[(E,2S,3R)-3-羟基-2-[[(Z)-十八碳-9-烯酰基]氨基]十八碳-4-烯基]2-三甲基铵乙基磷酸酯盐 | 108392-10-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 中文名称: [(E,2S,3R)-3-羟基-2-[[(Z)-十八碳-9-烯酰基]氨基]十八碳-4-烯基]2-三甲基铵乙基磷酸酯盐
• 中文别名: N-油酰-D-鞘磷脂；中文名称暂缺
• 英文名称: sphingomyelin d18:1(4E)/18:1(9Z)
• 英文别名: N-oleoyl-D-erythro-sphingosylphosphorylcholine；SM (d18:1/18:1)；N-(9Z-octadecenoyl)-sphing-4-enine-1-phosphocholine；[(E,2S,3R)-3-hydroxy-2-[[(Z)-octadec-9-enoyl]amino]octadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 108392-10-5
• 化学式: C₄₁H₈₁N₂O₆P
• 分子量: 729.078
• InChiKey: NBEADXWAAWCCDG-QDDWGVBQSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  50
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  油酸 、 D-赤藓-鞘氨醇磷酸胆碱 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(E,2S,3R)-3-羟基-2-[[(Z)-十八碳-9-烯酰基]氨基]十八碳-4-烯基]2-三甲基铵乙基磷酸酯盐
  参考文献：
  名称：

  水中天然和益生元 1,2-氨基醇两亲物的化学选择性酯化

  摘要：

  在细胞中，大量的膜脂是通过极性头基与酰化剂（例如脂肪酰辅酶A）的酶促O-酰化形成的。尽管这种含酯的脂质似乎是地球上生命的必需品，但尚不清楚在生命起源时缺乏酶机制的情况下是否可以自发形成类似类型的脂质。两亲物在水中进行无酶酯化的例子很少，而且没有一个可以在生理 pH 值下使用生化相关酰化剂在水中发生的例子。在这里，我们报道了 Cu(II) 和其他几种过渡金属离子引导下的 1,2-氨基醇两亲物在水中发生意外的化学选择性 O-酰化。在含有 Cu(II) 离子的缓冲液中，将生物 1,2-氨基醇两亲物（例如鞘氨酰磷酰胆碱）与生化相关的酰化剂（即酰基腺苷酸和酰基辅酶 A）混合，可形成高选择性的 O-酰化产物。由此产生的 O-酰化鞘脂自组装成囊泡，其生物物理特性与由 N-酰基对应物形成的囊泡明显不同。我们还证明 Cu(II) 可以指导替代 1,2-氨基醇的 O-酰化，包括益生元相关的 1,2-氨基醇两亲

  DOI：

  10.1021/jacs.3c12038

文献信息

• Method and use of metabolites for the diagnosis and differentiation of neonatal encephalopathy
  申请人：InfanDx AG

  公开号：EP2587264A1

  公开（公告）日：2013-05-01

  The invention generally relates to the identification metabolites and signatures (panels) of metabolites, which are applicable as biomarkers in clinical diagnosis, in particular for neonatal encephalopathy. They are useful tools in differential clinical diagnosis for early detection of brain injury, determination of brain areas affected by the insults and prediction of adverse neurological outcome and may also be applied in diagnosing disease progression and treatment effect. The present invention more particularly relates to an in vitro method for predicting the likelihood of neonatal encephalopathy of distinct brain areas, identification of affected brain area(s) of neonatal encephalopathy and risk of brain damage and prognosis and neurological outcome due to identification of the type and extent of damage of distinct brain tissues, in particular of hippocampus and / or basal ganglia.

  本发明一般涉及代谢物和代谢物特征（组）的鉴定，这些代谢物和代谢物特征可作为生物标志物用于临床诊断，特别是新生儿脑病的诊断。它们是临床鉴别诊断的有用工具，可用于早期发现脑损伤、确定受损伤影响的脑区和预测不良神经功能结果，还可用于诊断疾病进展和治疗效果。本发明尤其涉及一种体外方法，用于预测不同脑区发生新生儿脑病的可能性、确定新生儿脑病的受影响脑区以及脑损伤风险，并通过鉴定不同脑组织（尤其是海马和/或基底节）的损伤类型和程度来预测预后和神经系统结果。
• Diagnosis and treatment of neonatal encephalopathy
  申请人：InfanDx AG

  公开号：US10514383B2

  公开（公告）日：2019-12-24

  Metabolites and signatures (panels) of metabolites are applicable as biomarkers in clinical diagnosis, in particular for neonatal encephalopathy. They are useful tools in differential clinical diagnosis for early detection of brain injury, determination of brain areas affected by the insults and prediction of adverse neurological outcome and may also be applied in diagnosing disease progression and treatment effect. An in vitro method for predicting the likelihood of neonatal encephalopathy of distinct brain areas, identification of affected brain area(s) of neonatal encephalopathy and risk of brain damage and prognosis and neurological outcome due to identification of the type and extent of damage of distinct brain tissues, in particular of hippocampus and/or basal ganglia, is provided.

  代谢物和代谢物特征（组）可作为生物标记物用于临床诊断，尤其是新生儿脑病的诊断。它们是临床鉴别诊断的有用工具，可用于早期发现脑损伤、确定受损伤影响的脑区和预测不良神经系统结果，还可用于诊断疾病进展和治疗效果。本研究提供了一种体外方法，用于预测不同脑区发生新生儿脑病的可能性、确定新生儿脑病的受影响脑区、脑损伤风险以及由于确定不同脑组织（特别是海马和/或基底节）的损伤类型和程度而导致的预后和神经系统结局。
• METHOD AND USE OF METABOLITES FOR THE DIAGNOSIS AND DIFFERENTIATION OF NEONATAL ENCEPHALOPATHY
  申请人：InfanDx AG

  公开号：EP2771696A2

  公开（公告）日：2014-09-03
• METHODS MAKING USE OF PANELS OF METABOLITES FOR THE DIAGNOSIS AND DIFFERENTIATION OF NEONATAL ENCEPHALOPATHY
  申请人：InfanDx AG

  公开号：EP2771696B1

  公开（公告）日：2022-09-14
• Method and Use of Metabolites for the Diagnosis and Differentiation of Neonatal Encephalopathy
  申请人：InfanDx AG

  公开号：US20140308687A1

  公开（公告）日：2014-10-16

  Metabolites and signatures (panels) of metabolites are applicable as biomarkers in clinical diagnosis, in particular for neonatal encephalopathy. They are useful tools in differential clinical diagnosis for early detection of brain injury, determination of brain areas affected by the insults and prediction of adverse neurological outcome and may also be applied in diagnosing disease progression and treatment effect. An in vitro method for predicting the likelihood of neonatal encephalopathy of distinct brain areas, identification of affected brain area(s) of neonatal encephalopathy and risk of brain damage and prognosis and neurological outcome due to identification of the type and extent of damage of distinct brain tissues, in particular of hippocampus and/or basal ganglia, is provided.