Identification

Generic Name
(4S)-5-Fluoro-4-hydroxy-3,4-dihydro-2(1H)-pyrimidinone
DrugBank Accession Number
DB04135
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 132.0931
Monoisotopic: 132.033505619
Chemical Formula
C4H5FN2O2
Synonyms
  • (4S)-5-Fluoro-4-hydroxy-3,4-dihydropyrimidin-2(1H)-one

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCytosine deaminaseNot 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

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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Hydropyrimidines / Ureas / Fluorohydrins / Vinyl fluorides / Fluoroalkenes / Azacyclic compounds / Alkanolamines / Organopnictogen compounds / Organofluorides / Organic oxides
show 2 more
Substituents
1,2,3,4-tetrahydropyrimidine / Aliphatic heteromonocyclic compound / Alkanolamine / Azacycle / Carbonic acid derivative / Carbonyl group / Fluoroalkene / Fluorohydrin / Haloalkene / Halohydrin
show 14 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
organofluorine compound, hydroxypyrimidine, pyrimidone (CHEBI:42694)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
PRVUBDAKZJCBTI-VKHMYHEASA-N
InChI
InChI=1S/C4H5FN2O2/c5-2-1-6-4(9)7-3(2)8/h1,3,8H,(H2,6,7,9)/t3-/m0/s1
IUPAC Name
(4S)-5-fluoro-4-hydroxy-1,2,3,4-tetrahydropyrimidin-2-one
SMILES
[H]N1C=C(F)[C@H](O)N([H])C1=O

References

General References
Not Available
PubChem Compound
448302
PubChem Substance
46506652
ChemSpider
395142
ZINC
ZINC000005834564
PDBe Ligand
FPY
PDB Entries
1ra0 / 1ra5 / 1rak

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 Solubility36.1 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)10ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.36 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.97 m3·mol-1ChemAxon
Polarizability10.08 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9538
Blood Brain Barrier+0.9005
Caco-2 permeable-0.6007
P-glycoprotein substrateNon-substrate0.7169
P-glycoprotein inhibitor INon-inhibitor0.7824
P-glycoprotein inhibitor IINon-inhibitor0.9948
Renal organic cation transporterNon-inhibitor0.918
CYP450 2C9 substrateNon-substrate0.7588
CYP450 2D6 substrateNon-substrate0.8392
CYP450 3A4 substrateNon-substrate0.7215
CYP450 1A2 substrateNon-inhibitor0.7784
CYP450 2C9 inhibitorNon-inhibitor0.9058
CYP450 2D6 inhibitorNon-inhibitor0.9152
CYP450 2C19 inhibitorNon-inhibitor0.8292
CYP450 3A4 inhibitorNon-inhibitor0.9032
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9412
Ames testNon AMES toxic0.7374
CarcinogenicityNon-carcinogens0.8948
BiodegradationNot ready biodegradable0.9868
Rat acute toxicity2.3070 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9653
hERG inhibition (predictor II)Non-inhibitor0.9666
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

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of cytosine to uracil. Is involved in the pyrimidine salvage pathway, which allows the cell to utilize cytosine for pyrimidine nucleotide synthesis. Is also abl...
Gene Name
codA
Uniprot ID
P25524
Uniprot Name
Cytosine deaminase
Molecular Weight
47590.66 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