Np mrd loader

Record Information
Version2.0
Created at2022-05-11 16:32:49 UTC
Updated at2022-05-11 16:32:49 UTC
NP-MRD IDNP0086852
Secondary Accession NumbersNone
Natural Product Identification
Common Name8-Hydroxyguanosine
Description8-Hydroxyguanosine, also known as 8-oxoguo or 8-oxog nucleoside, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. 8-Hydroxyguanosine was first documented in 2002 (PMID: 12546425). 8-Hydroxyguanosine is a strong basic compound (based on its pKa) (PMID: 12499051) (PMID: 14607529).
Structure
Thumb
Synonyms
ValueSource
7,8-Dihydro-8-oxo-guanosineHMDB
8-OxoguanosineHMDB
Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-D-ribofuranosyl- (7ci,8ci)HMDB
Purine-6,8(1H,9H)-dione, 2-amino-9-.beta.-delta-ribofuranosyl- (7ci,8ci)HMDB
7,8-Dihydro-8-oxoguanosineHMDB
8-OxoGuoHMDB
8-oxo-7,8-DihydroguanosineHMDB
8-OxoG nucleosideHMDB
8-HydroxyguanosineMeSH
Chemical FormulaC10H13N5O6
Average Mass299.2401 Da
Monoisotopic Mass299.08658 Da
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7,8,9-tetrahydro-1H-purine-6,8-dione
Traditional Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(NC(=O)N2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
InChI=1S/C10H13N5O6/c11-9-13-6-3(7(19)14-9)12-10(20)15(6)8-5(18)4(17)2(1-16)21-8/h2,4-5,8,16-18H,1H2,(H,12,20)(H3,11,13,14,19)/t2-,4-,5-,8-/m1/s1
InChI KeyFPGSEBKFEJEOSA-UMMCILCDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Hydroxypyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-3ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)7.53ChemAxon
pKa (Strongest Basic)3.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area169.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.4 m³·mol⁻¹ChemAxon
Polarizability26.94 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002044
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022815
KNApSAcK IDNot Available
Chemspider ID58640
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link8-Hydroxyguanosine
METLIN IDNot Available
PubChem Compound65131
PDB IDNot Available
ChEBI ID1177182
Good Scents IDNot Available
References
General References
  1. Abe T, Isobe C, Murata T, Sato C, Tohgi H: Alteration of 8-hydroxyguanosine concentrations in the cerebrospinal fluid and serum from patients with Parkinson's disease. Neurosci Lett. 2003 Jan 16;336(2):105-8. doi: 10.1016/s0304-3940(02)01259-4. [PubMed:12499051 ]
  2. Harman SM, Liang L, Tsitouras PD, Gucciardo F, Heward CB, Reaven PD, Ping W, Ahmed A, Cutler RG: Urinary excretion of three nucleic acid oxidation adducts and isoprostane F(2)alpha measured by liquid chromatography-mass spectrometry in smokers, ex-smokers, and nonsmokers. Free Radic Biol Med. 2003 Nov 15;35(10):1301-9. doi: 10.1016/j.freeradbiomed.2003.07.003. [PubMed:14607529 ]
  3. Hayashi M, Arai N, Satoh J, Suzuki H, Katayama K, Tamagawa K, Morimatsu Y: Neurodegenerative mechanisms in subacute sclerosing panencephalitis. J Child Neurol. 2002 Oct;17(10):725-30. doi: 10.1177/08830738020170101101. [PubMed:12546425 ]