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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-10-29 21:45:23 UTC
HMDB IDHMDB00095
Secondary Accession NumbersNone
Metabolite Identification
Common NameCytidine monophosphate
DescriptionCytidine 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 ].
Structure
Thumb
Synonyms
  1. 5'-CMP
  2. 5-Cytidylate
  3. 5-Cytidylic acid
  4. CMP
  5. Cytidine 5'-monophosphate
  6. Cytidine 5'-monophosphorate
  7. Cytidine 5'-monophosphoric acid
  8. Cytidine 5'-phosphate
  9. Cytidine 5'-phosphorate
  10. Cytidine 5'-phosphoric acid
  11. Cytidine mono(dihydrogen phosphate)
  12. Cytidine monophosphate
  13. Cytidylate
  14. Cytidylic acid
Chemical FormulaC9H14N3O8P
Average Molecular Weight323.1965
Monoisotopic Molecular Weight323.051850951
IUPAC Name{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number63-37-6
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier
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
InChI KeyIERHLVCPSMICTF-XVFCMESISA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPyrimidine Nucleotides
Sub ClassPyrimidine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Glycosyl Compound
  • Hydropyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPyrimidine Ribonucleoside Monophosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Ganglioside biosynthesis
  • Component of Globoside metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Keratan sulfate biosynthesis
  • Component of N-Glycan biosynthesis
  • Component of O-Glycan biosynthesis
  • Component of Pyrimidine metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Lysosome
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point233 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.3 g/LALOGPS
logP-2ALOGPS
logP-3.3ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-0.62ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area175.14ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.42ChemAxon
Polarizability26.89ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Lysosome
  • Golgi apparatus
Biofluid Locations
  • Saliva
Tissue Location
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Phosphatidylinositol Phosphate MetabolismSMP00463map00562
Plasmalogen SynthesisSMP00479Not Available
Pyrimidine MetabolismSMP00046map00240
Transcription/TranslationSMP00019Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified1.27 +/- 0.75 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified0.0573 +/- 0.176 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.0965 +/- 0.0870 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.90 +/- 0.71 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified1.02 +/- 0.31 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified0.63 +/- 0.64 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011882
KNApSAcK IDNot Available
Chemspider ID5901
KEGG Compound IDC00055
BioCyc IDCMP
BiGG ID33689
Wikipedia LinkCytidine monophosphate
NuGOwiki LinkHMDB00095
Metagene LinkHMDB00095
METLIN ID5143
PubChem Compound6131
PDB IDC
ChEBI ID17361
References
Synthesis ReferenceZhou, Jingkang. Method for preparing cytidine 5'-monophosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 12 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Hirono A, Fujii H, Miyajima H, Kawakatsu T, Hiyoshi Y, Miwa S: Three families with hereditary hemolytic anemia and pyrimidine 5'-nucleotidase deficiency: electrophoretic and kinetic studies. Clin Chim Acta. 1983 May 30;130(2):189-97. Pubmed: 6307548
  3. Okahira S, Nishikawa F, Nishikawa S, Akazawa T, Seya T, Matsumoto M: Interferon-beta induction through toll-like receptor 3 depends on double-stranded RNA structure. DNA Cell Biol. 2005 Oct;24(10):614-23. Pubmed: 16225392
  4. Daunter B, Newlands J: Seminal plasma biochemistry II: seminal plasma and spermatozoal cytidine monophosphate-sialic acid synthetase and sialyltransferase activities. Andrologia. 1981 May-Jun;13(3):215-24. Pubmed: 6267956
  5. Schmukler M, Jewett PB, Levy CC: The effects of polyamines on a residue-specific human plasma ribonuclease. J Biol Chem. 1975 Mar 25;250(6):2206-12. Pubmed: 234961
