5-メチルウリジン
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
識別子と物理属性
| CAS No. | 1463-10-1 |
|---|---|
| 分子式 | C10H14N2O6 |
| 平均分子量 | 258.23 g/mol |
| 単同位体質量 | 258.08518617 g/mol |
| SMILES | Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O |
| InChIKey | DWRXFEITVBNRMK-JXOAFFINSA-N |
| PubChem CID | 445408 |
| ChEMBL | CHEMBL106175 |
| ChEBI | CHEBI:45996 |
| EC No. | 215-973-9 |
| DTXSID | DTXSID20163348 |
| 現地名 | 5-メチルウリジン |
化学・物理的性質
| XLogP | -1.6 |
|---|---|
| 極性表面積 | 119 |
| 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 |
| 融点 | 183 - 187 °C183-184 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 153.52 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| 密度 | 1.576±0.06 g/cm3(Predicted) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 溶解度 | メタノール（少量、加熱、超音波処理）、水（少量、超音波処理） |
| pKa（酸解離定数） | 9.55±0.10(Predicted) |
| 外観・状態 | 粉 |
| 色 | 白い |
| pH | 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 | 1463-10-1(CAS DataBase Reference) |
化学的特性
White Powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.WarningH315 (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. |
|---|---|
| 規制情報 | Status: Active Update: 09-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/31788 |
| Hazard Classes and Categories | Skin Irrit. 2 (33.3%) |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29349990 |
| 危険文句（R） | 26/27/28 |
| 化審法 | (5)-6843 |
| 危険表示 | T+ |
| 安全措置（S） | 24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
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.