NAV

5-fluoro-2'-deoxyuridine-5'-monophosphate

Identification

Generic Name
5-fluoro-2'-deoxyuridine-5'-monophosphate
DrugBank Accession Number
DB03761
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 326.1723
Monoisotopic: 326.031530087
Chemical Formula
C9H12FN2O8P
Synonyms
  • 5-fluorodeoxyuridine monophosphate
  • 5FdUMP
  • F-dUMP
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThymidylate synthaseNot AvailableEscherichia coli (strain K12)
UThymidylate synthaseNot AvailableLactobacillus casei
UThymidylate synthase ThyXNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UThymidylate synthase 1Not AvailableBacillus subtilis (strain 168)
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
Not Available
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 / Halopyrimidines / Monoalkyl phosphates / Aryl fluorides / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols
show 8 more
Substituents
Alcohol / Alkyl phosphate / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:2129)
Affected organisms
Not Available

Chemical Identifiers

UNII
7CJ707H131
CAS number
134-46-3
InChI Key
HFEKDTCAMMOLQP-RRKCRQDMSA-N
InChI
InChI=1S/C9H12FN2O8P/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18)/t5-,6+,7+/m0/s1
IUPAC Name
{[(2R,3S,5R)-5-(5-fluoro-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=C(F)C(=O)NC1=O

References

General References
Not Available
Human Metabolome Database
HMDB0060394
KEGG Compound
C04242
PubChem Compound
8642
PubChem Substance
46508904
ChemSpider
8321
BindingDB
50022238
ChEBI
2129
ChEMBL
CHEMBL886
ZINC
ZINC000003875881
PDBe Ligand
UFP
PDB Entries
1b02 / 1bjg / 1dnf / 1icg / 1id9 / 1o28 / 1o29 / 1tdb / 1tls / 1tsn …
show 31 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
logP-1.4Chemaxon
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
Refractivity62.13 m3·mol-1Chemaxon
Polarizability25.9 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6958
Blood Brain Barrier+0.8148
Caco-2 permeable-0.8028
P-glycoprotein substrateNon-substrate0.6785
P-glycoprotein inhibitor INon-inhibitor0.7377
P-glycoprotein inhibitor IINon-inhibitor0.9518
Renal organic cation transporterNon-inhibitor0.9041
CYP450 2C9 substrateNon-substrate0.7653
CYP450 2D6 substrateNon-substrate0.8386
CYP450 3A4 substrateSubstrate0.5186
CYP450 1A2 substrateNon-inhibitor0.8049
CYP450 2C9 inhibitorNon-inhibitor0.8183
CYP450 2D6 inhibitorNon-inhibitor0.889
CYP450 2C19 inhibitorNon-inhibitor0.7844
CYP450 3A4 inhibitorNon-inhibitor0.7365
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8032
Ames testAMES toxic0.5231
CarcinogenicityNon-carcinogens0.7826
BiodegradationNot ready biodegradable0.9638
Rat acute toxicity2.5320 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9584
hERG inhibition (predictor II)Non-inhibitor0.7017
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-MSsplash10-0002-9410000000-870fe831cb893d234c57
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0279000000-7924bcf36d9355cd0146
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-2009000000-10a804f759e56ce72016
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9001000000-2db2cd80a846faa9a126
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000t-7911000000-67bcc26fd9c46aa2601b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-9120000000-d1308f78d1abf0e16200
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2900000000-41cc28f8a75938278e0d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.021271
predicted
DarkChem Lite v0.1.0
[M-H]-164.73021
predicted
DeepCCS 1.0 (2019)
[M+H]+179.381771
predicted
DarkChem Lite v0.1.0
[M+H]+167.08842
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.159671
predicted
DarkChem Lite v0.1.0
[M+Na]+173.86111
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidylate synthase
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]
Details2. Thymidylate synthase
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]
Details3. Thymidylate synthase ThyX
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]
Details4. Thymidylate synthase 1
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Provides the sole de novo source of dTMP for DNA biosynthesis.
Gene Name
thyA1
Uniprot ID
P0CI79
Uniprot Name
Thymidylate synthase 1
Molecular Weight
32807.07 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