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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:40:56 UTC

Update Date

2023-02-21 17:28:58 UTC

HMDB ID

HMDB0041820

Secondary Accession Numbers

HMDB41820

Metabolite Identification

Common Name

8-Oxoguanine

Description

8-Oxoguanine belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 8-Oxoguanine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 8-oxoguanine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 8-Oxoguanine.

Structure

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

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.198  -2.843   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1    8    9                                                  
CONECT    3    1   10   11                                                  
CONECT    4    6    8   10                                                  
CONECT    5    7    9   12                                                  
CONECT    6    4                                                            
CONECT    7    1    5                                                       
CONECT    8    2    4                                                       
CONECT    9    2    5                                                       
CONECT   10    3    4                                                       
CONECT   11    3                                                            
CONECT   12    5                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-1H-purine-6,8-dione	HMDB
8-Oxyguanine	HMDB

Chemical Formula

C₅H₃N₅O₂

Average Molecular Weight

165.1096

Monoisotopic Molecular Weight

165.028674365

IUPAC Name

6-hydroxy-2-imino-8,9-dihydro-2H-purin-8-one

Traditional Name

8-oxoguanine

CAS Registry Number

82014-86-6

SMILES

OC1=NC(=N)N=C2NC(=O)N=C12

InChI Identifier

InChI=1S/C5H3N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H3,6,8,9,10,11,12)

InChI Key

UBKVUFQGVWHZIR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purinones. These are purines in which the purine moiety bears a C=O group. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Purinones

Alternative Parents

Substituents

Purinone
Hydropyrimidine
2,5-dihydropyrimidine
3-imidazoline
Carbonic acid derivative
Amidine
Carboxylic acid amidine
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organonitrogen compound
Organic oxide
Imine
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oxopurine (CHEBI:44605 )
2-aminopurines (CHEBI:44605 )

Ontology

Not Available

Endogenous (HMDB: HMDB0041820)

