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ニコチン酸アミドのリボース

Nicotinamide-beta-riboside

HCID 439924
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基本情報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
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基本情報

CAS
1341-23-7
標準SMILES
NC(=O)c1ccc[n+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1
InChIKey
JLEBZPBDRKPWTD-TURQNECASA-O
分子式
C11H15N2O5+
平均分子量
255.25 g/mol
単同位体質量
255.097548

名称と識別子

優先名称
Nicotinamide-beta-riboside
IUPAC
3-Carbamoyl-1-beta-D-ribofuranosylpyridin-1-ium
現地名
ニコチン酸アミドのリボース
英語名
Nicotinamide riboside
分子式
C11H15N2O5+
分子量
255.25

名称と別名

ニコチン酸アミドのリボースニコチンアミド-β-リボシド1-β-D-リボフラノシル-3-カルバモイルピリジニウム1-(β-D-リボフラノシル)ピリジニウム-3-カルボアミドニコチンアミドリボシド1-デオキシ-1-(3-カルバモイルピリジニオ)-β-D-リボフラノース3-カルバモイル-1-[(2R,3R,4S,5R)-3,4-ジヒドロキシ-5-(ヒドロキシメチル)オキソラン-2-イル]-1λ5-ピリジン-1-イリウム1-(β-D-リボフラノシル)-3-(アミノカルボニル)ピリジニウムN-ribosylnicotinamideBETA-nicotinamide riboseNicotinamide riboside (NR)3-Carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium
名称をさらに表示
Nicotinamide RibosePyridinium, 3-(aminocarbonyl)-1-β-D-ribofuranosyl-C:C&B64Niacinamide RiboseNicotiamide RibosideNicotinimide Riboside

データベース識別子

CAS
1341-23-7
PubChem CID
439924
DTXSID
DTXSID501010039
ChEMBL
CHEMBL438497
ChEBI
CHEBI:15927
UNII
0I8H2M0L7N
EC Number
811-511-0
Nikkaji
J490.568G

物性

物理化学的性質

貯蔵温度
-20 °C · Store at -20°C
溶解性
Water: Soluble
外見
A low-melting semi-solid
InChI
InChI=1/C11H14N2O5/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)/p+1/t7-,8-,9-,11-/s3
InChIKey
JLEBZPBDRKPWTD-XULPMDEONA-O
SMILES
O[C@@H]1[C@@H]([C@@H](CO)O[C@H]1[N+]1=CC=CC(C(=O)N)=C1)O |&1:1,2,3,7,r|
化学的性質 · 1 件

化学的特性Nicotinamide riboside (NR) is part of the B3 vitamin family. Like other forms of vitamin B3, nicotinamide riboside gets converted into nicotinamide adenine dinucleotide (NAD+), a coenzyme essential for life. For this reason, it is often called a NAD+ precursor because it is part of the series of chemical steps that are required to create NAD+.Different biosynthetic pathways are responsible for converting the different B3 vitamins into NAD+. The enzyme nicotinamide phosphoribosyltransferase (Nampt) catalyzes the rate-limiting step of the two-step pathway converting nicotinamide to NAD+. NR kinase enzymes can also function as a salvage pathway for NAD+, but this pathway is not essential.

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

危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302

化学と産業

応用分野 · 2 件

説明Nicotinamide Riboside (NR) is a next-generation vitamin B3 that has been found to be naturally-occurring in milk in trace amounts. The metabolism of NR is unique from that of other more commonly known forms of vitamin B3 , nicotinamide and nicotinic acid. Specifically, NR has been shown in a pre-clinical study to be the most effective form of vitamin B3 at increasing nicotinamide adenine dinucleotide (NAD+)2 .Nicotinic acid (also known as niacin) and nicotinamide (also known as niacinamide) were discovered in the 1930’s to be the factors that cured pellagra . Niacin is known to cause severe flushing . In 2004, nicotinamide riboside emerged as a newly discovered NAD+ precursor and does not bind to the receptor responsible for flushing.NR has pre-clinically demonstrated that it is superior to both niacin and nicotinamide, both of which are standard forms of vitamin B3 commonly used in vitamin supplements and foods, at boosting NAD+2 . This is due to the fact that NR is not reliant upon a conversion step requiring the enzyme “NAMPT” , see Figure below. The activity level of NAMPT determines the amount of nicotinamide that is converted into NAD+ , which is why this particular step in the process is often referred to as the “rate limiting step”. As normal aging occurs, the activity of NAMPT is thought to decrease. NR can be used by the cell to make NAD+ without this enzymatic step.NAD+ synthesis from nicotinic acid, nicotinamide, and nicotinamide riboside

使用Nicotinamide Riboside can be used in biological study of gene circadian reprogramming transcriptome in liver identified metabolic pathways of aging in mouse. It also increases NAD+ in the cerebral cortex and reduces cognitive deterioration in a transgenic mouse model of Alzheimer’s disease.

上流・下流製品情報

下流製品

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補足説明 · 1 件

定義ChEBI: Nicotinamide riboside is a pyridine nucleoside consisting of nicotinamide with a beta-D-ribofuranosyl moiety at the 1-position. It is a metabolite found in or produced by Saccharomyces cerevisiae. It is an orally available form of vitamin B3 and precursor of nicotinamide adenine dinucleotide (NAD+) with potential use in the treatment of chemotherapy induced peripheral neuropathy (CIPN).

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