2'-deoxy-5-(hydroxymethyl)uridine 5'-(dihydrogen phosphate)

Identification

Name
2'-deoxy-5-(hydroxymethyl)uridine 5'-(dihydrogen phosphate)
Accession Number
DB03846  (EXPT00248)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 5-hydroxymethyluridine-2'-deoxy-5'-monophosphate
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 338.2079
Monoisotopic: 338.0515166
Chemical Formula
C10H15N2O9P
InChI Key
WEBVWKFGRVLCNS-XLPZGREQSA-N
InChI
InChI=1S/C10H15N2O9P/c13-3-5-2-12(10(16)11-9(5)15)8-1-6(14)7(21-8)4-20-22(17,18)19/h2,6-8,13-14H,1,3-4H2,(H,11,15,16)(H2,17,18,19)/t6-,7+,8+/m0/s1
IUPAC Name
{[(2R,3S,5R)-3-hydroxy-5-[5-(hydroxymethyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl]oxolan-2-yl]methoxy}phosphonic acid
SMILES
[H]N1C(=O)N(C=C(CO)C1=O)[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidylate kinaseNot AvailableMycobacterium tuberculosis
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
447206
PubChem Substance
46505421
ChemSpider
394364
ChEMBL
CHEMBL1160818
ZINC
ZINC000013538464
PDBe Ligand
5HU
PDB Entries
1mrs / 1y6g / 1y8z / 4e9h / 4ea4 / 4ea5 / 4ew0

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
Water Solubility8.39 mg/mLALOGPS
logP-1.6ALOGPS
logP-2.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area165.86 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity68.06 m3·mol-1ChemAxon
Polarizability28.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8916
Blood Brain Barrier+0.8241
Caco-2 permeable-0.6913
P-glycoprotein substrateNon-substrate0.644
P-glycoprotein inhibitor INon-inhibitor0.6845
P-glycoprotein inhibitor IINon-inhibitor0.9371
Renal organic cation transporterNon-inhibitor0.8849
CYP450 2C9 substrateNon-substrate0.7507
CYP450 2D6 substrateNon-substrate0.832
CYP450 3A4 substrateNon-substrate0.5077
CYP450 1A2 substrateNon-inhibitor0.8732
CYP450 2C9 inhibitorNon-inhibitor0.8685
CYP450 2D6 inhibitorNon-inhibitor0.8912
CYP450 2C19 inhibitorNon-inhibitor0.833
CYP450 3A4 inhibitorNon-inhibitor0.9513
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9371
Ames testAMES toxic0.5334
CarcinogenicityNon-carcinogens0.8324
BiodegradationNot ready biodegradable0.672
Rat acute toxicity2.4301 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9013
hERG inhibition (predictor II)Non-inhibitor0.7312
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
Monoalkyl phosphates / Pyrimidones / Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Tetrahydrofurans / Secondary alcohols / Ureas / Lactams / Oxacyclic compounds
show 7 more
Substituents
Pyrimidine 2'-deoxyribonucleoside monophosphate / Pyrimidone / Monoalkyl phosphate / Hydropyrimidine / Organic phosphoric acid derivative / Phosphoric acid ester / Pyrimidine / Alkyl phosphate / Heteroaromatic compound / Tetrahydrofuran
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the reversible phosphorylation of deoxythymidine monophosphate (dTMP) to deoxythymidine diphosphate (dTDP), using ATP as its preferred phosphoryl donor. Situated at the junction of both de novo and salvage pathways of deoxythymidine triphosphate (dTTP) synthesis, is essential for DNA synthesis and cellular growth. Has a broad specificity for nucleoside triphosphates, being highly active with ATP or dATP as phosphate donors, and less active with ITP, GTP, CTP and UTP.
Specific Function
Atp binding
Gene Name
tmk
Uniprot ID
P9WKE1
Uniprot Name
Thymidylate kinase
Molecular Weight
22634.285 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 12, 2020 10:52

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