Summary

Full name5-taurinomethyluridine
Short nametm5U
MODOMICS code54U
Nature of the modified residueNatural
RNAMods codeÊ
Residue unique ID21
Found in RNAYes
Related nucleotides404
Found in phylogenyEukaryota
Found naturally in RNA typestRNA

Chemical information

Sum formulaC12H19N3O9S
Type of moietynucleoside
Degeneracynot applicable
SMILESOC[C@H]1O[C@@H]([n]2cc(CNCCS(O)(=O)=O)c(=O)[nH]c2=O)[C@H](O)[C@@H]1O
logP-2.4028
TPSA199.56
Number of atoms25
Number of Hydrogen Bond Acceptors 1 (HBA1)10
Number of Hydrogen Bond Acceptors 2 (HBA2)11
Number of Hydrogen Bond Donors (HBD)6
PDB no exac match , link to the most similar ligand TM2
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0011610
InChIInChI=1S/C12H19N3O9S/c16-5-7-8(17)9(18)11(24-7)15-4-6(10(19)14-12(15)20)3-13-1-2-25(21,22)23/h4,7-9,11,13,16-18H,1-3,5H2,(H,14,19,20)(H,21,22,23)/t7-,8-,9-,11-/m1/s1
InChIKeyVJKJOPUEUOTEBX-TURQNECASA-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(n2cc(CN=CCS(O)(O)=O)c(=O)[nH]c2=O)C(O)C1O tautomer #0
OCC1OC(n2cc(CNCCS(=O)(O)=O)c(=O)[nH]c2=O)C(O)C1O tautomer #1
OCC1OC(n2cc(CNC=CS(O)(O)=O)c(=O)[nH]c2=O)C(O)C1O tautomer #2
OCC1OC(n2cc(CNCC=[SH](O)(O)=O)c(=O)[nH]c2=O)C(O)C1O tautomer #3
OCC1OC(n2cc(CN=CCS(O)(O)=O)c(O)nc2=O)C(O)C1O tautomer #4
OCC1OC(n2cc(CN=CCS(O)(O)=O)c(=O)nc2O)C(O)C1O tautomer #5
OCC1OC(n2cc(CNCCS(=O)(O)=O)c(O)nc2=O)C(O)C1O tautomer #6
OCC1OC(n2cc(CNCCS(=O)(O)=O)c(=O)nc2O)C(O)C1O tautomer #7
OCC1OC(n2cc(CNC=CS(O)(O)=O)c(O)nc2=O)C(O)C1O tautomer #8
OCC1OC(n2cc(CNC=CS(O)(O)=O)c(=O)nc2O)C(O)C1O tautomer #9
OCC1OC(n2cc(CNCC=[SH](O)(O)=O)c(O)nc2=O)C(O)C1O tautomer #10
OCC1OC(n2cc(CNCC=[SH](O)(O)=O)c(=O)nc2O)C(O)C1O tautomer #11

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
tm5U tm5U tm5U

* 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 mass381.0842
Average mass381.359
[M+H]+382.092
Product ions250
Normalized LC elution time * not available
LC elution order/characteristics not available

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

Chemical groups contained

TypeSubtype
methyl groupmethyl at aromatic C
othertauryl

Reactions producing 5-taurinomethyluridine

Name
U:tm5U

Reactions starting from 5-taurinomethyluridine

Name
tm5U:tm5s2U

Last modification of this entry: Sept. 29, 2021


Copyright © Genesilico - All rights reserved
If you have any advice or suggestions for corrections or improvements, please contact: Andrea Cappannini - lp.vog.bcmii@ininnappaca