5-Fluoro-2'-Deoxyuridine-5'-Monophosphate

Identification

Name
5-Fluoro-2'-Deoxyuridine-5'-Monophosphate
Accession Number
DB03761  (EXPT03176)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 326.1723
Monoisotopic: 326.031530087
Chemical Formula
C9H12FN2O8P
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-4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
O[[email protected]]1C[[email protected]@H](O[[email protected]@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB60394
KEGG Compound
C04242
PubChem Compound
8642
PubChem Substance
46508904
ChemSpider
8321
BindingDB
50022238
ChEBI
2129
ChEMBL
CHEMBL886
HET
UFP
PDB Entries
1b02 / 1bjg / 1dnf / 1icg / 1id9 / 1o28 / 1o29 / 1tdb / 1tls / 1tsn
show 13 more

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.91 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.1ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area149.12 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.45 m3·mol-1ChemAxon
Polarizability25.42 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-MSNot Available
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

Taxonomy

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
Pyrimidine 2'-deoxyribonucleoside monophosphate / Halopyrimidine / Monoalkyl phosphate / Pyrimidone / Aryl fluoride / Aryl halide / Hydropyrimidine / Pyrimidine / Organic phosphoric acid derivative / Phosphoric acid ester
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:2129)

Targets

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. [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
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. [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
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. [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 November 09, 2017 03:32