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8-Oxo-dGMP

PubChem CID
135488904
Structure
8-Oxo-dGMP_small.png
8-Oxo-dGMP_3D_Structure.png
Molecular Formula
Synonyms
  • 8-oxo-dGMP
  • 8-Hydroxydeoxyguanosine 5'-monophosphate
  • 127027-50-3
  • 8-OH-Dgmp
  • 8-oxo-2'-deoxyguanosine-5'-monophosphate
Molecular Weight
363.22 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2019-01-15
  • Modify:
    2025-01-18
Description
8-oxo-dGMP is a purine 2'-deoxyribonucleoside 5'-monophosphate having 8-oxo-7,8-dihydroguanine as the nucleobase. It is a conjugate acid of an 8-oxo-dGMP(2-).
8-oxo-dGMP is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
8-Oxo-dGMP.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3S,5R)-5-(2-amino-6,8-dioxo-1,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H14N5O8P/c11-9-13-7-6(8(17)14-9)12-10(18)15(7)5-1-3(16)4(23-5)2-22-24(19,20)21/h3-5,16H,1-2H2,(H,12,18)(H2,19,20,21)(H3,11,13,14,17)/t3-,4+,5+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

AQIVLFLYHYFRKU-VPENINKCSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1[C@@H]([C@H](O[C@H]1N2C3=C(C(=O)NC(=N3)N)NC2=O)COP(=O)(O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H14N5O8P
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 ChEBI ID

2.3.3 DrugBank ID

2.3.4 DSSTox Substance ID

2.3.5 KEGG ID

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 8-hydroxydeoxyguanosine 5'-monophosphate
  • 8-OH-dGmp

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
363.22 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-4.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
363.05799942 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
363.05799942 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
196 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
701
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
3
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)

3.2 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

5 Chemical Vendors

6 Literature

6.1 Consolidated References

6.2 NLM Curated PubMed Citations

6.3 Chemical Co-Occurrences in Literature

6.4 Chemical-Gene Co-Occurrences in Literature

6.5 Chemical-Disease Co-Occurrences in Literature

7 Patents

7.1 Depositor-Supplied Patent Identifiers

7.2 WIPO PATENTSCOPE

7.3 Chemical Co-Occurrences in Patents

7.4 Chemical-Disease Co-Occurrences in Patents

7.5 Chemical-Gene Co-Occurrences in Patents

8 Interactions and Pathways

8.1 Protein Bound 3D Structures

8.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

8.2 Chemical-Target Interactions

9 Biological Test Results

9.1 BioAssay Results

10 Classification

10.1 MeSH Tree

10.2 ChEBI Ontology

10.3 ChemIDplus

10.4 NORMAN Suspect List Exchange Classification

10.5 EPA DSSTox Classification

10.6 MolGenie Organic Chemistry Ontology

11 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/
    2′-Deoxy-7,8-dihydro-8-oxo-5′-guanylic acid
    https://commonchemistry.cas.org/detail?cas_rn=127027-50-3
  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
  4. EPA DSSTox
    9-(2-Deoxy-5-O-phosphonopentofuranosyl)-2-imino-3,9-dihydro-2H-purine-6,8-diol
    https://comptox.epa.gov/dashboard/DTXSID40925768
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. ChEBI
  6. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  7. Japan Chemical Substance Dictionary (Nikkaji)
  8. 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
  9. Metabolomics Workbench
  10. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    9-(2-Deoxy-5-O-phosphonopentofuranosyl)-2-imino-3,9-dihydro-2H-purine-6,8-diol
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  11. Protein Data Bank in Europe (PDBe)
  12. 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
  13. Wikidata
  14. PubChem
  15. 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
    8-hydroxydeoxyguanosine 5'-monophosphate
    https://www.ncbi.nlm.nih.gov/mesh/67063477
  16. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  17. PATENTSCOPE (WIPO)
CONTENTS