3-[(3E)-3-(hydroxyimino)-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one

• ChemBase编号: 1817
• 分子式: C16H11N3O2
• 平均质量: 277.27744
• 单一同位素质量: 277.08512661
• SMILES: c12/C(=N\O)/C(=C\3/C(=O)Nc4c3cccc4)/Nc1cccc2
• Canonical SMILES: O/N=C\1/C(=C\2/C(=O)Nc3c2cccc3)/Nc2c1cccc2
• InChI: InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14+
• InChIKey: HBDSHCUSXQATPO-BGBJRWHRSA-N

名称和登记号

名称

• IUPAC标准名: 3-[(3E)-3-(hydroxyimino)-2,3-dihydro-1H-indol-2-ylidene]-2,3-dihydro-1H-indol-2-one
• IUPAC传统名: 3-[(3E)-3-(hydroxyimino)-1H-indol-2-ylidene]-1H-indol-2-one; indirubin-3'-monoxime
• 别名: Indirubin-3'-Monoxime; Indirubin-3′-monoxime; Indirubin-3′-oxime; Indirubin-3’-oxime; 3-[1,3-Dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one

登记号

• CAS号: 160807-49-8
• MDL号: MFCD02683594
• PubChem SID: 24278483; 46507166; 160965272
• PubChem CID: 5326739

理论计算性质

JChem

• Acid pKa: 8.309751
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 1.7936308
• LogD (pH = 7.4): 1.744158
• Log P: 1.7943468
• 摩尔折射率: 82.8171 cm^3
• 极化性: 29.389532 Å^3
• 极化表面积: 73.72 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.18
• LOG S: -3.38
• 溶解度: 1.17e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; DMSO: >10 mg/mL; H2O: insoluble; Methanol
• 外观: Dark Red Solid; solid
• 熔点: 247-249°C (dec.)

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: Light Sensitive
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98% (HPLC)
• Mol. Weight: mol wt 277.28

详细说明

DrugBank - DB02052

Drug information: experimental

Sigma Aldrich - I0404

Biochem/physiol Actions
Indirubin-3′-oxime is a cyclin-dependent kinase inhibitor which functions by competing with ATP for binding to the catalytic subunit; exhibits antiproliferative activity leading to G2/M arrest in many cell lines and G1/S arrest in Jurkat cells.

Toronto Research Chemicals - I527500

A potent inhibitor of GSK-3β (IC50=22nM). Also inhibits CDK1 (IC50=180nM) and CDK (IC50=100nM). It reversibly arrests asynchronous HBL-100 cells at G2. It induces apoptosis in the mammary carcinoma cell line MCF-7 (10μM).

参考文献

• Leclerc, S., et al.: J. Biol. Chem., 276, 251 (2001)
• Damiens, E., et al.: Oncogene, 20, 3786 (2001)
• Marko, D., et al.: Br. J. Cancer, 84, 283 (2001)