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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:55 UTC

HMDB ID

HMDB0000542

Secondary Accession Numbers

HMDB00542

Metabolite Identification

Common Name

8-Hydroxyadenine

Description

8-hydroxyadenine is an intermediate in the oxidation of adenine to 2,8-dihydroxyadenine by xanthine oxidase (EC 1.1.3.22). A controversy exists as to whether or not this metabolite is a marker of DNA damage. Several papers have reported an artifactual formation of a number of modified bases from intact DNA bases during derivatization of DNA hydrolysates to be analyzed by gas chromatography-mass spectrometry (GC/MS). These reports dealt with 8-hydroxyadenine (8-OH). It needs to be emphasized that the procedures for hydrolysis of DNA and derivatization of DNA hydrolysates used in these papers substantially differed from the established procedures previously described. Furthermore, a large number of relevant papers reporting the levels of these modified bases in DNA of various sources have been ignored. Interestingly, the levels of modified bases reported in the literature were not as high as those reported prior to prepurification. Levels of 8-OH-Ade were quite close to, or even the same as, or smaller than the level reported after prepurification. All these facts raise the question of the validity of the claims about the measurement of these modified DNA bases by GC/MS. Oxidative damage to DNA may play an important role in aging and neurodegenerative diseases such as Alzheimer's disease (AD). Attack on DNA by reactive oxygen species, particularly hydroxyl radicals, can lead to strand breaks, DNA-DNA and DNA-protein cross-linking, sister chromatid exchange and translocation, and formation of at least 20 oxidized base adducts. Modification of DNA bases can lead to mutation and altered protein synthesis. In late-stage AD brain, several studies have shown an elevation of the base adducts 8-hydroxyadenine (8-OHA). Several studies have shown a decline in repair of 8-OHG in AD. Most recently studies have shown elevated 8-OHA in nuclear and mitochondrial DNA in mild cognitive impairment, the earliest detectable form of AD, suggesting that oxidative damage to DNA is an early event in AD and not a secondary phenomenon. (PMID: 10098459 , 17034348 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
7,8-Dihydro-8-oxoadenine	ChEBI
8-oxo-7,8-Dihydroadenine	ChEBI
8-OxoA	ChEBI
Oxyadenine	ChEBI
6-Amino-1,7-dihydro-8H-purin-8-one	HMDB
6-Amino-8-hydroxypurine	HMDB
6-Amino-purin-8(9H)-one	HMDB
6-Amino-purin-8-ol	HMDB
8-Hydroxy-1H-purin-6-amine	HMDB
8-Oxoadenine	HMDB
Oksaden	HMDB
Oxaden	HMDB
7,8-DHOA	HMDB

Chemical Formula

C₅H₅N₅O

Average Molecular Weight

151.1261

Monoisotopic Molecular Weight

151.049409807

IUPAC Name

6-amino-7H-purin-8-ol

Traditional Name

6-amino-8-hydroxypurine

CAS Registry Number

21149-26-8

SMILES

NC1=NC=NC2=C1NC(O)=N2

InChI Identifier

InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11)

InChI Key

RGKBRPAAQSHTED-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

6-aminopurine
Purinone
Aminopyrimidine
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Urea
Azacycle
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000542)

Source

Endogenous

Endogenous (HMDB: HMDB0000542)

