ChemFOnt: Showing chemical card for 8-Hydroxyguanosine (CFc000001371)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:59 UTC

Chemfont ID

CFc000001371

Molecule Identification

Common Name

8-Hydroxyguanosine

Definition

8-hydroxyguanosine (8-OHG) is a marker for measuring the rate of oxidative damage to nucleic acids and lipids. Production of reactive oxygen species (ROS) damage proteins, lipid membranes, and nucleic acids (DNA and RNA), all critical functional components of living cells. The progressive accumulation of unrepaired free radical damage over time is believed to be a major contributor to the aging process and to a variety of age-related chronic diseases. Generation of most free radicals is a 'side effect' of normal metabolic processes, especially mitochondrial production of ROS, including superoxide anion, hydrogen peroxide, and hydroxyl radical, coincident to oxidative metabolism. (PMID 14607529 ). 8-OHG (marker of oxidative damage to RNA) was found in the cerebral cortex in three of six cases of neuropathologically examined autopsy of subacute sclerosing panencephalitis patients. Subacute sclerosing panencephalitis is caused by persistent brain infection of mutated measles virus, showing inflammation, neuronal loss, and demyelination. (PMID 12546425 ). The concentration of 8-OHG in CSF in Parkinson's disease (PD) patients is approximately three-fold that in controls. The concentration of 8-OHG in CSF decreased significantly with the duration of disease. However, the concentration of 8-OHG in serum was not significantly altered in PD patients compared to that in controls. (PMID 12499051 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7,8-dihydro-8-oxo-Guanosine	HMDB
8-Oxoguanosine	HMDB, MeSH
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-Oxoguanosine	MeSH, HMDB
8-OxoGuo	MeSH, HMDB
8-oxo-7,8-Dihydroguanosine	MeSH, HMDB
8-OxoG nucleoside	MeSH, HMDB
8-Hydroxyguanosine	MeSH

Chemical Formula

C₁₀H₁₃N₅O₆

Average Molecular Weight

299.2401

Monoisotopic Molecular Weight

299.086583173

IUPAC Name

2-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 Name

2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,7-dihydropurine-6,8-dione

CAS Registry Number

3868-31-3

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 Key

FPGSEBKFEJEOSA-UMMCILCDSA-N

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12391605)
Cerebrospinal Fluid (CSF) (PMID: 12391605)
Cerebrospinal fluid (HMDB: HMDB0002044)

Source

Endogenous

Endogenous (HMDB: HMDB0002044)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Alzheimer's Disease (MarkerDB: MDB00000371)
Parkinson's disease (MarkerDB: MDB00000371)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	9.79 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	3.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	169.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.4 m³·mol⁻¹	ChemAxon
Polarizability	26.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002044

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022815

KNApSAcK ID

Not Available

Chemspider ID

58640

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

8-Hydroxyguanosine

METLIN ID

Not Available

PubChem Compound

65131

PDB ID

Not Available

ChEBI ID

1177182

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Wong, Peter K.; Floyd, Robert A. photochemical synthesis of 8-hydroxyguanine nucleosides. Methods in Enzymology (1994), 234(Oxygen Radicals in Biological Systems, Pt. D), 59-65.

Showing chemical card for 8-Hydroxyguanosine (CFc000001371)

MOL for CFc000001371 (8-Hydroxyguanosine)

3D MOL for CFc000001371 (8-Hydroxyguanosine)

3D SDF for CFc000001371 (8-Hydroxyguanosine)

3D-SDF for CFc000001371 (8-Hydroxyguanosine)

PDB for CFc000001371 (8-Hydroxyguanosine)

3D PDB for CFc000001371 (8-Hydroxyguanosine)

SMILES for CFc000001371 (8-Hydroxyguanosine)

INCHI for CFc000001371 (8-Hydroxyguanosine)

Structure for CFc000001371 (8-Hydroxyguanosine)

3D Structure for CFc000001371 (8-Hydroxyguanosine)