Summary

Full nameN4-acetyl-2'-O-methylcytidine
IUPAC nameN-[1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
Short nameac4Cm
MODOMICS code042C
Synonyms
113886-71-8
Ac-2-OMe-C
Ac-2'-OMe-C
Ac-2/'-OMe-C
AC-32177
AKOS015899633
BS-19249
CID 10902616
CID10902616
CTK4A8501
CYDFBLGNJUNSCC-QCNRFFRDSA-N
Cytidine, N-acetyl-2'-O-methyl-
Cytidine,N-acetyl-2'-O-methyl-
DTXSID00447815
HG1334
I14-11183
I14-32546
J-700206
K-1012
MFCD15145149
N-[1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
N-(1-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide
N4 -acetyl-2'-O-methyl cytidine
N4-Acetyl-2'-O-methyl cytidine
N4-Acetyl-2'-O-methylcytidine
N4-ACETYL-2'-O-METHYL-CYTIDINE
N-Acetyl-2'-O-methylcytidine
SCHEMBL3499005
ST24045894
ZINC34556412

Nature of the modified residueNatural
RNAMods code
Residue unique ID106
Found in RNAYes
Related nucleotides257

Chemical information

Sum formulaC12H17N3O6
Type of moietynucleoside
Degeneracynot applicable
SMILESCO[C@H]1[C@H]([n]2c(=O)nc(NC(=O)C)cc2)O[C@H](CO)[C@H]1O
logP-1.4597
TPSA122.91
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)8
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 LHH
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0005923
InChIInChI=1S/C12H17N3O6/c1-6(17)13-8-3-4-15(12(19)14-8)11-10(20-2)9(18)7(5-16)21-11/h3-4,7,9-11,16,18H,5H2,1-2H3,(H,13,14,17,19)/t7-,9-,10-,11-/m1/s1
InChIKeyCYDFBLGNJUNSCC-QCNRFFRDSA-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(=NC(=O)C)cc2)OC(CO)C1O tautomer #0
COC1C(n2c(=O)nc(NC(=O)C)cc2)OC(CO)C1O tautomer #1
COC1C(n2c(=O)[nH]c(=NC(O)=C)cc2)OC(CO)C1O tautomer #2
COC1C(n2c(=O)nc(NC(O)=C)cc2)OC(CO)C1O tautomer #3
COC1C(n2c(O)nc(=NC(=O)C)cc2)OC(CO)C1O tautomer #4
COC1C(n2c(=O)nc(N=C(O)C)cc2)OC(CO)C1O tautomer #5
COC1C(n2c(O)nc(=NC(O)=C)cc2)OC(CO)C1O tautomer #6

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
ac4Cm ac4Cm ac4Cm

* 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 mass299.1117
Average mass299.28
[M+H]+300.1195
Product ions154/112
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
otheracetylamide

Reactions producing N4-acetyl-2'-O-methylcytidine

Name
Cm:ac4Cm
ac4C:ac4Cm

Last modification of this entry: Sept. 29, 2021


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