  6. Paglia DE, Valentine WN, Keitt AS, Brockway RA, Nakatani M: Pyrimidine nucleotidase deficiency with active dephosphorylation of dTMP: evidence for existence of thymidine nucleotidase in human erythrocytes. Blood. 1983 Nov;62(5):1147-9. Pubmed: 6313098
  7. Yates AJ, Warner JK: Behavior of sugar derivatives in procedures for ganglioside isolation. Lipids. 1984 Jul;19(7):562-9. Pubmed: 6748871
  8. Li YP, Curley G, Lopez M, Chavez M, Glew R, Aragon A, Kumar H, Baca OG: Protein-tyrosine phosphatase activity of Coxiella burnetii that inhibits human neutrophils. Acta Virol. 1996 Nov-Dec;40(5-6):263-72. Pubmed: 9171454
  9. Hirono A, Fujii H, Natori H, Kurokawa I, Miwa S: Chromatographic analysis of human erythrocyte pyrimidine 5'-nucleotidase from five patients with pyrimidine 5'-nucleotidase deficiency. Br J Haematol. 1987 Jan;65(1):35-41. Pubmed: 3028466
  10. Gella A, Ponce J, Cusso R, Durany N: Effect of the nucleotides CMP and UMP on exhaustion in exercise rats. J Physiol Biochem. 2008 Mar;64(1):9-17. Pubmed: 18663991

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
Reactions
Cytidine monophosphate + Water → Cytidine + Phosphoric aciddetails
General function:
Involved in ATP binding
Specific function:
Catalyzes specific phosphoryl transfer from ATP to UMP and CMP.
Gene Name:
CMPK1
Uniprot ID:
P30085
Molecular weight:
20180.12
Reactions
Adenosine triphosphate + Cytidine monophosphate → ADP + CDPdetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
Reactions
Cytidine monophosphate + Water → Cytidine + Phosphoric aciddetails
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
Reactions
Cytidine monophosphate + Water → Cytidine + Phosphoric aciddetails
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
Reactions
Cytidine monophosphate + Water → Cytidine + Phosphoric aciddetails
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
Reactions
Cytidine monophosphate + Water → Cytidine + Phosphoric aciddetails
General function:
Involved in hydrolase activity
Specific function:
In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:
ENTPD1
Uniprot ID:
P49961
Molecular weight:
58706.0
Reactions
CDP + Water → Cytidine monophosphate + Phosphoric aciddetails
General function:
Involved in calcium ion binding
Specific function:
Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Molecular weight:
44839.24
General function:
Involved in hydrolase activity
Specific function:
Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:
ENTPD3
Uniprot ID:
O75355
Molecular weight:
59104.76
Reactions
CDP + Water → Cytidine monophosphate + Phosphoric aciddetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Molecular weight:
22760.43
Reactions
Adenosine triphosphate + Cytidine → ADP + Cytidine monophosphatedetails
Uridine triphosphate + Cytidine → Uridine 5'-diphosphate + Cytidine monophosphatedetails
Guanosine triphosphate + Cytidine → Guanosine diphosphate + Cytidine monophosphatedetails
Inosine triphosphate + Cytidine → IDP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Cytidine → dADP + Cytidine monophosphatedetails
dGTP + Cytidine → dGDP + Cytidine monophosphatedetails
Thymidine 5'-triphosphate + Cytidine → dTDP + Cytidine monophosphatedetails
dCTP + Cytidine → dCDP + Cytidine monophosphatedetails
Deoxyuridine triphosphate + Cytidine → dUDP + Cytidine monophosphatedetails
General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of the NeuAc-alpha-2,3-Gal-beta-1,4-GlcNAc-, NeuAc-alpha-2,3-Gal-beta-1,3-GlcNAc- or NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- sequences found in terminal carbohydrate groups of glycoproteins and glycolipids. The highest activity is toward Gal-beta-1,3-GlcNAc and the lowest toward Gal-beta-1,3-GalNAc (By similarity).
Gene Name:
ST3GAL3
Uniprot ID:
Q11203
Molecular weight:
38741.57
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-(1->4)-N-acetyl-D-glucosaminyl-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-N-acetyl-D-glucosaminyl-glycoproteindetails
General function:
Involved in sialyltransferase activity
Specific function:
Involved in the production of gangliosides GD3 and GT3 from GM3; gangliosides are a subfamily of complex glycosphinglolipds that contain one or more residues of sialic acid.
