Summary

Full name5,2'-O-dimethylcytidine
IUPAC name4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-5-methylpyrimidin-2-one
Short namem5Cm
MODOMICS code05C
Synonyms
113886-70-7
2'-OME-5-ME-C
2'-O-Methyl-5-methylcytidine
2'-(O-METHYL)-5-METHYLCYTIDINE
2-(O-METHYL)-5-METHYLCYTIDINE
2/'-(O-METHYL)-5-METHYLCYTIDINE
4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-5-methylpyrimidin-2-one
4-amino-1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-5-methylpyrimidin-2(1H)-one
5,2'-O-dimethylcytidine
5-methyl-2'-o-methylcytidine
5-Methyl-2/'-o-methylcytidine
AC-32270
BRD-K51246933-001-01-2
CNVRVGAACYEOQI-FDDDBJFASA-N
CTK8E4105
Cytidine, 5-methyl-2'-O-methyl-
Cytidine,5-methyl-2'-O-methyl-
DTXSID60595381
MFCD04973693
RT-006662
SCHEMBL659090
VZ30458
ZINC43771799

Nature of the modified residueNatural
RNAMods codeτ
Residue unique ID2
Found in RNAYes
Related nucleotides350

Chemical information

Sum formulaC11H17N3O5
Type of moietynucleoside
Degeneracynot applicable
SMILESCO[C@H]1[C@H]([n]2c(=O)nc(N)c(C)c2)O[C@H](CO)[C@H]1O
logP-1.0193
TPSA119.83
Number of atoms19
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 LKC
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0000982
InChIInChI=1S/C11H17N3O5/c1-5-3-14(11(17)13-9(5)12)10-8(18-2)7(16)6(4-15)19-10/h3,6-8,10,15-16H,4H2,1-2H3,(H2,12,13,17)/t6-,7-,8-,10-/m1/s1
InChIKeyCNVRVGAACYEOQI-FDDDBJFASA-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(=N)c(C)c2)OC(CO)C1O tautomer #0
COC1C(n2c(=O)nc(N)c(C)c2)OC(CO)C1O tautomer #1
COC1C(n2c(O)nc(=N)c(C)c2)OC(CO)C1O tautomer #2

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
m5Cm m5Cm m5Cm

* 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 mass271.1168
Average mass271.27
[M+H]+272.1246
Product ions126
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
methyl groupmethyl at aromatic C

Reactions producing 5,2'-O-dimethylcytidine

Name
Cm:m5Cm
m5C:m5Cm

Last modification of this entry: Sept. 29, 2021


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