(2R,3R,4S,5R)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase编号: 156530
• 分子式: C11H14N4O4
• 平均质量: 266.25326
• 单一同位素质量: 266.10150495
• SMILES: c1cn(c2c1c(ncn2)N)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc2c1ncnc2N
• InChI: InChI=1S/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
• InChIKey: HDZZVAMISRMYHH-KCGFPETGSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R,4S,5R)-2-{4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC传统名: tubercidin
• 别名: 7-Deazaadenosine; Tubercidin

登记号

• CAS号: 69-33-0
• EC号: 200-703-4
• MDL号: MFCD00056012
• Beilstein号: 38498
• PubChem SID: 162250667
• PubChem CID: 6245

理论计算性质

• Acid pKa: 12.455672
• 质子受体: 7
• 质子供体: 4
• LogD (pH = 5.5): -2.802182
• LogD (pH = 7.4): -1.4864898
• Log P: -1.27846
• 摩尔折射率: 65.3716 cm^3
• 极化性: 25.36341 Å^3
• 极化表面积: 126.65 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

安全信息

• RTECS编号: UY8870000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 3462
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 28
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300
• GHS警示性声明: P264-P301 + P310
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2

产品相关信息

• 纯度: ≥99.0% (HPLC)
• 生物来源: from Streptomyces tubercidicus
• Empirical Formula (Hill Notation): C11H14N4O4

详细说明

Sigma Aldrich - 93747

Biochem/physiol Actions
Toxic adenosine analog with antiviral,1 antitrypanosomal,2 and antifungal functions. Mode of action: Inhibits multiple metabolic processes, including RNA processing, nucleic acid synthesis, protein synthesis, and methylation of tRNA through intracellular incorporation into nucleic acids. Tubercidin acts as a plant antifungal,3 inhibits mammalian SAH hydrolase (SAHH),4 and blocks purine biosynthesis in Candida famata.5