[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid

• ChemBase编号: 133324
• 分子式: C11H17N5O9P2
• 平均质量: 425.228302
• 单一同位素质量: 425.05015041
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(CP(=O)(O)O)O)O)O)N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(CP(=O)(O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C11H17N5O9P2/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/s1
• InChIKey: OLCWZBFDIYXLAA-IOSLPCCCSA-N

名称和登记号

名称

• IUPAC标准名: [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl]phosphonic acid
• IUPAC传统名: α,β-methylene adp
• 别名: α,β-Methyleneadenosine 5′-diphosphate; ADP[α,β-CH2]; AMP-CP; Adenosine 5′-(α,β-methylene)diphosphate

登记号

• CAS号: 3768-14-7
• EC号: 223-194-0
• MDL号: MFCD00042991
• Beilstein号: 633678
• PubChem SID: 162227601; 24896872
• PubChem CID: 92199

理论计算性质

• Acid pKa: 0.98112744
• 质子受体: 12
• 质子供体: 6
• LogD (pH = 5.5): -8.182416
• LogD (pH = 7.4): -8.16192
• Log P: -5.8846297
• 摩尔折射率: 87.2951 cm^3
• 极化性: 34.85279 Å^3
• 极化表面积: 223.37 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: false

分子性质

安全信息

• 德国WGK号: 3
• 安全公开号: 22-24/25
• 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: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C11H17N5O9P2

详细说明

Sigma Aldrich - M3763

Application
Adenosine 5′-(α,β-methylene)diphosphate (AMP-CP) is a CD73 inhibitor and is used to study adenosinergic signaling regulation via CD73/ecto-5′-nucleotidase.
Reconstitution
soluble in water up to Approx. 50 mg/ml with heating

Sigma Aldrich - 01920

Other Notes
Powerful inhibitor of 5′-nucleotidase from rat heart membranes1; Useful tool in kinetic studies with 5′-nucleotidase2