N4-Acetylcytidine
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MedKoo CAT#: 112006

CAS#: 3768-18-1

Description: N4-Acetylcytidine is a catabolite of cytidine. It activates BV-2 microglia when used at a concentration of 0.3 mM, an effect that can be blocked by the adenosine A2A receptor antagonist SCH 58261. It also increases protein levels of the NOD-like receptor protein 3 (NLRP3) inflammasome, an effect that can be blocked by high mobility group box 1 (HMGB1) siRNA in BV-2 microglia. Urine levels of N4-acetylcytidine are increased in mice with tumors induced by 3-methylcholanthrene. N4-Acetylcytidine is also found as a post-transcriptional modification in RNA.


Chemical Structure

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N4-Acetylcytidine
CAS# 3768-18-1

Theoretical Analysis

MedKoo Cat#: 112006
Name: N4-Acetylcytidine
CAS#: 3768-18-1
Chemical Formula: C11H15N3O6
Exact Mass: 285.10
Molecular Weight: 285.260
Elemental Analysis: C, 46.32; H, 5.30; N, 14.73; O, 33.65

Price and Availability

Size Price Availability Quantity
1g USD 240 2 Weeks
5g USD 500 2 Weeks
10g USD 740 2 Weeks
25g USD 1110 2 Weeks
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Synonym: ac4C; N4-Acetylcytidine; N4Acetylcytidine; N4 Acetylcytidine

IUPAC/Chemical Name: N-(1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide

InChi Key: NIDVTARKFBZMOT-PEBGCTIMSA-N

InChi Code: InChI=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

SMILES Code: O[C@H]1[C@@]([H])(O[C@@H]([C@H]1O)CO)N2C(N=C(NC(C)=O)C=C2)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 1.0 3.51
PBS (pH:7.2) 2.0 7.01

Preparing Stock Solutions

The following data is based on the product molecular weight 285.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bortolin-Cavaillé ML, Aurélie Q, Supuni TG, Thomas JM, Sas-Chen A, Sharma S, Plisson-Chastang C, Vandel L, Blader P, Lafontaine DLJ, Schwartz S, Meier JL, Cavaillé J. Probing small ribosomal subunit RNA helix 45 acetylation across eukaryotic evolution. Nucleic Acids Res. 2022 Jun 1:gkac404. doi: 10.1093/nar/gkac404. Epub ahead of print. PMID: 35648437.


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3: Wang G, Zhang M, Zhang Y, Xie Y, Zou J, Zhong J, Zheng Z, Zhou X, Zheng Y, Chen B, Liu C. NAT10-mediated mRNA N4-acetylcytidine modification promotes bladder cancer progression. Clin Transl Med. 2022 May;12(5):e738. doi: 10.1002/ctm2.738. PMID: 35522942; PMCID: PMC9076013.


4: Liu S, Zhang Y, Qiu L, Zhang S, Meng Y, Huang C, Chen Z, Zhang B, Han J. Uncovering N4-Acetylcytidine-Related mRNA Modification Pattern and Landscape of Stemness and Immunity in Hepatocellular Carcinoma. Front Cell Dev Biol. 2022 Apr 14;10:861000. doi: 10.3389/fcell.2022.861000. PMID: 35493106; PMCID: PMC9046676.


5: Geng Z, Liu P, Yuan L, Zhang K, Lin J, Nie X, Jiang H, Li B, Liu T, Zhang B. Electroacupuncture attenuates ac4C modification of P16 mRNA in the ovarian granulosa cells of a mouse model premature ovarian failure. Acupunct Med. 2022 Apr 27:9645284221085284. doi: 10.1177/09645284221085284. Epub ahead of print. PMID: 35475376.


6: Broly M, Polevoda BV, Awayda KM, Tong N, Lentini J, Besnard T, Deb W, O'Rourke D, Baptista J, Ellard S, Almannai M, Hashem M, Abdulwahab F, Shamseldin H, Al-Tala S, Alkuraya FS, Leon A, van Loon RLE, Ferlini A, Sanchini M, Bigoni S, Ciorba A, van Bokhoven H, Iqbal Z, Al-Maawali A, Al-Murshedi F, Ganesh A, Al- Mamari W, Lim SC, Pais LS, Brown N, Riazuddin S, Bézieau S, Fu D, Isidor B, Cogné B, O'Connell MR. THUMPD1 bi-allelic variants cause loss of tRNA acetylation and a syndromic neurodevelopmental disorder. Am J Hum Genet. 2022 Apr 7;109(4):587-600. doi: 10.1016/j.ajhg.2022.02.001. Epub 2022 Feb 22. PMID: 35196516; PMCID: PMC9069073.


7: Li N, Rana TM. Regulation of antiviral innate immunity by chemical modification of viral RNA. Wiley Interdiscip Rev RNA. 2022 Feb 12:e1720. doi: 10.1002/wrna.1720. Epub ahead of print. PMID: 35150188.


8: Wang K, Zhou LY, Liu F, Lin L, Ju J, Tian PC, Liu CY, Li XM, Chen XZ, Wang T, Wang F, Wang SC, Zhang J, Zhang YH, Tian JW, Wang K. PIWI-Interacting RNA HAAPIR Regulates Cardiomyocyte Death After Myocardial Infarction by Promoting NAT10-Mediated ac4 C Acetylation of Tfec mRNA. Adv Sci (Weinh). 2022 Mar;9(8):e2106058. doi: 10.1002/advs.202106058. Epub 2022 Feb 9. PMID: 35138696; PMCID: PMC8922123.


