{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase编号: 70591
• 分子式: C9H14N3O8P
• 平均质量: 323.196521
• 单一同位素质量: 323.05185105
• SMILES: P(=O)(O)(O)OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(=O)nc(cc1)N
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1ccc(nc1=O)N)COP(=O)(O)O
• InChI: InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
• InChIKey: IERHLVCPSMICTF-XVFCMESISA-N

名称和登记号

名称

• IUPAC标准名: {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC传统名: cytidine monophosphate
• 别名: Cytidine 5'-Phosphate; Cytidine 5'-Phosphoric Acid; Cytidine Monophosphate; Cytidine Mono(dihydrogen phosphate)(Ester); Cytidylic Acid; Cytosine 5'-Monophosphate; Cytidine 5'-Monophosphate; 5'-Cytidylic acid; ((2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate; 5'-Cytidylic acid; Cytidine monophosphate; 5′-CMP; 5′-Cytidylic acid; C-5′-P; Cytidine 5′-monophosphate

登记号

• CAS号: 63-37-6
• EC号: 200-556-6
• MDL号: MFCD00006544
• Beilstein号: 46982
• PubChem SID: 162036306; 24892358
• PubChem CID: 6131
• CHEBI ID: 17361
• CHEMBL: 307679
• Chemspider ID: 5901
• 维基百科标题: Cytidine_monophosphate

理论计算性质

• Acid pKa: 1.247557
• 质子受体: 9
• 质子供体: 5
• LogD (pH = 5.5): -5.362577
• LogD (pH = 7.4): -6.4509172
• Log P: -3.1532001
• 摩尔折射率: 65.4177 cm^3
• 极化性: 26.073345 Å^3
• 极化表面积: 175.14 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Water
• 外观: crystalline; White Solid
• 熔点: ~222 °C (dec.); 205-208°C
• 比旋光度: [α]20/D +9±0.5°, c = 1% in 0.5 M Na2HPO4
• pKa: 0.8, 4.5, 6.3

安全信息

• 保存条件: Refrigerator
• 保存注意事项: IRRITANT
• 德国WGK号: 3
• TSCA收录: false
• 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: ≥98.0% (HPLC); ≥99% (HPLC); 95+%
• 级别: Sigma Grade
• 杂质: ~3% water
• 生物来源: from yeast
• Empirical Formula (Hill Notation): C9H14N3O8P

详细说明

Sigma Aldrich - C1131

Application
Cytidine 5′-monophosphate (CMP) is used as a substrate of uridine monophosphate (UMP)/cytidine monophosphate (CMP) kinase (EC 2.7.4.4) to form CDP which upon phosphorylation to CTP supports DNA and RNA biosynthesis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1131.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C998305

A constituent of nucleic acids. It was isolated from yeast nucleic acid.

参考文献

• Parrou, J., et al.: Anal. Biochem., 248, 186 (1997)
• Phipps, A., et al.: Xenobiotica, 28, 527 (1997)
• Mohler, R., et al.: Anal. Chem., 78, 2700 (1997)