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

Solid

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	6.58 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-0.19	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	5.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.71 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	39.67 m³·mol⁻¹	ChemAxon
Polarizability	13.45 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]+	130.168	31661259
DarkChem	[M-H]-	127.374	31661259
AllCCS	[M+H]+	132.977	32859911
AllCCS	[M-H]-	126.237	32859911
DeepCCS	[M+H]+	129.877	30932474
DeepCCS	[M-H]-	126.346	30932474
DeepCCS	[M-2H]-	163.603	30932474
DeepCCS	[M+Na]+	138.913	30932474
AllCCS	[M+H]+	133.0	32859911
AllCCS	[M+H-H2O]+	128.3	32859911
AllCCS	[M+NH4]+	137.3	32859911
AllCCS	[M+Na]+	138.6	32859911
AllCCS	[M-H]-	126.2	32859911
AllCCS	[M+Na-2H]-	127.2	32859911
AllCCS	[M+HCOO]-	128.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyadenine	NC1=NC=NC2=C1NC(O)=N2	2769.4	Standard polar	33892256
8-Hydroxyadenine	NC1=NC=NC2=C1NC(O)=N2	2076.5	Standard non polar	33892256
8-Hydroxyadenine	NC1=NC=NC2=C1NC(O)=N2	1851.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyadenine,1TMS,isomer #1	C[Si](C)(C)OC1=NC2=NC=NC(N)=C2[NH]1	2008.9	Semi standard non polar	33892256
8-Hydroxyadenine,1TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O)=N2	2139.4	Semi standard non polar	33892256
8-Hydroxyadenine,1TMS,isomer #3	C[Si](C)(C)N1C(O)=NC2=NC=NC(N)=C21	1992.5	Semi standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C)=N2	1972.9	Semi standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C)=N2	1932.6	Standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C)=N2	3030.6	Standard polar	33892256
8-Hydroxyadenine,2TMS,isomer #2	C[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C	1984.9	Semi standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #2	C[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C	1913.2	Standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #2	C[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C	2793.0	Standard polar	33892256
8-Hydroxyadenine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C	2106.8	Semi standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C	2040.3	Standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #3	C[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C	2757.5	Standard polar	33892256
8-Hydroxyadenine,2TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2	2001.7	Semi standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2	1926.6	Standard non polar	33892256
8-Hydroxyadenine,2TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2	2716.1	Standard polar	33892256
8-Hydroxyadenine,3TMS,isomer #1	C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]1	2004.1	Semi standard non polar	33892256
8-Hydroxyadenine,3TMS,isomer #1	C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]1	1971.4	Standard non polar	33892256
8-Hydroxyadenine,3TMS,isomer #1	C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]1	2619.4	Standard polar	33892256
8-Hydroxyadenine,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	1996.0	Semi standard non polar	33892256
8-Hydroxyadenine,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	1922.6	Standard non polar	33892256
8-Hydroxyadenine,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N2	2671.9	Standard polar	33892256
8-Hydroxyadenine,3TMS,isomer #3	C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C	2009.0	Semi standard non polar	33892256
8-Hydroxyadenine,3TMS,isomer #3	C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C	1994.3	Standard non polar	33892256
8-Hydroxyadenine,3TMS,isomer #3	C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C	2413.1	Standard polar	33892256
8-Hydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C	2062.0	Semi standard non polar	33892256
8-Hydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C	2005.6	Standard non polar	33892256
8-Hydroxyadenine,4TMS,isomer #1	C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C	2320.1	Standard polar	33892256
8-Hydroxyadenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2[NH]1	2237.9	Semi standard non polar	33892256
8-Hydroxyadenine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O)=N2	2330.2	Semi standard non polar	33892256
8-Hydroxyadenine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(O)=NC2=NC=NC(N)=C21	2250.2	Semi standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N2	2395.3	Semi standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N2	2308.2	Standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N2	3067.8	Standard polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C(C)(C)C	2405.7	Semi standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C(C)(C)C	2308.2	Standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C(C)(C)C	2855.3	Standard polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C(C)(C)C	2530.3	Semi standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C(C)(C)C	2435.1	Standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C(C)(C)C	2765.7	Standard polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2	2450.0	Semi standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2	2290.8	Standard non polar	33892256
8-Hydroxyadenine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2	2798.5	Standard polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]1	2538.3	Semi standard non polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]1	2607.2	Standard non polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2[NH]1	2766.1	Standard polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2574.3	Semi standard non polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2544.5	Standard non polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=N2	2808.3	Standard polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2)[Si](C)(C)C(C)(C)C	2625.0	Semi standard non polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2)[Si](C)(C)C(C)(C)C	2601.2	Standard non polar	33892256
8-Hydroxyadenine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N2)[Si](C)(C)C(C)(C)C	2634.4	Standard polar	33892256
8-Hydroxyadenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N1[Si](C)(C)C(C)(C)C	2744.7	Semi standard non polar	33892256
8-Hydroxyadenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N1[Si](C)(C)C(C)(C)C	2828.5	Standard non polar	33892256
8-Hydroxyadenine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N1[Si](C)(C)C(C)(C)C	2685.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zmi-2900000000-15799f7dfde6b61d5e9d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (1 TMS) - 70eV, Positive	splash10-0kmi-5930000000-e3d510cf39e85c0d6c20	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	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-Hydroxyadenine 10V, Positive-QTOF	splash10-0udi-0900000000-d209f35bcb47000991e2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Positive-QTOF	splash10-0udi-0900000000-ccfafe3d723f793a566c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Positive-QTOF	splash10-0kai-9500000000-8441670cd85efff4fc68	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 10V, Negative-QTOF	splash10-0udi-0900000000-7396c5f39ca266e16ca2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Negative-QTOF	splash10-0udi-0900000000-fcac70e143de08e16c17	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Negative-QTOF	splash10-0006-9100000000-c317d7036a3bfb98fedb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 10V, Positive-QTOF	splash10-0udi-0900000000-361a2474138028086bb3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Positive-QTOF	splash10-0udi-0900000000-50d8e77d9b1fbd7cf4b1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Positive-QTOF	splash10-05ai-7900000000-40365895919344706a26	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 10V, Negative-QTOF	splash10-0udi-0900000000-062eb4a75a9800bdbe07	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Negative-QTOF	splash10-0ul0-0900000000-6b703dbbb8530abc9653	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Negative-QTOF	splash10-014l-9200000000-5a08d4210b257200ae71	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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

