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2′-O-Methyluridine

CAT: 0804-HY-W011824-01Size: 1 gDry Ice: NoHazardous: No
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CAT#:0804-HY-W011824-01Size:1 g
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Description
2’-O-Methyluridine is a modified nucleoside that can be found in T. thermophile tRNA. 2’-O-Methyluridine can be incorporated into siRNA targeting the gene encoding apolipoprotein B, which decreases ApoB protein levels in HepG2 and prevents IFN-α production in isolated human PBMCs. 2’-O-Methyluridine level in serum is decreased in patients with breast cancer[1][2][3].
CAS Number
2140-76-3
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apolipoprotein; Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Field of Research
Cancer; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/2-o-methyluridine.html
Purity
99.91
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O[C@H]1[C@@H](OC)[C@H](N2C(NC(C=C2)=O)=O)O[C@@H]1CO
Molecular Formula
C10H14N2O6
Molecular Weight
258.23
Precautions
H302, H315, H319, H335
References & Citations
[1]Aučynaitė A, et al. Identification of a 2'-O-Methyluridine Nucleoside Hydrolase Using the Metagenomic Libraries. Molecules. 2018;23 (11) :2904. Published 2018 Nov 7.|[2]Kuchino, Y., et al., (1985) . Tetrahymena thermophila glutamine tRNA and its gene that corresponds to UAA termination codon. Proceedings of the National Academy of Sciences of the United States of America, 82 (14), 4758–4762.|[3]Judge, A. D., et al., (2006) . Design of noninflammatory synthetic siRNA mediating potent gene silencing in vivo. Molecular therapy : the journal of the American Society of Gene Therapy, 13 (3), 494–505.|[4]Fang, Z., et al., (2021) . Mass Spectrometry-Based Targeted Serum Monomethylated Ribonucleosides Profiling for Early Detection of Breast Cancer. Frontiers in molecular biosciences, 8, 741603.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

2'-O-Methyluridine

2'-O-methyluridine is a methyluridine that consists of uridine bearing a single methyl substituent located at position O-2' on the ribose ring.

CAS Number2140-76-3
PubChem CID102212
IUPAC Name1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidine-2,4-dione
Molecular FormulaC10H14N2O6
Molecular Weight258.23
XLogP-1.4
Topological Polar Surface Area108
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Heavy Atom Count18
Formal Charge0
Complexity385
SMILES
CO[C@@H]1[C@@H]([C@H](O[C@H]1N2C=CC(=O)NC2=O)CO)O
InChI
InChI=1S/C10H14N2O6/c1-17-8-7(15)5(4-13)18-9(8)12-3-2-6(14)11-10(12)16/h2-3,5,7-9,13,15H,4H2,1H3,(H,11,14,16)/t5-,7-,8-,9-/m1/s1
InChIKey
SXUXMRMBWZCMEN-ZOQUXTDFSA-N
Chemical Structure
2D Structure
2D structure of 2'-O-Methyluridine
CAS: 2140-76-3
CID: 102212
Formula: C10H14N2O6
MW: 258.23
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight258.23
XLogP3-1.4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass258.08518617
Monoisotopic Mass258.08518617
Topological Polar Surface Area108 Ų
Heavy Atom Count18
Formal Charge0
Complexity385
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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CatalogName
B8927-2502′-O-Methyluridine
296247-012'-O-Methyluridine
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TNU0374-01N3-Methyl-2'-O-methyluridine
TNU0648-015-Bromo-2'-O-methyluridine
F5923005-Fluoro-2’-O-methyluridine
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