Summary

Full name1-methylinosine
IUPAC name9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpurin-6-one
Short namem1I
MODOMICS code19A
Synonyms
1-methyl-inosine
1-Methylinosine
2140-73-0
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methyl-6,9-dihydro-1H-purin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1-methylpurin-6-one
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1-methyl-1,9-dihydro-6H-purin-6-one
AC1L22KY
C6JR3HAB96
CHEBI:19065
CID65095
CS-0061842
DTXSID90175670
HY-113139
inosine, 1-methyl
Inosine, 1-methyl-
Inosine,1-methyl-
m(1)i
N1-Methylinosine
Q27109107
SCHEMBL19359092
UNII-C6JR3HAB96
WJNGQIYEQLPJMN-IOSLPCCCSA-N

Nature of the modified residueNatural
RNAMods codeO
Residue unique ID26
Found in RNAYes
Related nucleotides344
Enzymes Trm5 (Saccharomyces cerevisiae)
Found in phylogenyEukaryota
Found naturally in RNA typestRNA

Chemical information

Sum formulaC11H14N4O5
Type of moietynucleoside
Degeneracynot applicable
PubChem ID65095
SMILESC[n]1c(=O)c2c([n]([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)cn2)nc1
logP-2.2585
TPSA122.63
Number of atoms20
Number of Hydrogen Bond Acceptors 1 (HBA1)7
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)3
PDB no exac match , link to the most similar ligand NOS
HMDB (Human Metabolome Database) exact match HMDB0002721
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0002721
InChIInChI=1S/C11H14N4O5/c1-14-3-13-9-6(10(14)19)12-4-15(9)11-8(18)7(17)5(2-16)20-11/h3-5,7-8,11,16-18H,2H2,1H3/t5-,7-,8-,11-/m1/s1
InChIKeyWJNGQIYEQLPJMN-IOSLPCCCSA-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


Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m1I m1I m1I

* 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 mass282.0964
Average mass282.253
[M+H]+283.1042
Product ions151
Normalized LC elution time *1,24 (Kellner 2014)
LC elution order/characteristicsbetween G and A (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 -

Chemical groups contained

TypeSubtype
methyl groupmethyl at aromatic N
otherketo

Reactions producing 1-methylinosine

Name
I:m1I
m1A:m1I

Reactions starting from 1-methylinosine

Name
m1I:m1Im

Last modification of this entry: Sept. 29, 2021


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