2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione

• ChemBase编号: 106038
• 分子式: C15H14O3
• 平均质量: 242.26986
• 单一同位素质量: 242.09429431
• SMILES: CC1(C)CCC2=C(O1)c1c(cccc1)C(=O)C2=O
• Canonical SMILES: O=C1C2=C(OC(CC2)(C)C)c2c(C1=O)cccc2
• InChI: InChI=1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3
• InChIKey: QZPQTZZNNJUOLS-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2,2-dimethyl-2H,3H,4H,5H,6H-naphtho[1,2-b]pyran-5,6-dione
• IUPAC传统名: β-lapachone
• 别名: β-Lapachone; ARQ-501; Beta-Lapachone; 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-b]pyran-5,6-dione; ARQ 501; NSC 26326; NSC 629749; SL 11001; β-Lapachone; β-LAPACHONE; β-Lapachone

登记号

• CAS号: 4707-32-8
• MDL号: MFCD01712233
• PubChem SID: 162087653; 24278512
• PubChem CID: 3885

理论计算性质

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 2.6293175
• LogD (pH = 7.4): 2.6293175
• Log P: 2.6293175
• 摩尔折射率: 69.092 cm^3
• 极化性: 26.07847 Å^3
• 极化表面积: 43.37 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: Chloroform
• 外观: Orange Solid
• 熔点: >110°C (dec.)

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: QL6127400
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: Topoisomerase

产品相关信息

• 纯度: ≥98%; ≥98% (TLC)
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02196031

Purity: >98%
Novel DNA topoisomerase I inhibitor.

Sigma Aldrich - L2037

Biochem/physiol Actions
β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.1

Toronto Research Chemicals - L175300

β-Lapachone is a naturally occurring quinone obtained from the bark of the lapacho tree (Tabebuia avellanedae) with cancer chemopreventive properties. Induces apoptosis in HL-60 and human prostate cancer cells.

参考文献

• Renslo, A., et al.: Nat. Chem. Biol., 2, 701 (2006)
• Hopkins, A., et al.: Nat. Chem. Biol., 4, 682 (2006)
• Stuart, K., et al.: J. Clin. Invest., 118, 1301 (2006)
• Martin, R., et al.: Science, 25, 1680 (2006)