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6-Thioguanosine 5'-diphosphate

PubChem CID
3035439
Structure
6-Thioguanosine 5'-diphosphate_small.png
6-Thioguanosine 5'-diphosphate_3D_Structure.png
Molecular Formula
Synonyms
  • 6-thioguanosine 5'-diphosphate
  • Thiogdp
  • 16541-19-8
  • p(S)pg
  • [(2R,3S,4R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate
Molecular Weight
459.27 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-18

1 Structures

1.1 2D Structure

Chemical Structure Depiction
6-Thioguanosine 5'-diphosphate.png

1.2 3D Conformer

2 Biologic Description

IUPAC Condensed
P-P-s6Gua-Ribf
Sequence
N
HELM
RNA1{[*P(=O)(O)OP(=O)(O)O |$_R2;;;;;;;;|]R([*n1cnc2c1nc([nH]c2=S)N |$_R1;;;;;;;;;;;$|])}$$$$
IUPAC
5'-diphospho-6-thio-guanosine

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

[(2R,3S,4R)-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

3.1.2 InChI

InChI=1S/C10H15N5O10P2S/c11-10-13-7-4(8(28)14-10)12-2-15(7)9-6(17)5(16)3(24-9)1-23-27(21,22)25-26(18,19)20/h2-3,5-6,9,16-17H,1H2,(H,21,22)(H2,18,19,20)(H3,11,13,14,28)/t3-,5-,6-,9?/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.3 InChIKey

IUTNWRFYTFZSEK-LZGMGDPASA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

3.1.4 SMILES

C1=NC2=C(N1C3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)O)O)O)NC(=NC2=S)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C10H15N5O10P2S
Computed by PubChem 2.1 (PubChem release 2021.05.07)

3.3 Other Identifiers

3.3.1 CAS

16541-19-8

3.3.2 DSSTox Substance ID

3.3.3 PharmGKB ID

3.3.4 Wikidata

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • 6-thioguanosine 5'-diphosphate
  • 9-beta-ribofuranosyl-2-amino-6-mercaptopurine 5'-diphosphate
  • guanosine 5'-(beta-thio)diphosphate
  • p(S)pg
  • thioGDP

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
459.27 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3
Property Value
-3.9
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
459.00148686 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
459.00148686 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
263 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
765
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
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 2019.01.04)

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Biochemical Reactions

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Chemical Co-Occurrences in Literature

8.4 Chemical-Gene Co-Occurrences in Literature

8.5 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 Chemical Co-Occurrences in Patents

9.3 Chemical-Gene Co-Occurrences in Patents

10 Interactions and Pathways

10.1 Pathways

11 Classification

11.1 MeSH Tree

11.2 ChemIDplus

11.3 EPA DSSTox Classification

12 Information Sources

  1. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  2. EPA DSSTox
    Thiodeoxyguanosine 5'-diphosphate
    https://comptox.epa.gov/dashboard/DTXSID00937084
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  3. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  4. Wikidata
    9-{5-O-[Hydroxy(phosphonooxy)phosphoryl]pentofuranosyl}-2-imino-3,9-dihydro-2H-purine-6-thiol
    https://www.wikidata.org/wiki/Q82913285
  5. PubChem
  6. 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
    6-thioguanosine 5'-diphosphate
    https://www.ncbi.nlm.nih.gov/mesh/67032829
CONTENTS