ChemFOnt: Showing chemical card for 8-Hydroxyguanine (CFc000001362)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:58 UTC

Chemfont ID

CFc000001362

Molecule Identification

Common Name

8-Hydroxyguanine

Definition

Formation of 8-hydroxyguanine (8-OHG), a mutagenic base which is a marker for OH-mediated DNA damage, requires peroxidase and halides and occurs in the presence of transition metal chelators (DTPA +/- desferrioxamine), and is inhibited by catalase, superoxide dismutase (SOD), and scavengers of hypohalous acids. (PMID 10820020 ). 8-Hydroxyguanine is an oxidative stress marker for diagnosis of Alzheimer's disease (AD). (PMID 15977989 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8-Oxoguanine	ChEBI
1H-Purine-6,8-dione, 2-amino-7,9-dihydro-1H-purine-6,8-dione	HMDB
2-amino-6,8-Dihydroxypurine	HMDB, MeSH
2-amino-7,9-dihydro-1H-Purine-6,8-dione	HMDB
2-amino-Purine-6,8-diol	HMDB
2-Aminopurine-6,8-diol	HMDB
7,8-dihydro-8-Oxoguanine	HMDB
oxo-8-Gua	MeSH, HMDB
8-oxo-7,8-Dihydroguanine	MeSH, HMDB
8-Hydroxyguanine	ChEBI

Chemical Formula

C₅H₅N₅O₂

Average Molecular Weight

167.1255

Monoisotopic Molecular Weight

167.044324429

IUPAC Name

2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione

Traditional Name

8-hydroxyguanine

CAS Registry Number

5614-64-2

SMILES

NC1=NC2=C(NC(=O)N2)C(=O)N1

InChI Identifier

InChI=1S/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)

InChI Key

CLGFIVUFZRGQRP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purines and purine derivatives

Alternative Parents

Substituents

Purine
Hydroxypyrimidine
Pyrimidine
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:52617 )
an aromatic compound (CPD-12427 )

Functional Ontology

Physiological effect

Health effect

Endocrine system disorder

Diabetes mellitus type 2 (HMDB: HMDB0002032)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 11315839)
Cerebrospinal Fluid (CSF) (PMID: 11255442)
Cerebrospinal fluid (HMDB: HMDB0002032)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Source

Endogenous

Endogenous (HMDB: HMDB0002032)

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: MDB00000370)
Diabetes mellitus type 2 (MarkerDB: MDB00000370)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.94 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-1.5	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.35	ChemAxon
pKa (Strongest Basic)	3.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	108.61 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.81 m³·mol⁻¹	ChemAxon
Polarizability	14.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002032

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022809

KNApSAcK ID

Not Available

Chemspider ID

58661

KEGG Compound ID

C20155

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

8-Oxoguanine

METLIN ID

Not Available

PubChem Compound

65154

PDB ID

Not Available

ChEBI ID

52617

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Usacheva A M; Chernikov A V; Bruskov V I Formation of 8-hydroxyguanine upon damage of guanine nucleotides by gamma radiation. Molekuliarnaia biologiia (1995), 29(2), 446-51.

Showing chemical card for 8-Hydroxyguanine (CFc000001362)

MOL for CFc000001362 (8-Hydroxyguanine)

3D MOL for CFc000001362 (8-Hydroxyguanine)

3D SDF for CFc000001362 (8-Hydroxyguanine)

3D-SDF for CFc000001362 (8-Hydroxyguanine)

PDB for CFc000001362 (8-Hydroxyguanine)

3D PDB for CFc000001362 (8-Hydroxyguanine)

SMILES for CFc000001362 (8-Hydroxyguanine)

INCHI for CFc000001362 (8-Hydroxyguanine)

Structure for CFc000001362 (8-Hydroxyguanine)

3D Structure for CFc000001362 (8-Hydroxyguanine)