sodium (4aR,6R,7R,7aS)-6-(6-amino-9H-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: 102912
• 分子式: C10H11N5NaO6P
• 平均质量: 351.187771
• 单一同位素质量: 351.03446401
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O)N.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1ncnc2N.[Na+]
• InChI: InChI=1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1
• InChIKey: BXJBFCKTIWRKMQ-MCDZGGTQSA-M

名称和登记号

名称

• IUPAC标准名: sodium (4aR,6R,7R,7aS)-6-(6-amino-9H-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 3',5'-cyclic amp anion
• 别名: 环化腺苷酸 钠盐; 腺苷-3′,5′-环单磷酸 钠盐 一水合物; cAMP-Na; Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate; Adenosine-3',5'-Monophosphoric Acid; ADENOSINE-3',5'-cyclic-MONOPHOSPHATE SODIUM SALT; Adenosine Cyclic 3',5'-(Hydrogen Phosphate) Monosodium Salt; 3',5'-AMP Sodium Salt; Adenosine 3',5'-Phosphoric Acid Sodium Salt; Cyclic 3',5'-AMP Sodium Salt; Cyclic 3',5'-Adenosine Monophosphate Monosodium Salt; Cyclic AMP Sodium; Cyclic AMP Sodium Salt; cAMP Sodium Salt; Adenosine-3',5'-cyclic Monophosphate Sodium Salt; 3′,5′-Cyclic AMP sodium salt

登记号

• CAS号: 37839-81-9
• MDL号: MFCD00069736
• Beilstein号: 54612
• PubChem SID: 24891151; 162088780
• PubChem CID: 23669773

理论计算性质

• Acid pKa: 1.8324043
• 质子受体: 8
• 质子供体: 2
• LogD (pH = 5.5): -3.768807
• LogD (pH = 7.4): -3.6955175
• Log P: -4.0200067
• 摩尔折射率: 69.1678 cm^3
• 极化性: 27.794725 Å^3
• 极化表面积: 157.67 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: soluble50 mg/mL; H2O: soluble50 mg/mL, clear, colorless
• 外观: white powder

安全信息

• 保存条件: 0°C
• RTECS编号: AU7357900
• 德国WGK号: 2
• 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%; ≥98.0% (HPLC); ≥99.0% (HPLC)
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C10H11N5NaO6P · H2O

详细说明

MP Biomedicals - 02105460

Sodium Salt
Crystalline
Purity: Approx. 98%

Sigma Aldrich - A6885

Application
Adenosine-3′,5′-cyclic monophosphate (cAMP) is an activator of cyclic-AMP-dependent protein kinase A (PKA). The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis. Exogneous cAMP plays a role in the spontaneous activity and contraction of the heart muscle.
Biochem/physiol Actions
Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

Sigma Aldrich - 01894

Biochem/physiol Actions
Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

Toronto Research Chemicals - A280455

Adenosine-3’,5’-cyclic Monophosphate is an Adenosine (A280400) derivative useful as anticancer agent.

参考文献

• Keast, R., et al.: Pharma. Res., 19, 1019 (2002)