Identification
- Generic Name
- Adenosine 5'-[gamma-thio]triphosphate
- DrugBank Accession Number
- DB02930
- Background
A nucleoside triphosphate analogue that is ATP in which one of the oxygens attached to 3-phosphate group is replaced by sulfur.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Adenosine 5'-[gamma-thio]triphosphate (DB02930)
- Weight
- Average: 523.247
Monoisotopic: 522.972901227 - Chemical Formula
- C10H16N5O12P3S
- 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'-[γ-thio]triphosphate
- Adenosine 5'-O-(3-thiotriphosphate)
- ATP-gamma-S
- ATP-gammaS
- gamma-Thio-ATP
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UADP-ribosyl cyclase 2 Not Available Humans USynapsin-1 Not Available Humans U[3-methyl-2-oxobutanoate dehydrogenase [lipoamide]] kinase, mitochondrial Not Available Humans U6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1 Not Available Humans UMismatch repair endonuclease PMS2 Not Available Humans UProtein RecA Not Available Mycobacterium paratuberculosis (strain ATCC BAA-968 / K-10) UProtein RecA Not Available Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422) UProtein RecA Not Available Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155) UChloramphenicol 3-O phosphotransferase Not Available Streptomyces venezuelae (strain ATCC 10712 / CBS 650.69 / DSM 40230 / JCM 4526 / NBRC 13096 / PD 04745) UPhosphoribosylglycinamide formyltransferase 2 Not Available Escherichia coli (strain K12) UATP-dependent DNA helicase RecQ Not Available Escherichia coli (strain K12) UDNA polymerase III subunit tau Not Available Escherichia coli (strain K12) USerine/threonine-protein kinase PknB Not Available Mycobacterium tuberculosis UCag alpha Not Available Helicobacter 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-diol / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound show 32 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- nucleoside triphosphate analogue (CHEBI:27575)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 35094-46-3
- 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
- NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O
References
- General References
- Not Available
- External Links
- KEGG Compound
- C13742
- PubChem Compound
- 440317
- PubChem Substance
- 46507118
- ChemSpider
- 389291
- BindingDB
- 50118217
- ChEBI
- 27575
- ChEMBL
- CHEMBL131890
- ZINC
- ZINC000008295128
- PDBe Ligand
- AGS
- PDB Entries
- 1aux / 1bif / 1gjv / 1h74 / 1h7u / 1isg / 1k6m / 1kjj / 1kp8 / 1kwo … show 342 more
Clinical Trials
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
Property Value Source Water Solubility 2.26 mg/mL ALOGPS logP -0.5 ALOGPS logP -4.6 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 0.82 Chemaxon pKa (Strongest Basic) 4.9 Chemaxon Physiological Charge -4 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 7 Chemaxon Polar Surface Area 262.06 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 103.81 m3·mol-1 Chemaxon Polarizability 40.87 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7731 Blood Brain Barrier + 0.8388 Caco-2 permeable - 0.708 P-glycoprotein substrate Non-substrate 0.7019 P-glycoprotein inhibitor I Non-inhibitor 0.8871 P-glycoprotein inhibitor II Non-inhibitor 0.9916 Renal organic cation transporter Non-inhibitor 0.9567 CYP450 2C9 substrate Non-substrate 0.7877 CYP450 2D6 substrate Non-substrate 0.8238 CYP450 3A4 substrate Non-substrate 0.5758 CYP450 1A2 substrate Non-inhibitor 0.8599 CYP450 2C9 inhibitor Non-inhibitor 0.9002 CYP450 2D6 inhibitor Non-inhibitor 0.8954 CYP450 2C19 inhibitor Non-inhibitor 0.9057 CYP450 3A4 inhibitor Non-inhibitor 0.8962 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9734 Ames test Non AMES toxic 0.8038 Carcinogenicity Non-carcinogens 0.8791 Biodegradation Not ready biodegradable 0.9109 Rat acute toxicity 2.5484 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9834 hERG inhibition (predictor II) Non-inhibitor 0.762
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- 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
- 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
- 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
- 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
- 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
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52