(4aR,6R,7R,7aS)-6-{6-amino-8-[(6-aminohexyl)amino]-9H-purin-9-yl}-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-one

• ChemBase编号: 133921
• 分子式: C16H26N7O6P
• 平均质量: 443.394701
• 单一同位素质量: 443.16821822
• SMILES: c1nc(c2c(n1)n(c(n2)NCCCCCCN)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)O)O)N
• Canonical SMILES: NCCCCCCNc1nc2c(n1[C@@H]1O[C@H]3[C@H]([C@H]1O)OP(=O)(OC3)O)ncnc2N
• InChI: InChI=1S/C16H26N7O6P/c17-5-3-1-2-4-6-19-16-22-10-13(18)20-8-21-14(10)23(16)15-11(24)12-9(28-15)7-27-30(25,26)29-12/h8-9,11-12,15,24H,1-7,17H2,(H,19,22)(H,25,26)(H2,18,20,21)/t9-,11-,12-,15-/m1/s1
• InChIKey: WCWLOZYNRVLFOG-SDBHATRESA-N

名称和登记号

名称

• IUPAC标准名: (4aR,6R,7R,7aS)-6-{6-amino-8-[(6-aminohexyl)amino]-9H-purin-9-yl}-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• IUPAC传统名: (4aR,6R,7R,7aS)-6-{6-amino-8-[(6-aminohexyl)amino]purin-9-yl}-2,7-dihydroxy-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• 别名: 8-(6-Aminohexyl)aminoadenosine-3′,5′-cyclic monophosphate; 8-AHA-cAMP; 8-(6-Aminohexyl)aminoadenosine 3′:5′-cyclic monophosphate

登记号

• CAS号: 39824-30-1
• MDL号: MFCD00057125
• PubChem SID: 24724386; 162228198; 24891322
• PubChem CID: 16078938

理论计算性质

• Acid pKa: 1.8351647
• 质子受体: 10
• 质子供体: 5
• LogD (pH = 5.5): -1.5642824
• LogD (pH = 7.4): -1.5025132
• Log P: -1.5034121
• 摩尔折射率: 106.6184 cm^3
• 极化性: 41.470924 Å^3
• 极化表面积: 192.89 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: dilute NaOH: soluble
• 外观: white 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; -70°C

产品相关信息

• 纯度: ~98%; ≥98% (HPLC)
• 包装: vial of 25 μmol
• 运输包装: dry ice
• Empirical Formula (Hill Notation): C16H26N7O6P

详细说明

Sigma Aldrich - A2104

Biochem/physiol Actions
Selective cAMP-dependent protein kinase (PKA) activator. Site selective cAMP analog with preference for site B of RI of cAMP-dependent protein kinase. In combination with 8-piperidino-cAMP, which selects site A of RI and site B of RII, selective synergistic activation of protein kinase A type I can be obtained.

Sigma Aldrich - A8138

Application
Cyclic AMP analog which shows partially selective agonist activity with Type I cAMP-dependent protein kinase isozyme.1