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Identification
YMDB IDYMDB00406
NameCytidine monophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCytidine monophosphate, also known as CMP or cytidylic acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Cytidine monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine monophosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 5'-CMP
  • 5Cytidylate
  • 5Cytidylic acid
  • CMP
  • Cytidine 5'-monophosphate
  • Cytidine 5'-monophosphorate
  • Cytidine 5'-monophosphoric acid
  • Cytidine 5'-phosphate
  • Cytidine 5'-phosphorate
  • Cytidine 5'-phosphoric acid
  • Cytidine mono(dihydrogen phosphate)
  • Cytidine monophosphate
  • Cytidylate
  • Cytidylic acid
  • Cytidine-5'-monophosphate
  • pC
  • Cytidine-5'-monophosphoric acid
  • Cytidine monophosphoric acid
  • 5-Cytidylate
  • 5-Cytidylic acid
  • Acid, cytidylic
  • monoPhosphate, cytidine
  • 2' CMP
  • 2'-CMP
  • 3' CMP
  • Acids, cytidylic
  • Cytidylic acids
  • 3'-CMP
CAS number63-37-6
WeightAverage: 323.1965
Monoisotopic: 323.051850951
InChI KeyIERHLVCPSMICTF-XVFCMESISA-N
InChIInChI=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
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 IUPAC Namecytidine monophosphate
Chemical FormulaC9H14N3O8P
SMILES[H]O[C@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])N1C([H])=C([H])C(=NC1=O)N([H])[H])C([H])([H])OP(=O)(O[H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting point233 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 Area175.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.42 m³·mol⁻¹ChemAxon
Polarizability26.89 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin BiosynthesisPW002431 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/10:0/28:0)PW003484 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/10:0/30:0)PW003501 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/12:0/26:0)PW003502 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/12:0/28:0)PW003503 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Ether lipid metabolismec00565 Map00565
Glycerophospholipid metabolismec00564 Map00564
Pantothenate and CoA biosynthesisec00770 Map00770
Pyrimidine metabolismec00240 Map00240
beta-Alanine metabolismec00410 Map00410
SMPDB Reactions
D-4'-Phosphopantothenate + Cytidine triphosphate + L-CysteineCytidine monophosphate + Pyrophosphate + hydron + 4-Phosphopantothenoylcysteine
CDP-DG(16:0/16:0) + Glycerol 3-phosphatePGP(16:0/16:0) + hydron + Cytidine monophosphate
CDP-DG(16:0/16:0) + Glycerol 3-phosphate PGP(14:0/14:0) + hydron + Cytidine monophosphate
CDP-DG(16:0/16:0) + Glycerol 3-phosphatePGP(14:0/14:0) + hydron + Cytidine monophosphate
CDP-DG(14:0/14:0) + Glycerol 3-phosphatePGP(14:0/14:0) + hydron + Cytidine monophosphate
KEGG Reactions
water + 3',5'-cyclic CMPCytidine monophosphate + hydron
Cytidine monophosphate + waterphosphate + Cytidine
CDP-diacylglycerol + phosphatidylglycerol → cardiolipin + Cytidine monophosphate
CDP-Ethanolamine + DG(16:0/16:0/0:0)PE(14:0/16:1(9Z)) + Cytidine monophosphate + hydron
Citicoline + 1,2-dioleoylglycerolPC(18:1(9Z)/18:1(9Z)) + Cytidine monophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9511000000-b038dcf334a34dfe4149JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ot-9414000000-5835e3555d5546f12c1fJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0902000000-617172aee10f02d2ad2bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-ae1e8fc6db6222910637JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-2900000000-c9ec8c41f82341b9225eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0229-0409000000-f28cc32ecb27c7712081JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-03di-0902000000-9a79f63e713af4d035abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-1900000000-a5ef2297cb197b2d13e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9003000000-fed24d718a29a060134bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9003000000-331ea098a652ec08d560JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9003000000-fed24d718a29a060134bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9003000000-331ea098a652ec08d560JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0229-0409000000-f28cc32ecb27c7712081JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0902000000-9a79f63e713af4d035abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-1900000000-25254e2c3fbbfd5e145bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-75b42cbe789350bd13b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4900000000-fa026ae4d1a84f43102eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7900000000-5adaadd61efb1191857eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0200-9848000000-0ac0c37265bd767019b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-5dd0a8c928cf323e5d75JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-73255a3373b4f1f51b4dJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Hjelmstad, R. H., Bell, R. M. (1987). "Mutants of Saccharomyces cerevisiae defective in sn-1,2-diacylglycerol cholinephosphotransferase. Isolation, characterization, and cloning of the CPT1 gene." J Biol Chem 262:3909-3917.3029130
  • Hjelmstad, R. H., Bell, R. M. (1988). "The sn-1,2-diacylglycerol ethanolaminephosphotransferase activity of Saccharomyces cerevisiae. Isolation of mutants and cloning of the EPT1 gene." J Biol Chem 263:19748-19757.2848840
  • Nakanishi, T., Sekimizu, K. (2002). "SDT1/SSM1, a multicopy suppressor of S-II null mutant, encodes a novel pyrimidine 5'-nucleotidase." J Biol Chem 277:22103-22106.11934891
  • Marobbio, C. M., Di Noia, M. A., Palmieri, F. (2006). "Identification of a mitochondrial transporter for pyrimidine nucleotides in Saccharomyces cerevisiae: bacterial expression, reconstitution and functional characterization." Biochem J 393:441-446.16194150
  • Nikawa, J., Yamashita, S. (1997). "Phosphatidylinositol synthase from yeast." Biochim Biophys Acta 1348:173-178.9370330
  • Yamashita, S., Nikawa, J. (1997). "Phosphatidylserine synthase from yeast." Biochim Biophys Acta 1348:228-235.9370337
Synthesis Reference:Zhou, Jingkang. Method for preparing cytidine 5'-monophosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 12 pp.
External Links:
ResourceLink
CHEBI ID17361
HMDB IDHMDB00095
Pubchem Compound ID6131
Kegg IDC00055
ChemSpider ID5901
FOODB IDFDB011882
WikipediaCytidine_monophosphate
BioCyc IDCMP

