8-hydroxy-3-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl(4a-13C,5,9-15N2)-3H,5H,6H,7H,8H,10H-pyrimido[1,2-a]purin-10-one

• ChemBase编号: 173818
• 分子式: C14H19N5O5
• 平均质量: 340.31063263
• 单一同位素质量: 340.13604336
• SMILES: C1C([C@H](O[C@H]1n1c2c(nc1)c(=O)[15n]1[13c](n2)[15NH]C(CC1O)C)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](CC1O)n1cnc2c1n[13c]1[15NH]C(C)CC([15n]1c2=O)O
• InChI: InChI=1S/C14H19N5O5/c1-6-2-9(22)19-13(23)11-12(17-14(19)16-6)18(5-15-11)10-3-7(21)8(4-20)24-10/h5-10,20-22H,2-4H2,1H3,(H,16,17)/t6?,7?,8-,9?,10-/m1/s1/i14+1,16+1,19+1
• InChIKey: DKBDYPZFCQIHPX-UCOZRKTESA-N

名称和登记号

名称

• IUPAC标准名: 8-hydroxy-3-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl(4a-^1^3C,5,9-^1^5N₂)-3H,5H,6H,7H,8H,10H-pyrimido[1,2-a]purin-10-one
• IUPAC传统名: 8-hydroxy-3-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl(4a-^1^3C,5,9-^1^5N₂)-5H,6H,7H,8H-pyrimido[1,2-a]purin-10-one
• 别名: 3-(2-Deoxy-β-D-erythro-pentofuranosyl)-4,6,7,8-tetrahydro-8-hydroxy-6-methylpyrimido[1,2-a]purin-10(3H)-one-13C,15N2; α-Me-γ-OH-PdG-13C,15N2; Cr-PdG-13C,15N2; α-Methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine-13C,15N2(Mixture of Diastereomers)

登记号

• PubChem SID: 164229728
• PubChem CID: 71750392

理论计算性质

• Acid pKa: 13.230736
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -1.153203
• LogD (pH = 7.4): -1.1531665
• Log P: -1.1531655
• 摩尔折射率: 80.7132 cm^3
• 极化性: 30.867731 Å^3
• 极化表面积: 132.44 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; Methanol
• 外观: Pale Yellow Solid
• 熔点: 149-152°C

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - M312892

A genotoxic labelled cyclic adduct of 2'-deoxyguanosine with crotonaldehyde. Histones accelerate the cyclic 1,N2-propanoguanine adduct-formation of DNA by the primary metabolite of alcohol and carcinogenic crotonaldehyde.

参考文献

• Fang, J., et al.: Carcinogenesis, 18, 627 (1997)
• Wang, M., et al.: Chem. Res. Toxicol., 14, 1025 (1997)
• Kurtz, A., et al.: J. Biol. Chem., 278, 5970 (1997)