Basic information
- CAS
1445-07-4- Standard SMILES
O=c1[nH]cc([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1- InChIKey
PTJWIQPHWPFNBW-GBNDHIKLSA-N- Molecular formula
- C9H12N2O6
- Average molar mass
- 244.2 g/mol
- Monoisotopic mass
- 244.06953611
Overview
Pseudouridine is a C-glycosyl pyrimidine that consists of uracil having a beta-D-ribofuranosyl residue attached at position 5. The C-glycosyl isomer of the nucleoside uridine. It has a role as a fundamental metabolite.
Names & identifiers
- Preferred name
- Pseudouridine
- IUPAC
- 5-[(2S,3R,4S,5R)-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
PSEUDOURIDINE1445-07-4psi-Uridine5-(beta-D-Ribofuranosyl)uracil7R0R6H6KEG2,4(1H,3H)-Pyrimidinedione, 5-beta-D-ribofuranosyl-CHEBI:178025-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidine-2,4-dioneNSC-1624055-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione5-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1H-pyrimidine-2,4-dione5-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
Show more names
Pseudo-UTPβ-Pseudouridiney-UridineNSC 162405PseudoruidinePseudourindinePseudouricdine
RefChem:177010978-484-6beta-Pseudouridine5-Ribosyluracilbeta-D-Pseudouridine5-((2S,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dionePseudouridine CPseudouridin
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
Experimental & physicochemical properties
Physical DescriptionSolid
Collision Cross Section
150.77 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
159 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
150.3 Ų [M-H]-
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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
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
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
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
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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