9: Zhang G, Luo W, Lyu J, Yu ZG, Huang G. CNNLSTMac4CPred: A Hybrid Model for N4-Acetylcytidine Prediction. Interdiscip Sci. 2022 Jun;14(2):439-451. doi: 10.1007/s12539-021-00500-0. Epub 2022 Feb 1. PMID: 35106702.


10: Li K, Liu J, Yang X, Tu Z, Huang K, Zhu X. Pan-cancer analysis of N4-acetylcytidine adaptor THUMPD1 as a predictor for prognosis and immunotherapy. Biosci Rep. 2021 Dec 22;41(12):BSR20212300. doi: 10.1042/BSR20212300. PMID: 34762107; PMCID: PMC8655504.


11: Yang W, Li HY, Wu YF, Mi RJ, Liu WZ, Shen X, Lu YX, Jiang YH, Ma MJ, Shen HY. ac4C acetylation of RUNX2 catalyzed by NAT10 spurs osteogenesis of BMSCs and prevents ovariectomy-induced bone loss. Mol Ther Nucleic Acids. 2021 Jul 2;26:135-147. doi: 10.1016/j.omtn.2021.06.022. PMID: 34513300; PMCID: PMC8413676.


12: Wang C, Ju Y, Zou Q, Lin C. DeepAc4C: A convolutional neural network model with hybrid features composed of physicochemical patterns and distributed representation information for identification of N4-acetylcytidine in mRNA. Bioinformatics. 2021 Aug 24:btab611. doi: 10.1093/bioinformatics/btab611. Epub ahead of print. PMID: 34427581.


13: Xiang Y, Zhou C, Zeng Y, Guo Q, Huang J, Wu T, Liu J, Liang Q, Zeng H, Liang X. NAT10-Mediated N4-Acetylcytidine of RNA Contributes to Post-transcriptional Regulation of Mouse Oocyte Maturation in vitro. Front Cell Dev Biol. 2021 Jul 30;9:704341. doi: 10.3389/fcell.2021.704341. PMID: 34395433; PMCID: PMC8363255.


14: Shrimp JH, Jing Y, Gamage ST, Nelson KM, Han J, Bryson KM, Montgomery DC, Thomas JM, Nance KD, Sharma S, Fox SD, Andressen T, Sinclair WR, Wu H, Allali- Hassani A, Senisterra G, Vedadi M, Lafontaine D, Dahlin JL, Marmorstein R, Walters MA, Meier JL. Remodelin Is a Cryptic Assay Interference Chemotype That Does Not Inhibit NAT10-Dependent Cytidine Acetylation. ACS Med Chem Lett. 2020 Jul 27;12(6):887-892. doi: 10.1021/acsmedchemlett.0c00193. PMID: 34141066; PMCID: PMC8201477.


15: Yang C, Wu T, Zhang J, Liu J, Zhao K, Sun W, Zhou X, Kong X, Shi J. Prognostic and Immunological Role of mRNA ac4C Regulator NAT10 in Pan-Cancer: New Territory for Cancer Research? Front Oncol. 2021 May 19;11:630417. doi: 10.3389/fonc.2021.630417. PMID: 34094911; PMCID: PMC8170476.


16: Zhu Z, Xing X, Huang S, Tu Y. NAT10 Promotes Osteogenic Differentiation of Mesenchymal Stem Cells by Mediating N4-Acetylcytidine Modification of Gremlin 1. Stem Cells Int. 2021 Apr 12;2021:8833527. doi: 10.1155/2021/8833527. PMID: 33953754; PMCID: PMC8057913.


17: Thalalla Gamage S, Sas-Chen A, Schwartz S, Meier JL. Quantitative nucleotide resolution profiling of RNA cytidine acetylation by ac4C-seq. Nat Protoc. 2021 Apr;16(4):2286-2307. doi: 10.1038/s41596-021-00501-9. Epub 2021 Mar 26. PMID: 33772246; PMCID: PMC9103714.


18: Komal S, Zhang LR, Han SN. Potential regulatory role of epigenetic RNA methylation in cardiovascular diseases. Biomed Pharmacother. 2021 May;137:111376. doi: 10.1016/j.biopha.2021.111376. Epub 2021 Feb 13. PMID: 33588266.


19: Maran SR, de Lemos Padilha Pitta JL, Dos Santos Vasconcelos CR, McDermott SM, Rezende AM, Silvio Moretti N. Epitranscriptome machinery in Trypanosomatids: New players on the table? Mol Microbiol. 2021 May;115(5):942-958. doi: 10.1111/mmi.14688. Epub 2021 Feb 10. PMID: 33513291.


20: Bai H, Zhang Q. Role of N4-acetylcytidine for continuously activating NLRP3 inflammosome by HMGB1 pathway in microglia. Neural Regen Res. 2021 Jul;16(7):1427-1428. doi: 10.4103/1673-5374.301006. PMID: 33318439; PMCID: PMC8284255.