General Information of MET (ID: META00158)
Name Cytidine monophosphate
Synonyms   Click to Show/Hide Synonyms of This Metabolite
5-Cytidylic acid', Cytidine 5'-monophosphorate, Cytidine 5'-phosphate, Cytidine 5'-phosphorate, Cytidine 5'-phosphoric acid, 'Cytidine mono(dihydrogen phosphate); Acid, cytidylic; CMP', Cytidine-5'-monophosphate, 'Cytidylate; Cytidylic acid; pC', Cytidine-5'-monophosphoric acid, 'Cytidine monophosphoric acid', Cytidine 5'-monophosphate, Cytidine 5'-monophosphoric acid, 5'-CMP, '5-Cytidylate
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;TCM Ingredients;Microbial
Structure Type   Pyrimidine ribonucleotides  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Pyrimidine nucleotides
Pyrimidine ribonucleotides
PubChem CID
6131
HMDB ID
HMDB0000095
Formula
C9H14N3O8P
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C00055
DrugBank ID
DB03403
ChEBI ID
17361
FooDB ID
FDB030736
ChemSpider ID
5901
Physicochemical Properties Molecular Weight 323.2 Topological Polar Surface Area 175
XlogP -3.4 Complexity 531
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 8
Function
Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockdown (shRNA) of SULF1
                      Induced Change Cytidine monophosphate concentration: decrease (FC = 0.62 / 0.76)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of cytidine monophosphate levels compared with control group.
      Mitochondrial carrier (MC)
            Solute carrier family 25 member 36 (SLC25A36) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Recombinant protein addition of SLC25A36
                      Induced Change Cytidine monophosphate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that recombinant protein addition of SLC25A36 leads to the increase of cytidine monophosphate levels compared with control group.
      Nitrogen permease regulator (NPR)
            Natriuretic peptide receptor B (NPR2) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [3]
                      Introduced Variation Deletion of NPR2
                      Induced Change Cytidine monophosphate concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that deletion of NPR2 leads to the decrease of cytidine monophosphate levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [4]
                      Introduced Variation Knockout of TP53
                      Induced Change Cytidine monophosphate concentration: decrease (Log2 FC=0.74)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of cytidine monophosphate levels compared with control group.
      Sugar transporter (ST)
            Facilitated glucose transporter 1 (SLC2A1A) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Downregulation of slc2a1a caused by Yap loss-of-function mutation
                      Induced Change Cytidine monophosphate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that downregulation of slc2a1a caused by Yap loss-of-function mutation leads to the increase of cytidine monophosphate levels compared with control group.
      Transcriptional coactivator (TC)
            Transcriptional coactivator YAP1 (yap1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [5]
                      Introduced Variation Decrease of Yap mRNA caused by Yap loss-of-function mutation
                      Induced Change Cytidine monophosphate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that decrease of Yap mRNA caused by Yap loss-of-function mutation leads to the increase of cytidine monophosphate levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
2 The human SLC25A33 and SLC25A36 genes of solute carrier family 25 encode two mitochondrial pyrimidine nucleotide transporters. J Biol Chem. 2014 Nov 28;289(48):33137-48.
3 Npr2 inhibits TORC1 to prevent inappropriate utilization of glutamine for biosynthesis of nitrogen-containing metabolites. Sci Signal. 2014 Dec 16;7(356):ra120.
4 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
5 Yap regulates glucose utilization and sustains nucleotide synthesis to enable organ growth. EMBO J. 2018 Nov 15;37(22):e100294.

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