Uridine monophosphate

Identification

Name
Uridine monophosphate
Accession Number
DB03685  (EXPT03155)
Type
Small Molecule
Groups
Experimental
Description

5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position.

Structure
Thumb
Synonyms
  • 5'-uridylic acid
  • UMP
  • Uridine 5'-monophosphate
  • Uridine 5'-phosphoric acid
  • Uridine phosphate
  • Uridine-5'-monophosphate
Categories
Not Available
UNII
E2OU15WN0N
CAS number
58-97-9
Weight
Average: 324.1813
Monoisotopic: 324.035866536
Chemical Formula
C9H13N2O9P
InChI Key
DJJCXFVJDGTHFX-XVFCMESISA-N
InChI
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
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
SMILES
O[[email protected]]1[[email protected]@H](O)[[email protected]@H](O[[email protected]@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUridine-cytidine kinase-like 1Not AvailableHuman
UGalactose-1-phosphate uridylyltransferaseNot AvailableEscherichia coli (strain K12)
UThymidylate synthaseNot AvailableLactobacillus casei
UGlycosyltransferase 6 domain-containing protein 1Not AvailableHuman
UU6 snRNA-associated Sm-like protein LSm6Not AvailableHuman
UUracil phosphoribosyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UBeta-1,4-galactosyltransferase 1Not AvailableHuman
UInterferon-stimulated gene 20 kDa proteinNot AvailableHuman
UOrotidine 5'-phosphate decarboxylaseNot AvailableBacillus subtilis (strain 168)
UBifunctional protein PyrRNot AvailableBacillus caldolyticus
UUracil phosphoribosyltransferaseNot AvailableGeobacillus kaustophilus (strain HTA426)
UBifunctional polymyxin resistance protein ArnANot AvailableEscherichia coli (strain K12)
URibosomal small subunit pseudouridine synthase ANot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
Amikacin Action PathwayDrug action
Spectinomycin Action PathwayDrug action
Clindamycin Action PathwayDrug action
Gentamicin Action PathwayDrug action
Netilmicin Action PathwayDrug action
Doxycycline Action PathwayDrug action
Minocycline Action PathwayDrug action
Lymecycline Action PathwayDrug action
Tigecycline Action PathwayDrug action
Beta Ureidopropionase DeficiencyDisease
Dihydropyrimidinase DeficiencyDisease
UMP Synthase Deiciency (Orotic Aciduria)Disease
Lactose SynthesisMetabolic
Congenital disorder of glycosylation CDG-IIdDisease
Tobramycin Action PathwayDrug action
Arbekacin Action PathwayDrug action
Methacycline Action PathwayDrug action
Azithromycin Action PathwayDrug action
Telithromycin Action PathwayDrug action
Streptomycin Action PathwayDrug action
Demeclocycline Action PathwayDrug action
Oxytetracycline Action PathwayDrug action
Tetracycline Action PathwayDrug action
GLUT-1 deficiency syndromeDisease
Lincomycin Action PathwayDrug action
Troleandomycin Action PathwayDrug action
Josamycin Action PathwayDrug action
Pyrimidine MetabolismMetabolic
Clarithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB00288
KEGG Compound
C00105
ChemSpider
5808
BindingDB
50398699
ChEBI
16695
ChEMBL
CHEMBL214393
HET
U5P
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)202 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility12.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.44 m3·mol-1ChemAxon
Polarizability26.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9132
Blood Brain Barrier+0.8209
Caco-2 permeable-0.8159
P-glycoprotein substrateNon-substrate0.7686
P-glycoprotein inhibitor INon-inhibitor0.8844
P-glycoprotein inhibitor IINon-inhibitor0.9719
Renal organic cation transporterNon-inhibitor0.9445
CYP450 2C9 substrateNon-substrate0.6802
CYP450 2D6 substrateNon-substrate0.8553
CYP450 3A4 substrateNon-substrate0.5695
CYP450 1A2 substrateNon-inhibitor0.9039
CYP450 2C9 inhibitorNon-inhibitor0.9086
CYP450 2D6 inhibitorNon-inhibitor0.91
CYP450 2C19 inhibitorNon-inhibitor0.887
CYP450 3A4 inhibitorNon-inhibitor0.9167
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.959
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9005
BiodegradationReady biodegradable0.5346
Rat acute toxicity2.0585 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9698
hERG inhibition (predictor II)Non-inhibitor0.8041
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (5 TMS)GC-MSsplash10-014i-2953000000-f54596d9a11bbe82adc5
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-2953000000-f54596d9a11bbe82adc5
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-03fr-0194000000-c8bedd9fabaccee15ef6
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-03di-0910000000-da7fb1ddd74c36aec368
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-03di-0900000000-b2c9787a3d982ecb858e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-00ba-9102000000-f8b96709e62e0857c40a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-00ba-9102000000-f8b96709e62e0857c40a
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of chemical entities known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Nucleosides, nucleotides, and analogues
