sodium [(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2R,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl phosphate

• ChemBase编号: 132589
• 分子式: C20H30N4NaO16P
• 平均质量: 636.432931
• 单一同位素质量: 636.12921181
• SMILES: CC(=O)N[C@@H]1[C@H](C[C@](OC1[C@@H]([C@@H](CO)O)O)(C(=O)O)OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1ccc(nc1=O)N)O)O)O.[Na+]
• Canonical SMILES: OC[C@H]([C@H](C1O[C@](C[C@@H]([C@H]1NC(=O)C)O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(nc1=O)N)[O-])C(=O)O)O)O.[Na+]
• InChI: InChI=1S/C20H31N4O16P.Na/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34;/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34);/q;+1/p-1/t8-,9+,10+,12+,13+,14+,15+,16?,17+,20+;/m0./s1
• InChIKey: VFRHSOGUONIUOR-CTFMUGKASA-M

名称和登记号

名称

• IUPAC标准名: sodium [(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2R,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl phosphate
• IUPAC传统名: sodium [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (2R,4S,5R)-2-carboxy-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl phosphate
• 别名: CMP-NAN; CMP-NANA; CMP-NeuAc; CMP-Sialic acid; Cytidine-5′-monophospho-N-acetylneuraminic acid sodium salt; CMP-Neu5Ac

登记号

• CAS号: 3063-71-6
• MDL号: MFCD00151579
• Beilstein号: 4224251
• PubChem SID: 162226866; 24893038
• PubChem CID: 23679065

理论计算性质

• Acid pKa: 1.4845895
• 质子受体: 16
• 质子供体: 9
• LogD (pH = 5.5): -10.4701
• LogD (pH = 7.4): -11.445854
• Log P: -5.740562
• 摩尔折射率: 124.2984 cm^3
• 极化性: 51.02455 Å^3
• 极化表面积: 323.52 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

分子性质

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: -20°C

产品相关信息

• 纯度: ≥85% (HPCE); ≥85% (HPLC)
• 运输包装: wet ice
• 线性分子式: C20H31N4O16P

详细说明

Sigma Aldrich - C8271

Application
Substrate for sialyltransferases. Used for the enzymatic sialylation of glycans.
Cytidine-5′-monophospho-N-acetylneuraminic acid (CMP-Sialic acid) is a substrate for sialyltransferases. It is used for the enzymatic sialylation of glycans.
Preparation Note
Enzymatically prepared by the method of Schauer, R., et al., Hoppe Seyler′s Z. Physiol. Chem., 353, 883 (1972).CMP-NAN is very acid-labile.

Sigma Aldrich - 27562

Application
Substrate for sialyltransferases. Used for the enzymatic sialylation of glycans.