Record Information
Version1.0
Created at2020-04-17 18:42:00 UTC
Updated at2020-11-18 16:38:49 UTC
CannabisDB IDCDB004838
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameUridine 5'-monophosphate
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. Within humans, uridine 5'-monophosphate participates in a number of enzymatic reactions. In particular, uridine 5'-monophosphate can be converted into uridine 5'-diphosphate; which is catalyzed by the enzyme UMP-CMP kinase. In addition, uridine 5'-monophosphate can be biosynthesized from uridine 5'-diphosphate; which is catalyzed by the enzyme soluble calcium-activated nucleotidase 1. In humans, uridine 5'-monophosphate is involved in the metabolic disorder called the glut-1 deficiency syndrome pathway. Outside of the human body, Uridine 5'-monophosphate has been detected, but not quantified in, several different foods, such as naranjilla, cereals and cereal products, swedes, jicama, and chives. This could make uridine 5'-monophosphate a potential biomarker for the consumption of these foods. A pyrimidine ribonucleoside 5'-monophosphate having uracil as the nucleobase. Uridine 5'-monophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
5'-UMPChEBI
5'Uridylic acidChEBI
pUChEBI
UMPChEBI
Uridine 5'-(dihydrogen phosphate)ChEBI
Uridine 5'-phosphateChEBI
Uridine 5'-phosphoric acidChEBI
Uridine monophosphateChEBI
URIDINE-5'-monophosphATEChEBI
UridylateChEBI
Uridylic acidChEBI
5'UridylateGenerator
Uridine 5'-(dihydrogen phosphoric acid)Generator
Uridine monophosphoric acidGenerator
URIDINE-5'-monophosphoric acidGenerator
Uridine 5'-monophosphoric acidGenerator
Uridine 5'-phosphorateHMDB
Uridine mono(dihydrogen phosphate)HMDB
Uridine phosphateHMDB
Acids, uridylicHMDB
monoPhosphate, uridineHMDB
5'-monoPhosphate, uridineHMDB
Uridylic acidsHMDB
Acid, uridylicHMDB
Uridine 5' monophosphateHMDB
Chemical FormulaC9H13N2O9P
Average Molecular Weight324.18
Monoisotopic Molecular Weight324.0359
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 Nameuridine monophosphate
CAS Registry Number58-97-9
SMILES
O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O
InChI Identifier
InChI=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
InChI KeyDJJCXFVJDGTHFX-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
  • 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSUridine 5'-monophosphate, 5 TMS, GC-MS Spectrumsplash10-014i-2953000000-f54596d9a11bbe82adc5Spectrum
GC-MSUridine 5'-monophosphate, non-derivatized, GC-MS Spectrumsplash10-014i-2953000000-f54596d9a11bbe82adc5Spectrum
Predicted GC-MSUridine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002b-9611000000-d241a590ba092a9137caSpectrum
Predicted GC-MSUridine 5'-monophosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fza-5933100000-760b9e44040ca55554b3Spectrum
Predicted GC-MSUridine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUridine 5'-monophosphate, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03fr-0194000000-c8bedd9fabaccee15ef6Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0910000000-da7fb1ddd74c36aec368Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0900000000-b2c9787a3d982ecb858eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00ba-9102000000-f8b96709e62e0857c40aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ba-9102000000-f8b96709e62e0857c40aSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-05bb-9632000000-b8ba3967a5a4fa269881Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-9400000000-3d07e2fe57474fcd3e4bSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-5039000000-c23fa9bbd6fcb5cf53d9Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004j-9111000000-5b5b7e0858807d74c34aSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-00os-9700000000-963e2c76c3f98512da72Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-01r2-9510000000-b934a101047c97c33c7eSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-3019000000-1bc3f90d1e162da0bc3cSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004j-9211000000-5a9399a9558a148f349eSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004j-9111000000-47125abb177da73df355Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004j-9000000000-c462cab8b32dc6c50361Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9010000000-f3876f614e314a89ace6Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-ef91704ffebfee64c252Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004j-9100000000-585ad2bb25aaaee5854cSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-60d486fec926bde90d2cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1911000000-7963cbf4b5fd08b83e4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-5900000000-404805c9de28466c7072Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9800000000-5522394ff370886e5a5dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03mi-8934000000-b1f27b01000758ca974dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-c3e61932dae0623d3924Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4db5b2019eff03b12956Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
UMP-CMP kinaseCMPK11p32P30085 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Ectonucleoside triphosphate diphosphohydrolase 1ENTPD110q24P49961 details
Soluble calcium-activated nucleotidase 1CANT117q25.3Q8WVQ1 details
Ectonucleoside triphosphate diphosphohydrolase 3ENTPD33p21.3O75355 details
Uridine-cytidine kinase 1UCK19q34.13Q9HA47 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Beta-1,4-galactosyltransferase 1B4GALT19p13P15291 details
Inosine triphosphate pyrophosphataseITPA20pQ9BY32 details
Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]NUDT29p13P50583 details
Ectonucleoside triphosphate diphosphohydrolase 4ENTPD48p21.3Q9Y227 details
Ectonucleoside triphosphate diphosphohydrolase 6ENTPD620p11.21O75354 details
Ectonucleoside triphosphate diphosphohydrolase 5ENTPD514q24O75356 details
Uridine 5'-monophosphate synthaseUMPS3q13P11172 details
UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferaseDPAGT111q23.3Q9H3H5 details
Uridine diphosphate glucose pyrophosphataseNUDT1414q32.33O95848 details
Uridine-cytidine kinase 2UCK21q23Q9BZX2 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
ENTPD4 proteinENTPD48p21.3Q8NE73 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
UMP-CMP kinase 2, mitochondrialCMPK22p25.2Q5EBM0 details
Uridine-cytidine kinase-like 1UCKL120q13.33Q9NWZ5 details
Ectonucleoside triphosphate diphosphohydrolase 8ENTPD89q34.3Q5MY95 details
N-acetylglucosamine-1-phosphotransferase subunits alpha/betaGNPTAB12q23.2Q3T906 details
Uracil phosphoribosyltransferase homologUPRTQ96BW1 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Soluble calcium-activated nucleotidase 1CANT117q25.3Q8WVQ1 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Beta-1,4-galactosyltransferase 1B4GALT19p13P15291 details
Inosine triphosphate pyrophosphataseITPA20pQ9BY32 details
Uridine diphosphate glucose pyrophosphataseNUDT1414q32.33O95848 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
N-acetylglucosamine-1-phosphotransferase subunits alpha/betaGNPTAB12q23.2Q3T906 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 3ENPP36q22O14638 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
N-acetylglucosamine-1-phosphotransferase subunits alpha/betaGNPTAB12q23.2Q3T906 details
Concentrations Data
Not Available
HMDB IDHMDB0000288
DrugBank IDDB03685
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031248
KNApSAcK IDC00007311
Chemspider ID5808
KEGG Compound IDC00105
BioCyc IDUMP
BiGG ID33873
Wikipedia LinkUridine_monophosphate
METLIN IDNot Available
PubChem Compound6030
PDB IDNot Available
ChEBI ID16695
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 47 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
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
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
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
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
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
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
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
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

Only showing the first 10 proteins. There are 47 proteins in total.