5-メチルウリジン

5-Methyluridine

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基本情報

CAS: 1463-10-1
標準SMILES: Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
InChIKey: DWRXFEITVBNRMK-JXOAFFINSA-N
分子式: C10H14N2O6
平均分子量: 258.23 g/mol
単同位体質量: 258.08518617

概要

Ribothymidine is a methyluridine having a single methyl substituent at the 5-position on the uracil ring. It has a role as an antigen, an Escherichia coli metabolite and a human metabolite.

名称と識別子

優先名称: 5-Methyluridine
IUPAC: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
現地名: 5-メチルウリジン
英語名: 5-Methyluridine
分子式: C10H14N2O6
分子量: 258.23

名称と別名

5-Methyluridine1463-10-1RibothymidineThymine ribosideRibosylthymineribosylthymidine1-(beta-D-ribofuranosyl)thymineCHEBI:45996ZS1409014ADTXSID201633481-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

名称をさらに表示

5-メチルウリジンチミンリボクラノシド5-メチル-1-β-D-リボフラノシル-1,2,3,4-テトラヒドロピリミジン-2,4-ジオン1-β-D-リボフラノシルチミンリボチミジンチミンリボヌクレオシド2'α-ヒドロキシチミジン1-(β-D-リボフラノシル)チミン5-メチル-1-(β-D-リボフラノシル)ピリミジン-2,4(1H,3H)-ジオンリボシルチミンチミンリボシド5-メチルウリジン, 結晶1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dione5-Me-U5-Me-UrMethyluridine5-methyuridine5-methyl-uridinTHYMINERIBOSIDE

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-5-methylpyrimidine-2,4-dioneRefChem:898086DTXCID9085839215-973-9Uridine, 5-methyl-5-Methyl UridineThymine ribofuranoside

物性

構造計算による物性補完中

XLogP: -1.6
極性表面積: 119 Å²
水素結合供与体数: 4
水素結合受容体数: 6
回転可能結合数: 2
重原子数: 18
形式電荷: 0
複雑度: 409

実験および物理化学的性質

Melting Point183 - 187 °C

Physical DescriptionSolid

Collision Cross Section153.52 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

物理化学的性質

融点: 183 · 183-184 °C(lit.)
比重(密度): 1.576 · 1.576±0.06 g/cm3(Predicted)
貯蔵温度: Keep in dark place,Sealed in dry,Room Temperature
溶解性: メタノール（少量、加熱、超音波処理）、水（少量、超音波処理）
酸解離定数(Pka): 9.55 · 9.55±0.10(Predicted)
外見: 粉
色: 白い
PH: 9.7 · 9.7
InChI: InChI=1S/C10H14N2O6/c1-4-2-12(10(17)11-8(4)16)9-7(15)6(14)5(3-13)18-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,17)/t5-,6-,7-,9-/m1/s1
InChIKey: DWRXFEITVBNRMK-JXOAFFINSA-N
SMILES: OC[C@H]1O[C@@H](N2C=C(C)C(=O)NC2=O)[C@H](O)[C@@H]1O
CAS データベース

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。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.

Warning

H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationStatus: Active Update: 09-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/31788

Hazard Classes and CategoriesSkin Irrit. 2 (33.3%)

安全データ

wgk: 3
hs_code: 29349990
risk_code: 26/27/28
化審法: (5)-6843
hazard_code: T+
safety_code: 24/25
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Tissue LocationsPlacenta

Cellular LocationsCytoplasm

応用分野 · 4 件

解説1-β-D-ribofuranosylthimine．C10H14N2O6(258.23)．5-メチルウリジンは，大腸菌tRNAをはじめ，多くのtRNA中に存在する修飾ヌクレオシドの一種．トリメチルシリルチミンとO-ベンゾイル-D-リボフラノシルクロリドとを縮合させたのち，保護基をはずすと得られる．白色の粉末．融点184～185 ℃．[α]17D－10.0°(水)．水に可溶．λmax 267 nm(ε 9800，pH 7)．森北出版「化学辞典（第2版）

用途有機合成原料。

説明5-Methyluridine is a pyrimidine nucleoside and methylated form of uridine. It is the ribonucleoside counterpart to the deoxyribonucleoside thymidine, which lacks a hydroxyl group at the 2' position. 5-Methyluridine contains a thymine base joined to a ribose pentose sugar. It is an endogenous methylated nucleoside found in human fluids. In cells, 5-methyluridine is present in tRNA, formed during its post-transcriptional modification by the methylation of uridine.

使用A primary degradation product of tRNA, an urinary nucleoside as biological marker for patients with colorectal cancer.It enhances the antitumor activity of 5-fluorouracil in a mouse Erlich solid carcinoma model and a P388 murine leukemia model. It has been used to characterize the activity of a variety of enzymes, including uridine nucleosidase.

上流・下流製品情報

上流原料

化合物ノート

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基本情報

CAS: 1463-10-1
標準SMILES: Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O
InChIKey: DWRXFEITVBNRMK-JXOAFFINSA-N
分子式: C10H14N2O6
平均分子量: 258.23 g/mol
単同位体質量: 258.08518617

概要

Ribothymidine is a methyluridine having a single methyl substituent at the 5-position on the uracil ring. It has a role as an antigen, an Escherichia coli metabolite and a human metabolite.