Enzymes

General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P40506
Molecular weight:
41892.69922
Reactions
CTP + (R)-4'-phosphopantothenate + L-cysteine → CMP + PPi + N-((R)-4'-phosphopantothenoyl)-L-cysteine.
General function:
Involved in ATP binding
Specific function:
ATP + uridine = ADP + UMP
Gene Name:
Not Available
Uniprot ID:
Q12084
Molecular weight:
26594.80078
Reactions
ATP + uridine → ADP + UMP.
ATP + cytidine → ADP + CMP.
General function:
Involved in catalytic activity
Specific function:
Could be an enzyme that inactivates 6-azauracil by modifying it
Gene Name:
SDT1
Uniprot ID:
P53078
Molecular weight:
31968.40039
Reactions
General function:
Involved in ATP binding
Specific function:
Catalyzes the conversion of uridine into UMP and cytidine into CMP in the pyrimidine salvage pathway
Gene Name:
URK1
Uniprot ID:
P27515
Molecular weight:
56295.5
Reactions
ATP + uridine → ADP + UMP.
ATP + cytidine → ADP + CMP.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Essential for the viability of mitochondrial petite mutant. Catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:
PGS1
Uniprot ID:
P25578
Molecular weight:
59369.69922
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate → CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:
CPT1
Uniprot ID:
P17898
Molecular weight:
44829.0
Reactions
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl ethanolamine to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the ethanolaminephosphotransferase might participate in the transport process. EPT1 catalyzes both choline- and ethanolamine-phosphotransferase reactions
Gene Name:
EPT1
Uniprot ID:
P22140
Molecular weight:
44559.30078
Reactions
CDP-ethanolamine + 1,2-diacylglycerol → CMP + a phosphatidylethanolamine.
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.
General function:
Involved in catalytic activity
Specific function:
Controls the level of cAMP in yeast cells, together with the low-affinity cAMP phosphodiesterase (PDE1)
Gene Name:
PDE2
Uniprot ID:
P06776
Molecular weight:
60999.19922
Reactions
Adenosine 3',5'-cyclic phosphate + H(2)O → adenosine 5'-phosphate.
General function:
Involved in CDP-diacylglycerol-serine O-phosphatidyltransferase activity
Specific function:
CDP-diacylglycerol + L-serine = CMP + (3-sn- phosphatidyl)-L-serine
Gene Name:
CHO1
Uniprot ID:
P08456
Molecular weight:
30804.19922
Reactions
CDP-diacylglycerol + L-serine → CMP + (3-sn-phosphatidyl)-L-serine.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
CDP-diacylglycerol + myo-inositol = CMP + phosphatidyl-1D-myo-inositol
Gene Name:
PIS1
Uniprot ID:
P06197
Molecular weight:
24823.5
Reactions
CDP-diacylglycerol + myo-inositol → CMP + phosphatidyl-1D-myo-inositol.
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol
Gene Name:
CRD1
Uniprot ID:
Q07560
Molecular weight:
32019.30078
Reactions
2 Phosphatidylglycerol → diphosphatidylglycerol + glycerol.

Transporters

General function:
Involved in binding
Specific function:
Not Available
Gene Name:
RIM2
Uniprot ID:
P38127
Molecular weight:
42101.39844