5-Bromo-2'-deoxyuridine 5'-(dihydrogen phosphate)

Identification

Name
5-Bromo-2'-deoxyuridine 5'-(dihydrogen phosphate)
Accession Number
DB01903  (EXPT00758)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
51432-32-7
Weight
Average: 387.078
Monoisotopic: 385.951464529
Chemical Formula
C9H12BrN2O8P
InChI Key
LHLHVDBXXZVYJT-RRKCRQDMSA-N
InChI
InChI=1S/C9H12BrN2O8P/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-bromo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid
SMILES
O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=C(Br)C(=O)NC1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidylate synthase ThyXNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
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
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

References

General References
Not Available
External Links
PubChem Compound
93036
PubChem Substance
46506735
ChemSpider
83989
BindingDB
50010238
ChEMBL
CHEMBL1160593
ZINC
ZINC000006090961
PDBe Ligand
BRU
PDB Entries
115d / 165d / 1a35 / 1aio / 1awc / 1cs7 / 1d3r / 1d9r / 1da1 / 1dcr
show 112 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
logP-0.81ChemAxon
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.63 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.54 m3·mol-1ChemAxon
Polarizability28.84 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7648
Blood Brain Barrier+0.7372
Caco-2 permeable-0.7844
P-glycoprotein substrateNon-substrate0.6884
P-glycoprotein inhibitor INon-inhibitor0.745
P-glycoprotein inhibitor IINon-inhibitor0.9172
Renal organic cation transporterNon-inhibitor0.8918
CYP450 2C9 substrateNon-substrate0.7632
CYP450 2D6 substrateNon-substrate0.8381
CYP450 3A4 substrateSubstrate0.5133
CYP450 1A2 substrateNon-inhibitor0.7903
CYP450 2C9 inhibitorNon-inhibitor0.8209
CYP450 2D6 inhibitorNon-inhibitor0.8851
CYP450 2C19 inhibitorNon-inhibitor0.7835
CYP450 3A4 inhibitorNon-inhibitor0.758
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7526
Ames testNon AMES toxic0.6163
CarcinogenicityNon-carcinogens0.7908
BiodegradationNot ready biodegradable0.9106
Rat acute toxicity2.3169 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9541
hERG inhibition (predictor II)Non-inhibitor0.729
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 bromides / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Secondary alcohols
show 8 more
Substituents
Pyrimidine 2'-deoxyribonucleoside monophosphate / Halopyrimidine / Monoalkyl phosphate / Pyrimidone / Aryl bromide / Aryl halide / Hydropyrimidine / Pyrimidine / Organic phosphoric acid derivative / Phosphoric acid ester
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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]

Drug created on June 13, 2005 07:24 / Updated on May 02, 2020 03:35

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