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Identification
YMDB IDYMDB00049
NameUridine 5'-monophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUridine 5'-monophosphate, also known as uridylic acid or uridylate, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Uridine 5'-monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine 5'-monophosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • 5'-Monophosphate, uridine
  • 5'-UMP
  • 5'Uridylate
  • 5'Uridylic acid
  • Acid, uridylic
  • Acids, uridylic
  • Monophosphate, uridine
  • pU
  • UMP
  • Uridine 5' monophosphate
  • Uridine 5'-(dihydrogen phosphate)
  • Uridine 5'-(dihydrogen phosphoric acid)
  • Uridine 5'-monophosphate
  • Uridine 5'-monophosphic acid
  • Uridine 5'-monophosphoric acid
  • Uridine 5'-phosphate
  • Uridine 5'-phosphorate
  • Uridine 5'-phosphoric acid
  • Uridine mono(dihydrogen phosphate)
  • Uridine monophosphate
  • Uridine monophosphoric acid
  • Uridine phosphate
  • Uridine-5'-monophosphate
  • URIDINE-5'-monophosphoric acid
  • Uridylate
  • Uridylic acid
  • Uridylic acids
CAS number58-97-9
WeightAverage: 324.1813
Monoisotopic: 324.035866536
InChI KeyDJJCXFVJDGTHFX-XVFCMESISA-N
InChIInChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Nameuridine monophosphate
Chemical FormulaC9H13N2O9P
SMILES[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]1([H])O[H])N1C([H])=C([H])C(=O)N([H])C1=O
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
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • 1,2-diol
  • Urea
  • Secondary alcohol
  • Lactam
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point202 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility12 g/LALOGPS
logP-1.8ALOGPS
logP-2.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.44 m³·mol⁻¹ChemAxon
Polarizability26.3 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • nucleus
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
N-Glycan biosynthesisPW002501 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
N-Glycan biosynthesisec00510 Map00510
Pyrimidine metabolismec00240 Map00240
SMPDB Reactions
Orotidylic acid + hydronCarbon dioxide + Uridine 5'-monophosphate
Uridine 5'-monophosphate + Adenosine triphosphateADP + Uridine 5'-diphosphate
Dolichol phosphate + Uridine diphosphate-N-acetylglucosamineUridine 5'-monophosphate + N-acetyl-α-D-glucosaminyl-diphosphodolichol
KEGG Reactions
water + Uridine 5'-monophosphatephosphate + Uridine
Uridine 5'-diphosphate + waterphosphate + hydron + Uridine 5'-monophosphate
hydron + Orotidylic acidCarbon dioxide + Uridine 5'-monophosphate
Adenosine triphosphate + Uridine 5'-monophosphateUridine 5'-diphosphate + ADP
Uracil + Phosphoribosyl pyrophosphatePyrophosphate + Uridine 5'-monophosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-014i-2953000000-f54596d9a11bbe82adc5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2953000000-f54596d9a11bbe82adc5JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9611000000-d241a590ba092a9137caJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fza-5933100000-760b9e44040ca55554b3JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03fr-0194000000-c8bedd9fabaccee15ef6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0910000000-da7fb1ddd74c36aec368JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0900000000-b2c9787a3d982ecb858eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9102000000-f8b96709e62e0857c40aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9102000000-f8b96709e62e0857c40aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1911000000-7963cbf4b5fd08b83e4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-404805c9de28466c7072JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9800000000-5522394ff370886e5a5dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-8934000000-b1f27b01000758ca974dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-c3e61932dae0623d3924JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4db5b2019eff03b12956JSpectraViewer
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
  • Levine, H. L., Brody, R. S., Westheimer, F. H. (1980). "Inhibition of orotidine-5'-phosphate decarboxylase by 1-(5'-phospho-beta-d-ribofuranosyl)barbituric acid, 6-azauridine 5'-phosphate, and uridine 5'-phosphate." Biochemistry 19:4993-4999.7006681
  • Kurtz, J. E., Exinger, F., Erbs, P., Jund, R. (1999). "New insights into the pyrimidine salvage pathway of Saccharomyces cerevisiae: requirement of six genes for cytidine metabolism." Curr Genet 36:130-136.10501935
  • 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
  • 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
  • Gao, X. D., Kaigorodov, V., Jigami, Y. (1999). "YND1, a homologue of GDA1, encodes membrane-bound apyrase required for Golgi N- and O-glycosylation in Saccharomyces cerevisiae." J Biol Chem 274:21450-21456.10409709
Synthesis Reference:Wang Xing; Wang Xiuwen; Yin Mengxin; Xiao Zijun; Ma Cuiqing; Lin Zhixin; Wang Peng George; Xu Ping Production of uridine 5'-monophosphate by Corynebacterium ammoniagenes ATCC 6872 using a statistically improved biocatalytic process. Applied microbiolo
External Links:
ResourceLink
CHEBI ID16695
HMDB IDHMDB00288
Pubchem Compound ID6030
Kegg IDC00105
ChemSpider ID5808
FOODB IDFDB007508
WikipediaUridine_monophosphate
BioCyc IDUMP

