Details of Metabolite

General Information of MET (ID: META00383)
Name CMP-N-Acetylneuraminate
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Acid, CMP acetylneuraminic; Acid, CMP-sialic; CMP Acetylneuraminate; CMP Acetylneuraminic acid; CMP Sialic acid; CMP-N-Acetyl-b-neuraminic acid; CMP-N-Acetylneuraminic acid; CMP-N-Acylneuraminate', Cytidine 5'-monophosphate N-acetylneuraminic acid, 'Acetylneuraminic acid, CMP; CMP-Nana; CMP-Neu5ac; CMP-NeuNAc; CMP-Sialate', CYTIDINE-5'-monophosphate-5-N-acetylneuraminate, CYTIDINE-5'-monophosphoric acid-5-N-acetylneuraminic acid, Cytidine-5'-monophospho-N-acetylneuraminate, Cytidine-5'-monophosphono-N-acetylneuraminate, 'CMP-N-Acetyl-b-neuraminate; CMP-Sialic acid', CYTIDINE-5'-monophosphATE-5-N-acetylneuraminIC ACID, Cytidine-5'-monophospho-N-acetylneuraminic acid, Cytidine-5'-monophosphono-N-acetylneuraminic acid, 'CMP-N-Acetyl-beta-neuraminate; CMP-beta-Neu5ac; Cytidine monophosphate N acetylneuraminic acid; Cytidine monophosphate N-acetylneuraminate; Cytidine monophosphate N-acetylneuraminic acid; Cytidine monophosphic acid N-acetylneuraminic acid; Cytidine monophosphoric acid N-acetylneuraminic acid
Source Endogenous;Escherichia Coli Metabolite;Food;Microbial
Structure Type   Pyrimidine nucleotide sugars  (Click to Show/Hide the Complete Structure Type Hierarchy)
Nucleosides, nucleotides, and analogues
Pyrimidine nucleotides
Pyrimidine nucleotide sugars
PubChem CID
448209
HMDB ID
HMDB0001176
Formula
C20H31N4O16P
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
C00128
DrugBank ID
DB02485
ChEBI ID
16556
FooDB ID
FDB022466
ChemSpider ID
395082
Physicochemical Properties Molecular Weight 614.5 Topological Polar Surface Area 321
XlogP -6.7 Complexity 1120
Heavy Atom Count 41 Rotatable Bond Count 11
Hydrogen Bond Donor Count 10 Hydrogen Bond Acceptor Count 16
Function
Cytidine 5'-monophosphate-N-acetylneuraminic acid (CMP-Neu5Ac), also known as CMP-N-acetyl--neuraminic acid, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. CMP-Neu5Ac is an extremely weak basic (essentially neutral) compound (based on its pKa). CMP-Neu5Ac donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            N-acylneuraminate-9-phosphatase (NANP) 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 Knockout of NANP
                      Induced Change CMP-N-Acetylneuraminate concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Carbohydrate metabolism disorders [ICD-11: 5C51]
                      Details It is reported that knockout of NANP leads to the decrease of CMP-N-acetylneuraminate 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 [2]
                      Introduced Variation Knockout of TP53
                      Induced Change CMP-N-Acetylneuraminate concentration: increase (Log2 FC=1.34)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of CMP-N-acetylneuraminate levels compared with control group.
      Transcription factor (TF)
            Forkhead box protein O1 (FOXO1) 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 Overexpression of Foxo1
                      Induced Change CMP-N-Acetylneuraminate concentration: increase (FC = 1.20)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Foxo1 leads to the increase of CMP-N-acetylneuraminate levels compared with control group.
      Transferases (EC 2)
            Acetylglucosaminyltransferase 5 (MGAT5) 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 Mgat5
                      Induced Change CMP-N-Acetylneuraminate concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Mgat5 leads to the decrease of CMP-N-acetylneuraminate levels compared with control group.
References
1 Activity of N-acylneuraminate-9-phosphatase (NANP) is not essential for de novo sialic acid biosynthesis. Biochim Biophys Acta Gen Subj. 2019 Oct;1863(10):1471-1479.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.
3 Metabolomic analysis of C2C12 myoblasts induced by the transcription factor FOXO1. FEBS Lett. 2019 Jun;593(12):1303-1312.
4 N-glycan remodeling on glucagon receptor is an effector of nutrient sensing by the hexosamine biosynthesis pathway. J Biol Chem. 2014 Jun 6;289(23):15927-41.

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