Adenosine-5'-[Beta, Gamma-Methylene]Triphosphate

Identification

Name
Adenosine-5'-[Beta, Gamma-Methylene]Triphosphate
Accession Number
DB03909  (EXPT00416)
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: 505.2082
Monoisotopic: 505.016480601
Chemical Formula
C11H18N5O12P3
InChI Key
UFZTZBNSLXELAL-IOSLPCCCSA-N
InChI
InChI=1S/C11H18N5O12P3/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(27-11)1-26-31(24,25)28-30(22,23)4-29(19,20)21/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H,24,25)(H2,12,13,14)(H2,19,20,21)/t5-,7-,8-,11-/m1/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}methyl)phosphonic acid
SMILES
[H][[email protected]]1(COP(O)(=O)OP(O)(=O)CP(O)(O)=O)O[[email protected]@]([H])(N2C=NC3=C(N)N=CN=C23)[[email protected]]([H])(O)[[email protected]]1([H])O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFolylpolyglutamate synthaseNot AvailableLactobacillus casei
UChemotaxis protein CheANot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UUDP-N-acetylmuramate--L-alanine ligaseNot AvailableHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
UThermoresistant gluconokinaseNot AvailableEscherichia coli (strain K12)
UPhosphoribosylglycinamide formyltransferase 2Not AvailableEscherichia coli (strain K12)
UInsulin receptorNot AvailableHuman
USarcoplasmic/endoplasmic reticulum calcium ATPase 1Not AvailableHuman
UPyridoxal kinaseNot AvailableHuman
UPhosphoglycerate kinase 1Not AvailableHuman
USerine/threonine-protein kinase PknBNot AvailableMycobacterium tuberculosis
URibokinaseNot AvailableEscherichia coli (strain K12)
UPutative sugar kinaseNot AvailableSalmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
UProbable butyrate kinase 2Not AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
UKinesin-like protein KIF1ANot AvailableHuman
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
C13741
PubChem Compound
91532
PubChem Substance
46506243
ChemSpider
82651
BindingDB
18135
ChEBI
40532
ChEMBL
CHEMBL133463
HET
ACP
PDB Entries
1dag / 1dah / 1e22 / 1g3r / 1gll / 1gqt / 1gqy / 1i44 / 1i58 / 1i5a
show 216 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 Solubility4.45 mg/mLALOGPS
logP-1.1ALOGPS
logP-6.6ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.38ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area269.9 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity98.17 m3·mol-1ChemAxon
Polarizability39.97 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9077
Blood Brain Barrier+0.8625
Caco-2 permeable-0.7248
P-glycoprotein substrateNon-substrate0.588
P-glycoprotein inhibitor INon-inhibitor0.8872
P-glycoprotein inhibitor IINon-inhibitor0.9751
Renal organic cation transporterNon-inhibitor0.9607
CYP450 2C9 substrateNon-substrate0.8709
CYP450 2D6 substrateNon-substrate0.8323
CYP450 3A4 substrateNon-substrate0.5648
CYP450 1A2 substrateNon-inhibitor0.8555
CYP450 2C9 inhibitorNon-inhibitor0.9178
CYP450 2D6 inhibitorNon-inhibitor0.8662
CYP450 2C19 inhibitorNon-inhibitor0.9061
CYP450 3A4 inhibitorNon-inhibitor0.7692
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9622
Ames testNon AMES toxic0.8044
CarcinogenicityNon-carcinogens0.8801
BiodegradationNot ready biodegradable0.9514
Rat acute toxicity2.5963 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9661
hERG inhibition (predictor II)Non-inhibitor0.7883
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 purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Bisphosphonates / Aminopyrimidines and derivatives / Monoalkyl phosphates / Imidolactams / N-substituted imidazoles / Heteroaromatic compounds
show 11 more
Substituents
Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Monosaccharide phosphate / Pentose monosaccharide / Bisphosphonate / Imidazopyrimidine
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
nucleoside triphosphate analogue (CHEBI:40532)

Targets

Kind
Protein
Organism
Lactobacillus casei
Pharmacological action
Unknown
General Function
Tetrahydrofolylpolyglutamate synthase activity
Specific Function
Conversion of folates to polyglutamate derivatives. It prefers 5,10-methylenetetrahydrofolate, rather than 10-formyltetrahydrofolate as folate substrate.
Gene Name
fgs
Uniprot ID
P15925
Uniprot Name
Folylpolyglutamate synthase
Molecular Weight
46588.815 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
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Phosphorelay sensor kinase activity
Specific Function
Involved in the transmission of sensory signals from the chemoreceptors to the flagellar motors. CheA is autophosphorylated; it can transfer its phosphate group to either CheB or CheY (By similarity).
Gene Name
cheA
Uniprot ID
Q56310
Uniprot Name
Chemotaxis protein CheA
Molecular Weight
75555.3 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
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Unknown
General Function
Udp-n-acetylmuramate-l-alanine ligase activity
Specific Function
Cell wall formation.
Gene Name
murC
Uniprot ID
P45066
Uniprot Name
UDP-N-acetylmuramate--L-alanine ligase
Molecular Weight
51993.93 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Gluconokinase activity
Specific Function
Not Available
Gene Name
gntK
Uniprot ID
P46859
Uniprot Name
Thermoresistant gluconokinase
Molecular Weight
19543.13 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Phosphoribosylglycinamide formyltransferase activity
Specific Function
Catalyzes two reactions: the first one is the production of beta-formyl glycinamide ribonucleotide (GAR) from formate, ATP and beta GAR; the second, a side reaction, is the production of acetyl pho...
Gene Name
purT
Uniprot ID
P33221
Uniprot Name
Phosphoribosylglycinamide formyltransferase 2
Molecular Weight
42433.335 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
Receptor signaling protein tyrosine kinase activity
Specific Function
Receptor tyrosine kinase which mediates the pleiotropic actions of insulin. Binding of insulin leads to phosphorylation of several intracellular substrates, including, insulin receptor substrates (...
Gene Name
INSR
Uniprot ID
P06213
Uniprot Name
Insulin receptor
Molecular Weight
156331.465 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
Protein homodimerization activity
Specific Function
Key regulator of striated muscle performance by acting as the major Ca(2+) ATPase responsible for the reuptake of cytosolic Ca(2+) into the sarcoplasmic reticulum. Catalyzes the hydrolysis of ATP c...
Gene Name
ATP2A1
Uniprot ID
O14983
Uniprot Name
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
Molecular Weight
110251.36 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
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Required for synthesis of pyridoxal-5-phosphate from vitamin B6.
Gene Name
PDXK
Uniprot ID
O00764
Uniprot Name
Pyridoxal kinase
Molecular Weight
35102.105 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
Human
Pharmacological action
Unknown
General Function
Phosphoglycerate kinase activity
Specific Function
In addition to its role as a glycolytic enzyme, it seems that PGK-1 acts as a polymerase alpha cofactor protein (primer recognition protein).
Gene Name
PGK1
Uniprot ID
P00558
Uniprot Name
Phosphoglycerate kinase 1
Molecular Weight
44614.36 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
Protein kinase that regulates many aspects of mycobacterial physiology, and is critical for growth in vitro and survival of the pathogen in the host (PubMed:24706757). Is a key component of a signal transduction pathway that regulates cell growth, cell shape and cell division via phosphorylation of target proteins such as GarA, GlmU, PapA5, PbpA, FhaB (Rv0019c), FhaA (Rv0020c), MviN, PstP, EmbR, Rv1422, Rv1747 and RseA (PubMed:15978616, PubMed:15985609, PubMed:15987910, PubMed:16436437, PubMed:16817899, PubMed:16980473, PubMed:19121323, PubMed:19826007, PubMed:20025669, PubMed:21423706, PubMed:22275220). Also catalyzes the phosphorylation of the core proteasome alpha-subunit (PrcA), and thereby regulates the proteolytic activity of the proteasome (PubMed:25224505). Is a major regulator of the oxygen-dependent replication switch since PknB activity is necessary for reactivation of cells from the hypoxic state (PubMed:24409094). Shows a strong preference for Thr versus Ser as the phosphoacceptor. Overexpression of PknB alters cell morphology and leads to cell death (PubMed:24706757) (PubMed:24409094).
Specific Function
Atp binding
Gene Name
pknB
Uniprot ID
P9WI81
Uniprot Name
Serine/threonine-protein kinase PknB
Molecular Weight
66509.265 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Ribokinase activity
Specific Function
Not Available
Gene Name
rbsK
Uniprot ID
P0A9J6
Uniprot Name
Ribokinase
Molecular Weight
32290.19 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
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Pharmacological action
Unknown
General Function
Ribokinase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8ZKR2
Uniprot Name
Putative sugar kinase
Molecular Weight
34237.43 Da
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Butyrate kinase activity
Specific Function
Not Available
Gene Name
buk2
Uniprot ID
Q9X278
Uniprot Name
Probable butyrate kinase 2
Molecular Weight
42022.04 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Motor activity
Specific Function
Motor for anterograde axonal transport of synaptic vesicle precursors.
Gene Name
KIF1A
Uniprot ID
Q12756
Uniprot Name
Kinesin-like protein KIF1A
Molecular Weight
191062.325 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:20