Identification
Name5-Fluoro-2'-Deoxyuridine-5'-Monophosphate
Accession NumberDB03761  (EXPT03176)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 326.1723
Monoisotopic: 326.031530087
Chemical FormulaC9H12FN2O8P
InChI KeyHFEKDTCAMMOLQP-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[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(F)C(O)=NC1=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Thymidylate synthaseProteinunknownNot AvailableEscherichia coli (strain K12)P0A884 details
Thymidylate synthaseProteinunknownNot AvailableLactobacillus caseiP00469 details
Thymidylate synthase ThyXProteinunknownNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)Q9WYT0 details
Thymidylate synthase 1ProteinunknownNot AvailableBacillus subtilis (strain 168)P0CI79 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleotides
Direct ParentPyrimidine 2'-deoxyribonucleoside monophosphates
Alternative ParentsPyrimidones / Halopyrimidines / Monoalkyl phosphates / Aryl fluorides / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols
SubstituentsPyrimidine 2'-deoxyribonucleoside monophosphate / Halopyrimidine / Monoalkyl phosphate / Pyrimidone / Aryl fluoride / Aryl halide / Hydropyrimidine / Pyrimidine / Organic phosphoric acid derivative / Phosphoric acid ester
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptorspyrimidine 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 June 11, 2017 16:24