2'-デオキシウリジン

Deoxyuridine

HCID 13712CAS 951-78-0
部分構造検索類似構造を探す

基本情報

標準SMILES
O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1
InChIKey
MXHRCPNRJAMMIM-SHYZEUOFSA-N
分子式
C9H12N2O5
平均分子量
228.2 g/mol
単同位体質量
228.07462148

概要

2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is functionally related to a uracil.

名称と識別子

優先名称
Deoxyuridine
IUPAC
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
現地名
2'-デオキシウリジン
英語名
2'-Deoxyuridine
分子式
C9H12N2O5
分子量
228.2

名称と別名

2'-DEOXYURIDINE951-78-0deoxyuridineUracil deoxyriboside2-DeoxyuridinedURDDeoxyribose uracil2'-DesoxyuridineUridine, 2'-deoxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione1-(2-deoxy-beta-D-erythro-pentofuranosyl)uracilW78I7AY22C
名称をさらに表示
2'-デオキシウリジンデオキシウリジンデスオキシリボースウラシルウラシルデオキシリボシド5-デメチルチミジン2-デオキシウリジン2′‐デオキシウリジン(+)-2'-デオキシウリジン2'-デオキシウリジン-1'-D2′-デオキシウリジンDU1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione2'-dUNSC 23615UracildeoxyrDeoxy-uridinDEOXYURIDINE-2'
1-(2-Deoxy-beta-D-erythro-pentofuranoxyl)uracilCHEBI:164502,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-DTXSID308836212,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-erythro-ribofuranosyl)-NSC-236151-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidine-2,4-dione

データベース識別子

CAS
951-78-0
PubChem CID
13712
DTXSID
DTXSID30883621
ChEMBL
CHEMBL353955
ChEBI
CHEBI:16450
UNII
W78I7AY22C
EC Number
213-455-7
Nikkaji
J7.186B

物性

構造計算による物性

XLogP
-1.6
極性表面積
99.1 Ų
水素結合供与体数
3
水素結合受容体数
5
回転可能結合数
2
重原子数
16

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure
LogP-1.51
Melting Point167 °C
Physical DescriptionSolid
Collision Cross Section · 4 件

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

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

156.4 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

157.3 Ų [M+Na]+

物理化学的性質

融点
167 · 167-169 °C(lit.)
比旋光度
22 · D22 +50° (c = 1.1 in N NaOH)
沸点
370.01 °C · 370.01°C (rough estimate)
比重(密度)
1.3705 · 1.3705 (rough estimate)
屈折率
52 ° · 52 ° (C=1, 1mol/L NaOH)
貯蔵温度
2 · Inert atmosphere,2-8°C

化学的性質

化学的特性White crystalline powder

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.

Warning

H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 5 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 CategoriesAcute Tox. 4 (40%)

安全データ

F
10-23
wgk
3
tsca
TSCA listed
rtecs
YU7490000
hs_code
29349990
risk_code
36/37/38

化学と産業

薬理情報

MeSH Pharmacological ClassificationDrugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
Tissue LocationsBladder
Cellular LocationsExtracellular
Metabolite PathwaysBeta Ureidopropionase Deficiency

用途と製造

General Manufacturing InformationUridine, 2'-deoxy-: ACTIVE
応用分野 · 3 件

用途核酸関連研究用。

説明2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. It has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. It is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.

使用2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.

上流・下流製品情報

サプライヤー50 社

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
補足説明 · 1 件

定義ChEBI: 2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a uracil.

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