CMP (CHEM042155)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:52:50 UTC
Update Date2016-11-09 01:22:37 UTC
Accession NumberCHEM042155
Identification
Common NameCMP
ClassSmall Molecule
DescriptionA pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass323.197 g/mol
Monoisotopic Mass323.052 g/mol
CAS Registry NumberNot Available
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
SMILESNC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility16.3 g/LALOGPS
logP-2ALOGPS
logP-3.2ChemAxon
logS-1.3ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9511000000-b038dcf334a34dfe4149Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9414000000-5835e3555d5546f12c1fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0902000000-617172aee10f02d2ad2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-ae1e8fc6db6222910637Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-2900000000-c9ec8c41f82341b9225eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0229-0409000000-f28cc32ecb27c7712081Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-03di-0902000000-9a79f63e713af4d035abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-1900000000-a5ef2297cb197b2d13e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9003000000-fed24d718a29a060134bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9003000000-331ea098a652ec08d560Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9003000000-fed24d718a29a060134bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9003000000-331ea098a652ec08d560Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0229-0409000000-f28cc32ecb27c7712081Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0902000000-9a79f63e713af4d035abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-1900000000-25254e2c3fbbfd5e145bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-54c9c74aa59c00f506b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0902000000-9a79f63e713af4d035abSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-263b7b1f82f6bb15409eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-6900000000-b27523b9f2ac3b9d00b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-75b42cbe789350bd13b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4900000000-fa026ae4d1a84f43102eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7900000000-5adaadd61efb1191857eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0200-9848000000-0ac0c37265bd767019b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-5dd0a8c928cf323e5d75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-73255a3373b4f1f51b4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0911000000-88e415850bae3999df10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-46d7ab7a98d3be427e4bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB03403
HMDB IDHMDB0000095
FooDB IDFDB030736
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID33689
BioCyc IDCMP
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCytidine monophosphate
Chemspider ID5901
ChEBI ID17361
PubChem Compound ID6131
Kegg Compound IDC00055
YMDB IDYMDB00406
ECMDB IDECMDB00095
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21968653
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22991951
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24053133
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2559771
5. Zhou, Jingkang. Method for preparing cytidine 5'-monophosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 12 pp.
6. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
7. Zhou, Jingkang. Method for preparing cytidine 5'-monophosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 12 pp.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. Yates AJ, Warner JK: Behavior of sugar derivatives in procedures for ganglioside isolation. Lipids. 1984 Jul;19(7):562-9.
14. 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.
15. 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.
16. 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.
17. 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.