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

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-0.61	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	-0.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	110.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	13.51 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.9	31661259
DarkChem	[M-H]-	130.443	31661259
DeepCCS	[M-2H]-	169.219	30932474
DeepCCS	[M+Na]+	144.61	30932474
AllCCS	[M+H]+	133.9	32859911
AllCCS	[M+H-H2O]+	129.4	32859911
AllCCS	[M+NH4]+	138.1	32859911
AllCCS	[M+Na]+	139.3	32859911
AllCCS	[M-H]-	128.1	32859911
AllCCS	[M+Na-2H]-	128.6	32859911
AllCCS	[M+HCOO]-	129.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Oxoguanine	OC1=NC(=N)N=C2NC(=O)N=C12	3515.0	Standard polar	33892256
8-Oxoguanine	OC1=NC(=N)N=C2NC(=O)N=C12	2097.0	Standard non polar	33892256
8-Oxoguanine	OC1=NC(=N)N=C2NC(=O)N=C12	2017.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Oxoguanine,1TMS,isomer #1	C[Si](C)(C)OC1=NC(=N)N=C2NC(=O)N=C21	2276.6	Semi standard non polar	33892256
8-Oxoguanine,1TMS,isomer #2	C[Si](C)(C)N=C1N=C(O)C2=NC(=O)NC2=N1	2241.2	Semi standard non polar	33892256
8-Oxoguanine,1TMS,isomer #3	C[Si](C)(C)N1C(=O)N=C2C(O)=NC(=N)N=C21	2193.1	Semi standard non polar	33892256
8-Oxoguanine,2TMS,isomer #1	C[Si](C)(C)N=C1N=C2NC(=O)N=C2C(O[Si](C)(C)C)=N1	2248.3	Semi standard non polar	33892256
8-Oxoguanine,2TMS,isomer #1	C[Si](C)(C)N=C1N=C2NC(=O)N=C2C(O[Si](C)(C)C)=N1	2049.3	Standard non polar	33892256
8-Oxoguanine,2TMS,isomer #2	C[Si](C)(C)OC1=NC(=N)N=C2C1=NC(=O)N2[Si](C)(C)C	2173.2	Semi standard non polar	33892256
8-Oxoguanine,2TMS,isomer #2	C[Si](C)(C)OC1=NC(=N)N=C2C1=NC(=O)N2[Si](C)(C)C	2050.4	Standard non polar	33892256
8-Oxoguanine,2TMS,isomer #3	C[Si](C)(C)N=C1N=C(O)C2=NC(=O)N([Si](C)(C)C)C2=N1	2110.7	Semi standard non polar	33892256
8-Oxoguanine,2TMS,isomer #3	C[Si](C)(C)N=C1N=C(O)C2=NC(=O)N([Si](C)(C)C)C2=N1	2098.7	Standard non polar	33892256
8-Oxoguanine,3TMS,isomer #1	C[Si](C)(C)N=C1N=C(O[Si](C)(C)C)C2=NC(=O)N([Si](C)(C)C)C2=N1	2133.6	Semi standard non polar	33892256
8-Oxoguanine,3TMS,isomer #1	C[Si](C)(C)N=C1N=C(O[Si](C)(C)C)C2=NC(=O)N([Si](C)(C)C)C2=N1	2032.3	Standard non polar	33892256
8-Oxoguanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC(=N)N=C2NC(=O)N=C21	2403.7	Semi standard non polar	33892256
8-Oxoguanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1N=C(O)C2=NC(=O)NC2=N1	2407.5	Semi standard non polar	33892256
8-Oxoguanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(=O)N=C2C(O)=NC(=N)N=C21	2337.2	Semi standard non polar	33892256
8-Oxoguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C2NC(=O)N=C2C(O[Si](C)(C)C(C)(C)C)=N1	2502.3	Semi standard non polar	33892256
8-Oxoguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C2NC(=O)N=C2C(O[Si](C)(C)C(C)(C)C)=N1	2505.0	Standard non polar	33892256
8-Oxoguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(=N)N=C2C1=NC(=O)N2[Si](C)(C)C(C)(C)C	2428.2	Semi standard non polar	33892256
8-Oxoguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC(=N)N=C2C1=NC(=O)N2[Si](C)(C)C(C)(C)C	2510.2	Standard non polar	33892256
8-Oxoguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C1N=C(O)C2=NC(=O)N([Si](C)(C)C(C)(C)C)C2=N1	2457.3	Semi standard non polar	33892256
8-Oxoguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C1N=C(O)C2=NC(=O)N([Si](C)(C)C(C)(C)C)C2=N1	2557.3	Standard non polar	33892256
8-Oxoguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(O[Si](C)(C)C(C)(C)C)C2=NC(=O)N([Si](C)(C)C(C)(C)C)C2=N1	2583.2	Semi standard non polar	33892256
8-Oxoguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(O[Si](C)(C)C(C)(C)C)C2=NC(=O)N([Si](C)(C)C(C)(C)C)C2=N1	2651.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Oxoguanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-2900000000-e99f3dd9822e1a78a4cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Oxoguanine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9870000000-c791b36d46cd9f79af83	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Oxoguanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Oxoguanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 10V, Positive-QTOF	splash10-014i-0900000000-49fdcb115c2330bfaba4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 20V, Positive-QTOF	splash10-014i-0900000000-5f8e486e356c71e32636	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 40V, Positive-QTOF	splash10-01b9-1900000000-347bd9e7e8ffaf28fcd0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 10V, Negative-QTOF	splash10-03di-1900000000-ec51c8ce6fdbaa61f9a3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 20V, Negative-QTOF	splash10-0006-9300000000-af4aa5c1323cb084f11b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 40V, Negative-QTOF	splash10-0006-9000000000-d66d571572d63a249158	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 10V, Negative-QTOF	splash10-03di-0900000000-e6ab8887b99ffd819d24	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 20V, Negative-QTOF	splash10-03di-0900000000-e6ab8887b99ffd819d24	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 40V, Negative-QTOF	splash10-03dl-6900000000-dcce14ef4d49b9ac36d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 10V, Positive-QTOF	splash10-014i-0900000000-6783a1f89318f3eb168a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 20V, Positive-QTOF	splash10-014i-0900000000-6783a1f89318f3eb168a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Oxoguanine 40V, Positive-QTOF	splash10-014i-9500000000-102b909edd37935ce4e2	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111670

KNApSAcK ID

Not Available

Chemspider ID

106574

KEGG Compound ID

C20155

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

8-Oxoguanine

METLIN ID

Not Available

PubChem Compound

119315

PDB ID

OXG

ChEBI ID

44605

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 8-Oxoguanine (HMDB0041820)

MOL for HMDB0041820 (8-Oxoguanine)

3D MOL for HMDB0041820 (8-Oxoguanine)

3D SDF for HMDB0041820 (8-Oxoguanine)

3D-SDF for HMDB0041820 (8-Oxoguanine)

PDB for HMDB0041820 (8-Oxoguanine)

3D PDB for HMDB0041820 (8-Oxoguanine)

SMILES for HMDB0041820 (8-Oxoguanine)

INCHI for HMDB0041820 (8-Oxoguanine)

Structure for HMDB0041820 (8-Oxoguanine)

3D Structure for HMDB0041820 (8-Oxoguanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra