P1-(5'-Adenosyl)P5-(5'-Thymidyl)Pentaphosphate

Identification

Name
P1-(5'-Adenosyl)P5-(5'-Thymidyl)Pentaphosphate
Accession Number
DB03280  (EXPT02996)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 891.3541
Monoisotopic: 891.008112861
Chemical Formula
C20H30N7O23P5
InChI Key
JCFDSPQTEMXXLO-SLFMBYJQSA-N
InChI
InChI=1S/C20H30N7O23P5/c1-8-3-26(20(32)25-18(8)31)12-2-9(28)10(45-12)4-43-51(33,34)47-53(37,38)49-55(41,42)50-54(39,40)48-52(35,36)44-5-11-14(29)15(30)19(46-11)27-7-24-13-16(21)22-6-23-17(13)27/h3,6-7,9-12,14-15,19,28-30H,2,4-5H2,1H3,(H,33,34)(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,22,23)(H,25,31,32)/t9-,10+,11+,12+,14+,15+,19+/m0/s1
IUPAC Name
[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid
SMILES
[H][[email protected]]1(O)C[[email protected]@]([H])(O[[email protected]]1([H])COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[[email protected]@]1([H])O[[email protected]@]([H])(N2C=NC3=C(N)N=CN=C23)[[email protected]]([H])(O)[[email protected]]1([H])O)N1C=C(C)C(O)=NC1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidine kinaseNot AvailableHHV-1
UThymidylate kinaseNot AvailableMycobacterium tuberculosis
UThymidylate kinaseNot AvailableHuman
UThymidylate kinaseNot AvailableShigella flexneri
UThymidine kinaseNot AvailableEHV-4
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
447202
PubChem Substance
46505960
ChemSpider
394363
BindingDB
50366828
ChEMBL
CHEMBL1236157
HET
T5A
PDB Entries
1mrn / 1p75 / 1p7c / 2wwh / 3tmk / 4tmk / 4uxh

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 Solubility9.73 mg/mLALOGPS
logP0.41ALOGPS
logP-6.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.41ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area443.55 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity169.51 m3·mol-1ChemAxon
Polarizability68.76 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5164
Blood Brain Barrier-0.566
Caco-2 permeable-0.7013
P-glycoprotein substrateSubstrate0.6839
P-glycoprotein inhibitor INon-inhibitor0.7984
P-glycoprotein inhibitor IINon-inhibitor0.9887
Renal organic cation transporterNon-inhibitor0.9393
CYP450 2C9 substrateNon-substrate0.7549
CYP450 2D6 substrateNon-substrate0.8312
CYP450 3A4 substrateSubstrate0.5879
CYP450 1A2 substrateNon-inhibitor0.8746
CYP450 2C9 inhibitorNon-inhibitor0.8961
CYP450 2D6 inhibitorNon-inhibitor0.8944
CYP450 2C19 inhibitorNon-inhibitor0.9016
CYP450 3A4 inhibitorNon-inhibitor0.7679
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9201
Ames testNon AMES toxic0.7782
CarcinogenicityNon-carcinogens0.8204
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.4775 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9149
hERG inhibition (predictor II)Inhibitor0.5092
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/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 (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
(5'->5')-dinucleotides
Sub Class
Not Available
Direct Parent
(5'->5')-dinucleotides
Alternative Parents
Purine ribonucleoside polyphosphates / Pyrimidine 2'-deoxyribonucleoside polyphosphates / Purine nucleotide sugars / Purine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates
show 16 more
Substituents
(5'->5')-dinucleotide / Purine ribonucleoside polyphosphate / Pyrimidine 2'-deoxyribonucleoside polyphosphate / Purine nucleotide sugar / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine
show 36 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
HHV-1
Pharmacological action
Unknown
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
P03176
Uniprot Name
Thymidine kinase
Molecular Weight
40971.555 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]
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]
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
Shigella flexneri
Pharmacological action
Unknown
General Function
Thymidylate kinase activity
Specific 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 d...
Gene Name
tmk
Uniprot ID
P0A721
Uniprot Name
Thymidylate kinase
Molecular Weight
23782.93 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]
Kind
Protein
Organism
EHV-4
Pharmacological action
Unknown
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
P24425
Uniprot Name
Thymidine kinase
Molecular Weight
38784.035 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 15:11