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ナイアシンアミドリボシドクロリド

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyridin-1-ium-3-carboxamide;chloride

HCID 175647717
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
23111-00-4
標準SMILES
Cl.N=C([O-])c1ccc[n+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1
InChIKey
YABIFCKURFRPPO-IVOJBTPCSA-N
分子式
C11H15ClN2O5
平均分子量
290.7 g/mol
単同位体質量
290.0669493

概要

See other relationships...

名称と識別子

優先名称
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyridin-1-ium-3-carboxamide;chloride
IUPAC
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridin-1-ium-3-carboximidate;hydrochloride
現地名
ナイアシンアミドリボシドクロリド
英語名
Nicotinamide riboside chloride
分子式
C11H15ClN2O5
分子量
290.7

名称と別名

F7967651-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyridin-1-ium-3-carboxamide;chlorideナイアシンアミドリボシドクロリドNICOTINAMIDE RIBOSIDENRCNR-CLNicotinamide B-D Riboside Chloride(WX900111)NRCI3-carbamoyChemicalbookl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-iumchlorideNicotinamide ribose chloride3-Carbamoyl-1-beta-D-ribofuranosylpyridinium chloride3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium chloride
名称をさらに表示
NR-CL70%

データベース識別子

CAS
23111-00-4
PubChem CID
175647717

物性

構造計算による物性

極性表面積
121 Ų
水素結合供与体数
5
水素結合受容体数
6
回転可能結合数
3
重原子数
19
形式電荷
0
複雑度
314

物理化学的性質

貯蔵温度
2 · under inert gas (nitrogen or Argon) at 2-8°C
溶解性
100 mM、水に100 · DMSOに100 mM、水に100 mMまで可溶
外見
solid
色
White
由来生物
milk
水溶解度
10 mg/mL, · 10mg/mL, clear, colorless
安定性
Hygroscopic
化粧品成分の機能
抗酸化物質肌を保護する
InChI
InChI=1/C11H14N2O5.ClH/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11;/h1-4,7-9,11,14-16H,5H2,(H-,12,17);1H/t7-,8-,9-,11-;/s3
InChIKey
YABIFCKURFRPPO-TUHHAUDNNA-N
SMILES
O[C@@H]1[C@@H]([C@@H](CO)O[C@H]1[N+]1=CC=CC(C(=O)N)=C1)O.[Cl-] |&1:1,2,3,7,r|
化学的性質 · 1 件

化学的特性Nicotinamide riboside chloride (NR-CL) is structurally a quaternary ammonium salt containing a sensitive N-glycosidic bond that spontaneously cleaves in aqueous solution, yielding nicotinamide and d-ribose degradation products (Figure 1). NR-CL exhibits three crystalline forms: Type A, Type B, and Type C. Forms A and B represent true polymorphs of the anhydrous form, whereas form C constitutes a pseudo-polymorphic form as a methanesulfonate solvate. The B form exhibits a higher crystal density (1.591 Mg/m³) and a higher melting/decomposition temperature (123°C) compared to the A form (1.512 Mg/m³, 119°C), making it the most stable crystalline form. The crystal structure of Form B(Figure 2) is orthorhombic P212121 space group, with a = 7.0008(11) Å, b = 9.6465(15) Å, c = 17.971(3) Å, V = 1213.7(3) ų, and Z = 4.

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

安全データ

wgk
WGK 3
hs_code
2938909090
ストレージクラス
13 - Non Combustible Solids

化学と産業

応用分野 · 3 件

説明Nicotinamide Riboside Chloride is the chloride salt form of nicotinamide riboside (NR). NR is a pyridine nucleoside form of vitamin B3 that functions as a precursor to nicotinamide adenine dinucleotide (NAD+). Nicotinamide riboside chloride is a crystalline form of nicotinamide riboside (NR) chloride. Nicotinamide riboside chloride increases NAD+ levels and activates SIRT1 and SIRT3, thereby enhancing oxidative metabolism and protecting against high-fat diet-induced metabolic abnormalities. Nicotinamide riboside chloride is used in dietary supplements.

来歴Nicotinamide riboside (NR) was first described in 1944 as a growth factor, termed Factor V, for Haemophilus influenza, a bacterium that lives in and depends on blood. Factor V, purified from blood, was shown to exist in three forms: NAD+, NMN and NR. NR was the compound that led to the most rapid growth of this bacterium.Notably, H. influenza cannot grow on nicotinic acid, nicotinamide, tryptophan or aspartic acid, which were the previously known precursors of NAD+.In 2000, yeast Sir2 was shown to be an NAD+-dependent protein lysine deacetylase, which led several research groups to probe yeast NAD+ metabolism for genes and enzymes that might regulate lifespan. Biosynthesis of NAD+ in yeast was thought to flow exclusively through NAMN (nicotinic acid mononucleotide).When NAD+ synthase (glutamine-hydrolysing) was deleted from yeast cells, NR permitted yeast cells to grow. Thus, these Dartmouth College investigators proceeded to clone yeast and human nicotinamide riboside kinases and demonstrate the conversion of NR to NMN by nicotinamide riboside kinases in vitro and in vivo. They also demonstrated that NR is a natural product found in cow’s milk.

使用Nicotinamide Riboside Chloride is a crystal form of Nicotinamide riboside (NR) chloride termed NIAGEN, generally recognized as safe (GRAS) for use in foods and in dietary supplements. Nicotinamide Riboside Chloride is a source of vitamin B3 (niacin) and enhances oxidative metabolism, protection against high fat diet-induced metabolic abnormalities. Nicotinamide riboside is a newly discovered NAD (NAD+) precursor vitamin.

上流・下流製品情報

上流原料

α-D-Ribofuranosyl chloride, 2,3,5-triacetate

関連反応

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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
D-Ribofuranosyl chloride, 2,3,5-triacetate
1,4-dihydronicotinaMide riboside
ニコチン酸アミドのリボース
3-(Aminocarbonyl)-1-beta-D-ribofuranosylpyridinium bromide

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