2-amino-9-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase编号: 154349
• 分子式: C10H13N5O5
• 平均质量: 283.24072
• 单一同位素质量: 283.09166854
• SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@H]([C@@H]([C@H](O1)CO)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1
• InChIKey: NYHBQMYGNKIUIF-FJFJXFQQSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-9-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC传统名: 2-amino-9-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• 别名: 9-β-D-Arabinofuranosyl guanine hydrate; Ara-G hydrate

登记号

• CAS号: 38819-10-2(anhydrous)
• MDL号: MFCD00065486
• PubChem SID: 162248488
• PubChem CID: 65412

理论计算性质

• Acid pKa: 10.155725
• 质子受体: 8
• 质子供体: 5
• LogD (pH = 5.5): -2.7063062
• LogD (pH = 7.4): -2.7068908
• Log P: -2.7062182
• 摩尔折射率: 64.6211 cm^3
• 极化性: 24.328236 Å^3
• 极化表面积: 155.22 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: >10 mg/mL; H2O: insoluble
• 外观: solid

安全信息

• RTECS编号: MF8301000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-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: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C10H13N5O5 · xH2O

详细说明

Sigma Aldrich - A4233

Application
Ara-G is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. This active form of Ara-G induces apoptosis and inhibits DNA synthesis. Ara-G is also an antineoplastic and antimetabolite.
Biochem/physiol Actions
Ara-G is an inducer of apoptosis; inhibitor of DNA synthesis; antineoplastic; and antimetabolite. Ara-G is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. Incorporation of Ara-GTP into DNA leads to inhibition of DNA synthesis and apoptosis.