5-(ヒドロキシメチル)ウラシル

5-(Hydroxymethyl)uracil

HCID 78168CAS 4433-40-3

基本情報

標準SMILES
O=c1[nH]cc(CO)c(=O)[nH]1
InChIKey
JDBGXEHEIRGOBU-UHFFFAOYSA-N
分子式
C5H6N2O3
平均分子量
142.11 g/mol
単同位体質量
142.03784205

概要

5-hydroxymethyluracil is a primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position. It has a role as a human metabolite. It is a primary alcohol and a pyrimidone. It is functionally related to a uracil.

名称と識別子

優先名称
5-(Hydroxymethyl)uracil
IUPAC
5-(hydroxymethyl)-1H-pyrimidine-2,4-dione
現地名
5-(ヒドロキシメチル)ウラシル
英語名
5-Hydroxymethyluracil
分子式
C5H6N2O3
分子量
142.11

名称と別名

5-Hydroxymethyluracil4433-40-35-(Hydroxymethyl)uracil2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)-Uracil, 5-(hydroxymethyl)-5-(Hydroxymethyl)-2,4(1H,3H)-pyrimidinedionehydroxymethyluracil5-(hydroxymethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione590TQ3GL34NSC-20901DTXSID9063455CHEBI:16964
名称をさらに表示
5-ヒドロキシメチル-2,4(1H,3H)-ピリミジンジオン5-(ヒドロキシメチル)-1,2,3,4-テトラヒドロピリミジン-2,4-ジオン5-ヒドロキシメチルウラシル5-(ヒドロキシメチル)ピリミジン-2,4(1H,3H)-ジオン5-(ヒドロキシメチル)ウラシルNSC 20901AURORA KA-5475-methyloluracilα-HydroxythyMinea-Hydroxythymineuracil-5-methanolTIMTEC-BB SBB000084RARECHEM AH CK 0115HYDROXYMETHYL URACIL
RefChem:536253DTXCID8040307224-636-55-(HYDROXYMETHYL)PYRIMIDINE-2,4(1H,3H)-DIONE5-(Hydroxymethyl)pyrimidine-2,4-diol5-Oxymethyluracil5-Hydroxymethyl uracil5-(hydroxymethyl)-1H-pyrimidine-2,4-dione

データベース識別子

CAS
4433-40-3
PubChem CID
78168
DTXSID
DTXSID9063455
ChEMBL
CHEMBL1233360
ChEBI
CHEBI:16964
UNII
590TQ3GL34
EC Number
224-636-5
Nikkaji
J58.058I

物性

構造計算による物性

XLogP
-1.9
極性表面積
78.4 Ų
水素結合供与体数
3
水素結合受容体数
3
回転可能結合数
1
重原子数
10

実験および物理化学的性質

LogP-1.94
Solubility44 mg/mL
Physical DescriptionSolid
Collision Cross Section · 3 件

119.21 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

124.5 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

124.1 Ų [M-H]-

物理化学的性質

融点
300 °C · >300 °C(lit.)
比重(密度)
1.401 · 1.401±0.06 g/cm3(Predicted)
貯蔵温度
Sealed in dry,Room Temperature
溶解性
DMSO(微熱)、メタノール(微熱)、水(微熱)
酸解離定数(Pka)
8.46 · 8.46±0.10(Predicted)
外見
個体

化学的性質

化学的特性White Powder

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H315 (66.7%): 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 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)

安全データ

wgk
3
tsca
TSCA listed
rtecs
YR0513000
hs_code
29335990
hazard_code
Xi
safety_code
22-24/25

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.

Cellular LocationsCytoplasm

用途と製造

General Manufacturing Information2,4(1H,3H)-Pyrimidinedione, 5-(hydroxymethyl)-: INACTIVE
応用分野 · 3 件

解説C5H6N2O3(142.11).5-(ヒドロキシメチル)ウラシルは,ウラシルにホルムアルデヒドを付加させると得られる.分解点260~300 ℃.λmax 261 nm(ε 8×103,pH 7).枯草菌に感染するファージ ψe のDNAでは,チミンのすべてがこの塩基で置換されている.異常に高い浮遊密度(1.742 g cm-3)と低い融解温度(77.5 ℃)の原因物質であるとみられている.森北出版「化学辞典(第2版)

説明5-Hydroxymethyluracil is a product of oxidative damage to DNA, predominantly by hydroxyl radical via the Fenton reaction. It can be used as a potential epigenetic mark enhancing or inhibiting transcription with bacterial RNA polymerase.

使用5-Hydroxymethyluracil (cas# 4433-40-3) is a compound useful in organic synthesis.

サプライヤー50 社

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補足説明

定義ChEBI: 5-hydroxymethyluracil is a primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position. It has a role as a human metabolite. It is a primary alcohol and a pyrimidone. It derives from a uracil.

関連反応

20 件

関連ノート

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