5-{[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid

• ChemBase编号: 105103
• 分子式: C21H19NO6
• 平均质量: 381.37866
• 单一同位素质量: 381.12123733
• SMILES: OC(=O)c1cc(ccc1O)N(Cc1ccccc1O)Cc1cc(O)ccc1O
• Canonical SMILES: Oc1ccc(c(c1)CN(c1ccc(c(c1)C(=O)O)O)Cc1ccccc1O)O
• InChI: InChI=1S/C21H19NO6/c23-16-6-8-19(25)14(9-16)12-22(11-13-3-1-2-4-18(13)24)15-5-7-20(26)17(10-15)21(27)28/h1-10,23-26H,11-12H2,(H,27,28)
• InChIKey: ULTTYPMRMMDONC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-{[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid
• IUPAC传统名: 5-{[(2,5-dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino}-2-hydroxybenzoic acid
• 别名: 5-[[(2,5-Dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxy-benzoic Acid; NSC 678027; LAVENDUSTIN A; 5-[[(2,5-Dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid; Lavendustin A

登记号

• CAS号: 125697-92-9
• MDL号: MFCD00153822
• PubChem SID: 162091859; 24896314
• PubChem CID: 3894

理论计算性质

• Acid pKa: 3.4733346
• 质子受体: 7
• 质子供体: 5
• LogD (pH = 5.5): 2.5796022
• LogD (pH = 7.4): 1.2225813
• Log P: 4.452512
• 摩尔折射率: 104.8916 cm^3
• 极化性: 39.10215 Å^3
• 极化表面积: 121.46 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble; Methanol; methanol: soluble
• 外观: crystalline; Off-White to Pale Yellow Solid
• 熔点: 206-208°C

安全信息

• 保存条件: 0°C, Desiccate, Protect from light; -20°C Freezer
• 保存注意事项: Moisture Sensitive: Hygroscopic
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... EGFR(1956), ERBB2(2064), LCK(3932)

产品相关信息

• 纯度: ~85% (TLC)

详细说明

MP Biomedicals - 02158815

Lavendustin A is a potent and selective inhibitor of the EGF receptor tyrosine kinase (IC₅₀ =11 nM)^1 . It binds to a site on the kinase which is distinct from the ATP and peptide substrate binding sites^2 .

Sigma Aldrich - L2400

Biochem/physiol Actions
Cell-permeable tyrosine kinase inhibitor with little effect on protein kinase A or C. Inhibits NMDA-stimulated cGMP production. Inhibits VEGF-induced angiogenesis.
Physical form
Photosensitive

Toronto Research Chemicals - L215000

A potent tyrosine kinase inhibitor. Inhibition is competitive with ATP and is noncompetitive with the peptide.

参考文献

• Onada, T., et al., J. Nat. Prod. , 52 : 1252, (1989).
• Hsu, C.-Y.J., et al., J. Biol. Chem. , 266 : 21105, (1991).
• Onoda, T., et al.: Journal of Natural Products, 52, 6, 1252 (1989)