72-89-9

• 常用中文名：乙酰辅酶A
• 常用英文名：Acetyl-CoA
• CAS号：72-89-9
• 分子式：C₂₃H₃₈N₇O₁₇P₃S
• 分子量：809.571
• 相关类别： 医药中间体 杂环化合物 吡喃类化合物
• 发布时间：2018-07-19 16:26:43
• 更新时间：2024-01-01 18:03:44
• 乙酰辅酶A(Acetyl CoA)是一种不透膜的中枢代谢中间体,参与TCA循环和氧化磷酸化代谢。乙酰辅酶A通过向蛋白质的翻译后乙酰化反应的目标氨基酸残基提供(唯一供体)乙酰基来调节各种细胞机制。乙酰辅酶A也是脂质合成的关键前体[1][2][3][4]。

名称

• 中文名: 乙酰辅酶A
• 英文名: acetyl-CoA
• 英文别名: acetylocholine; Azetylcholin; ac-CoA; Choline acetate; S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3λ,5λ-diphosphaheptadecan-17-yl} ethanethioate (non-preferred name); Acetyl-CoenzymeA; S-ACETYL COENZYME A; acetyl CoA; Acetyl-CoA,Tri-Na; O-Acetylcholine; S-acetylcoenzyme A; [3H]-Acetylcholine; Acetyl choline ion; [14C]-Acetyl-Coenzyme A; S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3λ,5λ-diphosphaheptadecan-17-yl} ethanethioate (non-preferred name); Adenosine, 5'-O-[[[[(3R)-4-[[3-[[2-(acetylthio)ethyl]amino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]hydroxyphosphinyl]oxy]hydroxyphosphinyl]-, 3'-(dihydrogen phosphate); Coenzyme A S-Acetate; Choline acetate (ester); trilithium,[2-[[[[4-[[3-(2-acetylsulfanylethylamino)-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl] hydrogen phosphate,trihydrate; Acetyl coenzyme A; coenzyme A, acetyl-; ac-S-CoA; S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3λ,5λ-diphosphaheptadecan-17-yl} ethanethioate; S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydro-2-furanyl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3λ,5λ- diphosphaheptadecan-17-yl} ethanethioate; [3H]-Acetyl-Coenzyme A; (2-Acetoxyethyl)trimethylammonium; Ach; acetyl-S-CoA; Acetylcholinum; acetylCoA; Acetyl-Coenzyme A; [14C]-Acetylcholine; Coenzyme A, S-acetate; acetylcholine; acetylcholine cation

物化性质

• 密度: 1.9±0.1 g/cm3
• 分子式: C₂₃H₃₈N₇O₁₇P₃S
• 分子量: 809.571
• 精确质量: 809.125793
• PSA: 425.34000
• LogP: -3.89
• 折射率: 1.718

生物活性

• 描述: 乙酰辅酶A(Acetyl CoA)是一种不透膜的中枢代谢中间体,参与TCA循环和氧化磷酸化代谢。乙酰辅酶A通过向蛋白质的翻译后乙酰化反应的目标氨基酸残基提供(唯一供体)乙酰基来调节各种细胞机制。乙酰辅酶A也是脂质合成的关键前体[1][2][3][4]。
• 相关类别:
  研究领域 >> 心血管疾病
  信号通路 >> 自噬 >> 自噬
  研究领域 >> 代谢疾病
• 靶点:

  Human Endogenous Metabolite

• 体外研究: 乙酰辅酶A在饥饿的 U2OS公司细胞中增加细胞质蛋白乙酰化,同时减少饥饿诱导的自噬通量。(U2OS)细胞稳定表达 绿色荧光蛋白-LC3并显微注射乙酰辅酶A；在无营养条件下,用 100 nM挡板A1孵育 3小时后固定)[2]。
• 体内研究: 乙酰辅酶A通过抑制适应不良的自噬来抑制压力超负荷诱导的小鼠心肌病[2][3]。被剥夺食物 (但可以随意饮水) 24小时的小鼠在几个器官 (包括心脏和肌肉) 中表现出总 乙酰辅酶A水平显着降低,对应于蛋白质乙酰化水平的降低。相同的实验条件对大脑中 乙酰辅酶A的浓度没有重大影响,实际上会增加肝脏 乙酰辅酶A和蛋白质乙酰化水平[4]。
• 参考文献:

  [1]. Choudhary C, et al. The growing landscape of lysine acetylation links metabolism and cell signalling. Nat Rev Mol Cell Biol. 2014 Aug;15(8):536-50.

  [2]. Mariño G, et al. Regulation of autophagy by cytosolic acetyl-coenzyme A. Mol Cell. 2014 Mar 6;53(5):710-25.

  [3]. Zhu H, et al. Cardiac autophagy is a maladaptive response to hemodynamic stress. J Clin Invest. 2007 Jul;117(7):1782-93.

  [4]. Pietrocola F, et al. Acetyl coenzyme A: a central metabolite and second messenger. Cell Metab. 2015 Jun 2;21(6):805-21.

合成路线

108-24-7 85-61-0 ~% 72-89-9

文献：Journal of the American Chemical Society, , vol. 75, p. 2520 Journal of Biological Chemistry, , vol. 203, p. 869,872, 877

75-07-0 ~% 72-89-9

文献：US2013/66035 A1, ; Page/Page column ;

85-61-0 ~% 72-89-9

文献：Biochemische Zeitschrift, , vol. 329, p. 175 Journal of Biological Chemistry, , vol. 199, p. 65,66

2466-76-4 85-61-0 ~% 72-89-9

文献：Bioscience, biotechnology, and biochemistry, , vol. 67, # 10 p. 2106 - 2114

34832-35-4 85-61-0 ~% 72-89-9

文献：Journal of the American Chemical Society, , vol. 74, p. 3205

113-24-6 85-61-0 ~% 72-89-9

文献：Biochemistry, , vol. 51, # 13 p. 2795 - 2803

1420-36-6 ~% 72-89-9

文献：Organic Letters, , vol. 9, # 20 p. 3877 - 3880

75-07-0 85-61-0 ~% 72-89-9

文献：Biochemistry, , vol. 50, # 39 p. 8407 - 8416

64-19-7 604-98-8 ~% 72-89-9

文献：Biochemistry, , vol. 51, # 42 p. 8422 - 8434

上下游产品

上游产品  9
108-24-7 85-61-0 75-07-0 2466-76-4
34832-35-4 113-24-6 1420-36-6 64-19-7
604-98-8
下游产品  9
480-64-8 543-24-8 85-61-0 5147-00-2
2140-48-9 140-11-4 26157-58-4 1420-36-6
27548-93-2