Gene Name:
ST8SIA1
Uniprot ID:
Q92185
Molecular weight:
40518.655
Reactions
Cytidine monophosphate N-acetylneuraminic acid + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->8)-alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-Rdetails
General function:
Involved in lipopolysaccharide biosynthetic process
Specific function:
Catalyzes the activation of N-acetylneuraminic acid (NeuNAc) to cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuNAc), a substrate required for the addition of sialic acid. Has some activity toward NeuNAc, N-glycolylneuraminic acid (Neu5Gc) or 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN).
Gene Name:
CMAS
Uniprot ID:
Q8NFW8
Molecular weight:
48378.835
General function:
Involved in catalytic activity
Specific function:
Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Required for cell growth
Gene Name:
SGMS2
Uniprot ID:
Q8NHU3
Molecular weight:
42279.8
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the biosynthesis of phosphatidylinositol (PtdIns) as well as PtdIns:inositol exchange reaction. May thus act to reduce an excessive cellular PtdIns content. The exchange activity is due to the reverse reaction of PtdIns synthase and is dependent on CMP, which is tightly bound to the enzyme.
Gene Name:
CDIPT
Uniprot ID:
O14735
Molecular weight:
23538.47
Reactions
CDP-diacylglycerol + Myoinositol → Cytidine monophosphate + phosphatidyl-1D-myo-inositoldetails
CDP-diacylglycerol + Myoinositol → Cytidine monophosphate + 1-Phosphatidyl-D-myo-inositoldetails
General function:
Involved in sialyltransferase activity
Specific function:
Catalyzes the formation of ganglioside GM3 (alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1, 4-beta-D-glucosylceramide).
Gene Name:
ST3GAL5
Uniprot ID:
Q9UNP4
Molecular weight:
45584.69
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide → Cytidine monophosphate + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
General function:
Involved in sialyltransferase activity
Specific function:
Involved in the synthesis of sialyl-paragloboside, a precursor of sialyl-Lewis X determinant. Has a alpha-2,3- sialyltransferase activity toward Gal-beta1,4-GlcNAc structure on glycoproteins and glycolipids. Has a restricted substrate specificity, it utilizes Gal-beta1,4-GlcNAc on glycoproteins, and neolactotetraosylceramide and neolactohexaosylceramide, but not lactotetraosylceramide, lactosylceramide or asialo-GM1
Gene Name:
ST3GAL6
Uniprot ID:
Q9Y274
Molecular weight:
38213.3
General function:
Involved in catalytic activity
Specific function:
Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Suppresses BAX-mediated apoptosis and also prevents cell death in response to stimuli such as hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. May protect against cell death by reversing the stress-inducible increase in levels of proapoptotic ceramide. Required for cell growth
Gene Name:
SGMS1
Uniprot ID:
Q86VZ5
Molecular weight:
49207.3
General function:
Involved in beta-galactoside alpha-2,3-sialyltransferas
Specific function:
It may be responsible for the synthesis of the sequence NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- found on sugar chains O-linked to Thr or Ser and also as a terminal sequence on certain gangliosides. SIAT4A and SIAT4B sialylate the same acceptor substrates but exhibit different Km values.
Gene Name:
ST3GAL1
Uniprot ID:
Q11201
Molecular weight:
39074.745
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-Rdetails
General function:
Involved in ATP binding
Specific function:
Phosphorylates uridine and cytidine to uridine monophosphate and cytidine monophosphate. Does not phosphorylate deoxyribonucleosides or purine ribonucleosides. Can use ATP or GTP as a phosphate donor. Can also phosphorylate cytidine and uridine nucleoside analogs such as 6-azauridine, 5-fluorouridine, 4-thiouridine, 5-bromouridine, N(4)-acetylcytidine, N(4)-benzoylcytidine, 5-fluorocytidine, 2-thiocytidine, 5-methylcytidine, and N(4)-anisoylcytidine.
