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Phosphothiophosphoric acid-adenylate ester

PubChem CID
440317
Structure
Phosphothiophosphoric acid-adenylate ester_small.png
Phosphothiophosphoric acid-adenylate ester_3D_Structure.png
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.
A nucleoside triphosphate analogue that is ATP in which one of the oxygens attached to 3-phosphate group is replaced by sulfur.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Phosphothiophosphoric acid-adenylate ester.png

1.2 3D Conformer

2 Biologic Description

IUPAC Condensed
sP-P-P-rAdo
Sequence
A

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

[[(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)

3.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

NLTUCYMLOPLUHL-KQYNXXCUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

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)

3.2 Molecular Formula

C10H16N5O12P3S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

117750-47-7

3.3.2 ChEBI ID

3.3.3 ChEMBL ID

3.3.4 DrugBank ID

3.3.5 DSSTox Substance ID

3.3.6 KEGG ID

3.3.7 Metabolomics Workbench ID

3.3.8 Nikkaji Number

3.3.9 Pharos Ligand ID

3.3.10 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • (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

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

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)

5 Spectral Information

5.1 1D NMR Spectra

5.1.1 31P NMR Spectra

1 of 2
Instrument Name
Bruker HX-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker HX-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

7 Chemical Vendors

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

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.)

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Chemical Co-Occurrences in Literature

9.4 Chemical-Gene Co-Occurrences in Literature

9.5 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 Chemical Co-Occurrences in Patents

10.3 Chemical-Disease Co-Occurrences in Patents

10.4 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Protein Bound 3D Structures

11.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

11.2 Chemical-Target Interactions

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChemIDplus

13.4 ChEMBL Target Tree

13.5 EPA DSSTox Classification

13.6 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The 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 acid
    https://commonchemistry.cas.org/detail?cas_rn=35094-46-3
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
    Adenosine 5'-[gamma-thio]triphosphate
    https://www.drugbank.ca/drugs/DB02930
  4. EPA DSSTox
    Adenosine 5'-(trihydrogen diphosphate), P'-anhydride with phosphorothioic acid
    https://comptox.epa.gov/dashboard/DTXSID301138619
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. ChEBI
  6. ChEMBL
    LICENSE
    Access 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.html
  7. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It 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.jsp
    adenosine 5'-O-(3-thiotriphosphate)
    https://ctdbase.org/detail.go?type=chem&acc=C022571
  8. Japan Chemical Substance Dictionary (Nikkaji)
  9. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  10. Metabolomics Workbench
  11. Pharos
    LICENSE
    Data 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
  12. Protein Data Bank in Europe (PDBe)
  13. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data 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
  14. SpectraBase
    ADENOSINE-5'-GAMMA-THIONOTRIPHOSPHATE
    https://spectrabase.com/spectrum/FhdLQHMoFeM
    ADENOSINE-5'-GAMMA-THIONOTRIPHOSPHATE
    https://spectrabase.com/spectrum/3nDTOKmUiMN
  15. Wikidata
    [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] dihydroxyphosphinothioyl hydrogen phosphate
    https://www.wikidata.org/wiki/Q76100175
  16. PubChem
  17. Medical Subject Headings (MeSH)
    LICENSE
    Works 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.html
    adenosine 5'-O-(3-thiotriphosphate)
    https://www.ncbi.nlm.nih.gov/mesh/67022571
  18. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS