(4R,6R,8R,9Z,11Z)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione

• ChemBase编号: 132458
• 分子式: C18H17ClO6
• 平均质量: 364.77698
• 单一同位素质量: 364.07136594
• SMILES: C[C@@H]1C[C@@H]2[C@H](O2)/C=C\C=C/C(=O)Cc2c(c(cc(c2Cl)O)O)C(=O)O1
• Canonical SMILES: C[C@@H]1C[C@H]2O[C@@H]2/C=C\C=C/C(=O)Cc2c(C(=O)O1)c(O)cc(c2Cl)O
• InChI: InChI=1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2-,5-3-/t9-,14-,15-/m1/s1
• InChIKey: WYZWZEOGROVVHK-WSGSENCDSA-N

名称和登记号

名称

• IUPAC标准名: (4R,6R,8R,9Z,11Z)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.0^6,^8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
• IUPAC传统名: (4R,6R,8R,9Z,11Z)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.0^6,^8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
• 别名: Monorden; [1aS-(1aR*,2Z,4E,14*,15aR*)]-8-Chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-6H-oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione; Radicicol from Diheterospora chlamydosporia

登记号

• CAS号: 12772-57-5
• MDL号: MFCD06795865
• PubChem SID: 24899351; 162226735
• PubChem CID: 45933581

理论计算性质

• Acid pKa: 7.022605
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 3.6637928
• LogD (pH = 7.4): 3.1545846
• Log P: 3.6765287
• 摩尔折射率: 93.5609 cm^3
• 极化性: 35.18881 Å^3
• 极化表面积: 96.36 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: ethanol: soluble10 mg/mL
• 外观: yellow solid

安全信息

• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 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): 3
• 危险公开号: 45-46-22-36/37/38
• 安全公开号: 53-26-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335-H340-H350
• GHS警示性声明: P201-P261-P301 + P310-P305 + P351 + P338-P308 + P313
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... HSP90AA1(3320), SRC(6714)rat ... Src(83805)

详细说明

Sigma Aldrich - R2146

Biochem/physiol Actions
Antifungal macrolactone antibiotic that inhibits protein tyrosine kinase. Radicicol induces the differentiation of HL-60 cells into macrophages, blocking cell cycle at G1 and G2. It suppresses NIH 3T3 cell transformation by diverse oncogenes such as src, ras and mos and also suppresses the expression of mitogen-inducible cyclooxygenase-2. As a cell differentiation modulator, radicicol has anti-angiogenic activity in vivo, inhibiting the proliferation of and plasminogen activator production by vascular endothelial cells.
Caution
Photosensitive