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Molecular weight:
29298.92
Reactions
Adenosine triphosphate + Cytidine → ADP + Cytidine monophosphatedetails
Uridine triphosphate + Cytidine → Uridine 5'-diphosphate + Cytidine monophosphatedetails
Guanosine triphosphate + Cytidine → Guanosine diphosphate + Cytidine monophosphatedetails
Inosine triphosphate + Cytidine → IDP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Cytidine → dADP + Cytidine monophosphatedetails
dGTP + Cytidine → dGDP + Cytidine monophosphatedetails
Thymidine 5'-triphosphate + Cytidine → dTDP + Cytidine monophosphatedetails
dCTP + Cytidine → dCDP + Cytidine monophosphatedetails
Deoxyuridine triphosphate + Cytidine → dUDP + Cytidine monophosphatedetails
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes.
Gene Name:
CHPT1
Uniprot ID:
Q8WUD6
Molecular weight:
45096.535
Reactions
Citicoline + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylcholinedetails
Citicoline + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylcholinedetails
Citicoline + 1-Alkyl-2-acetyl-sn-glycerol → Cytidine monophosphate + 2-Acetyl-1-alkyl-sn-glycero-3-phosphocholinedetails
CMP-N-trimethyl-2-aminoethylphosphonate + Diacylglycerol → Cytidine monophosphate + Diacylglyceryl-N-trimethyl-2-aminoethylphosphonatedetails
1-Alkyl-2-acylglycerol + Citicoline → 1-Radyl-2-acyl-sn-glycero-3-phosphocholine + Cytidine monophosphatedetails
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the first step in the biosynthesis of coenzyme A from vitamin B5, where cysteine is conjugated to 4'-phosphopantothenate to form 4-phosphopantothenoylcysteine.
Gene Name:
PPCS
Uniprot ID:
Q9HAB8
Molecular weight:
15645.035
Reactions
Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + N-((R)-4'-phosphopantothenoyl)-L-cysteinedetails
Cytidine triphosphate + D-4'-Phosphopantothenate + L-Cysteine → Cytidine monophosphate + Pyrophosphate + 4-Phosphopantothenoylcysteinedetails
General function:
Involved in sialyltransferase activity
Specific function:
It may catalyze the formation of the NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- or NeuAc-alpha-2,3-Gal-beta-1,3-GlcNAc-sequences found in terminal carbohydrate groups of glycoproteins and glycolipids. It may be involved in the biosynthesis of the sialyl Lewis X determinant. Also acts on the corresponding 1,3-galactosyl derivative.
Gene Name:
ST3GAL4
Uniprot ID:
Q11206
Molecular weight:
38045.1
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoproteindetails
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
Reactions
Cytidine monophosphate + Water → Cytidine + Phosphoric aciddetails
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes both phosphatidylcholine and phosphatidylethanolamine biosynthesis from CDP-choline and CDP-ethanolamine, respectively. Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. Has a higher cholinephosphotransferase activity than ethanolaminephosphotransferase activity.
Gene Name:
CEPT1
Uniprot ID:
Q9Y6K0
Molecular weight:
46553.135
Reactions
CDP-Ethanolamine + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylethanolaminedetails
Citicoline + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylcholinedetails
Citicoline + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylcholinedetails
CDP-Ethanolamine + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylethanolaminedetails
Citicoline + 1-Alkyl-2-acetyl-sn-glycerol → Cytidine monophosphate + 2-Acetyl-1-alkyl-sn-glycero-3-phosphocholinedetails
CMP-2-aminoethylphosphonate + Diacylglycerol → Cytidine monophosphate + Diacylglyceryl-2-aminoethylphosphonatedetails
CMP-N-trimethyl-2-aminoethylphosphonate + Diacylglycerol → Cytidine monophosphate + Diacylglyceryl-N-trimethyl-2-aminoethylphosphonatedetails
CDP-Ethanolamine + 1-Alkyl-2-acylglycerol → Cytidine monophosphate + 1-Alkyl-2-acylglycerophosphoethanolaminedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Cytidine monophosphate → 1-Alkenyl-2-acylglycerol + CDP-Ethanolaminedetails
1-Alkyl-2-acylglycerol + Citicoline → 1-Radyl-2-acyl-sn-glycero-3-phosphocholine + Cytidine monophosphatedetails
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin (By similarity).