FDB022105

KNApSAcK ID

C00043227

Chemspider ID

4511108

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5527

PubChem Compound

95215

PDB ID

Not Available

ChEBI ID

134104

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Makarieva, Tatyana N.; Guzii, Alla G.; Dmitrenok, Andrei S.; Dmitrenok, Pavel S.; Krasokhin, Vladimir B.; Stonik, Valentin A. 8-Oxoadenine, 9-methyl-8-oxoadenine, and trihydroxylated sterols from a Far Eastern thorectidae sponge. Natural Product Communications (2006), 1(9), 711-714.

Material Safety Data Sheet (MSDS)

Not Available

General References

Bartlett GR: Metabolism by man of intravenously administered adenine. Transfusion. 1977 Jul-Aug;17(4):367-73. [PubMed:878002 ]
Ravanat JL, Guicherd P, Tuce Z, Cadet J: Simultaneous determination of five oxidative DNA lesions in human urine. Chem Res Toxicol. 1999 Sep;12(9):802-8. [PubMed:10490501 ]
Stillwell WG, Xu HX, Adkins JA, Wishnok JS, Tannenbaum SR: Analysis of methylated and oxidized purines in urine by capillary gas chromatography-mass spectrometry. Chem Res Toxicol. 1989 Mar-Apr;2(2):94-9. [PubMed:2519715 ]
Webb AL, Singh RH, Kennedy MJ, Elsas LJ: Verbal dyspraxia and galactosemia. Pediatr Res. 2003 Mar;53(3):396-402. [PubMed:12595586 ]
WYNGAARDEN JB, DUNN JT: 8-Hydroxyadenine as the intermediate in the oxidation of adenine to 2, 8-dihydroxyadenine by xanthine oxidase. Arch Biochem Biophys. 1957 Jul;70(1):150-6. [PubMed:13445250 ]
Dizdaroglu M: Facts about the artifacts in the measurement of oxidative DNA base damage by gas chromatography-mass spectrometry. Free Radic Res. 1998 Dec;29(6):551-63. [PubMed:10098459 ]
Markesbery WR, Lovell MA: DNA oxidation in Alzheimer's disease. Antioxid Redox Signal. 2006 Nov-Dec;8(11-12):2039-45. [PubMed:17034348 ]

Showing metabocard for 8-Hydroxyadenine (HMDB0000542)

MOL for HMDB0000542 (8-Hydroxyadenine)

3D MOL for HMDB0000542 (8-Hydroxyadenine)

3D SDF for HMDB0000542 (8-Hydroxyadenine)

3D-SDF for HMDB0000542 (8-Hydroxyadenine)

PDB for HMDB0000542 (8-Hydroxyadenine)

3D PDB for HMDB0000542 (8-Hydroxyadenine)

SMILES for HMDB0000542 (8-Hydroxyadenine)

INCHI for HMDB0000542 (8-Hydroxyadenine)

Structure for HMDB0000542 (8-Hydroxyadenine)

3D Structure for HMDB0000542 (8-Hydroxyadenine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra