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Cytidine 5'-monophosphate (cytidylic acid; 5'-Cytidylic acid; 5'-CMP)

Cat No.:V72313 Purity: ≥98%
Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide used as a monomer in RNA.
Cytidine 5'-monophosphate (cytidylic acid; 5'-Cytidylic acid; 5'-CMP)
Cytidine 5'-monophosphate (cytidylic acid; 5'-Cytidylic acid; 5'-CMP) Chemical Structure CAS No.: 63-37-6
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5g
Other Sizes
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Product Description
Cytidine 5'-monophosphate (5'-Cytidylic acid) is a nucleotide used as a monomer in RNA. Cytidine 5'-monophosphate consists of the nucleobases cytosine, pentose ribose, and a phosphate group.
Cytidine 5'-monophosphate (5'-CMP) is a nucleoside monophosphate used as a substrate of uridine monophosphate (UMP)/cytidine monophosphate (CMP) kinase (EC 2.7.4.4) to form CDP, which upon phosphorylation to CTP supports DNA and RNA biosynthesis. It is a key intermediate in RNA biosynthesis and nucleotide metabolism.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite Microbial Metabolite
5'-CMP targets UMP/CMP kinase (EC 2.7.4.4), serving as a substrate for the formation of CDP. It inhibits alpha-2,3-sialyltransferase and alpha-2,6-sialyltransferase from rat liver with Ki values of 65,000 nM and 64,000 nM, respectively. It is involved in the activation of sialic acid for glycoprotein biosynthesis.
ln Vitro
In vitro, 5'-CMP exhibits a wide range of inhibitory and growth inhibition bioactivities across various assays and cell types. It inhibits alpha-2,3-sialyltransferase and alpha-2,6-sialyltransferase with Ki values of 65 µM and 64 µM, respectively. It is used as a substrate for UMP/CMP kinase in biochemical assays.
ln Vivo
In vivo, 5'-CMP is a key intermediate in RNA biosynthesis and nucleotide metabolism. It is involved in the synthesis of nucleic acids and phospholipids. It plays a central role in the activation of sialic acid for glycoprotein biosynthesis. UMP-CMP kinase 2 inhibits Zika virus replication via activation of the type I interferon signaling pathway.
Enzyme Assay
In vitro enzyme assays for UMP/CMP kinase involve incubating the enzyme with 5'-CMP and ATP as phosphate donor in Tris-HCl buffer at pH 7.4, typically at 37°C. The reaction product, CDP, is quantified by HPLC or LC-MS/MS. Kinetic parameters are determined by varying 5'-CMP concentrations.
Cell Assay
For in vitro cell assays, cells are cultured and treated with 5'-CMP at concentrations ranging from 0.1-10 mM. Cellular nucleotide levels are analyzed by LC-MS/MS. The compound's effects on RNA and DNA synthesis are assessed by measuring nucleotide incorporation. Sialyltransferase activity is measured in cell lysates using fluorescent substrates.
Animal Protocol
For in vivo animal studies, 5'-CMP is typically administered to rodents via oral gavage or intravenous injection in pharmacokinetic and metabolic studies. Blood and tissue samples are collected, and nucleotide levels are quantified by LC-MS/MS. The compound's effects on nucleotide metabolism and nucleic acid synthesis are assessed. Antiviral activity is evaluated in models of Zika virus infection.
ADME/Pharmacokinetics
Cytidine 5'-monophosphate (MW 323.20) has the molecular formula C9H14N3O8P. It is a white, water-soluble powder. The compound is stable under recommended storage conditions. It is a nucleoside monophosphate and a key intermediate in RNA biosynthesis and nucleotide metabolism. It is used as a substrate for UMP/CMP kinase.
Toxicity/Toxicokinetics
The compound is for research use only. No specific toxicity data are available. As an endogenous nucleotide, it is expected to have low toxicity at physiological concentrations. Standard laboratory safety precautions should be followed when handling this compound.
References
[1]. Hernández AG, et, al. The determination of acid-soluble nucleotides in milk by improved enzymic methods: a comparison with the ion-exchange column chromatography procedure. J Sci Food Agric. 1981 Nov;32(11):1123-31.
Additional Infomation
Cytidine 5'-monophosphate is a pyrimidine nucleoside 5'-monophosphate with cytosine as its nucleobase. It is a metabolite in humans, as well as in E. coli and mice. It is both a pyrimidine nucleoside 5'-monophosphate and a cytidine 5'-phosphate. It is the conjugate acid of cytidine 5'-monophosphate (2-). A pyrimidine ribonucleoside 5'-monophosphate with cytosine as its nucleobase. Cytidine monophosphate is a metabolite found or produced in E. coli (K12 strain, MG1655 strain). It has also been reported in Drosophila melanogaster, Mycoplasma gallisepticum, and other organisms with relevant data. Cytidine monophosphate is a metabolite found or produced in Saccharomyces cerevisiae. Cytidine (dihydrogen phosphate). A cytosine nucleotide with a phosphate group esterified at the 2', 3', or 5' position of its sugar moiety. See also: Low molecular weight polyinosinic acid-polycytidylic acid (monomer); High molecular weight polyinosinic acid-polycytidylic acid (monomer)... See more...
Cytidine 5'-monophosphate (CAS# 63-37-6) is a nucleoside monophosphate and key intermediate in RNA biosynthesis and nucleotide metabolism. It has not been approved as a therapeutic drug but is widely used in biochemical, molecular biology, and pharmaceutical research. The compound is used as a substrate for UMP/CMP kinase and in studies of nucleotide metabolism, sialylation, and antiviral responses.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H14N3O8P
Molecular Weight
323.20
Exact Mass
323.051
CAS #
63-37-6
Related CAS #
Cytidine 5′-monophosphate-15N3 disodium
PubChem CID
6131
Appearance
White to off-white solid powder
Density
2.2±0.1 g/cm3
Boiling Point
662.8±65.0 °C at 760 mmHg
Melting Point
233 °C
Flash Point
354.6±34.3 °C
Vapour Pressure
0.0±4.6 mmHg at 25°C
Index of Refraction
1.775
LogP
-2.03
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
4
Heavy Atom Count
21
Complexity
531
Defined Atom Stereocenter Count
4
SMILES
C1=CN(C(=O)N=C1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
InChi Key
IERHLVCPSMICTF-XVFCMESISA-N
InChi Code
InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
Chemical Name
[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O: 18.33 mg/mL (56.71 mM)
DMSO: 1.1 mg/mL (3.40 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 11.11 mg/mL (34.37 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0941 mL 15.4703 mL 30.9406 mL
5 mM 0.6188 mL 3.0941 mL 6.1881 mL
10 mM 0.3094 mL 1.5470 mL 3.0941 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
Title:CMP vs Fascia Iliaca Block
Status:Unknown status
updateDate:2022-04-20
Ctid:NCT04426058

Link: https://clinicaltrials.gov/ct2/show/NCT04426058

Conditions:Pain, Postoperative|Hip Arthroplasty
Interventions:Fascia Illica
Phase:N/A
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