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3-吲哚基-beta-D-吡喃葡萄糖苷 | 487-60-5

中文名称
3-吲哚基-beta-D-吡喃葡萄糖苷
中文别名
靛甙水合物;吲哚葡糖苷水合物;3-吲哚氧基-Β-葡糖苷;吲苷;3-吲哚基-Β-D-吡喃葡萄糖苷;吲哚苷;3-吲哚基-Beta-D-吡喃葡萄糖苷;3-吲哚基-β-D-吡喃葡萄糖苷
英文名称
3-indoxyl-β-D-glucopyranoside
英文别名
indoxyl-β-D-glucopyranoside;indoxyl β-D-glucoside;indican (glucoside);indican;indoxyl-β-D-glucoside;indol-3-yl-β-D-glucopyranoside;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(1H-indol-3-yloxy)oxane-3,4,5-triol
3-吲哚基-beta-D-吡喃葡萄糖苷化学式
CAS
487-60-5
化学式
C14H17NO6
mdl
——
分子量
295.292
InChiKey
XVARCVCWNFACQC-RKQHYHRCSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 熔点:
    57-58 °C
  • 沸点:
    606.7±55.0 °C(Predicted)
  • 密度:
    1.562±0.06 g/cm3(Predicted)
  • 溶解度:
    H2O:0.1 Mat 20 °C,清澈至略微浑浊,无色至淡黄绿色
  • 最大波长(λmax):
    280nm(DMSO)(lit.)

计算性质

  • 辛醇/水分配系数(LogP):
    -0.1
  • 重原子数:
    21
  • 可旋转键数:
    3
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.43
  • 拓扑面积:
    115
  • 氢给体数:
    5
  • 氢受体数:
    6

ADMET

代谢
尿素毒素往往会因为饮食过量或者肾脏过滤功能不佳而在血液中积聚。大多数尿素毒素是代谢废物,通常通过尿液或粪便排出。
Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 毒性总结
尿毒症毒素,如靛蓝,通过有机离子转运体(特别是OAT3)积极运输到肾脏中。尿毒症毒素水平的增加可以刺激活性氧种类的产生。这似乎是通过尿毒症毒素直接结合或抑制NADPH氧化酶酶(特别是肾脏和心脏中丰富的NOX4)(A7868)来介导的。活性氧种类可以诱导几种不同的DNA甲基转移酶(DNMTs),这些酶参与沉默一种名为KLOTHO的蛋白质。KLOTHO已被确定在抗衰老、矿物质代谢和维生素D代谢中具有重要作用。许多研究表明,在急性或慢性肾脏疾病中,由于局部活性氧种类水平较高,KLOTHO mRNA和蛋白质水平会降低(A7869)。
Uremic toxins such as indican are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 致癌物分类
对人类不具有致癌性(未被国际癌症研究机构IARC列名)。
No indication of carcinogenicity to humans (not listed by IARC).
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 健康影响
长期暴露于尿毒症毒素可能会导致多种疾病,包括肾脏损伤、慢性肾病和心血管疾病。
Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 暴露途径
内源性的,摄入,皮肤(接触)
Endogenous, Ingestion, Dermal (contact)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
  • 症状
作为尿毒症毒素,这种化合物可以导致尿毒症综合征。尿毒症综合征可能影响身体的任何部位,并可能导致恶心、呕吐、食欲丧失和体重减轻。它还可能引起精神状态的变化,如混乱、意识降低、激动、精神疾病、癫痫和昏迷。异常出血也可能发生,例如在非常轻微的损伤后自发或大量出血。心脏问题,如心律不齐、心脏周围囊炎症(心包炎)和心脏压力增加,也可能出现在尿毒症综合征患者中。由于肺部和胸壁之间的空间(胸腔积液)积聚液体导致的呼吸急促也可能出现。
As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.
来源:Toxin and Toxin Target Database (T3DB)

安全信息

  • 安全说明:
    S22,S24/25
  • WGK Germany:
    3
  • 海关编码:
    2934999090
  • 危险品运输编号:
    OTH

SDS

SDS:5b693f9f35003de37e76a57f9861243d
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上下游信息

  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    3-吲哚基-beta-D-吡喃葡萄糖苷 在 air 、 β-glucosidase 作用下, 以 aq. phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂, 反应 6.0h, 以97%的产率得到indigo
    参考文献:
    名称:
    [EN] CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF
    [FR] COMPOSÉS DE RÉTICULATION ET MÉTHODES D'UTILISATION DE CEUX-CI
    摘要:
    本文描述了式IA、IB、II、III、IV和/或V的化合物以及它们的使用方法。本发明的化合物可能在生理条件和/或体内发生交联。
    公开号:
    WO2021092287A1
  • 作为产物:
    描述:
    alkaline earth salt of/the/ methylsulfuric acid 在 sodium methylate 作用下, 生成 3-吲哚基-beta-D-吡喃葡萄糖苷
    参考文献:
    名称:
    Freudenberg et al., Chemische Berichte, 1952, vol. 85, p. 641,644
    摘要:
    DOI:
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文献信息

