2'-Desoxyuridin
Deoxyuridine
Grundinformationen
- CAS
951-78-0- 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
- 228,07462149
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-DeoxyuridineUridine, 2'-deoxy-dURDDeoxyribose uracil2'-Desoxyuridine1-(2-deoxy-beta-D-erythro-pentofuranosyl)uracil1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione1-(2-Deoxy-beta-D-erythro-pentofuranoxyl)uracil
Weitere Namen anzeigen
DU1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione2'-dUNSC 23615UracildeoxyrDeoxy-uridinDEOXYURIDINE-2'
W78I7AY22CDTXSID308836212,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-beta-D-ribofuranosyl)-CHEBI:164502,4(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-dione(beta 1-(2-Deoxyribopyranosyl))thymidine
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
- Formalladung
- 0
- Komplexität
- 343
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure
LogP
-1.51
-1.51
Melting Point167 °C
Physical DescriptionSolid
Collision Cross Section
156 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
159.45 Ų [M+Na]+ [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)]
150 Ų [M-H]-
Physikochemische Eigenschaften
- Schmelzpunkt
- 167 · 167-169 °C(lit.)
- Siedepunkt
- 370.01 °C · 370.01°C (rough estimate)
- Dichte
- 1.3705 · 1.3705 (rough estimate)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
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
- hazard_code
- Xn
- hazard_note
- Air Sensitive
- safety_code
- 22-24/25-37/39-36/37/39-26
- Speicherklasse
- 11 - Combustible Solids
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
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.
Zugehörige Reaktionen
35
Notizen zur Verbindung
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