2'-Desoxyuridin

Deoxyuridine

HCID 13712CAS 951-78-0
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Grundinformationen

Standard-SMILES
O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1
InChIKey
MXHRCPNRJAMMIM-SHYZEUOFSA-N
Summenformel
C9H12N2O5
Durchschnittliche Molmasse
228,2 g/mol
Monoisotopische Masse
228,07462148

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Deoxyuridine
IUPAC
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Lokaler Name
2'-Desoxyuridin
Englischer Name
2'-Deoxyuridine
Summenformel
C9H12N2O5
Molmasse
228.2

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1,6
Polarare Oberfläche (TPSA)
99,1 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
2
Schwere Atome
16

Experimentelle und physikochemische Eigenschaften

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

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]+

Physikochemische Eigenschaften

Schmelzpunkt
167 · 167-169 °C(lit.)
Siedepunkt
370.01 °C · 370.01°C (rough estimate)
Dichte
1.3705 · 1.3705 (rough estimate)
Brechungsindex
52 ° · 52 ° (C=1, 1mol/L NaOH)
storage temp.
2 · Inert atmosphere,2-8°C
Löslichkeit
DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (40%)

Sicherheitsdaten

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

Chemie und Industrie

Pharmakologische Informationen

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

Verwendung und Herstellung

General Manufacturing InformationUridine, 2'-deoxy-: ACTIVE
Anwendungen · 2 Einträge

Beschreibung2'-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.

Verwenden2'-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.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

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]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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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