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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:48:15 UTC
HMDB IDHMDB0000095
Secondary Accession Numbers
  • HMDB00095
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
Data?1582752111
Synonyms
ValueSource
CMPChEBI
Cytidine-5'-monophosphateChEBI
CytidylateChEBI
Cytidylic acidChEBI
pCChEBI
Cytidine-5'-monophosphoric acidGenerator
Cytidine monophosphoric acidGenerator
Cytidine 5'-monophosphateHMDB
Cytidine 5'-monophosphoric acidHMDB
5'-CMPHMDB
5-CytidylateHMDB
5-Cytidylic acidHMDB
Cytidine 5'-monophosphorateHMDB
Cytidine 5'-phosphateHMDB
Cytidine 5'-phosphorateHMDB
Cytidine 5'-phosphoric acidHMDB
Cytidine mono(dihydrogen phosphate)HMDB
Acid, cytidylicHMDB
monoPhosphate, cytidineHMDB
5’-CMPHMDB
Cytidine 5’-monophosphateHMDB
Cytidine 5’-monophosphoric acidHMDB
Cytidine 5’-phosphateHMDB
Cytidine 5’-phosphoric acidHMDB
Cytidine monophosphateHMDB
Cytosine 5'-monophosphateHMDB
Cytosine 5’-monophosphateHMDB
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 Namecytidine monophosphate
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
Description Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine ribonucleotides
Direct ParentPyrimidine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Pyrimidine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Aminopyrimidine
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point233 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
AllCCS[M-H]-Not Available164.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00000148
AllCCS[M+H]+Not Available167.3http://allccs.zhulab.cn/database/detail?ID=AllCCS00000148
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.3 g/LALOGPS
logP10(-2) g/LALOGPS
logP10(-3.2) g/LChemAxon
logS10(-1.3) g/LALOGPS
pKa (Strongest Acidic)1.25ChemAxon
pKa (Strongest Basic)-0.15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area175.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.42 m³·mol⁻¹ChemAxon
Polarizability26.9 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.04231661259
DarkChem[M-H]-167.42931661259
AllCCS[M+H]+169.34632859911
AllCCS[M-H]-164.39132859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cytidine monophosphate,1TMS,#1C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O2794.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TMS,#2C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=CC(N)=NC1=O2777.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TMS,#3C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O2901.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TMS,#4C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C12884.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#1C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C2703.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#2C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O2848.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#3C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C)[C@H]2O)C=C12818.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#4C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O[C@H]1N1C=CC(N)=NC1=O2834.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#5C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C)C=C12803.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#6C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C2890.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#7C[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@@H](O)[C@H]2O)C=C12936.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TMS,#8C[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1)[Si](C)(C)C2830.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O3068.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1N1C=CC(N)=NC1=O3045.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#3CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O3140.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,1TBDMS,#4CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C13143.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3195.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O3300.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#3CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13288.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#4CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=CC(N)=NC1=O3290.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#5CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13271.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#6CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3338.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#7CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C13400.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Cytidine monophosphate,2TBDMS,#8CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3260.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cytidine monophosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9511000000-b038dcf334a34dfe41492016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytidine monophosphate GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9414000000-5835e3555d5546f12c1f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytidine monophosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytidine monophosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-0902000000-617172aee10f02d2ad2b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-03di-0900000000-ae1e8fc6db62229106372012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-03di-2900000000-c9ec8c41f82341b9225e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0229-0409000000-f28cc32ecb27c77120812012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-03di-0902000000-9a79f63e713af4d035ab2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-03di-1900000000-a5ef2297cb197b2d13e22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-00ba-9003000000-fed24d718a29a060134b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-00ba-9003000000-331ea098a652ec08d5602012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , negative-QTOFsplash10-00ba-9003000000-fed24d718a29a060134b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , negative-QTOFsplash10-00ba-9003000000-331ea098a652ec08d5602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , positive-QTOFsplash10-0229-0409000000-f28cc32ecb27c77120812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , positive-QTOFsplash10-03di-0902000000-9a79f63e713af4d035ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate LC-ESI-QTOF , positive-QTOFsplash10-03di-1900000000-25254e2c3fbbfd5e145b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate 10V, Positive-QTOFsplash10-03di-0900000000-54c9c74aa59c00f506b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate 30V, Positive-QTOFsplash10-03di-0902000000-9a79f63e713af4d035ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate 20V, Positive-QTOFsplash10-03di-1900000000-263b7b1f82f6bb15409e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Cytidine monophosphate 40V, Positive-QTOFsplash10-03di-6900000000-b27523b9f2ac3b9d00b72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 10V, Positive-QTOFsplash10-03di-0901000000-75b42cbe789350bd13b02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 20V, Positive-QTOFsplash10-03di-4900000000-fa026ae4d1a84f43102e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 40V, Positive-QTOFsplash10-03di-7900000000-5adaadd61efb1191857e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 10V, Negative-QTOFsplash10-0200-9848000000-0ac0c37265bd767019b22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 20V, Negative-QTOFsplash10-004i-9200000000-5dd0a8c928cf323e5d752016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 40V, Negative-QTOFsplash10-004i-9000000000-73255a3373b4f1f51b4d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 10V, Positive-QTOFsplash10-03di-0911000000-88e415850bae3999df102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytidine monophosphate 20V, Positive-QTOFsplash10-03di-0900000000-46d7ab7a98d3be427e4b2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
  • Nucleus
  • Lysosome
  • Golgi apparatus
Biospecimen Locations
  • Feces
  • Saliva
Tissue Locations
  • All Tissues
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
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 References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Associated OMIM IDs
DrugBank IDDB03403
Phenol Explorer Compound IDNot Available
FooDB IDFDB030736
KNApSAcK IDNot Available
Chemspider ID5901
KEGG Compound IDC00055
BioCyc IDCMP
BiGG ID33689
Wikipedia LinkCytidine monophosphate
METLIN IDNot Available
PubChem Compound6131
PDB IDNot Available
ChEBI ID17361
Food Biomarker OntologyNot Available
VMH IDCMP
MarkerDB IDMDB00029866
Good Scents IDNot Available
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. doi: 10.1038/nature07762. [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 ]
  11. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 39 proteins in total.

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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails
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 + Phosphatedetails
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

Only showing the first 10 proteins. There are 39 proteins in total.