Gene Name:
PGS1
Uniprot ID:
Q32NB8
Molecular weight:
62729.745
Reactions
CDP-diacylglycerol + Glycerol 3-phosphate → Cytidine monophosphate + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphatedetails
CDP-diacylglycerol + Glycerol 3-phosphate → Cytidine monophosphate + Phosphatidylglycerophosphatedetails
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2
Reactions
Cytidine monophosphate + Water → Cytidine + Phosphoric aciddetails
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the formation of phosphatidylethanolamine via 'Kennedy' pathway.
Gene Name:
EPT1
Uniprot ID:
Q9C0D9
Molecular weight:
45228.42
Reactions
CDP-Ethanolamine + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylethanolaminedetails
CDP-Ethanolamine + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylethanolaminedetails
CMP-2-aminoethylphosphonate + Diacylglycerol → Cytidine monophosphate + Diacylglyceryl-2-aminoethylphosphonatedetails
CDP-Ethanolamine + 1-Alkyl-2-acylglycerol → Cytidine monophosphate + 1-Alkyl-2-acylglycerophosphoethanolaminedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Cytidine monophosphate → 1-Alkenyl-2-acylglycerol + CDP-Ethanolaminedetails
General function:
Involved in thymidylate kinase activity
Specific function:
May participate in dUTP and dCTP synthesis in mitochondria. Is able to phosphorylate dUMP, dCMP, CMP, UMP and monophosphates of the pyrimidine nucleoside analogs ddC, dFdC, araC, BVDU and FdUrd with ATP as phosphate donor. Efficacy is highest for dUMP followed by dCMP; CMP and UMP are poor substrates. May be involved in mtDNA depletion caused by long term treatment with ddC or other pyrimidine analogs.
Gene Name:
CMPK2
Uniprot ID:
Q5EBM0
Molecular weight:
44958.27
Reactions
Adenosine triphosphate + Cytidine monophosphate → ADP + CDPdetails
General function:
Involved in ATP binding
Specific function:
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Molecular weight:
59465.77
Reactions
Adenosine triphosphate + Cytidine → ADP + Cytidine monophosphatedetails
Uridine triphosphate + Cytidine → Uridine 5'-diphosphate + Cytidine monophosphatedetails
Guanosine triphosphate + Cytidine → Guanosine diphosphate + Cytidine monophosphatedetails
Inosine triphosphate + Cytidine → IDP + Cytidine monophosphatedetails
Deoxyadenosine triphosphate + Cytidine → dADP + Cytidine monophosphatedetails
dGTP + Cytidine → dGDP + Cytidine monophosphatedetails
Thymidine 5'-triphosphate + Cytidine → dTDP + Cytidine monophosphatedetails
dCTP + Cytidine → dCDP + Cytidine monophosphatedetails
Deoxyuridine triphosphate + Cytidine → dUDP + Cytidine monophosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Canalicular ectonucleoside NTPDase responsible for the main hepatic NTPDase activity. Ectonucleoside NTPDases catalyze the hydrolysis of gamma- and beta-phosphate residues of nucleotides, playing a central role in concentration of extracellular nucleotides. Has activity toward ATP, ADP, UTP and UDP, but not toward AMP.
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Molecular weight:
53903.14
Reactions
CDP + Water → Cytidine monophosphate + Phosphoric aciddetails
General function:
Not Available
Specific function:
Involved in the biosynthesis of ganglioside GD1A from GM1B. Transfers CMP-NeuAc with an alpha-2,6-linkage to GalNAc residue on NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc of glycoproteins and glycolipids. Prefers glycoproteins to glycolipids (By similarity).
