NAV

1-{(2S,5S)-4-FLUORO-5-[(TRITYLOXY)METHYL]TETRAHYDROFURAN-2-YL}PYRIMIDINE-2,4(1H,3H)-DIONE

Identification

Generic Name
1-{(2S,5S)-4-FLUORO-5-[(TRITYLOXY)METHYL]TETRAHYDROFURAN-2-YL}PYRIMIDINE-2,4(1H,3H)-DIONE
DrugBank Accession Number
DB04685
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 472.5075
Monoisotopic: 472.179835503
Chemical Formula
C28H25FN2O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDeoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrialNot AvailableHumans
UDeoxyuridine 5'-triphosphate nucleotidohydrolase, putativeNot AvailablePlasmodium falciparum (isolate 3D7)
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 triphenyl compounds. These are aromatic compounds containing a triphenyl moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Triphenyl compounds
Sub Class
Not Available
Direct Parent
Triphenyl compounds
Alternative Parents
Pyrimidine 2',3'-dideoxyribonucleosides / Benzylethers / Pyrimidones / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Tetrahydrofurans / Lactams / Ureas / Azacyclic compounds
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Substituents
Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Azacycle / Benzylether / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organofluorine compound, pyrimidine 2',3'-dideoxyribonucleoside (CHEBI:42311)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GJNIPWYJQUGERM-BFLUCZKCSA-N
InChI
InChI=1S/C28H25FN2O4/c29-23-18-26(31-17-16-25(32)30-27(31)33)35-24(23)19-34-28(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-17,23-24,26H,18-19H2,(H,30,32,33)/t23-,24+,26+/m0/s1
IUPAC Name
1-[(2R,4S,5R)-4-fluoro-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
[H][C@]1(F)C[C@@]([H])(O[C@]1([H])COC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)N1C=CC(=O)NC1=O

References

General References
Not Available
PubChem Compound
4369390
PubChem Substance
46507952
ChemSpider
3571965
BindingDB
50190544
ChEMBL
CHEMBL209720
ZINC
ZINC000012504465
PDBe Ligand
DUX
PDB Entries
1vyq

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 Solubility0.00117 mg/mLALOGPS
logP4.3ALOGPS
logP5.18Chemaxon
logS-5.6ALOGPS
pKa (Strongest Acidic)9.86Chemaxon
pKa (Strongest Basic)-4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area67.87 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity129.16 m3·mol-1Chemaxon
Polarizability48.78 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9848
Blood Brain Barrier+0.9766
Caco-2 permeable-0.7197
P-glycoprotein substrateNon-substrate0.6847
P-glycoprotein inhibitor IInhibitor0.6644
P-glycoprotein inhibitor IIInhibitor0.577
Renal organic cation transporterNon-inhibitor0.7149
CYP450 2C9 substrateNon-substrate0.7997
CYP450 2D6 substrateNon-substrate0.8646
CYP450 3A4 substrateSubstrate0.6115
CYP450 1A2 substrateNon-inhibitor0.7767
CYP450 2C9 inhibitorInhibitor0.5645
CYP450 2D6 inhibitorNon-inhibitor0.8685
CYP450 2C19 inhibitorInhibitor0.5426
CYP450 3A4 inhibitorInhibitor0.5271
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7171
Ames testNon AMES toxic0.5222
CarcinogenicityNon-carcinogens0.7734
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4522 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9611
hERG inhibition (predictor II)Non-inhibitor0.6032
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0020900000-740bd6bbefdb53883a2b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-0322900000-2b53f1ef660a9771a8c8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1910100000-8fcfefd04515e573c137
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ffx-5310900000-a1903987fe60e5431a8f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-090r-3911300000-b2cbacc9d68d9a63b29b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fr6-4941300000-fc2786a35793c0329e4e
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]-203.15059
predicted
DeepCCS 1.0 (2019)
[M+H]+205.046
predicted
DeepCCS 1.0 (2019)
[M+Na]+210.82472
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Deoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Poly(a) rna 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
P33316
Uniprot Name
Deoxyuridine 5'-triphosphate nucleotidohydrolase, mitochondrial
Molecular Weight
26562.975 Da
References
  1. 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]
Details2. Deoxyuridine 5'-triphosphate nucleotidohydrolase, putative
Kind
Protein
Organism
Plasmodium falciparum (isolate 3D7)
Pharmacological action
Unknown
General Function
Dutp diphosphatase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8II92
Uniprot Name
Deoxyuridine 5'-triphosphate nucleotidohydrolase, putative
Molecular Weight
19572.98 Da

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52