Bis(Adenosine)-5'-Pentaphosphate

Identification

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Name
Bis(Adenosine)-5'-Pentaphosphate
Accession Number
DB01717  (EXPT00535)
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: 916.3669
Monoisotopic: 916.014595222
Chemical Formula
C20H29N10O22P5
InChI Key
OIMACDRJUANHTJ-XPWFQUROSA-N
InChI
InChI=1S/C20H29N10O22P5/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(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]phosphinic acid
SMILES
[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAdenylate kinaseNot AvailableBacillus subtilis (strain 168)
UAdenylate kinaseNot AvailableGeobacillus stearothermophilus
UAdenylate kinaseNot AvailableBacillus globisporus
UAdenylate kinase 2, mitochondrialNot AvailableHumans
UAdenylate kinase 8Not AvailableHumans
UAdenylate kinaseNot AvailableEscherichia coli (strain K12)
UAdenylate kinase isoenzyme 1Not AvailableHumans
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
KEGG Compound
C04058
PubChem Compound
440210
PubChem Substance
46505205
ChemSpider
389195
BindingDB
50435017
ChEBI
28898
ChEMBL
CHEMBL437508
HET
AP5
PDB Entries
1ake / 1aky / 1e4v / 1e4y / 1p3j / 1s3g / 1z83 / 1zak / 1zin / 1zio
show 50 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 Solubility6.92 mg/mLALOGPS
logP-0.2ALOGPS
logP-11ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.41ChemAxon
pKa (Strongest Basic)5.3ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area480.5 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity176.98 m3·mol-1ChemAxon
Polarizability72.12 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8092
Blood Brain Barrier+0.8289
Caco-2 permeable-0.7292
P-glycoprotein substrateNon-substrate0.6
P-glycoprotein inhibitor INon-inhibitor0.825
P-glycoprotein inhibitor IINon-inhibitor0.949
Renal organic cation transporterNon-inhibitor0.9328
CYP450 2C9 substrateNon-substrate0.8508
CYP450 2D6 substrateNon-substrate0.834
CYP450 3A4 substrateNon-substrate0.517
CYP450 1A2 substrateNon-inhibitor0.8771
CYP450 2C9 inhibitorNon-inhibitor0.9107
CYP450 2D6 inhibitorNon-inhibitor0.9012
CYP450 2C19 inhibitorNon-inhibitor0.9003
CYP450 3A4 inhibitorNon-inhibitor0.7715
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.891
Ames testNon AMES toxic0.878
CarcinogenicityNon-carcinogens0.9115
BiodegradationNot ready biodegradable0.9936
Rat acute toxicity2.8102 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9512
hERG inhibition (predictor II)Non-inhibitor0.594
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 / Purine nucleotide sugars / Purine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / N-substituted imidazoles
show 10 more
Substituents
(5'->5')-dinucleotide / Purine ribonucleoside polyphosphate / Purine nucleotide sugar / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Monosaccharide phosphate
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
diadenosyl pentaphosphate (CHEBI:28898)

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism.
Gene Name
adk
Uniprot ID
P16304
Uniprot Name
Adenylate kinase
Molecular Weight
24119.24 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
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism.
Gene Name
adk
Uniprot ID
P27142
Uniprot Name
Adenylate kinase
Molecular Weight
24142.65 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
Bacillus globisporus
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism.
Gene Name
adk
Uniprot ID
P84139
Uniprot Name
Adenylate kinase
Molecular Weight
23888.06 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
Humans
Pharmacological action
Unknown
General Function
Atp binding
Specific Function
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism. Adenylate kinase ...
Gene Name
AK2
Uniprot ID
P54819
Uniprot Name
Adenylate kinase 2, mitochondrial
Molecular Weight
26477.44 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
Humans
Pharmacological action
Unknown
General Function
Nucleoside diphosphate kinase activity
Specific Function
Nucleoside monophosphate (NMP) kinase that catalyzes the reversible transfer of the terminal phosphate group between nucleoside triphosphates and monophosphates. Has highest activity toward AMP, an...
Gene Name
AK8
Uniprot ID
Q96MA6
Uniprot Name
Adenylate kinase 8
Molecular Weight
54925.01 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism.
Gene Name
adk
Uniprot ID
P69441
Uniprot Name
Adenylate kinase
Molecular Weight
23585.845 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
Humans
Pharmacological action
Unknown
General Function
Nucleoside diphosphate kinase activity
Specific Function
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Also displays broad nucleoside diphosphate kinase activity. Plays an important role in cellular energy homeost...
Gene Name
AK1
Uniprot ID
P00568
Uniprot Name
Adenylate kinase isoenzyme 1
Molecular Weight
21634.725 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 04, 2019 05:21