Summary

Full namepseudouridine
Short nameY
MODOMICS code9U
Nature of the modified residueNatural
RNAMods codeP
Residue unique ID118
Found in RNAYes
Related nucleotides185
Enzymes Cbf5 (Saccharomyces cerevisiae)
Pus1 (Saccharomyces cerevisiae)
Pus1 (Homo sapiens)
Pus10 (Pyrococcus furiosus)
Pus2 (Saccharomyces cerevisiae)
Pus3 (Saccharomyces cerevisiae)
Pus4 (Saccharomyces cerevisiae)
Pus5 (Saccharomyces cerevisiae)
Pus6 (Saccharomyces cerevisiae)
Pus7 (Saccharomyces cerevisiae)
Pus8 (Saccharomyces cerevisiae)
Pus9 (Saccharomyces cerevisiae)
RluA (Escherichia coli)
RluB (Escherichia coli)
RluB (Bacillus subtilis)
RluC (Escherichia coli)
RluD (Escherichia coli)
RluE (Escherichia coli)
RluF (Escherichia coli)
RsuA (Escherichia coli)
TruA (Escherichia coli)
TruB (Escherichia coli)
TruC (Escherichia coli)
TruD (Escherichia coli)
Found in phylogenyArchaea, Eubacteria, Eukaryota
Found naturally in RNA typesrRNA, snRNA, snoRNA, tRNA

Chemical information

Sum formulaC9H12N2O6
Type of moietynucleoside
Degeneracynot applicable
PubChem ID15047
SMILESOC[C@H]1O[C@@H](c2c[nH]c(=O)[nH]c2=O)[C@H](O)[C@@H]1O
logP-2.7828
TPSA135.64
Number of atoms17
Number of Hydrogen Bond Acceptors 1 (HBA1)6
Number of Hydrogen Bond Acceptors 2 (HBA2)6
Number of Hydrogen Bond Donors (HBD)5
PDB no exac match , link to the most similar ligand FJF
PDB exact match , link to the most similar ligand FJF
HMDB (Human Metabolome Database) exact match HMDB0000767
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000767
InChIInChI=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
InChIKeyPTJWIQPHWPFNBW-GBNDHIKLSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)


Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
OCC1OC(C2C=NC(=O)NC2=O)C(O)C1O tautomer #0
OCC1OC(c2c[nH]c(=O)[nH]c2=O)C(O)C1O tautomer #1
OCC1OC(c2cnc(=O)[nH]c2O)C(O)C1O tautomer #2
OCC1OC(c2cnc(O)nc2O)C(O)C1O tautomer #3
OCC1OC(c2cnc(O)[nH]c2=O)C(O)C1O tautomer #4
OCC1OC(C2C=NC(=O)N=C2O)C(O)C1O tautomer #5
OCC1OC(c2c[nH]c(=O)nc2O)C(O)C1O tautomer #6
OCC1OC(c2cnc(O)nc2O)C(O)C1O tautomer #7
OCC1OC(C2C=NC(O)=NC2=O)C(O)C1O tautomer #8
OCC1OC(c2c[nH]c(O)nc2=O)C(O)C1O tautomer #9
Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
Y Y Y

* CYP Metabolic sites predicted with SMARTCyp. SMARTCyp is a method for prediction of which sites in a molecule that are most liable to metabolism by Cytochrome P450. It has been shown to be applicable to metabolism by the isoforms 1A2, 2A6, 2B6, 2C8, 2C19, 2E1, and 3A4 (CYP3A4), and specific models for the isoform 2C9 (CYP2C9) and isoform 2D6 (CYP2D6). CYP3A4, CYP2D6, and CYP2C9 are the three of the most important enzymes in drug metabolism since they are involved in the metabolism of more than half of the drugs used today. The three top-ranked atoms are highlighted. See: SmartCYP and SmartCYP - background; Patrik Rydberg, David E. Gloriam, Lars Olsen, The SMARTCyp cytochrome P450 metabolism prediction server, Bioinformatics, Volume 26, Issue 23, 1 December 2010, Pages 2988–2989 (link)


LC-MS Information

Monoisotopic mass244.0695
Average mass244.201
[M+H]+245.0773
Product ions209/179/155
Normalized LC elution time *0,34 (Kellner 2014); 0,37 (Kellner 2014)
LC elution order/characteristicsbefore C (Kellner 2014)

* normalized to guanosine (G), measured with a RP C-18 column with acetonitrile/ammonium acetate as mobile phase.


LC-MS Publications

Title Authors Journal Details PubMed Id DOI
Profiling of RNA modifications by multiplexed stable isotope labelling. Kellner S, Neumann J, Rosenkranz D, Lebedeva S, Ketting RF, Zischler H, Schneider D, Helm M. Chem Commun (Camb). [details] 24567952 -
Quantitative analysis of ribonucleoside modifications in tRNA by HPLC-coupled mass spectrometry. Su D, Chan CT, Gu C, Lim KS, Chionh YH, McBee ME, Russell BS, Babu IR, Begley TJ, Dedon PC... Nat Protoc [details] 24625781 -
Absolute and relative quantification of RNA modifications via biosynthetic isotopomers. Kellner S, Ochel A, Thuring K, Spenkuch F, Neumann J, Sharma S, Entian KD, Schneider D, Helm M... Nucleic Acids Res [details] 25129236 -

Comments

It is called pseudouridine because the ring structure is the same as in U, just attached by a different atom.

Chemical groups contained

TypeSubtype
ring modificationpseudouridine

Reactions producing pseudouridine

Name
U:Y

Reactions starting from pseudouridine

Name
Y:m3Y
Y:Ym
Y:m1Y
Y:acp3Y

Last modification of this entry: Oct. 4, 2021


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