(2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid

• ChemBase编号: 133647
• 分子式: C15H23N7O5
• 平均质量: 381.38702
• 单一同位素质量: 381.17606687
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)C[C@H](CC[C@@H](C(=O)O)N)N)O)O)N
• Canonical SMILES: N[C@H](C[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C15H23N7O5/c16-6(1-2-7(17)15(25)26)3-8-10(23)11(24)14(27-8)22-5-21-9-12(18)19-4-20-13(9)22/h4-8,10-11,14,23-24H,1-3,16-17H2,(H,25,26)(H2,18,19,20)/t6-,7-,8+,10+,11+,14+/m0/s1
• InChIKey: LMXOHSDXUQEUSF-YECHIGJVSA-N

名称和登记号

名称

• IUPAC标准名: (2S,5S)-2,5-diamino-6-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]hexanoic acid
• IUPAC传统名: sinefungin
• 别名: 5′-Deoxy-5′-(1,4-diamino-4-carboxybutyl)adenosine; A-9145; Adenosylornithine; Antibiotic 32232RP; Sinefungin

登记号

• CAS号: 58944-73-3
• PubChem SID: 24899800; 162227924
• PubChem CID: 65482

理论计算性质

• Acid pKa: 1.9477124
• 质子受体: 11
• 质子供体: 6
• LogD (pH = 5.5): -7.964581
• LogD (pH = 7.4): -6.847281
• Log P: -5.1386905
• 摩尔折射率: 92.6784 cm^3
• 极化性: 36.682793 Å^3
• 极化表面积: 208.65 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: H2O: soluble
• 外观: white to yellow powder

安全信息

• RTECS编号: HE3140000
• 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
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 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: 95% (HPLC)

详细说明

Sigma Aldrich - S8559

Biochem/physiol Actions
Sinefungin blocks the methylation of bases in DNA and RNA, such as 5-methylcytosine or N6-methyladenosine, suggesting a role in gene expression. In addition, sinefugin is involved in physiological processes such as aging and carcinogenesis.
Sinefungin blocks the methylation of bases in DNA and RNA, such as 5-methylcytosine or N6-methyladenosine, suggesting a role in gene expression. In addition, sinefugin is involved in physiological processes such as aging and carcinogenesis.Methylation inhibition by sinefugin is often accompanied by an altered rate of cytosine deamination that is coupled to transition mutation in the DNA. Sinefugin inhibits Epstein-Barr viral activity and this inhibition is related to the change in DNA methylation and gene expression. It can cause a rate change in several restriction DNA endonuclease activities, including Mme I, which is not connected to the inhibition of the methytransferase activity.