Structure via PubChem · Public domain (PubChem)
pseudouridine
Sign in to saveAlso known as Psi-uridine, (1S)-1,4-anhydro-1-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-D-ribitol, p, 5-(beta-D-ribofuranosyl)uracil, beta-Pseudouridine, beta-delta-Pseudouridine, Pseudouridine C, b-Pseudouridine
Pseudouridine (5-ribosyluracil, abbreviated by the Greek letter psi- Ψ) is an isomer of the nucleoside uridine in which the uracil is attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond.
Chemical data
- Formula
- C9H12N2O6
- Molecular weight
- 244.2 g/mol
- IUPAC name
- 5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidine-2,4-dione
- SMILES
- C1=C(C(=O)NC(=O)N1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
- InChIKey
- PTJWIQPHWPFNBW-GBNDHIKLSA-N
- XLogP
- -2.8
- Polar surface area
- 128 Ų
- H-bond donors
- 5
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,046 papers- Incorporation of pseudouridine into mRNA yields superior nonimmunogenic vector with increased translational capacity and biological stability.Molecular therapy : the journal of the American Society of Gene Therapy · 2008
- RNA pseudouridine modification in plants.Journal of experimental botany · 2023
- Pseudouridine as a novel biomarker in prostate cancer.Urologic oncology · 2021
- Incorporation of pseudouridine into mRNA enhances translation by diminishing PKR activation.Nucleic acids research · 2010
- Pseudouridine Synthase 7 in Cancer: Functions, Mechanisms, and Therapeutic Potential.Cells · 2025
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 244.069536
Show 5 more facts
- subject has role
- primary metabolite
- chemical formula
- C₉H₁₂N₂O₆
- canonical SMILES
- C1=C(C(=O)NC(=O)N1)C2C(C(C(O2)CO)O)O
- isomeric SMILES
- C1=C(C(=O)NC(=O)N1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
- Commons category
- Pseudouridine
via Wikidata · CC0
~13 min read
Encyclopedic overview
15 sectionsContents
- Effects and modification on different RNA
- tRNA
- mRNA
- rRNA
- snRNA
- Synthases
- TruA
- TruB
- TruD
- RluA
- Techniques in genome sequencing for pseudouridine
- Medical relevance
- Vaccines
- See also
- References
Pseudouridine (5-ribosyluracil, abbreviated by the Greek letter psi- Ψ) is an isomer of the nucleoside uridine in which the uracil is attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond.
Pseudouridine is the most abundant RNA modification in cellular RNA and one of over 100 chemically distinct modifications that may affect translation or other functions of RNA. Pseudouridine is the C5-glycoside isomer of uridine that contains a C-C bond between C1 of the ribose sugar and C5 of uracil, rather than usual C1-N1 bond found in uridine. Uridine is converted to pseudouridine by rotating the uridine molecule 180° across its N3-C6 axis. The C-C bond gives it more rotational freedom and conformational flexibility. In addition, pseudouridine has an extra hydrogen bond donor at the N1 position.
Excerpted from Wikipedia’s “pseudouridine” article, available under the CC BY-SA 4.0 licence.