beta-Pseudouridine
Basic information
- CAS
1445-07-4- Standard SMILES
O=c1[nH]cc(C2OC(CO)C(O)C2O)c(=O)[nH]1- InChIKey
PTJWIQPHWPFNBW-UHFFFAOYSA-N- Molecular formula
- C9H12N2O6
- Average molar mass
- 244.2 g/mol
- Monoisotopic mass
- 244.06953611
Overview
Beta-pseudouridine is a metabolite found in or produced by Saccharomyces cerevisiae.
Names & identifiers
- Preferred name
- beta-Pseudouridine
- IUPAC
- 5-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidine-2,4-dione
- English name
- Pseudouridine
- Molecular formula
- C9H12N2O6
- Molecular weight
- 244.2
Names & synonyms
.psi.-Uridine.beta.-Pseudouridinebeta-Pseudouridine.beta.-D-PseudouridinePseudouridine CUracil, 5-.beta.-D-ribofuranosyl-b-PseudouridinePSEUDOURIDINE NATURAL B ISOMER*FROM WHEAT BRANNSC162405NSC 1624055-beta-D-Ribofuranosyl-2,4(1H,3H)-PyrimidinedioneSCHEMBL1755664
Show more names
PSEUDOURIDINEPseudo-UTPβ-Pseudouridine5-((2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione5-Ribosyluracily-UridinePseudoruidinePseudourindinePseudouricdine
SCHEMBL6674859PTJWIQPHWPFNBW-UHFFFAOYSA-NAKOS0302415232,3H)-Pyrimidinedione, 5-.beta.-D-ribofuranosyl-5-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione
Database identifiers
- CAS
1445-07-4- PubChem CID
- 294335
Properties
Computed structural properties
- XLogP
- -2.8
- Topological polar surface area
- 128 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 382
Physicochemical properties
- Melting point
- 222 °C · 222 °C
- Density
- 1.641 · 1.641±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Methanol (Very Slightly, Heated), Water (Slightly, Sonicated, Heated)
- pka
- 8.52 · 8.52±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- PH
- 9 · ~9.0
- biological source
- synthetic (chemical)
- Water Solubility
- water: soluble
- λmax
- 264 nm · 264nm(MeOH)(lit.)
- InChI
- InChI=1/C9H12N2O6/c12-2-4-5(13)6(14)7(17-4)3-1-10-9(16)11-8(3)15/h1,4-7,12-14H,2H2,(H2,10,11,15,16)/t4-,5-,6-,7+/s3
- InChIKey
- PTJWIQPHWPFNBW-IZFRNLNUNA-N
- SMILES
- O[C@@H]1[C@@H]([C@@H](CO)O[C@H]1C1=CNC(=O)NC1=O)O |&1:1,2,3,7,r|
- FDA UNII
- 7 R0R6H6KEG · 7R0R6H6KEG
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
- wgk
- WGK 3
- hs_code
- 2934.99.9001
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Descriptionβ-Pseudouridine is the C-5 glycoside isomer of the nucleoside uridine. It is formed when uridine in RNA undergoes site-specific isomerization by a pseudouridine synthase enzyme. Pseudouridine is found in tRNAs from bacteria, archaea, and eukaryotes. In vitro, it reduces the number of X-ray-induced chromosomal aberrations in human lymphocytes isolated from whole blood in a dose-dependent manner.
UsesAn isomer of the nucleoside uridine found in all species and in many classes of RNA except mRNA. It is formed by enzymes called Ψ synthases, which post-transcriptionally isomerize specific uridine residues in RNA in a process termed pseudouridylation. Studies suggest that β-Pseudouridine reduces radiation-induced chromosome aberrations in human lymphocytes.
Upstream & downstream products
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