Summary

Full name2'-O-methylinosine
IUPAC name9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-1H-purin-6-one
Short nameIm
MODOMICS code09A
Synonyms
2-Chloro-6-fluorobenzotrichloride
2'-O-METHYL-D-INOSINE
2?O-Methylinosine
2'-(o-Methyl)-inosine
2'-O-methylinosine
2'-O-Methyl-inosine
2-(O-METHYL)-INOSINE
3881-21-8
3'-O-Methyl-Inosine
881M218
9-[(2R,3R,4R,5R)-4-HYDROXY-5-(HYDROXYMETHYL)-3-METHOXYOXOLAN-2-YL]-1H-PURIN-6-ONE
9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one
9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-tetrahydrofuran-2-yl]-3H-purin-6-one
9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-9H-purin-6-ol
9-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-oxolan-2-yl]-3H-purin-6-one
AC-8215
AKOS025402340
AN-8215
CHEBI:68467
CID10062287
CTK8F4496
DTXSID00435030
HPHXOIULGYVAKW-IOSLPCCCSA-N
J-700080
MFCD01631008
NS00014739
Q15632692
SCHEMBL658713
VZ21766
ZINC34149906

Nature of the modified residueNatural
RNAMods code
Residue unique ID128
Found in RNAYes
Related nucleotides367

Chemical information

Sum formulaC11H14N4O5
Type of moietynucleoside
Degeneracynot applicable
SMILESCO[C@H]1[C@H]([n]2cnc3c2nc[nH]c3=O)O[C@H](CO)[C@H]1O
logP-1.6148
TPSA122.49
Number of atoms20
Number of Hydrogen Bond Acceptors 1 (HBA1)7
Number of Hydrogen Bond Acceptors 2 (HBA2)8
Number of Hydrogen Bond Donors (HBD)3
PDB no exac match , link to the most similar ligand NOS
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000195
InChIInChI=1S/C11H14N4O5/c1-19-8-7(17)5(2-16)20-11(8)15-4-14-6-9(15)12-3-13-10(6)18/h3-5,7-8,11,16-17H,2H2,1H3,(H,12,13,18)/t5-,7-,8-,11-/m1/s1
InChIKeyHPHXOIULGYVAKW-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

Tautomers

Tautomers SMILES
COC1C(n2cnc3c2ncnc3O)OC(CO)C1O tautomer #0
COC1C(n2cnc3c2[nH]cnc3=O)OC(CO)C1O tautomer #1
COC1C(n2cnc3c2nc[nH]c3=O)OC(CO)C1O tautomer #2
COC1C(n2cnc3c2ncnc3O)OC(CO)C1O tautomer #3
COC1C(N2C=NC3C2=NC=NC3=O)OC(CO)C1O tautomer #4

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
Im Im Im

* 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 ions137
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 O2
otherketo

Reactions producing 2'-O-methylinosine

Name
I:Im
Am:Im

Reactions starting from 2'-O-methylinosine

Name
Im:m1Im

Last modification of this entry: Sept. 29, 2021


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