (nuclear export inhibitor). NES containing proteins include HIV-1 REV; actin, c-Abl, cyclin B1, MDM2/p53, I?B, MPF, PKA and MEK.