Adenosine 5'-[γ-thio]triphosphate

Identification

Name
Adenosine 5'-[γ-thio]triphosphate
Accession Number
DB02930  (EXPT02847, EXPT00458, DB01660)
Type
Small Molecule
Groups
Experimental
Description

A nucleoside triphosphate analogue that is ATP in which one of the oxygens attached to 3-phosphate group is replaced by sulfur.

Structure
Thumb
Synonyms
  • (gamma-S)ATP
  • Adenosine 5-O-(3-thiotriphophate)
  • Adenosine 5'-(3-thio)triphosphate
  • Adenosine 5'-(gamma-thio)triphosphate
  • adenosine 5'-[gamma-thio]triphosphate
  • Adenosine 5'-O-(3-thiotriphosphate)
  • ATP-gamma-S
  • ATP-gammaS
  • gamma-Thio-ATP
Categories
Not Available
UNII
Not Available
CAS number
35094-46-3
Weight
Average: 523.247
Monoisotopic: 522.972901227
Chemical Formula
C10H16N5O12P3S
InChI Key
NLTUCYMLOPLUHL-KQYNXXCUSA-N
InChI
InChI=1S/C10H16N5O12P3S/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(25-10)1-24-28(18,19)26-29(20,21)27-30(22,23)31/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H,20,21)(H2,11,12,13)(H2,22,23,31)/t4-,6-,7-,10-/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}oxy)phosphonothioic acid
SMILES
[H][[email protected]]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=S)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
UADP-ribosyl cyclase 2Not AvailableHuman
USynapsin-1Not AvailableHuman
U[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrialNot AvailableHuman
U6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1Not AvailableHuman
UMismatch repair endonuclease PMS2Not AvailableHuman
UProtein RecANot AvailableMycobacterium paratuberculosis (strain ATCC BAA-968 / K-10)
UProtein RecANot AvailableDeinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
UProtein RecANot AvailableMycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
UChloramphenicol 3-O phosphotransferaseNot AvailableStreptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)
UPhosphoribosylglycinamide formyltransferase 2Not AvailableEscherichia coli (strain K12)
UATP-dependent DNA helicase RecQNot AvailableEscherichia coli (strain K12)
UDNA polymerase III subunit tauNot AvailableEscherichia coli (strain K12)
USerine/threonine-protein kinase PknBNot AvailableMycobacterium tuberculosis
UCag alphaNot AvailableHelicobacter pylori
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
C13742
PubChem Compound
440317
PubChem Substance
46507118
ChemSpider
389291
BindingDB
50118217
ChEBI
27575
ChEMBL
CHEMBL131890
HET
AGS
PDB Entries
1aux / 1bif / 1gjv / 1h74 / 1h7u / 1isg / 1k6m / 1kjj / 1kp8 / 1kwo
show 123 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 Solubility2.26 mg/mLALOGPS
logP-0.5ALOGPS
logP-4.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.03ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area262.06 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity103.81 m3·mol-1ChemAxon
Polarizability40.88 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7731
Blood Brain Barrier+0.8388
Caco-2 permeable-0.708
P-glycoprotein substrateNon-substrate0.7019
P-glycoprotein inhibitor INon-inhibitor0.8871
P-glycoprotein inhibitor IINon-inhibitor0.9916
Renal organic cation transporterNon-inhibitor0.9567
CYP450 2C9 substrateNon-substrate0.7877
CYP450 2D6 substrateNon-substrate0.8238
CYP450 3A4 substrateNon-substrate0.5758
CYP450 1A2 substrateNon-inhibitor0.8599
CYP450 2C9 inhibitorNon-inhibitor0.9002
CYP450 2D6 inhibitorNon-inhibitor0.8954
CYP450 2C19 inhibitorNon-inhibitor0.9057
CYP450 3A4 inhibitorNon-inhibitor0.8962
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9734
Ames testNon AMES toxic0.8038
CarcinogenicityNon-carcinogens0.8791
BiodegradationNot ready biodegradable0.9109
Rat acute toxicity2.5484 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9834
hERG inhibition (predictor II)Non-inhibitor0.762
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 diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside diphosphates
Alternative Parents
Purine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Organic pyrophosphates / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / Imidolactams / Organic thiophosphoric acids and derivatives
show 11 more
Substituents
Purine ribonucleoside diphosphate / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Monosaccharide phosphate / Organic pyrophosphate / Pentose monosaccharide
show 32 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
nucleoside triphosphate analogue (CHEBI:27575)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity
Specific Function
Synthesizes the second messagers cyclic ADP-ribose and nicotinate-adenine dinucleotide phosphate, the former a second messenger that elicits calcium release from intracellular stores. May be involv...
Gene Name
BST1
Uniprot ID
Q10588
Uniprot Name
ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 2
Molecular Weight
35723.545 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
Transporter activity
Specific Function
Neuronal phosphoprotein that coats synaptic vesicles, binds to the cytoskeleton, and is believed to function in the regulation of neurotransmitter release. The complex formed with NOS1 and CAPON pr...
Gene Name
SYN1
Uniprot ID
P17600
Uniprot Name
Synapsin-1
Molecular Weight
74110.97 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
Protein serine/threonine kinase activity
Specific Function
Catalyzes the phosphorylation and inactivation of the branched-chain alpha-ketoacid dehydrogenase complex, the key regulatory enzyme of the valine, leucine and isoleucine catabolic pathways. Key en...
Gene Name
BCKDK
Uniprot ID
O14874
Uniprot Name
[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrial
Molecular Weight
46359.955 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
Identical protein binding
Specific Function
Synthesis and degradation of fructose 2,6-bisphosphate.
Gene Name
PFKFB1
Uniprot ID
P16118
Uniprot Name
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1
Molecular Weight
54680.86 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
Single base insertion or deletion binding
Specific Function
Component of the post-replicative DNA mismatch repair system (MMR). Heterodimerizes with MLH1 to form MutL alpha. DNA repair is initiated by MutS alpha (MSH2-MSH6) or MutS beta (MSH2-MSH6) binding ...
Gene Name
PMS2
Uniprot ID
P54278
Uniprot Name
Mismatch repair endonuclease PMS2
Molecular Weight
95795.875 Da
Kind
Protein
Organism
Mycobacterium paratuberculosis (strain ATCC BAA-968 / K-10)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
recA
Uniprot ID
P62219
Uniprot Name
Protein RecA
Molecular Weight
37464.435 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
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Pharmacological action
Unknown
General Function
Single-stranded dna binding
Specific Function
Can catalyze the hydrolysis of ATP in the presence of single-stranded DNA, the ATP-dependent uptake of single-stranded DNA by duplex DNA, and the ATP-dependent hybridization of homologous single-st...
Gene Name
recA
Uniprot ID
P42443
Uniprot Name
Protein RecA
Molecular Weight
38144.36 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]
Kind
Protein
Organism
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
Pharmacological action
Unknown
General Function
Single-stranded dna binding
Specific Function
Required for homologous recombination (HR) and the bypass of mutagenic DNA lesions (double strand breaks, DSB) by the SOS response. Can catalyze the hydrolysis of ATP in the presence of single-stra...
Gene Name
recA
Uniprot ID
Q59560
Uniprot Name
Protein RecA
Molecular Weight
37300.27 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
Streptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)
Pharmacological action
Unknown
General Function
Kinase activity
Specific Function
Inactivates chloramphenicol by catalyzing the transfer of the gamma-phosphate of ATP to the antibiotic's C-3' hydroxyl group.
Gene Name
Not Available
Uniprot ID
Q56148
Uniprot Name
Chloramphenicol 3-O phosphotransferase
Molecular Weight
18816.255 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Involved in the RecF recombination pathway; its gene expression is under the regulation of the SOS system. It is a DNA helicase.
Gene Name
recQ
Uniprot ID
P15043
Uniprot Name
ATP-dependent DNA helicase RecQ
Molecular Weight
68362.98 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
Nucleoside-triphosphatase activity
Specific Function
DNA polymerase III is a complex, multichain enzyme responsible for most of the replicative synthesis in bacteria. This DNA polymerase also exhibits 3' to 5' exonuclease activity.Isoform tau: serves...
Gene Name
dnaX
Uniprot ID
P06710
Uniprot Name
DNA polymerase III subunit tau
Molecular Weight
71136.99 Da
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
Helicobacter pylori
Pharmacological action
Unknown
General Function
Atp binding
Specific Function
Not Available
Gene Name
cag-alfa
Uniprot ID
Q7BK04
Uniprot Name
Cag alpha
Molecular Weight
37579.485 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:05