sodium 1-[(2S,3S,4R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ5-pyridin-1-ylium

• ChemBase编号: 134350
• 分子式: C21H26N6NaO18P3
• 平均质量: 766.371593
• 单一同位素质量: 766.04141219
• SMILES: c1cc(c[n+](c1)[C@@H]1[C@H]([C@H](C(O1)COP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)OP(=O)(O)O)O)O)O)C(=O)O.[Na+]
• Canonical SMILES: O[C@H]1[C@@H](O)C(O[C@@H]1[n+]1cccc(c1)C(=O)O)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)(O)O)n1cnc2c1ncnc2N)[O-])[O-].[Na+]
• InChI: InChI=1S/C21H27N6O18P3.Na/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(44-46(33,34)35)14(29)11(43-20)6-41-48(38,39)45-47(36,37)40-5-10-13(28)15(30)19(42-10)26-3-1-2-9(4-26)21(31)32;/h1-4,7-8,10-11,13-16,19-20,28-30H,5-6H2,(H6-,22,23,24,31,32,33,34,35,36,37,38,39);/q;+1/p-1/t10?,11-,13+,14-,15+,16-,19+,20-;/m1./s1
• InChIKey: KKCRODBDXQTAPI-NZNNTXIPSA-M

名称和登记号

名称

• IUPAC标准名: sodium 1-[(2S,3S,4R)-5-({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ^5-pyridin-1-ylium
• IUPAC传统名: sodium 1-[(2S,3S,4R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methyl phosphonato}oxyphosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1λ^5-pyridin-1-ylium
• 别名: β-NAADP; Nicotinic acid adenine dinucleotide phosphate sodium salt

登记号

• CAS号: 5502-96-5
• MDL号: MFCD00274064
• PubChem SID: 162228626; 24897746
• PubChem CID: 16219758

理论计算性质

• Acid pKa: 0.6518583
• 质子受体: 18
• 质子供体: 7
• LogD (pH = 5.5): -14.441434
• LogD (pH = 7.4): -16.141619
• Log P: -9.643525
• 摩尔折射率: 148.8042 cm^3
• 极化性: 60.219505 Å^3
• 极化表面积: 364.66 Å^2
• 可自由旋转的化学键: 13
• 里宾斯基五规则: false

分子性质

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

产品相关信息

• 纯度: ≥92.5%

详细说明

Sigma Aldrich - N5655

Other Notes
Note: Should not be confused with nicotinamide adenine dinucleotide phosphate (NADP).
Preparation Note
Enzymatically prepared analog of β-NADP+.
Biochem/physiol Actions
Potent activator of intracellular Ca2+ release via an IP3 and cyclic ADP ribose-independent mechanism.