sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase编号: 131320
• 分子式: C10H10BrN5NaO7P
• 平均质量: 446.083231
• 单一同位素质量: 444.9398906
• SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)n2c3c(c(=O)[nH]c(n3)N)nc2Br)O)OP(=O)(O1)[O-].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Br)nc2c1nc(N)[nH]c2=O.[Na+]
• InChI: InChI=1S/C10H11BrN5O7P.Na/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5;/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18);/q;+1/p-1/t2-,4-,5-,8-;/m1./s1
• InChIKey: ZJRFCXHKYQVNFK-YEOHUATISA-M

名称和登记号

名称

• IUPAC标准名: sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• IUPAC传统名: sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-1H-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• 别名: 8-Br-cGMP; 8-Bromoguanosine-3′,5′-cyclomonophosphate sodium salt; 8-Bromo-cyclic GMP; 8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt

登记号

• CAS号: 51116-01-9
• EC号: 256-993-8
• MDL号: MFCD00070128
• Beilstein号: 8378760
• PubChem SID: 24278021; 162225598
• PubChem CID: 23702959

理论计算性质

• Acid pKa: 1.9035653
• 质子受体: 8
• 质子供体: 3
• LogD (pH = 5.5): -3.215349
• LogD (pH = 7.4): -3.245903
• Log P: -1.1080263
• 摩尔折射率: 78.2181 cm^3
• 极化性: 30.848368 Å^3
• 极化表面积: 173.35 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: soluble0.1 g/mL, clear, slightly yellow; H2O: soluble50 mg/mL
• 外观: powder

安全信息

• 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

产品相关信息

• 纯度: ≥98% (HPLC); ≥99.0% (HPLC)
• 杂质: ≤1% guanosine 3′,5′-cyclophosphate (HPLC); ≤8% water(2 mol/mol)
• Empirical Formula (Hill Notation): C10H10BrN5NaO7P

详细说明

Sigma Aldrich - B1381

Biochem/physiol Actions
Cell-permeable cGMP analog having greater resistance to hydrolysis by phosphodiesterases than cGMP. Activates cGMP-dependent protein kinase. Slows or inhibits the intracellular calcium oscillations of tracheal smooth muscle cells in response to acetylcholine. Reported to mimic the effect of nitric oxide generating drugs.

Sigma Aldrich - 17110

Other Notes
A membrane-permeable cGMP derivative. Induces HL-60 cells to differentiate along the granulocytic pathway1