β-Nicotinamide adenine dinucleotide hydrate 烟酰胺腺嘌呤双核苷酸

CAS 53-84-9 MFCD00036253

化学结构图

53-84-9
SMILES: NC(=O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)([O-])OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c1

化学属性

Mol. FormulaC21H27N7O14P2
Mol. Weight663.43
Density1.422
SolubilitySoluble in water (200 mg/ml).
Stability对湿度敏感
Melting Point140-142°C

别名和识别编码

Chemical Nameβ-Nicotinamide adenine dinucleotide hydrate
Synonym Adenine Dinucleotide, Dihydronicotinamide Adenosine 5'-(trihydrogen diphosphate), 5'->5'-ester with 3-(aminocarbony Adenosine 5'-(trihydrogen diphosphate), 5'->5'-ester with 3-(aminocarbonyl)-1-β-D-ribofuranosylpyridinium hydroxide, inner salt Adenosine 5'-(trihydrogen diphosphate), 5'->5'-ester with 3-(aminocarbonyl)-1β-D-ribofuranosylpyridinium hydroxide, inner salt Adenosine 5'-(trihydrogen diphosphate), P C CO-1 Coenzyme I Cozymase DPN Dihydronicotinamide Adenine Dinucleotide Dinucleotide, Dihydronicotinamide Adenine Dinucleotide, Nicotinamide-Adenine Diphosphopyridine Nucleotide Diphosphopyridine nucleotide Diphosphopyridinnucleotid NAD NAD+ {PubChem} Nadide Nicotinamide Ade {} {PubChem} N
CAS Number53-84-9
EC Number200-184-4
Beilstein Registry Number3584133
MDL NumberMFCD00036253
PubChem Substance ID5892
Reaxys-RN3584133
Merck Number6344
Chemical Name Translation烟酰胺腺嘌呤双核苷酸
Wiswesser Line NotationT56 BN DN GN INJ FZ B- BT5OJ CQ DQ E1OPWOPWO1- BT5OTJCQ DQ E- AT6KJ CVZ
LabNetwork Molecule IDLN01315733
InChIInChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
Canonical SMILESO[C@H]([C@@H]1O)[C@@H](O[C@@H]1COP(OP(OC[C@H]2O[C@@H]([N+]3=CC=CC(C(N)=O)=C3)[C@H](O)[C@@H]2O)([O-])=O)(O)=O)N4C(N=CN=C5N)=C5N=C4
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分类

  • {SNA} Biochemicals and Reagents, NAD, NAD(P)(H) and Analogs, Nucleosides, Nucleotides, Oligonucleotides, Single-use vials
  • {SNA} Biochemicals and Reagents, Bulk vials, Core Bioreagents, NAD, NAD(P)(H) and Analogs, Nucleosides, Nucleotides, Oligonucleotides,
  • {SNA} Bulk vials, Chemical Synthesis, Cofactors,

产品应用

  • 烟酰胺腺嘌呤二核苷酸是一种转递質子（更准确来说是氢离子）的辅酶，它出现在细胞很多代谢反应中。NADH或更准确NADH + H+是它的还原形式。它可以被还原，最多携带两个質子（写为NADH + H+）。NAD+是脱氢酶的辅酶，如乙醇脱氢酶(ADH)，用于氧化乙醇。它在糖酵解、糖异生、三羧酸循环及呼吸链中发挥着不可替代的作用。中间产物会将脱下的氢递给NAD，使之成为NADH + H+。而NADH + H+则会作为氢的载体，在呼吸链中通过化学渗透偶联的方式，合成ATP。
  • 在吸光方面，NADH+H+在260nm和340nm处各有一吸收峰，而NAD+则只有260nm一处吸收峰，这是区别两者的重要属性。这同时也是很多代谢试验中，测量代谢率的物理依据。NAD在260nm的吸光系数为1.78*104L /(mol*cm)，而NADH在340nm的吸光系数为6.2*10³ L/(mol*cm)。

相关文献及参考

  • [2]. Brandt, U., Energy converting NADH:quinone oxidoreductase (complex I). Annu Rev Biochem, 2006. 75: p. 69-92.
  • [3]. Kussmaul, L. and J. Hirst, The mechanism of superoxide production by NADH:ubiquinone oxidoreductase (complex I) from bovine heart mitochondria. Proc Natl Acad Sci U S A, 2006. 103(20): p. 7607-12.
  • Merck: 14,6344
  • Short: II/27B
  • Short: II/3
  • [1]. Viollet, B., et al., Cellular and molecular mechanisms of metformin: an overview. Clin Sci (Lond), 2012. 122(6): p. 253-70.
  • [1]. Viollet, B., et al., Cellular and molecular mechanisms of metformin: an overview. Clin Sci (Lond), 2012. 122(6): p. 253-70.
  • [2]. Brandt, U., Energy converting NADH:quinone oxidoreductase (complex I). Annu Rev Biochem, 2006. 75: p. 69-92.
  • [3]. Kussmaul, L. and J. Hirst, The mechanism of superoxide production by NADH:ubiquinone oxidoreductase (complex I) from bovine heart mitochondria. Proc Natl Acad Sci U S A, 2006. 10

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
Risk Statements
  • R68/20/21/22
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P352
  • P304+P340
  • P305+P351+P338
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P332+P313
  • P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服，清洗后方可重新使用
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
RTECSUU3450000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Storage condition 0-10 0-10°C 2-8°C 储存温度：2-8℃ 极易吸潮，储存温度-20℃
Hazard Codes Xn
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H371 May cause damage to organs 可能导致器官损伤
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 4333 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   PCJOAU Pharmaceutical Chemistry Journal (English Translation).  Translation
   of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013)  No.1-
   1967-  Volume(issue)/page/year: 20,160,1986

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 100 ug/plate
REFERENCE :
   ABCHA6 Agricultural and Biological Chemistry.  (Maruzen Co. Ltd., POB 5050,
   Tokyo International, Tokyo 100-31, Japan)  V.25-    1961-
   Volume(issue)/page/year: 45,327,1981

其他信息

  • 极易吸湿。固体在干燥器内0℃或室温时稳定。中性或微酸性溶液（pH3～7)，在0℃时可稳定2周以上，碱性溶液中极易变质，加热易分解。溶于水，不溶于丙酮等有机溶剂。pH7.5时最大吸收波长259nm(ε17800)。最小吸收波长230nm(ε8000)。

系列性分类

  1. Research Essentials 基础科研
  2. Core Bioreagents - Research Essentials
  3. Vitamins and Coenzymes - Core Bioreagents
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. NAD and Analogs - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Cofactors - Enzymes, Inhibitors, and Substrates
  5. Oxidation-Reduction - Cofactors
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Cofactors - Enzymes, Inhibitors, and Substrates
  5. Oxidation-Reduction - Cofactors
  1. Life Science 生命科学
  2. Metabolomics 代谢组学
  3. Metabolic Pathways - Metabolomics
  4. Electron Transport and Cellular Respiration - Metabolic Pathways
  5. Cofactors and Substrates - Electron Transport and Cellular Respiration
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Building Blocks 手性分子砌块
  4. Heterocyclic Building Blocks - Chiral Building Blocks
  5. Purines - Heterocyclic Building Blocks
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. NAD and Analogs - Nucleosides, Nucleotides, Oligonucleotides
  5. NAD - NAD(P)(H) and Analogs
  6. Bulk vials - NAD
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. NAD and Analogs - Nucleosides, Nucleotides, Oligonucleotides
  5. NAD - NAD(P)(H) and Analogs
  6. Single-use vials - NAD
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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