Summary

Full nameN4-acetylcytidine
IUPAC nameN-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
Short nameac4C
MODOMICS code42C
Synonyms
3597-45-3
3768-18-1
4-[(1-Hydroxyethylidene)amino]-1-pentofuranosylpyrimidin-2(1H)-one
4-Acetyl-1-(beta-delta-ribofuranosyl)cytosine
4-Acetyl-1-(beta-D-ribofuranosyl)cytosine
4-Acetylcytidine
4-N-acetyl-cytidine
768A181
AC1L326V
AC1Q5JLE
AC-32170
Acetamide, N-(1,2-dihydro-2-oxo-1-beta-D-ribofuranosyl-4-pyrimidinyl)
Acetamide, N-(1,2-dihydro-2-oxo-1-.beta.-D-ribofuranosyl-4-pyrimidinyl)-
acetyl cytosine
Acetylcytidine
AJ-50600
AKOS015896940
AN-20958
AR-1K5740
AS-12329
C11-H15-N3-O6
C11H15N3O6
C22293
CA-237
CHEBI:70989
CID107461
CJ-11922
CS-0030784
CTK1C3669
Cytidine, N-acetyl-
DTXSID40958718
EINECS 223-195-6
HY-W019670
K-8298
MFCD00006540
N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide
N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide
N-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide
N-{1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide
N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-4-yl]acetamide
N4 -Acetylcytidine
n4-acetyl cytidine
N-4-Acetylcytidine
N4-Acetylcytidine
n(4)-acetylcytidine
N4-Acetylcytidine, 97.5% - 1G 1g
N4-Acetylcytidine, >=98%
n4-Acetylcytidine;n-acetylcytidine
n-acetyl-Cytidine
N-Acetylcytidine
NIDVTARKFBZMOT-PEBGCTIMSA-N
NS00014881
Q20890503
RT-001601
SC-09055
SCHEMBL453447
ST2419678
TL8002770
ZINC4321512

Nature of the modified residueNatural
RNAMods codeM
Residue unique ID81
Found in RNAYes
Related nucleotides200
Enzymes NAT10 (Homo sapiens)
Rra1 (Saccharomyces cerevisiae)
TmcA (Escherichia coli)
Found in phylogenyEubacteria, Eukaryota
Found naturally in RNA typesrRNA, tRNA

Chemical information

Sum formulaC11H15N3O6
Type of moietynucleoside
Degeneracynot applicable
SMILESCC(Nc1nc(=O)[n]([C@H]2[C@H](O)[C@H](O)[C@@H](CO)O2)cc1)=O
logP-2.1138
TPSA133.91
Number of atoms20
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)9
Number of Hydrogen Bond Donors (HBD)4
PDB no exac match , link to the most similar ligand 4AC
HMDB (Human Metabolome Database) exact match HMDB0005923
HMDB (Human Metabolome Database) no exac match, link to the most similar ligand HMDB0005923
InChIInChI=1S/C11H15N3O6/c1-5(16)12-7-2-3-14(11(19)13-7)10-9(18)8(17)6(4-15)20-10/h2-3,6,8-10,15,17-18H,4H2,1H3,(H,12,13,16,19)/t6-,8-,9-,10-/m1/s1
InChIKeyNIDVTARKFBZMOT-PEBGCTIMSA-N
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs
3259595
10234296
15047006
24891274
44436504
49832701
75499853
85257106
89744260
103839939
104379012
117570010
126675178
128705906
135063459
135684809
140033841
143178688
152036359
160646142
162174992
162225930
162516973
184819159
204364817
223497276
223559771
223669059
224430192
226773627
249716391
249839719
250214780
251897802
252228349
252316684
252354262
252400619
252411664
252452559
253666544
255437480
257237187
273528943
275918858
310265507
312226908
312595118
315445664
318050073
319138785
319450154
321933960
322082121
329864972
340563856
341251339
341837340
342526826
346699370
347797336
348276786
349017553
350078846
354266649
363671310
373739268
374046241
374171812
375136892
375556673
375668547
375736649
376152865
381013522
381374964
382370911
383452029
384515736
385647742
386484148
387128589
403600999
404623074
404826326
405111379
406168202
406529169
406675444
419541135
433774500
433774889
433775453
433840436
434384512
438515913
439455783
440703668
441087788
441133466
443523017

* 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
CC(N=c1[nH]c(=O)n(C2C(O)C(O)C(CO)O2)cc1)=O tautomer #0
CC(Nc1nc(=O)n(C2C(O)C(O)C(CO)O2)cc1)=O tautomer #1
C=C(N=c1[nH]c(=O)n(C2C(O)C(O)C(CO)O2)cc1)O tautomer #2
C=C(Nc1nc(=O)n(C2C(O)C(O)C(CO)O2)cc1)O tautomer #3
CC(N=c1nc(O)n(C2C(O)C(O)C(CO)O2)cc1)=O tautomer #4
CC(=Nc1nc(=O)n(C2C(O)C(O)C(CO)O2)cc1)O tautomer #5
C=C(N=c1nc(O)n(C2C(O)C(O)C(CO)O2)cc1)O tautomer #6

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
ac4C ac4C ac4C

* 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 mass285.0961
Average mass285.253
[M+H]+286.1039
Product ions154/112
Normalized LC elution time *1,35 (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 -
Absolute and relative quantification of RNA modifications via biosynthetic isotopomers. Kellner S, Ochel A, Thuring K, Spenkuch F, Neumann J, Sharma S, Entian KD, Schneider D, Helm M... Nucleic Acids Res [details] 25129236 -

Chemical groups contained

TypeSubtype
otheracetylamide

Reactions producing N4-acetylcytidine

Name
C:ac4C

Reactions starting from N4-acetylcytidine

Name
ac4C:ac4Cm

Last modification of this entry: Sept. 29, 2021


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