3a,6,7,7a-四氢-5-(羟基甲基)-2-甲基-(3aR,5R,6S,7R,7aR)-5H-吡喃并[3,2-d]噻唑-6,7-二醇

• 常用名: 3a,6,7,7a-四氢-5-(羟基甲基)-2-甲基-(3aR,5R,6S,7R,7aR)-5H-吡喃并[3,2-d]噻唑-6,7-二醇
• 英文名: NAG-thiazoline
• CAS号: 179030-22-9
• 分子量: 219.26
• 密度: 1.8±0.1 g/cm3
• 沸点: 443.0±45.0 °C at 760 mmHg
• 分子式: C₈H₁₃NO₄S
• 熔点: N/A
• 闪点: 221.7±28.7 °C

用途

NAG噻唑啉是具有180nM Ki的O-GlcNAcase抑制剂。NAG噻唑啉是一种强效GH20-GlcNAcase(VhGlcNAcase)抑制剂,IC50为11.9μM,Ki为62µM[1]。

名称

• 中文名: 3a,6,7,7a-四氢-5-(羟基甲基)-2-甲基-(3aR,5R,6S,7R,7aR)-5H-吡喃并[3,2-d]噻唑-6,7-二醇
• 英文名: (3aR,5R,6S,7R,7aR)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol

生物活性

• 描述: NAG噻唑啉是具有180nM Ki的O-GlcNAcase抑制剂。NAG噻唑啉是一种强效GH20-GlcNAcase(VhGlcNAcase)抑制剂,IC50为11.9μM,Ki为62µM[1]。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 体外研究: NAG噻唑啉完全抑制 V.坎贝尔650菌株的生长,麦克风值为 0.5µM[1]
• 参考文献:

  [1]. Macauley MS, et al. Increasing O-GlcNAc levels: An overview of small-molecule inhibitors of O-GlcNAcase. Biochim Biophys Acta. 2010 Feb;1800(2):107-21.

  [2]. Piyanat Meekrathok, et al. NAG-thiazoline is a potent inhibitor of the Vibrio campbellii GH20 β-N-Acetylglucosaminidase. FEBS J. 2020 Nov;287(22):4982-4995.

物理化学性质

• 密度: 1.8±0.1 g/cm3
• 沸点: 443.0±45.0 °C at 760 mmHg
• 分子式: C₈H₁₃NO₄S
• 分子量: 219.26
• 闪点: 221.7±28.7 °C
• 精确质量: 219.056534
• PSA: 107.58000
• LogP: -0.44
• InChIKey: DRHXTSWSUAJOJZ-FMDGEEDCSA-N
• SMILES: CC1=NC2C(OC(CO)C(O)C2O)S1
• 蒸汽压: 0.0±2.4 mmHg at 25°C
• 折射率: 1.742

靶点实验

查看更多实验

实验名称：Activation of PDK1 来源：ChEMBL 靶标：[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial External Id：CHEMBL1251511

实验名称：Pharmacological chaperone effect on beta Hex A beta-P504S/delta16kb mutant in fibrobl... 来源：ChEMBL 靶标：Beta-hexosaminidase subunit beta External Id：CHEMBL983119

实验名称：Inhibition of insulin-induced GLUT4 translocation into plasma membrane of mouse diffe... 来源：ChEMBL 靶标：Solute carrier family 2, facilitated glucose transporter member 4 External Id：CHEMBL1251510

实验名称：Induction of hyper-O-GlcNAc-ylation in human HeLa cells assessed as increase of O-Glc... 来源：ChEMBL 靶标：HeLa External Id：CHEMBL1251509

实验名称：Pharmacological chaperone effect on beta Hex A beta-P504S/delta16kb mutant in fibrobl... 来源：ChEMBL 靶标：Beta-hexosaminidase subunit beta External Id：CHEMBL983121

实验名称：Induction of hyper-O-GlcNAc-ylation in human HT-29 cells assessed as increase of O-Gl... 来源：ChEMBL 靶标：HT-29 External Id：CHEMBL1251508

实验名称：Experimentally measured binding affinity data (Ki) for protein-ligand complexes deriv... 来源：Shanghai Institute of Organic Chemistry 靶标：N/A External Id：PDBbind-Ki for protein-ligand complexes

实验名称：Pharmacological chaperone effect on beta Hex A beta-R505Q/IVS11 + 5G>A mutant in fibr... 来源：ChEMBL 靶标：Beta-hexosaminidase subunit alpha External Id：CHEMBL983115

实验名称：Experimentally measured binding affinity data (Kd) for protein-ligand complexes deriv... 来源：Shanghai Institute of Organic Chemistry 靶标：N/A External Id：PDBbind-Kd for protein-ligand complexes

实验名称：Pharmacological chaperone effect on beta Hex A beta-R505Q/IVS11 + 5G>A mutant in fibr... 来源：ChEMBL 靶标：Beta-hexosaminidase subunit alpha External Id：CHEMBL983117

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英文别名

• (3aR,5R,6S,7R,7aR)-5-(Hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
• 3AR,5R,6S,7R,7AR-5-HYDROXYMETHYL-2-METHYL-5,6,7,7A-TETRAHYDRO-3AH-PYRANO[3,2-D]THIAZOLE-6,7-DIOL
• (5R,6S,7R)-5-(Hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
• NAG-thiazoline
• N-Acetylglucosamine Thiazoline
• UNII-ML5FHL557A
• 2epn
• NGT
• 1hp5