  • [EN] CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE RÉTICULATION ET PROCÉDÉS D'UTILISATION
    申请人:UNIV NORTH CAROLINA STATE
    公开号:WO2021016537A1
    公开(公告)日:2021-01-28
    Compounds comprising a cross-linking moiety and a protecting group are described herein along with their methods of use. The cross-linking moiety may comprise an indoxyl and the protecting group may comprise a sugar (e.g., a glucuronide or glucoside), phosphoester, or sulfoester group. The cross-linking moiety and protecting group may be attached to each other via an oxygen atom, sulfur atom, or linker. In some embodiments, the linker attaching the cross-linking moiety and protecting group is a self-immolative linker. A compound of the present invention may cross-link under physiological conditions and/or in vivo.
    本文描述了包含交联基团和保护基团的化合物,以及它们的使用方法。交联基团可能包括吲哚基团,保护基团可能包括糖类(例如葡萄糖醛酸盐或葡萄糖苷)、磷酸酯或磺酸酯基团。交联基团和保护基团可以通过氧原子、硫原子或连接剂相互连接。在某些实施例中,连接交联基团和保护基团的连接剂是自解离连接剂。本发明的化合物可能在生理条件和/或体内发生交联。
  • Elucidating Cysteine-Assisted Synthesis of Indirubin by a Flavin-Containing Monooxygenase
    作者:Joonwon Kim、Jeongchan Lee、Pyung-Gang Lee、Eun-Jung Kim、Wolfgang Kroutil、Byung-gee Kim
    DOI:10.1021/acscatal.9b02613
    日期:2019.10.4
    inhibiting the dimerization of indoxyl. Second, the reducing power of cysteine allows MaFMO to additionally hydroxylate indoxyl toward isatin, overcoming the problem in biased distribution of two different precursors. Third, cysteine activates isatin to react with 2-cysteinylindoleninone to form indirubin. Based on this revealed mechanism, indirubin derivatives with different indole ring components were synthesized
    靛玉红是在当归龙辉湾中发现的一种生物活性化合物,该物质是治疗慢性粒细胞白血病的传统中药。在靛玉红的生物合成中,作为靛玉红的立体异构体的靛蓝的形成是主要的副反应。最近的发现表明,半胱氨酸的补充使产物的选择性从靛蓝转变为靛玉红。在这里,我们公开了半胱氨酸如何使用来自甲基邻苯二甲硫醚的含黄素的单加氧酶来增强靛玉红合成中的产物选择性。(MaFMO)。首先,半胱氨酸与吲哚基反应以合成2-半胱氨酸林多烯酮,从而抑制了吲哚基的二聚化。其次,半胱氨酸的还原能力使MaFMO可以将吲哚酚进一步羟化为靛红,从而克服了两种不同前体的偏向分布问题。第三,半胱氨酸激活靛红与2-半胱氨酸林多烯酮反应形成靛玉红。基于这一揭示的机理,合成了具有不同吲哚环成分的靛玉红衍生物。
  • Compositions and methods for enhanced mucosal delivery of Y2 receptor-binding peptides and methods for treating and preventing obesity
    申请人:Nastech Pharmaceutical Company Inc.
    公开号:US20040157777A1
    公开(公告)日:2004-08-12
    Pharmaceutical compositions and methods are described comprising at least one Y2 receptor-binding peptide, such as peptide YY(PYY), Neuropeptide Y (NPY) or Pancreatic Peptide (PP) and one or more mucosal delivery-enhancing agents for enhanced nasal mucosal delivery of the peptide YY, for treating a variety of diseases and conditions in mammalian subjects, including obesity.
    描述了包含至少一种Y2受体结合肽(如肽YY(PYY)、神经肽Y(NPY)或胰岛素肽(PP))和一种或多种黏膜传递增强剂的药物组合物和方法,以增强肽YY在鼻黏膜中的传递,用于治疗哺乳动物主体中的多种疾病和病况,包括肥胖。
  • Intranasal administration of glucose-regulating peptides
    申请人:Quay C. Steven
    公开号:US20050143303A1
    公开(公告)日:2005-06-30
    Pharmaceutical compositions and methods are described comprising at least one glucose-regulating peptide, such as amylin, glucagon-like peptide-1 (GLP), pramlintide or exendin-4 and one or more mucosal delivery-enhancing agents for enhanced nasal mucosal delivery of the amylin, for treating a variety of diseases and conditions in mammalian subjects, including obesity and diabetes mellitus.
    本文介绍了一种药物组合和方法,其中包括至少一种调节葡萄糖的肽类,如降淀粉样肽、胰高血糖素样肽-1(GLP)、普拉林肽或外肽-4,以及一种或多种黏膜传递增强剂,以增强降淀粉样肽在鼻黏膜上的传递,用于治疗哺乳动物主体中的多种疾病和病况,包括肥胖和糖尿病。
  • METHOD FOR PRODUCING GLUCOSIDES
    申请人:Motokucho Suguru
    公开号:US20130060015A1
    公开(公告)日:2013-03-07
    The present invention relates to methods for producing glucosides directly from glucose or a polysaccharide comprising glucose as a structural unit. The present invention provides a method comprising reacting glucose or a polysaccharide comprising glucose as a structural unit with a compound represented by R—OH in the presence of a supercritical or subcritical carbon dioxide to produce glucosides and a method comprising dissolving or suspending glucose or a polysaccharide comprising glucose as a structural unit in an organic solvent containing a compound represent by R—OH and reacting the glucose or polysaccharide with the compound represented by R—OH in the presence of a supercritical or subcritical carbon dioxide to produce glucosides.
    本发明涉及从葡萄糖或包含葡萄糖作为结构单元的多糖直接生产葡萄糖苷的方法。本发明提供了一种方法,包括在超临界或亚临界二氧化碳存在下,将葡萄糖或包含葡萄糖作为结构单元的多糖与表示为R-OH的化合物反应,以产生葡萄糖苷;以及一种方法,包括在含有表示为R-OH的化合物的有机溶剂中溶解或悬浮葡萄糖或包含葡萄糖作为结构单元的多糖,并在超临界或亚临界二氧化碳存在下,将葡萄糖或多糖与表示为R-OH的化合物反应,以产生葡萄糖苷。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
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ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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