Enzymes

General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
Catalyzes the initial step in the synthesis of dolichol- P-P-oligosaccharides
Gene Name:
ALG7
Uniprot ID:
P07286
Molecular weight:
50367.39844
Reactions
UDP-N-acetyl-D-glucosamine + dolichyl phosphate → UMP + N-acetyl-D-glucosaminyl-diphosphodolichol.
General function:
Involved in catalytic activity
Specific function:
Orotidine 5'-phosphate = UMP + CO(2)
Gene Name:
URA3
Uniprot ID:
P03962
Molecular weight:
29239.30078
Reactions
Orotidine 5'-phosphate → UMP + CO(2).
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP2 and PHO5
Gene Name:
NPP1
Uniprot ID:
P25353
Molecular weight:
84733.20313
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
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 hydrolase activity
Specific function:
Catalyzes the hydrolysis of phosphoanhydride bonds of nucleoside tri- and di-phosphates. Has equal high activity toward ADP/ATP, GDP/GTP, and UDP/UTP and approximately 50% less toward CDP/CTP and thiamine pyrophosphate. Has no activity toward GMP. Required for Golgi glycosylation and cell wall integrity. Together with CDC55, required for adenovirus E4orf4 (early region 4 open reading frame 4) induced toxicity, the apyrase activity is not required for this function. Plays a role in sphingolipid synthesis
Gene Name:
YND1
Uniprot ID:
P40009
Molecular weight:
71851.20313
Reactions
ATP + 2 H(2)O → AMP + 2 phosphate.
General function:
Involved in catalytic activity
Specific function:
Mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and PHO5
Gene Name:
NPP2
Uniprot ID:
P39997
Molecular weight:
57354.10156
Reactions
A dinucleotide + H(2)O → 2 mononucleotides.
General function:
Involved in ATP binding
Specific function:
Furnishes the cell with pyrimidines. Accepts UMP, and dUMP as phosphate acceptors with high activity; to a lesser extent, it can also use IMP, GMP, dGMP, 5-iodo-dUMP, XMP, and dTMP as substrates. ATP and dATP are the best phosphate donors; can use GTP, dGTP, dCTP, and dTTP to some degree (30-50%)
Gene Name:
URA6
Uniprot ID:
P15700
Molecular weight:
22933.0
Reactions
ATP + UMP → ADP + UDP.
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 transferase activity, transferring hexosyl groups
Specific function:
Involved in protein N-glycosylation. Essential for the second step of the dolichol-linked oligosaccharide pathway
Gene Name:
ALG13
Uniprot ID:
P53178
Molecular weight:
22660.90039
Reactions
UDP-N-acetyl-D-glucosamine + N-acetyl-D-glucosaminyl-diphosphodolichol → UDP + N,N'-diacetylchitobiosyl-diphosphodolichol.
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:
Nucleotide transport and metabolism
Specific function:
Catalyzes the conversion of uracil and 5-phospho-alpha- D-ribose 1-diphosphate (PRPP) to UMP and diphosphate
Gene Name:
FUR1
Uniprot ID:
P18562
Molecular weight:
24594.19922
Reactions
UMP + diphosphate → uracil + 5-phospho-alpha-D-ribose 1-diphosphate.

Transporters

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