(2R,3R,4S,5R)-2-[2-chloro-6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase编号: 105640
• 分子式: C15H20ClN5O4
• 平均质量: 369.8034
• 单一同位素质量: 369.12038183
• SMILES: OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(NC3CCCC3)nc(Cl)nc12
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2NC1CCCC1
• InChI: InChI=1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1
• InChIKey: XSMYYYQVWPZWIZ-IDTAVKCVSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R,4S,5R)-2-[2-chloro-6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC传统名: ccpa (biochemistry)
• 别名: CCPA (biochemistry); CCPA; 2-Chloro-N6-cyclopentyladenosine; 2-CHLORO-N^6-CYCLO-PENTYLADENOSINE

登记号

• CAS号: 37739-05-2
• MDL号: MFCD00078574
• PubChem SID: 24892583; 162093815
• PubChem CID: 123807
• CHEMBL: 284969
• Chemspider ID: 110356
• IUPHAR配体索引: 379
• 医学主题词(MeSH): 2-chloro-N(6)cyclopentyladenosine
• 维基百科标题: CCPA_(biochemistry)

理论计算性质

• Acid pKa: 12.45397
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): 0.47398627
• LogD (pH = 7.4): 0.4739885
• Log P: 0.4739924
• 摩尔折射率: 90.6008 cm^3
• 极化性: 35.012794 Å^3
• 极化表面积: 125.55 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

安全信息

• RTECS编号: AU7357555
• 德国WGK号: 3
• 安全公开号: R
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

详细说明

MP Biomedicals - 02193632

(CCPA)
A very selective A₁ Adenosine receptor agonist.

Sigma Aldrich - C7938

Biochem/physiol Actions
A1 adenosine receptor agonist with high selectivity: reportedly 10,000-fold for A1 over A2 receptors.
Application
2-Chloro-N6-cyclopentyladenosine (CCPA) may be used as an A1 adenosine receptor agonist with high selectivity. CCPA is often used with other adenosine receptor agonists and antagonist to resolve A(1), A(2A) and A(3) receptor functions. These include DPCPX (A(1) receptor antagonist), 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-α][1,3,5]triazin-5-ylamino]ethyl)phenol (A(2A) receptor antagonist), and 4-[2-[[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid hydrochloride (A(2A) receptor agonist), and Cl-IB-MECA, (A(3)) receptor agonist).