(2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid
| 中文名称 | (2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid |
|---|---|
| 中文同义词 | 化合物 T16837;N-琥珀酰-5-氨基咪唑-4-甲酰胺核糖5'-磷酸;N-[[5-氨基-1-(5-O-膦酰基-B-D-呋喃核糖基)-1H-咪唑-4-基]羰基]-L-天冬氨酸;化合物 SAICAR |
| 英文名称 | (2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid |
| 英文同义词 | (2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid;N-[[5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-yl]carbonyl]-L-aspartic acid;Succino-AICAR;2-[[1-(5-O-Phosphono-β-D-ribofuranosyl)-5-amino-1H-imidazol]-4-ylcarbonylamino]succinic acid;5-Aminoimidazole-4-N-succinocarboxamide ribonucleotide;5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole;N-Succinyl-5-aMinoiMidazole-4-carboxaMide Ribose 5'-Phosphate;L-Aspartic acid, N-[[5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-yl]carbonyl]- |
| CAS号 | 3031-95-6 |
| 分子式 | C13H19N4O12P |
| 分子量 | 454.28 |
| EINECS号 | |
| 相关类别 | |
| Mol文件 | 3031-95-6.mol |
| 结构式 | ![(2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid 结构式](CAS/GIF/3031-95-6.gif) |
(2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid 性质
| 熔点 | >189°C (dec.) |
|---|---|
| 密度 | 2.18±0.1 g/cm3(Predicted) |
| 储存条件 | Hygroscopic, -20°C Freezer, Under inert atmosphere |
| 溶解度 | 甲醇（微溶）、水（微溶） |
| 形态 | 固体 |
| 酸度系数(pKa) | 1.86±0.10(Predicted) |
| 颜色 | 白色至类白色 |
| 生物来源 | synthetic |
| 稳定性 | 吸湿性 |
| 主要应用 | 代谢组学 |
| InChIKey | NAQGHJTUZRHGAC-ZZZDFHIKSA-N |
| SMILES | NC1=C(N=CN1[C@H]2[C@H](O)[C@H](O)[C@@H](COP(O)(O)=O)O2)C(N[C@@H](CC(O)=O)C(O)=O)=O |
(2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid 用途与合成方法
N-琥珀酰基-5-氨基咪唑-4-羧酰胺5'-磷酸核糖是嘌呤代谢产物。 由于腺苷是神经元功能的有效抑制剂，可抑制几种兴奋递质的释放并引发神经元的直接过级化，因此腺苷琥珀酸裂合酶（ASase）缺乏症患者出现的症状可能反映了琥珀酰嘌呤对神经传递的干扰。
SAICAR 是嘌呤核苷酸从头合成的中间体，以同工酶选择性性方式激活 PKM2，EC50 为 0.3 mM。SAICAR 刺激 PKM2 并促进癌细胞在葡萄糖限制条件下的存活。|
Human Endogenous Metabolite
|
SAICAR accumulation induces nuclear localization of PKM2. PKM2-SAICAR phosphorylates and activates Erk1/2, which in turn sensitizes PKM2 for SAICAR binding through phosphorylation. Additionally, PKM2-SAICAR was necessary to induce sustained Erk1/2 activation and mitogen-induced cell proliferation. SAICAR-PKM2 interaction is necessary and sufficient to induce H3 T11 and Erk1/2 phosphorylation.
Upon glucose starvation, cellular SAICAR concentration increases in an oscillatory manner and stimulates PKM2 activity in cancer cells. The SAICAR-PKM2 interaction also promotes cancer cell survival in glucose-limited conditions. In glucose-limited conditions, cells with higher SAICAR concentrations (
adsl-kd
cells or cells overexpressing PAICS) survive better while
paics-kd
cells died earlier than control-kd cells. SAICAR promotes cancer cell survival in glucose-limited conditions.
安全信息
| WGK Germany | WGK 3 |
|---|---|
| 存储类别 | 11 - 可燃固体 |
| 更新日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
|---|---|---|---|---|---|
| 2026/06/05 | HY-126585 | (2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid SAICAR | 3031-95-6 | 500μg | 2000元 |
| 2026/06/05 | HY-126585 | (2S)-2-[[5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carbonyl]amino]butanedioic acid SAICAR | 3031-95-6 | 1mg | 3400元 |