| Identification | More | [Name]
Cytidylic acid | [CAS]
63-37-6 | [Synonyms]
5'-CMP
5'-CYTIDINE MONOPHOSPHATE
5'-CYTIDYLIC ACID
5'-CYTIDYLIC ACID MONOHYDRATE
C-5'-P
C-5-P
CMP
CMP MONOHYDRATE
CYTIDINE 5'-MONOPHOSPHATE
CYTIDINE-5'-MONOPHOSPHATE MONOHYDRATE
CYTIDINE-5'-MONOPHOSPHORIC ACID
CYTIDYLIC ACID
cmp(nucleotide)
cytidine5’-(dihydrogenphosphate)
cytidine5’-phosphate
cytidine5’-phosphoricacid
cytidinemonophosphate
Cytidine Monophosphate and salts
Cytidine 5'-monophate
CYTIDINE 5'-MONOPHOSPHATE FREE ACIDSIGMA GRADE FRO | [EINECS(EC#)]
200-556-6 | [Molecular Formula]
C9H14N3O8P | [MDL Number]
MFCD00006544 | [Molecular Weight]
323.2 | [MOL File]
63-37-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
~222 °C (dec.)
| [Boiling point ]
678.1±65.0 °C(Predicted) | [density ]
2.15±0.1 g/cm3(Predicted) | [refractive index ]
9.8 ° (C=1, 0.5mol/L Na2HPO4) | [storage temp. ]
2-8°C
| [solubility ]
Water (Slightly, Heated) | [form ]
crystalline
| [pka]
pK2:4.39(0);pK3:6.62(+1) (25°C) | [color ]
White | [biological source]
synthetic | [Water Solubility ]
soluble | [BRN ]
46982 | [InChI]
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 | [InChIKey]
IERHLVCPSMICTF-JDNPWWSISA-N | [SMILES]
P(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)(O)(O)=O | [CAS DataBase Reference]
63-37-6(CAS DataBase Reference) | [EPA Substance Registry System]
63-37-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
HA3980000
| [F ]
10-21 | [HS Code ]
29349900 | [Toxicity]
LD50 intraperitoneal in mouse: > 1gm/kg |
| Hazard Information | Back Directory | [Description]
Cytidine 5'-monophosphate, also known as 5'-CMP, is a nucleotide that is used as a monomer in RNA. 5'-CMP is a key intermediate in the preparation of several nucleotide derivatives and is widely used in food and pharmaceutical industries. | [Chemical Properties]
white crystalline powder | [Uses]
A constituent of nucleic acids. It was isolated from yeast nucleic acid. | [Definition]
ChEBI: A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase. | [Production Methods]
As a key intermediate in preparing several nucleotide derivatives, cytidine 5′-monophosphate (5′-CMP) is widely applied in food and pharmaceutical industries. Enzymatic synthesis of 5′-CMP is catalyzed by cytidine kinase (CK, EC 2.7.1.213), a type of nucleoside kinase that belongs to the PfkB family. Li et al. constructed a highly efficient biosynthesis system for manufacturing 5′-CMP in vitro. CK was used for the biotransformation of cytidine to 5′-CMP, while polyphosphate kinase (PPK) was coupled for adenosine triphosphate regeneration. Both CK and PPK were selected from extremophiles, possessing great potential for biocatalytic synthesis. After optimization, 96 mM 5′-CMP was produced within 6 h, and the yield reached nearly 100%[1]. | [benefits]
Cytidine 5’-monophosphate (CMP) is a nucleotide supplement with potential benefits such as improved muscle function, immune support, and enhanced neuronal growth. CMP is a component of RNA and phospholipids and sometimes pairs with uridine and other nutrients to produce synergistic effects, particularly in brain health. Studies have shown that adding CMP as a supplement to fish feed can contribute to their growth, health performance, and immune response. | [Biochem/physiol Actions]
Cytidine 5′-monophosphate (CMP) is 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. | [Side effects]
Cytidine 5’-monophosphate (CMP) is a naturally occurring substance and is considered relatively safe, with no adverse health effects or respiratory irritation. No serious adverse reactions have been reported when CMP is used as a supplement; the most common side effects are gastrointestinal reactions, including nausea, vomiting, diarrhea, abdominal pain, and decreased appetite. Headaches may occur with long-term use. | [storage]
Store at -20°C, protect from light | [References]
[1] Zonglin Li. “Efficient One-Pot Synthesis of Cytidine 5′-Monophosphate Using an Extremophilic Enzyme Cascade System.” Journal of Agricultural and Food Chemistry 68 34 (2020): 9188–9194.
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