Basic information
- CAS
951-78-0- Standard SMILES
O=c1ccn(C2CC(O)C(CO)O2)c(=O)[nH]1- InChIKey
MXHRCPNRJAMMIM-UHFFFAOYSA-N- Molecular formula
- C9H12N2O5
- Average molar mass
- 228.2 g/mol
- Monoisotopic mass
- 228.07462149
Overview
2'-Desoxyuridine has been reported in Acanthaster planci with data available.
Names & identifiers
- Preferred name
- 1-(2-Deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione
- IUPAC
- 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
- English name
- 2'-Deoxyuridine
- Molecular formula
- C9H12N2O5
- Molecular weight
- 228.2
Names & synonyms
DTXSID608624841-(2-Deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dioneRefChem:1053964DTXCID00811239[2'-13C]2'-DEOXYURIDINENSC23615[5',5''-2H2]2'-DEOXYURIDINE[5'-13C]2'-DEOXYURIDINEDesoxyuridine1-(2-deoxypentofuranosyl)-4-hydroxypyrimidin-2(1H)-oneUracil desoxyuridinedU, 2'-dU
Show more names
DUdeoxyuridine1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dioneURACIL DEOXYRIBOSIDE2'-dUdurdUracildeoxyrDeoxy-uridinDEOXYURIDINE-2'
NSC 23615s55051-(2-Deoxy-beta-D-ribofuranosyl)uracilURIDINE, 2-DEOXY-orb1307628SCHEMBL2641582SCHEMBL27146729MXHRCPNRJAMMIM-UHFFFAOYSA-N
Database identifiers
- CAS
951-78-0- PubChem CID
Properties
Computed structural properties
- XLogP
- -1.6
- Topological polar surface area
- 99.1 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 343
Physicochemical properties
- Melting point
- 167 · 167-169 °C(lit.)
- alpha
- 22 · D22 +50° (c = 1.1 in N NaOH)
- Boiling point
- 370.01 °C · 370.01°C (rough estimate)
- Density
- 1.3705 · 1.3705 (rough estimate)
- refractive index
- 52 ° · 52 ° (C=1, 1mol/L NaOH)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
- form
- Powder
- pka
- 9.3 · pKa 9.3(H2O t = 25) (Uncertain)
- color
- White to off-white
- biological source
- synthetic (organic)
- Water Solubility
- 300 g/L · 300 g/L (20 ºC)
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,2910
- BRN
- 24433 · 24433
- InChI
- 1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YU7490000
- hs_code
- 29349990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- hazard_note
- Air Sensitive
- safety_code
- 22-24/25-37/39-36/37/39-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Description2'-Deoxyuridine is a natural deoxynucleoside, which can be directly used to prepare combined deoxynucleoside drugs or used as chemical reagents for biochemical research. At the same time, it can be used as an intermediate to synthesize some antiviral nucleoside drugs and molecular markers, such as 8-bromo-2-deoxyuridine and 8-hydroxy-2-deoxyuridine from 2'-Deoxyuridine.
Description2'-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.
Uses2'-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.
UsesAn uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease
Upstream & downstream products
Downstream products
Related reactions
7 records
Compound notes
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