MiMeDB: Showing metabocard for 8-oxoguanine (MMDBc0054310)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:06:21 UTC

Update Date

2024-04-30 20:52:29 UTC

Metabolite ID

MMDBc0054310

Metabolite Identification

Common Name

8-oxoguanine

Description

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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      29.299 -19.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.529 -18.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.839 -19.968   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      29.299 -17.300   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      31.609 -18.634   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      30.839 -17.300   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      27.022 -18.954   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      26.861 -20.486   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      28.268 -21.112   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      31.609 -15.966   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      31.609 -21.301   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.527 -21.256   0.000  0.00  0.00           O+0
CONECT    1    3    2    9                                                  
CONECT    2    4    7    1                                                  
CONECT    3    1    5   11                                                  
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   10                                                  
CONECT    7    8    2                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    1                                                       
CONECT   10    6                                                            
CONECT   11    3                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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

Molecular Formula

C₅H₅N₅O₂

Average Mass

167.1255

Monoisotopic Mass

167.044324429

IUPAC Name

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

Traditional Name

8-hydroxyguanine

CAS Registry Number

Not Available

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

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3900000000-58549cee828db799d7b5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-6a4117b10e5530095707	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-89fdc38268686eaba66a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-107l-9600000000-7c79695abe7a15874725	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-ac22897692beb4981ede	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2900000000-f3b3767a022d716580d1	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-9a8d26eff2e742411cb2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-d3890f3472d103400e66	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ri-1900000000-59a4be35534659234b6b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-7d9830f9bdf455a84283	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-2907e7cb009d3747cf21	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-5795d2965bc15c5daf00	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00us-9200000000-fd1acc84bba1739821db	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11255442
Diabetes mellitus type 2	Increased	Association	Human Blood	HMDB	11315839

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.19		0.15	0.23	uM	Adult (>18 years old)	Not Specified	Alzheimer's disease	HMDB	11255442
Human Blood	Detected and Quantified	0.005	0.0007			uM	Adult (>18 years old)	Both	Diabetes	HMDB	11315839
Human Blood	Detected and Quantified	0.0001	0.00015			uM	Adult (>18 years old)	Both	Normal	HMDB	11315839
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.68		0.49	0.87	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	11255442
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

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

Not Available

General References

Shen Z, Wu W, Hazen SL: Activated leukocytes oxidatively damage DNA, RNA, and the nucleotide pool through halide-dependent formation of hydroxyl radical. Biochemistry. 2000 May 9;39(18):5474-82. doi: 10.1021/bi992809y. [PubMed:10820020 ]
Lovell MA, Markesbery WR: Ratio of 8-hydroxyguanine in intact DNA to free 8-hydroxyguanine is increased in Alzheimer disease ventricular cerebrospinal fluid. Arch Neurol. 2001 Mar;58(3):392-6. doi: 10.1001/archneur.58.3.392. [PubMed:11255442 ]
Flirski M, Sobow T: Biochemical markers and risk factors of Alzheimer's disease. Curr Alzheimer Res. 2005 Jan;2(1):47-64. doi: 10.2174/1567205052772704. [PubMed:15977989 ]

Showing metabocard for 8-oxoguanine (MMDBc0054310)

MOL for #<Metabolite:0x00007fecd8021be8>

3D MOL for #<Metabolite:0x00007fecd8021be8>

3D SDF for #<Metabolite:0x00007fecd8021be8>

3D-SDF for #<Metabolite:0x00007fecd8021be8>

PDB for #<Metabolite:0x00007fecd8021be8>

3D PDB for #<Metabolite:0x00007fecd8021be8>

SMILES for #<Metabolite:0x00007fecd8021be8>

INCHI for #<Metabolite:0x00007fecd8021be8>

Structure for #<Metabolite:0x00007fecd8021be8>

3D Structure for #<Metabolite:0x00007fecd8021be8>