Identification
NameAdenosine 5'-[γ-thio]triphosphate
Accession NumberDB02930  (EXPT02847, EXPT00458, DB01660)
TypeSmall Molecule
GroupsExperimental
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
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS number35094-46-3
WeightAverage: 523.247
Monoisotopic: 522.972901227
Chemical FormulaC10H16N5O12P3S
InChI KeyNLTUCYMLOPLUHL-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][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=S)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
ADP-ribosyl cyclase/cyclic ADP-ribose hydrolase 2ProteinunknownNot AvailableHumanQ10588 details
Synapsin-1ProteinunknownNot AvailableHumanP17600 details
[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrialProteinunknownNot AvailableHumanO14874 details
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1ProteinunknownNot AvailableHumanP16118 details
Mismatch repair endonuclease PMS2ProteinunknownNot AvailableHumanP54278 details
Protein RecAProteinunknownNot AvailableMycobacterium paratuberculosis (strain ATCC BAA-968 / K-10)P62219 details
Protein RecAProteinunknownNot AvailableDeinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)P42443 details
Protein RecAProteinunknownNot AvailableMycobacterium smegmatis (strain ATCC 700084 / mc(2)155)Q59560 details
Chloramphenicol 3-O phosphotransferaseProteinunknownNot AvailableStreptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745)Q56148 details
Phosphoribosylglycinamide formyltransferase 2ProteinunknownNot AvailableEscherichia coli (strain K12)P33221 details
ATP-dependent DNA helicase RecQProteinunknownNot AvailableEscherichia coli (strain K12)P15043 details
DNA polymerase III subunit tauProteinunknownNot AvailableEscherichia coli (strain K12)P06710 details
Serine/threonine-protein kinase PknBProteinunknownNot AvailableMycobacterium tuberculosisP9WI81 details
Cag alphaProteinunknownNot AvailableHelicobacter pyloriQ7BK04 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside diphosphates
Alternative ParentsPurine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Organic pyrophosphates / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / Primary aromatic amines / Imidolactams
SubstituentsPurine ribonucleoside diphosphate / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Monosaccharide phosphate / Organic pyrophosphate / Pentose monosaccharide
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsnucleoside 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 involved in pre-B-cell growth.
Gene Name:
BST1
Uniprot ID:
Q10588
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 proteins is necessary for specific nitric-oxid functions at a presynaptic level.
Gene Name:
SYN1
Uniprot ID:
P17600
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 enzyme that regulate the activity state of the BCKD complex.
Gene Name:
BCKDK
Uniprot ID:
O14874
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
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 to a dsDNA mismatch, then MutL alpha is recruited to the heteroduplex. Assembly of the MutL-MutS-heteroduplex ternary complex in presence of RFC and PCNA is sufficient to activate endonuclease activit...
Gene Name:
PMS2
Uniprot ID:
P54278
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
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-stranded DNAs. It interacts with LexA causing its activation and leading to its autocatalytic cleavage.
Gene Name:
recA
Uniprot ID:
P42443
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-stranded DNA, the ATP-dependent uptake of single-stranded DNA by duplex DNA, and the ATP-dependent hybridization of homologous single-stranded DNAs. Numerous X-ray crystals have been resolved under differ...
Gene Name:
recA
Uniprot ID:
Q59560
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
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 phosphate and ADP from acetate and ATP.
Gene Name:
purT
Uniprot ID:
P33221
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
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 as a scaffold to help in the dimerization of the core complex.Isoform gamma: seems to interact with the delta subunit. to transfer the beta subunit on the DNA.
Gene Name:
dnaX
Uniprot ID:
P06710
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
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
Molecular Weight:
37579.485 Da
Drug created on June 13, 2005 07:24 / Updated on June 11, 2017 20:43