Deoxyuridine monophosphate

Identification

Generic Name
Deoxyuridine monophosphate
DrugBank Accession Number
DB03800
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 308.1819
Monoisotopic: 308.040951914
Chemical Formula
C9H13N2O8P
Synonyms
  • 2'-deoxyuridine 5'-monophosphate
  • 2'-Deoxyuridine 5'-phosphate
  • Deoxyuridine 5'-phosphate
  • Deoxyuridylate
  • Deoxyuridylic acid
  • dUMP

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDeoxyuridine 5'-triphosphate nucleotidohydrolaseNot AvailableEscherichia coli (strain K12)
UThymidylate synthaseNot AvailableLactobacillus casei
UThymidylate synthaseNot AvailableEscherichia coli (strain K12)
UThymidylate synthaseNot AvailableHumans
UThymidylate synthase ThyXNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UPol polyproteinNot AvailableFIV
UDeoxyuridine 5'-triphosphate nucleotidohydrolaseNot AvailableMycobacterium tuberculosis
UThymidylate synthaseNot AvailablePneumocystis carinii
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Pyrimidine MetabolismMetabolic
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)Disease
beta-Ureidopropionase DeficiencyDisease
Dihydropyrimidinase DeficiencyDisease
UMP Synthase Deficiency (Orotic Aciduria)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleoside monophosphates. These are pyrimidine nucleotides with a monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine deoxyribonucleotides
Direct Parent
Pyrimidine 2'-deoxyribonucleoside monophosphates
Alternative Parents
Pyrimidones / Monoalkyl phosphates / Hydroxypyrimidines / Hydropyrimidines / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Hydroxypyrimidine / Monoalkyl phosphate / Organic nitrogen compound
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate, deoxyuridine phosphate (CHEBI:17622) / Deoxyribonucleotides (C00365)
Affected organisms
Not Available

Chemical Identifiers

UNII
N9J10KFG94
CAS number
964-26-1
InChI Key
JSRLJPSBLDHEIO-SHYZEUOFSA-N
InChI
InChI=1S/C9H13N2O8P/c12-5-3-8(11-2-1-7(13)10-9(11)14)19-6(5)4-18-20(15,16)17/h1-2,5-6,8,12H,3-4H2,(H,10,13,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
IUPAC Name
{[(2R,3S,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=CC(=O)NC1=O

