Summary

Full name5-(isopentenylaminomethyl)-2-thiouridine
IUPAC name1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(3-methylbut-2-enylamino)methyl]-2-sulfanylidenepyrimidin-4-one
Short nameinm5s2U
MODOMICS code2583U
Nature of the modified residueNatural
RNAMods code½
Residue unique ID146
Found in RNAYes
Related nucleotides353

Chemical information

Sum formulaC15H23N3O5S
Type of moietynucleoside
Degeneracynot applicable
SMILESCC(=CCNCc1c(=O)[nH]c(=S)[n]([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)c1)C
logP-0.0359
TPSA151.83
Number of atoms24
Number of Hydrogen Bond Acceptors 1 (HBA1)7
Number of Hydrogen Bond Acceptors 2 (HBA2)8
Number of Hydrogen Bond Donors (HBD)5
PDB no exac match , link to the most similar ligand U8U
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0011610
InChIInChI=1S/C15H23N3O5S/c1-8(2)3-4-16-5-9-6-18(15(24)17-13(9)22)14-12(21)11(20)10(7-19)23-14/h3,6,10-12,14,16,19-21H,4-5,7H2,1-2H3,(H,17,22,24)/t10-,11-,12-,14-/m1/s1
InChIKeyKZNMUKLEOMANLY-HKUMRIAESA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs

* 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
CC(=CCNCc1c(=O)[nH]c(=S)n(C2C(O)C(O)C(CO)O2)c1)C tautomer #0
CC(=CCNCc1c(=O)nc(S)n(C2C(O)C(O)C(CO)O2)c1)C tautomer #1
CC(=CCNCc1c(O)nc(=S)n(C2C(O)C(O)C(CO)O2)c1)C tautomer #2

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
inm5s2U inm5s2U inm5s2U

* 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 mass357.1358
Average mass357.425
[M+H]+358.1436
Product ions226
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.

Comments

5-(isopentenylaminomethyl)uridine and 2-thio-5-(isopentenylaminomethyl)uridine were identified in tRNA of Thermodesulfobacterium commune. Their identities were determined by mass spectrometry and confirmed by chemical synthesis. Data were presented at the tRNA meeting in Banz, Germany (1985) by P.F. Crain, D.R. Phillips, T. Hashizume and F. Widdel. Since then, beside the Banz-meeting abstract, no paper was published about these modified nucleosides.

Reactions producing 5-(isopentenylaminomethyl)-2-thiouridine

Name
nm5s2U:inm5s2U

Last modification of this entry: Sept. 29, 2021


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