Gene Name:
ST6GALNAC4
Uniprot ID:
Q9H4F1
Molecular weight:
34200.255
Reactions
Cytidine monophosphate N-acetylneuraminic acid + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-D-galactosaminyl-R → Cytidine monophosphate + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-(N-acetyl-alpha-neuraminyl-(2->6))-N-acetyl-D-galactosaminyl-Rdetails
General function:
Not Available
Specific function:
Hydrolyzes ADP-ribose, IDP-ribose, CDP-glycerol, CDP-choline and CDP-ethanolamine, but not other non-reducing ADP-sugars or CDP-glucose. May be involved in immune cell signaling as suggested by the second-messenger role of ADP-ribose, which activates TRPM2 as a mediator of oxidative/nitrosative stress (By similarity).
Gene Name:
ADPRM
Uniprot ID:
Q3LIE5
Molecular weight:
39529.105
Reactions
Citicoline + Water → Cytidine monophosphate + Phosphorylcholinedetails
CDP-glycerol + Water → Cytidine monophosphate + Glycerol 3-phosphatedetails
General function:
Not Available
Specific function:
It may be responsible for the synthesis of the sequence NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc- found in terminal carbohydrate groups of certain glycoproteins, oligosaccharides and glycolipids. SIAT4A and SIAT4B sialylate the same acceptor substrates but exhibit different Km values.
Gene Name:
ST3GAL2
Uniprot ID:
Q16842
Molecular weight:
40172.565
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-R → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-alpha-D-galactosaminyl-Rdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
ST6GALNAC1
Uniprot ID:
Q9NSC7
Molecular weight:
68563.845
Reactions
Cytidine monophosphate N-acetylneuraminic acid + glycano-(1->3)-(N-acetyl-alpha-D-galactosaminyl)-glycoprotein → Cytidine monophosphate + glycano-((2->6)-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoproteindetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
ST6GALNAC2
Uniprot ID:
Q9UJ37
Molecular weight:
41938.815
Reactions
Cytidine monophosphate N-acetylneuraminic acid + glycano-beta-D-galactosyl-1,3-(N-acetyl-D-galactosaminyl)-glycoprotein → Cytidine monophosphate + glycano-beta-D-galactosyl-(2,6-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoproteindetails
General function:
Not Available
Specific function:
Involved in the biosynthesis of ganglioside GD1A from GM1B. Transfers CMP-NeuAc with an alpha-2,6-linkage to GalNAc residue on NeuAc-alpha-2,3-Gal-beta-1,3-GalNAc of glycoproteins and glycolipids. ST6GalNAcIII prefers glycolipids to glycoproteins (By similarity).
Gene Name:
ST6GALNAC3
Uniprot ID:
Q8NDV1
Molecular weight:
24021.865
Reactions
Cytidine monophosphate N-acetylneuraminic acid + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-(N-acetyl-D-galactosaminyl)-glycoprotein → Cytidine monophosphate + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-(2,6-alpha-N-acetylneuraminyl)-(N-acetyl-D-galactosaminyl)-glycoproteindetails
General function:
Not Available
Specific function:
Transfers sialic acid from the donor of substrate CMP-sialic acid to galactose containing acceptor substrates.
Gene Name:
ST6GAL1
Uniprot ID:
P15907
Molecular weight:
46604.235
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine → Cytidine monophosphate + (N-acetylneuraminosyl(a2-6)lactosamine)details
General function:
Not Available
Specific function:
Transfers sialic acid from the donor of substrate CMP-sialic acid to galactose containing acceptor substrates. Has alpha-2,6-sialyltransferase activity toward oligosaccharides that have the Gal-beta-1,4-GlcNAc sequence at the non-reducing end of their carbohydrate groups, but it has weak or no activities toward glycoproteins and glycolipids.
Gene Name:
ST6GAL2
Uniprot ID:
Q96JF0
Molecular weight:
60157.39
Reactions
Cytidine monophosphate N-acetylneuraminic acid + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine → Cytidine monophosphate + (N-acetylneuraminosyl(a2-6)lactosamine)details