References

General References
Not Available
Human Metabolome Database
HMDB0001409
KEGG Compound
C00365
PubChem Compound
65063
PubChem Substance
46506977
ChemSpider
58574
BindingDB
50028108
ChEBI
17622
ChEMBL
CHEMBL211312
ZINC
ZINC000004228260
PDBe Ligand
UMP
Wikipedia
Deoxyuridine_monophosphate
PDB Entries
1aiq / 1axw / 1bid / 1bp0 / 1bp6 / 1bpj / 1bq1 / 1ci7 / 1dna / 1f28
show 211 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.97 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.6Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.23Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area145.63 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity61.93 m3·mol-1Chemaxon
Polarizability25.86 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.736
Blood Brain Barrier+0.8502
Caco-2 permeable-0.7964
P-glycoprotein substrateNon-substrate0.6961
P-glycoprotein inhibitor INon-inhibitor0.7951
P-glycoprotein inhibitor IINon-inhibitor0.9467
Renal organic cation transporterNon-inhibitor0.903
CYP450 2C9 substrateNon-substrate0.715
CYP450 2D6 substrateNon-substrate0.8507
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8951
CYP450 2C9 inhibitorNon-inhibitor0.8857
CYP450 2D6 inhibitorNon-inhibitor0.9161
CYP450 2C19 inhibitorNon-inhibitor0.8741
CYP450 3A4 inhibitorNon-inhibitor0.8089
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9289
Ames testNon AMES toxic0.5863
CarcinogenicityNon-carcinogens0.8247
BiodegradationNot ready biodegradable0.5481
Rat acute toxicity2.2793 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9497
hERG inhibition (predictor II)Non-inhibitor0.8131
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-9410000000-3abd5b4815950ff662f5
MS/MS Spectrum - Quattro_QQQ 10V, N/ALC-MS/MSsplash10-001i-9100000000-c9b7092bb72f342d372f
MS/MS Spectrum - Quattro_QQQ 25V, N/ALC-MS/MSsplash10-001i-9000000000-d2272878a49bc62c1955
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-001i-9000000000-69451d809e5517ef09cb
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-01ta-9803000000-f0e26cbfb75f3fb7b36e
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-01ta-9803000000-f0e26cbfb75f3fb7b36e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-4459000000-f364a8cd597ae8fc74c0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-4920000000-b43d72f4e45a2e7306a2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-7009000000-5e3d4695b1742d303ce9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9010000000-b14f5b56f26fc4eb9196
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dr-3900000000-121e7f54f767a62ae98a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-163331d827e39ba13a45
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-180.3062736
predicted
DarkChem Lite v0.1.0
[M-H]-181.4470736
predicted
DarkChem Lite v0.1.0
[M-H]-181.3449736
predicted
DarkChem Lite v0.1.0
[M-H]-158.5781
predicted
DeepCCS 1.0 (2019)
[M+H]+179.3222736
predicted
DarkChem Lite v0.1.0
[M+H]+182.1023736
predicted
DarkChem Lite v0.1.0
[M+H]+183.3472736
predicted
DarkChem Lite v0.1.0
[M+H]+160.93663
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.5498736
predicted
DarkChem Lite v0.1.0
[M+Na]+181.3186736
predicted
DarkChem Lite v0.1.0
[M+Na]+181.3285736
predicted
DarkChem Lite v0.1.0
[M+Na]+167.5205
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
This enzyme is involved in nucleotide metabolism: it produces dUMP, the immediate precursor of thymidine nucleotides and it decreases the intracellular concentration of dUTP so that uracil cannot b...
Gene Name
dut
Uniprot ID
P06968
Uniprot Name
Deoxyuridine 5'-triphosphate nucleotidohydrolase
Molecular Weight
16155.34 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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis. This protein also binds to its mRNA thus repressing its own translation.
Gene Name
thyA
Uniprot ID
P0A884
Uniprot Name
Thymidylate synthase
Molecular Weight
30479.475 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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name
TYMS
Uniprot ID
P04818
Uniprot Name
Thymidylate synthase
Molecular Weight
35715.65 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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Thymidylate synthase (fad) activity
Specific Function
Catalyzes the formation of dTMP and tetrahydrofolate from dUMP and methylenetetrahydrofolate.
Gene Name
thyX
Uniprot ID
Q9WYT0
Uniprot Name
Thymidylate synthase ThyX
Molecular Weight
26003.785 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. [Article]
  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. [Article]
Kind
Protein
Organism
FIV
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
During replicative cycle of retroviruses, the reverse-transcribed viral DNA is integrated into the host chromosome by the viral integrase enzyme. RNase H activity is associated with the reverse tra...
Gene Name
pol
Uniprot ID
P16088
Uniprot Name
Pol polyprotein
Molecular Weight
127493.025 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. [Article]
  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. [Article]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
This enzyme is involved in nucleotide metabolism: it produces dUMP, the immediate precursor of thymidine nucleotides and it decreases the intracellular concentration of dUTP so that uracil cannot be incorporated into DNA.
Specific Function
Dutp diphosphatase activity
Gene Name
dut
Uniprot ID
P9WNS5
Uniprot Name
Deoxyuridine 5'-triphosphate nucleotidohydrolase
Molecular Weight
15802.815 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. [Article]
  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. [Article]
Kind
Protein
Organism
Pneumocystis carinii
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Not Available
Gene Name
THYA
Uniprot ID
P13100
Uniprot Name
Thymidylate synthase
Molecular Weight
34361.99 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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52