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5-Hydroxymethyl xylouridine

CAT: 0804-HY-152496Size: 1 EachDry Ice: NoHazardous: No
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Description
5-Hydroxymethyl xylouridine is a thymidine analog. Analogs of this series have insertional activity towards replicated DNA. They can be used to label cells and track DNA synthesis[1].
CAS Number
52448-09-6
UNSPSC
12352005
Target
Nucleoside Antimetabolite/Analog
Type
Oligonucleotides
Related Pathways
Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/5-hydroxymethyl-xylouridine.html
Solubility
10 mM in DMSO
Smiles
OC[C@@H]1[C@H](O)[C@@H](O)[C@H](N(C(N2)=O)C=C(CO)C2=O)O1
Molecular Formula
C10H14N2O7
Molecular Weight
274.23
References & Citations
[1]Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18 (23) :3373-88.|[2]Cavanagh BL, et al. Thymidine analogues for tracking DNA synthesis. Molecules. 2011 Sep 15;16 (9) :7980-93.
Shipping Conditions
Room temperature
Scientific Category
Oligonucleotides
Clinical Information
No Development Reported

Chemical Information

5-Hydroxymethyl xylouridine
CAS Number52448-09-6
PubChem CID13052735
IUPAC Name1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)pyrimidine-2,4-dione
Molecular FormulaC10H14N2O7
Molecular Weight274.23
XLogP-2.3
Topological Polar Surface Area140
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Heavy Atom Count19
Formal Charge0
Complexity424
SMILES
C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@H]([C@H](O2)CO)O)O)CO
InChI
InChI=1S/C10H14N2O7/c13-2-4-1-12(10(18)11-8(4)17)9-7(16)6(15)5(3-14)19-9/h1,5-7,9,13-16H,2-3H2,(H,11,17,18)/t5-,6+,7-,9-/m1/s1
InChIKey
VQAJJNQKTRZJIQ-JVZYCSMKSA-N
Chemical Structure
2D Structure
2D structure of 5-Hydroxymethyl xylouridine
CAS: 52448-09-6
CID: 13052735
Formula: C10H14N2O7
MW: 274.23
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight274.23
XLogP3-2.3
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass274.08010079
Monoisotopic Mass274.08010079
Topological Polar Surface Area140 Ų
Heavy Atom Count19
Formal Charge0
Complexity424
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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