Phosphothiophosphoric acid-adenylate ester
PubChem CID
440317
Structure
Molecular Formula
Synonyms
- gamma-Thio-ATP
- (gamma-S)ATP
- ATP-gammaS
- 35094-46-3
- phosphothiophosphoric acid-adenylate ester
Molecular Weight
523.25 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
- Create:2005-06-24
- Modify:2025-01-18
Description
Adenosine 5'-[gamma-thio]triphosphate is a nucleoside triphosphate analogue that is ATP in which one of the oxygens attached to 3-phosphate group is replaced by sulfur. It is functionally related to an ATP and a ({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(9H-purin-9-yl)oxolan-2-yl]methyl phosphonato}oxy)(phosphonatooxy)phosphinate.
Chemical Structure Depiction
IUPAC Condensed
sP-P-P-rAdo
Sequence
A
[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] dihydroxyphosphinothioyl hydrogen phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
NLTUCYMLOPLUHL-KQYNXXCUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=S)(O)O)O)O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C10H16N5O12P3S
Computed by PubChem 2.2 (PubChem release 2021.10.14)
117750-47-7
- (gamma-S)ATP
- adenosine 5'-(3-thio)triphosphate
- adenosine 5'-(gamma-S)triphosphate
- adenosine 5'-O-(3-thiotriphosphate)
- adenosine 5'-O-(gamma-thiotriphosphate)
- adenosine 5'-O-thiotriphosphate
- adenosine 5'-thiotriphosphate
- adenosine-5'-(3-thiotriphosphate)
- ATP gamma-S
- ATPgammaS
- gamma-thio-ATP
- gamma-Thio-ATP
- (gamma-S)ATP
- ATP-gammaS
- 35094-46-3
- phosphothiophosphoric acid-adenylate ester
- ATP-gamma-S
- ATPgammaS
- Adenosine 5'-(3-thio)triphosphate
- alpha-Thio-ATP
- Adenosine 5'-O-(3-thiotriphosphate)
- adenosine 5'-[gamma-thio]triphosphate
- 117750-47-7
- Adenosine 5'-thiotriphosphate
- Adenosine 5'-(gamma-S)triphosphate
- alpha-Thioadenosine triphosphate
- Adenosine 5'-O-(gamma-thiotriphosphate)
- Adenosine 5-O-(3-thiotriphophate)
- Adenosine 5'-(gamma-thio)triphosphate
- CHEMBL131890
- [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] dihydroxyphosphinothioyl hydrogen phosphate
- CHEBI:27575
- Adenosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid
- Adenosine 5'-(trihydrogen diphosphate), p'-anhydride with phosphorothioic acid
- Adenosine 5'-[gamma-S]triphosphate
- 5'-O-(hydroxy{[hydroxy(thiophosphonooxy)phosphoryl]oxy}phosphoryl)adenosine
- Adenosine, 5'-P''-ester with thiotriphosphoric acid ((HO)2P(O)OP(O)(OH)OP(35S)(OH)2)
- Adenosine-5'-(3-thiotriphosphate)
- adenosine 5'-O-thiotriphosphate
- 1njf
- 1xxh
- Gamma Thio ATP
- ATP.gamma.S
- 1w1w
- SCHEMBL77440
- SCHEMBL20164791
- DTXSID301138619
- Adenosine 5'-(3-thiotriphosphate)
- BDBM50118217
- Adenosine 5'-(gamma-thiotriphosphate)
- Adenosine 5'-(.gamma.-S)triphosphate
- DB02930
- [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-sulfanylphosphinic acid
- ADENOSINE-5''-DIPHOSPHATE MONOTHIOPHOSPHATE
- Adenosine 5 inverted exclamation marka-(3-thiotriphosphate)
- 5'-O-[(S)-hydroxy{[(S)-hydroxy(thiophosphonooxy)phosphoryl]oxy}phosphoryl]adenosine
- Adenosine 5'-(trihydrogen diphosphate), P'-anhydride with phosphorothioic acid (9CI)
- Adenosine 5a(2)-(trihydrogen diphosphate), Pa(2)-anhydride with phosphorothioic acid
- adenosine, 5'-O-[[[[(dihydroxyphosphinothioyl)oxy]hydroxyphosphinyl]oxy]hydroxyphosphinyl]-
- [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-sulfanyl-phosphinic acid
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
523.25 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
17
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
522.97290313 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
522.97290313 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
294 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
805
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
4
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Stereo Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Stereo Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
Affinity Labels
Analogs of those substrates or compounds which bind naturally at the active sites of proteins, enzymes, antibodies, steroids, or physiological receptors. These analogs form a stable covalent bond at the binding site, thereby acting as inhibitors of the proteins or steroids. (See all compounds classified as Affinity Labels.)
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/Adenosine 5′-(trihydrogen diphosphate), P′-anhydride with phosphorothioic acidhttps://commonchemistry.cas.org/detail?cas_rn=35094-46-3
- ChemIDplusAdenosine 5'-O-(3-thiotriphosphate)https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0035094463alpha-Thioadenosine triphosphatehttps://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0117750477ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useAdenosine 5'-[gamma-thio]triphosphatehttps://www.drugbank.ca/drugs/DB02930
- EPA DSSToxAdenosine 5'-(trihydrogen diphosphate), P'-anhydride with phosphorothioic acidhttps://comptox.epa.gov/dashboard/DTXSID301138619CompTox Chemicals Dashboard Chemical Listshttps://comptox.epa.gov/dashboard/chemical-lists/
- ChEBIAdenosine 5'-[gamma-thio]triphosphatehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:27575
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.htmlChEMBL Protein Target Treehttps://www.ebi.ac.uk/chembl/g/#browse/targets
- Comparative Toxicogenomics Database (CTD)LICENSEIt is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.http://ctdbase.org/about/legal.jspadenosine 5'-O-(3-thiotriphosphate)https://ctdbase.org/detail.go?type=chem&acc=C022571
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.html
- Metabolomics WorkbenchAdenosine 5'-[gamma-thio]triphosphatehttps://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=51375
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/about
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.https://www.rcsb.org/pages/policies
- SpectraBaseADENOSINE-5'-GAMMA-THIONOTRIPHOSPHATEhttps://spectrabase.com/spectrum/FhdLQHMoFeMADENOSINE-5'-GAMMA-THIONOTRIPHOSPHATEhttps://spectrabase.com/spectrum/3nDTOKmUiMN
- Wikidata[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] dihydroxyphosphinothioyl hydrogen phosphatehttps://www.wikidata.org/wiki/Q76100175
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmladenosine 5'-O-(3-thiotriphosphate)https://www.ncbi.nlm.nih.gov/mesh/67022571Affinity Labelshttps://www.ncbi.nlm.nih.gov/mesh/68000345
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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