Showing Compound 8-Hydroxyguanosine (FDB022815)

Record Information

Version

1.0

Creation date

2011-09-21 00:20:04 UTC

Update date

2015-07-21 06:57:22 UTC

Primary ID

FDB022815

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

8-Hydroxyguanosine

Description

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) [HMDB]

CAS Number

3868-31-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
7,8-dihydro-8-oxo-Guanosine	HMDB
7,8-dihydro-8-Oxoguanosine	MeSH, HMDB
8-Hydroxyguanosine	MeSH
8-hydroxyguanosine	hmdb
8-oxo-7,8-Dihydroguanosine	MeSH, HMDB
8-OxoG nucleoside	MeSH, HMDB
8-Oxoguanosine	HMDB, MeSH
8-OxoGuo	MeSH, HMDB
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.-D-ribofuranosyl- (7CI,8CI)	hmdb

Showing 1 to 10 of 12 entries

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

Chemical Formula

C10H13N5O6

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

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

Isomeric SMILES

NC1=NC2=C(NC(=O)N2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1

Average Molecular Weight

299.2401

Monoisotopic Molecular Weight

299.086583173

Classification

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

Ontology

Disposition

Biological location:

Biofluid and excreta:

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	8-Hydroxyguanosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9160000000-b5d214bf9c0982dbbe63	Spectrum
Predicted GC-MS	8-Hydroxyguanosine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uec-6902330000-d183539e2e438b4d7c80	Spectrum
Predicted GC-MS	8-Hydroxyguanosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-0f5c81fc8d1ea968575d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-0cbf4ce2e5de074bf971	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v6r-0900000000-625b8c3fb826dde8502a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-0490000000-d4f85e8ee7d5857f5de9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0920000000-8df43d9931a862018046	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dm-3900000000-5f141ad8cdd5265bd2e2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-0590000000-1ad5ee29954e5c959115	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0930000000-d9cf1a8f55c39625b8e2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xs-1900000000-6be5e18238989f501180	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0908000000-df8fac03f541fd5e932a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-1b32e9ca2d9b8052067d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-1910000000-36cbcf5ae3cd08917674	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

58640

ChEMBL ID

CHEMBL1688964

KEGG Compound ID

Not Available

Pubchem Compound ID

65131

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02044

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB