3'-Azido-3'-Deoxythymidine-5'-Monophosphate

Identification

Name
3'-Azido-3'-Deoxythymidine-5'-Monophosphate
Accession Number
DB03666  (EXPT00583)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
97YMU05VPJ
CAS number
Not Available
Weight
Average: 347.2212
Monoisotopic: 347.063084339
Chemical Formula
C10H14N5O7P
InChI Key
OIFWQOKDSPDILA-XLPZGREQSA-N
InChI
InChI=1S/C10H14N5O7P/c1-5-3-15(10(17)12-9(5)16)8-2-6(13-14-11)7(22-8)4-21-23(18,19)20/h3,6-8H,2,4H2,1H3,(H,12,16,17)(H2,18,19,20)/t6-,7+,8+/m0/s1
IUPAC Name
{[(2S,3S,5R)-3-azido-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid
SMILES
[H][[email protected]@]1(C[[email protected]]([H])(N=[N+]=[N-])[[email protected]@]([H])(COP(O)(O)=O)O1)N1C=C(C)C(O)=NC1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidylate kinaseNot AvailableHuman
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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
65374
PubChem Substance
46506173
ChemSpider
58846
ChEMBL
CHEMBL257695
HET
ATM
PDB Entries
1e98 / 1e99 / 1e9b / 1e9d / 1n5y / 1n6q / 1w2h / 2jau / 2tmk / 2wwi
show 9 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
Water Solubility3.56 mg/mLALOGPS
logP-0.07ALOGPS
logP-0.055ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.26ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area158.32 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity72.9 m3·mol-1ChemAxon
Polarizability29.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7915
Blood Brain Barrier+0.5952
Caco-2 permeable-0.7704
P-glycoprotein substrateNon-substrate0.6451
P-glycoprotein inhibitor INon-inhibitor0.8248
P-glycoprotein inhibitor IINon-inhibitor0.9404
Renal organic cation transporterNon-inhibitor0.8913
CYP450 2C9 substrateNon-substrate0.6349
CYP450 2D6 substrateNon-substrate0.8583
CYP450 3A4 substrateSubstrate0.5607
CYP450 1A2 substrateNon-inhibitor0.8664
CYP450 2C9 inhibitorNon-inhibitor0.8531
CYP450 2D6 inhibitorNon-inhibitor0.9123
CYP450 2C19 inhibitorNon-inhibitor0.8415
CYP450 3A4 inhibitorNon-inhibitor0.8089
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9245
Ames testAMES toxic0.6044
CarcinogenicityNon-carcinogens0.8076
BiodegradationReady biodegradable0.7501
Rat acute toxicity2.4191 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8615
hERG inhibition (predictor II)Non-inhibitor0.8032
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 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
Monoalkyl phosphates / Hydropyrimidines / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Ureas / Lactams / Azo imides / Azo compounds / Oxacyclic compounds
show 5 more
Substituents
Pyrimidone / Monoalkyl phosphate / Hydropyrimidine / Organic phosphoric acid derivative / Phosphoric acid ester / Alkyl phosphate / Tetrahydrofuran / Heteroaromatic compound / Vinylogous amide / Azo compound
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Uridylate kinase activity
Specific Function
Catalyzes the conversion of dTMP to dTDP.
Gene Name
DTYMK
Uniprot ID
P23919
Uniprot Name
Thymidylate kinase
Molecular Weight
23819.105 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]
  3. 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. [PubMed:10592235]
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 December 01, 2017 15:17