Summary

Full name5-(isopentenylaminomethyl)-2'-O-methyluridine
IUPAC name1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-5-[(3-methylbut-2-enylamino)methyl]pyrimidine-2,4-dione
Short nameinm5Um
MODOMICS code0583U
Nature of the modified residueNatural
RNAMods code¼
Residue unique ID145
Found in RNAYes
Related nucleotides352

Chemical information

Sum formulaC16H25N3O6
Type of moietynucleoside
Degeneracynot applicable
SMILESCO[C@H]1[C@H]([n]2c(=O)[nH]c(=O)c(CNCC=C(C)C)c2)O[C@H](CO)[C@H]1O
logP-0.7511
TPSA125.81
Number of atoms25
Number of Hydrogen Bond Acceptors 1 (HBA1)7
Number of Hydrogen Bond Acceptors 2 (HBA2)8
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand 38T
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000884
InChIInChI=1S/C16H25N3O6/c1-9(2)4-5-17-6-10-7-19(16(23)18-14(10)22)15-13(24-3)12(21)11(8-20)25-15/h4,7,11-13,15,17,20-21H,5-6,8H2,1-3H3,(H,18,22,23)/t11-,12-,13-,15-/m1/s1
InChIKeyLUZQNJKKCXNVPW-RGCMKSIDSA-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
COC1C(n2c(=O)[nH]c(=O)c(CNCC=C(C)C)c2)OC(CO)C1O tautomer #0
COC1C(n2c(O)nc(=O)c(CNCC=C(C)C)c2)OC(CO)C1O tautomer #1
COC1C(n2c(=O)nc(O)c(CNCC=C(C)C)c2)OC(CO)C1O tautomer #2

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
inm5Um inm5Um inm5Um

* 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 mass355.1743
Average mass355.386
[M+H]+356.1821
Product ions210
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'-O-methyluridine

Name
inm5U:inm5Um

Last modification of this entry: Sept. 29, 2021


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