1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

• ChemBase编号: 2771
• 分子式: C9H12N2O5
• 平均质量: 228.20198
• 单一同位素质量: 228.07462149
• SMILES: OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cccnc1=O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cccnc1=O
• InChI: InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1
• InChIKey: RPQZTTQVRYEKCR-WCTZXXKLSA-N

名称和登记号

名称

• IUPAC标准名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC传统名: zebularine
• 别名: 1-(β-D-Ribofuranosyl)-1,2-dihydropyrimidin-2-one; 2-Pyrimidone-1-β-D-riboside; Zebularine; pyrimidin-2-one beta-ribofuranoside; Pyrimidin-2-one ribonucleoside; Pyrimidin-2-one beta-D-ribofuranoside; 1-beta-D-ribofuranosyl-2(1H)-pyrimidinone; 1-beta-D-ribofuranosylpyrimidin-2(1H)-one; DHZ; Zebularine; Pyrimidin-2-one β-D-ribofuranoside

登记号

• CAS号: 3690-10-6
• MDL号: MFCD04973699
• PubChem SID: 160966219; 46504541
• PubChem CID: 100016
• Chemspider ID: 90372
• 维基百科标题: Zebularine

理论计算性质

JChem

• Acid pKa: 12.553243
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): -2.2063577
• LogD (pH = 7.4): -2.2063606
• Log P: -2.2063575
• 摩尔折射率: 51.6751 cm^3
• 极化性: 20.316578 Å^3
• 极化表面积: 102.59 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.3
• LOG S: -0.59
• 溶解度: 5.82e+01 g/l

分子性质

理化性质

• 溶解度: DMSO: soluble16 mg/mL
• 外观: solid

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C9H12N2O5

详细说明

DrugBank - DB03068

• Drug Groups: experimental
• Description: A chemically stable, cytidine analog that displays anti-tumor properties. Acts as a transition state analog inhibitor of cytidine deaminase by binding to the active size as covalent hydrates. Also shown to inhibit DNA methylation and tumor growth both in vitro and in vivo.

Sigma Aldrich - Z4775

Biochem/physiol Actions
Zebularine is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.