Sub Class
Pyrimidine nucleotides
Direct Parent
Pyrimidine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / Monosaccharide phosphates / Pyrimidones / Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Oxolanes / Heteroaromatic compounds / Ureas
show 9 more
Substituents
Pyrimidine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Pentose monosaccharide / Pyrimidone / Monoalkyl phosphate / Hydropyrimidine
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidine ribonucleoside 5'-monophosphate, uridine 5'-phosphate (CHEBI:16695 ) / Ribonucleotides (C00105 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Uridine kinase activity
Specific Function
May contribute to UTP accumulation needed for blast transformation and proliferation.
Gene Name
UCKL1
Uniprot ID
Q9NWZ5
Uniprot Name
Uridine-cytidine kinase-like 1
Molecular Weight
61140.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
galT
Uniprot ID
P09148
Uniprot Name
Galactose-1-phosphate uridylyltransferase
Molecular Weight
39645.395 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Lactobacillus casei
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis.
Gene Name
thyA
Uniprot ID
P00469
Uniprot Name
Thymidylate synthase
Molecular Weight
36579.235 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity, transferring hexosyl groups
Specific Function
Not Available
Gene Name
GLT6D1
Uniprot ID
Q7Z4J2
Uniprot Name
Glycosyltransferase 6 domain-containing protein 1
Molecular Weight
36273.575 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Component of LSm protein complexes, which are involved in RNA processing and may function in a chaperone-like manner, facilitating the efficient association of RNA processing factors with their sub...
Gene Name
LSM6
Uniprot ID
P62312
Uniprot Name
U6 snRNA-associated Sm-like protein LSm6
Molecular Weight
9127.525 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Uracil phosphoribosyltransferase activity
Specific Function
Catalyzes the conversion of uracil and 5-phospho-alpha-D-ribose 1-diphosphate (PRPP) to UMP and diphosphate.
Gene Name
upp
Uniprot ID
Q9WZI0
Uniprot Name
Uracil phosphoribosyltransferase
Molecular Weight
23320.02 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Udp-galactosyltransferase activity
Specific Function
The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoprot...
Gene Name
B4GALT1
Uniprot ID
P15291
Uniprot Name
Beta-1,4-galactosyltransferase 1
Molecular Weight
43919.895 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
U3 snorna binding
Specific Function
Interferon-induced antiviral exoribonuclease that acts on single-stranded RNA and also has minor activity towards single-stranded DNA. Exhibits antiviral activity against RNA viruses including hepa...
Gene Name
ISG20
Uniprot ID
Q96AZ6
Uniprot Name
Interferon-stimulated gene 20 kDa protein
Molecular Weight
20363.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Orotidine-5'-phosphate decarboxylase activity
Specific Function
Catalyzes the decarboxylation of orotidine 5'-monophosphate (OMP) to uridine 5'-monophosphate (UMP).
Gene Name
pyrF
Uniprot ID
P25971
Uniprot Name
Orotidine 5'-phosphate decarboxylase
Molecular Weight
25991.84 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Bacillus caldolyticus
Pharmacological action
Unknown
General Function
Uracil phosphoribosyltransferase activity
Specific Function
Regulates transcriptional attenuation of the pyrimidine nucleotide (pyr) operon by binding in a uridine-dependent manner to specific sites on pyr mRNA. This disrupts an antiterminator hairpin in th...
Gene Name
pyrR
Uniprot ID
P41007
Uniprot Name
Bifunctional protein PyrR
Molecular Weight
19937.85 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Geobacillus kaustophilus (strain HTA426)
Pharmacological action
Unknown
General Function
Uracil phosphoribosyltransferase activity
Specific Function
Catalyzes the conversion of uracil and 5-phospho-alpha-D-ribose 1-diphosphate (PRPP) to UMP and diphosphate.
Gene Name
upp
Uniprot ID
Q5KUI3
Uniprot Name
Uracil phosphoribosyltransferase
Molecular Weight
22831.48 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Udp-glucuronate decarboxylase activity
Specific Function
Bifunctional enzyme that catalyzes the oxidative decarboxylation of UDP-glucuronic acid (UDP-GlcUA) to UDP-4-keto-arabinose (UDP-Ara4O) and the addition of a formyl group to UDP-4-amino-4-deoxy-L-a...
Gene Name
arnA
Uniprot ID
P77398
Uniprot Name
Bifunctional polymyxin resistance protein ArnA
Molecular Weight
74288.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Rna binding
Specific Function
Responsible for synthesis of pseudouridine from uracil-516 in 16S ribosomal RNA.
Gene Name
rsuA
Uniprot ID
P0AA43
Uniprot Name
Ribosomal small subunit pseudouridine synthase A
Molecular Weight
25865.12 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:25