NAV

5-Bromothienyldeoxyuridine

Identification

Generic Name
5-Bromothienyldeoxyuridine
DrugBank Accession Number
DB03804
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 389.222
Monoisotopic: 387.972854873
Chemical Formula
C13H13BrN2O5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThymidine kinase
ligand
HHV-1
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 pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleosides
Sub Class
Pyrimidine 2'-deoxyribonucleosides
Direct Parent
Pyrimidine 2'-deoxyribonucleosides
Alternative Parents
Pyrimidones / 2,5-disubstituted thiophenes / Aryl bromides / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols / Lactams
show 8 more
Substituents
2,5-disubstituted thiophene / Alcohol / Aromatic heteromonocyclic compound / Aryl bromide / Aryl halide / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
IGUZFFOBAZCVRK-VAOFZXAKSA-N
InChI
InChI=1S/C13H13BrN2O5S/c14-10-2-1-9(22-10)6-4-16(13(20)15-12(6)19)11-3-7(18)8(5-17)21-11/h1-2,4,7-8,11,17-18H,3,5H2,(H,15,19,20)/t7-,8+,11+/m0/s1
IUPAC Name
5-(5-bromothiophen-2-yl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])CO)N1C=C(C2=CC=C(Br)S2)C(=O)NC1=O

References

General References
Not Available
PubChem Compound
446725
PubChem Substance
46507054
ChemSpider
394009
ChEMBL
CHEMBL1231486
ZINC
ZINC000003802687
PDBe Ligand
BTD
PDB Entries
1ki4

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 Solubility0.14 mg/mLALOGPS
logP0.68ALOGPS
logP1Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.69Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area99.1 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity79.18 m3·mol-1Chemaxon
Polarizability33.17 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9373
Blood Brain Barrier+0.5774
Caco-2 permeable-0.796
P-glycoprotein substrateNon-substrate0.6935
P-glycoprotein inhibitor INon-inhibitor0.8686
P-glycoprotein inhibitor IINon-inhibitor0.9066
Renal organic cation transporterNon-inhibitor0.8917
CYP450 2C9 substrateNon-substrate0.736
CYP450 2D6 substrateNon-substrate0.8496
CYP450 3A4 substrateNon-substrate0.5665
CYP450 1A2 substrateNon-inhibitor0.8183
CYP450 2C9 inhibitorNon-inhibitor0.7663
CYP450 2D6 inhibitorNon-inhibitor0.8865
CYP450 2C19 inhibitorNon-inhibitor0.7999
CYP450 3A4 inhibitorNon-inhibitor0.7929
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6264
Ames testNon AMES toxic0.8369
CarcinogenicityNon-carcinogens0.7499
BiodegradationNot ready biodegradable0.8797
Rat acute toxicity1.9001 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Non-inhibitor0.7707
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/MSsplash10-000i-0049000000-8f3da9ff05b15690f218
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-9044000000-b1f2f6626368fe821676
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00ds-1169000000-cb476c96b9a4bb4ccc64
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0190000000-916216b48c246f218ea4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0191000000-f37af1c40ec0003cca59
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fv-3593000000-c67d09a71c1e80cb5a43
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]-171.45341
predicted
DeepCCS 1.0 (2019)
[M+H]+173.84898
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.7615
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidine kinase
Kind
Protein
Organism
HHV-1
Pharmacological action
Unknown
Actions
Ligand
General Function
Thymidine kinase activity
Specific Function
In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate the...
Gene Name
TK
Uniprot ID
Q9QNF7
Uniprot Name
Thymidine kinase
Molecular Weight
40896.475 Da
References
  1. Champness JN, Bennett MS, Wien F, Visse R, Summers WC, Herdewijn P, de Clerq E, Ostrowski T, Jarvest RL, Sanderson MR: Exploring the active site of herpes simplex virus type-1 thymidine kinase by X-ray crystallography of complexes with aciclovir and other ligands. Proteins. 1998 Aug 15;32(3):350-61. [Article]

Drug created at June 13, 2005 13:24 / Updated at April 30, 2023 10:33