Common NamePseudouridine
DescriptionPseudouridine, also known as psi-uridine or 5-ribosyluracil, belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides, such as phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides. Pseudouridine specifically has its uracil attached via a carbon-carbon instead of a nitrogen-carbon glycosidic bond to the ribofuranose. It is the most prevalent of the over one hundred different modified nucleosides found in RNA (PMID: 17113994 ). Pseudouridine is a solid that is soluble in water. Pseudouridine exists in all living species, ranging from bacteria to humans, and is in all classes of RNA except mRNA. It is formed by enzymes called pseudouridine synthases, which post-transcriptionally isomerize specific uridine residues in RNA.
Structure
Molecular FormulaC9H12N2O6
Average Mass244.20140
Monoisotopic Mass244.06954
IUPAC Name5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
Traditional NamePseudouridine
CAS Registry Number1445-07-4
SMILESO=c1[nH]cc([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)[nH]1
InChI IdentifierInChI=1S/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+/m1/s1
InChI KeyPTJWIQPHWPFNBW-GBNDHIKLSA-N
CHEBI IDCHEBI:17802
HMDB IDHMDB0000767
StateNot Available
Water Solubility6.38e+01 g/l
logP-2.01
logS-0.58
pKa (Strongest Acidic)9.55
pKa (Strongest Basic)-2.98
Hydrogen Acceptor Count6
Hydrogen Donor Count5
Polar Surface Area128.12 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity52.44 m³·mol⁻¹
Polarizability21.81

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