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Showing metabocard for 8-Hydroxyadenine (HMDB0000542)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:55 UTC
HMDB IDHMDB0000542
Secondary Accession Numbers
  • HMDB00542
Metabolite Identification
Common Name8-Hydroxyadenine
Description8-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
Data?1676999695
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000542 (8-Hydroxyadenine)

8-Hydroxyadenine.mol
  Mrv0541 02231218352D          

 11 12  0  0  0  0            999 V2000
   -1.7624    0.0022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7598    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309    0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    1.0753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9374    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504   -0.2596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624    0.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  6  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0000542 (8-Hydroxyadenine)

HMDB0000542
     RDKit          3D
8-Hydroxyadenine
 16 17  0  0  0  0  0  0  0  0999 V2000
   -0.8858    2.2841   -0.2591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621    0.8733   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2949    0.3316   -0.0469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -1.0017    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -1.8412    0.0551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -1.3831   -0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -1.9499   -0.0744 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859   -0.9832   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544   -1.1809   -0.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097    0.1907   -0.2355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041   -0.0165   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5257    2.8746   -0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0988    2.7745    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982   -1.4117    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9257   -0.6603    0.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135    1.0997   -0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11  2  1  0
 11  6  2  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  9 15  1  0
 10 16  1  0
M  END
Download

3D SDF for HMDB0000542 (8-Hydroxyadenine)

8-Hydroxyadenine.mol
  Mrv0541 02231218352D          

 11 12  0  0  0  0            999 V2000
   -1.7624    0.0022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7598    0.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309    0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3334   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0517   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545    1.0753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9374    0.4063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504   -0.2596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7624    0.4038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  6  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000542

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C5H5N5O

> <MOLECULAR_WEIGHT>
151.1261

> <EXACT_MASS>
151.049409807

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
13.450917479326169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-7H-purin-8-ol

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
-0.19278554733333342

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.000640902975775

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.891531635117873

> <JCHEM_PKA_STRONGEST_BASIC>
5.111952418949486

> <JCHEM_POLAR_SURFACE_AREA>
100.71

> <JCHEM_REFRACTIVITY>
39.6737

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-amino-8-hydroxypurine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000542 (8-Hydroxyadenine)

HMDB0000542
     RDKit          3D
8-Hydroxyadenine
 16 17  0  0  0  0  0  0  0  0999 V2000
   -0.8858    2.2841   -0.2591 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0621    0.8733   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2949    0.3316   -0.0469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -1.0017    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4276   -1.8412    0.0551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -1.3831   -0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -1.9499   -0.0744 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859   -0.9832   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544   -1.1809   -0.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097    0.1907   -0.2355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041   -0.0165   -0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5257    2.8746   -0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0988    2.7745    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982   -1.4117    0.1394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9257   -0.6603    0.4222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135    1.0997   -0.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11  2  1  0
 11  6  2  0
  1 12  1  0
  1 13  1  0
  4 14  1  0
  9 15  1  0
 10 16  1  0
M  END
Download

PDB for HMDB0000542 (8-Hydroxyadenine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 8-Hydroxyadenine.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -3.290   0.004   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -3.285   1.544   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.949   2.310   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.618   1.536   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.622  -0.004   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.959  -0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.963  -2.310   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       0.848   2.007   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.750   0.758   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.841  -0.485   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       3.290   0.754   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    1                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0000542 (8-Hydroxyadenine)

COMPND    HMDB0000542
HETATM    1  N1  UNL     1      -0.886   2.284  -0.259  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.062   0.873  -0.152  1.00  0.00           C  
HETATM    3  N2  UNL     1      -2.295   0.332  -0.047  1.00  0.00           N  
HETATM    4  C2  UNL     1      -2.479  -1.002   0.055  1.00  0.00           C  
HETATM    5  N3  UNL     1      -1.428  -1.841   0.055  1.00  0.00           N  
HETATM    6  C3  UNL     1      -0.175  -1.383  -0.045  1.00  0.00           C  
HETATM    7  N4  UNL     1       1.063  -1.950  -0.074  1.00  0.00           N  
HETATM    8  C4  UNL     1       1.986  -0.983  -0.192  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.354  -1.181  -0.253  1.00  0.00           O  
HETATM   10  N5  UNL     1       1.310   0.191  -0.236  1.00  0.00           N  
HETATM   11  C5  UNL     1      -0.004  -0.017  -0.149  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.526   2.875  -0.815  1.00  0.00           H  
HETATM   13  H2  UNL     1      -0.099   2.775   0.223  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.498  -1.412   0.139  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.926  -0.660   0.422  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.813   1.100  -0.326  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3   11
CONECT    3    4
CONECT    4    5    5   14
CONECT    5    6
CONECT    6    7   11   11
CONECT    7    8    8
CONECT    8    9   10
CONECT    9   15
CONECT   10   11   16
END
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SMILES for HMDB0000542 (8-Hydroxyadenine)

NC1=NC=NC2=C1NC(O)=N2
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INCHI for HMDB0000542 (8-Hydroxyadenine)

InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-3)10-5(11)9-2/h1H,(H4,6,7,8,9,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
7,8-Dihydro-8-oxoadenineChEBI
8-oxo-7,8-DihydroadenineChEBI
8-OxoAChEBI
OxyadenineChEBI
6-Amino-1,7-dihydro-8H-purin-8-oneHMDB
6-Amino-8-hydroxypurineHMDB
6-Amino-purin-8(9H)-oneHMDB
6-Amino-purin-8-olHMDB
8-Hydroxy-1H-purin-6-amineHMDB
8-OxoadenineHMDB
OksadenHMDB
OxadenHMDB
7,8-DHOAHMDB
Chemical FormulaC5H5N5O
Average Molecular Weight151.1261
Monoisotopic Molecular Weight151.049409807
IUPAC Name6-amino-7H-purin-8-ol
Traditional Name6-amino-8-hydroxypurine
CAS Registry Number21149-26-8
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 KeyRGKBRPAAQSHTED-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurinones
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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.58 g/LALOGPS
logP-0.82ALOGPS
logP-0.19ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.89ChemAxon
pKa (Strongest Basic)5.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.71 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.67 m³·mol⁻¹ChemAxon
Polarizability13.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.16831661259
DarkChem[M-H]-127.37431661259
AllCCS[M+H]+132.97732859911
AllCCS[M-H]-126.23732859911
DeepCCS[M+H]+129.87730932474
DeepCCS[M-H]-126.34630932474
DeepCCS[M-2H]-163.60330932474
DeepCCS[M+Na]+138.91330932474
AllCCS[M+H]+133.032859911
AllCCS[M+H-H2O]+128.332859911
AllCCS[M+NH4]+137.332859911
AllCCS[M+Na]+138.632859911
AllCCS[M-H]-126.232859911
AllCCS[M+Na-2H]-127.232859911
AllCCS[M+HCOO]-128.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.27 minutes32390414
Predicted by Siyang on May 30, 20228.6294 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.41 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid253.3 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid613.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid318.7 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid42.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid211.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid103.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid282.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid234.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)737.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid558.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid36.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid591.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid182.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid228.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate602.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA368.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water226.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-HydroxyadenineNC1=NC=NC2=C1NC(O)=N22769.4Standard polar33892256
8-HydroxyadenineNC1=NC=NC2=C1NC(O)=N22076.5Standard non polar33892256
8-HydroxyadenineNC1=NC=NC2=C1NC(O)=N21851.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxyadenine,1TMS,isomer #1C[Si](C)(C)OC1=NC2=NC=NC(N)=C2[NH]12008.9Semi standard non polar33892256
8-Hydroxyadenine,1TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O)=N22139.4Semi standard non polar33892256
8-Hydroxyadenine,1TMS,isomer #3C[Si](C)(C)N1C(O)=NC2=NC=NC(N)=C211992.5Semi standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C)=N21972.9Semi standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C)=N21932.6Standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #1C[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C)=N23030.6Standard polar33892256
8-Hydroxyadenine,2TMS,isomer #2C[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C1984.9Semi standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #2C[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C1913.2Standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #2C[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C2793.0Standard polar33892256
8-Hydroxyadenine,2TMS,isomer #3C[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C2106.8Semi standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #3C[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C2040.3Standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #3C[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C2757.5Standard polar33892256
8-Hydroxyadenine,2TMS,isomer #4C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O)=N22001.7Semi standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #4C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O)=N21926.6Standard non polar33892256
8-Hydroxyadenine,2TMS,isomer #4C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O)=N22716.1Standard polar33892256
8-Hydroxyadenine,3TMS,isomer #1C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]12004.1Semi standard non polar33892256
8-Hydroxyadenine,3TMS,isomer #1C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]11971.4Standard non polar33892256
8-Hydroxyadenine,3TMS,isomer #1C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2[NH]12619.4Standard polar33892256
8-Hydroxyadenine,3TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N21996.0Semi standard non polar33892256
8-Hydroxyadenine,3TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N21922.6Standard non polar33892256
8-Hydroxyadenine,3TMS,isomer #2C[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C)C(O[Si](C)(C)C)=N22671.9Standard polar33892256
8-Hydroxyadenine,3TMS,isomer #3C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C2009.0Semi standard non polar33892256
8-Hydroxyadenine,3TMS,isomer #3C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C1994.3Standard non polar33892256
8-Hydroxyadenine,3TMS,isomer #3C[Si](C)(C)N(C1=NC=NC2=C1N([Si](C)(C)C)C(O)=N2)[Si](C)(C)C2413.1Standard polar33892256
8-Hydroxyadenine,4TMS,isomer #1C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C2062.0Semi standard non polar33892256
8-Hydroxyadenine,4TMS,isomer #1C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C2005.6Standard non polar33892256
8-Hydroxyadenine,4TMS,isomer #1C[Si](C)(C)OC1=NC2=NC=NC(N([Si](C)(C)C)[Si](C)(C)C)=C2N1[Si](C)(C)C2320.1Standard polar33892256
8-Hydroxyadenine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2[NH]12237.9Semi standard non polar33892256
8-Hydroxyadenine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O)=N22330.2Semi standard non polar33892256
8-Hydroxyadenine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(O)=NC2=NC=NC(N)=C212250.2Semi standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N22395.3Semi standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N22308.2Standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1[NH]C(O[Si](C)(C)C(C)(C)C)=N23067.8Standard polar33892256
8-Hydroxyadenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C(C)(C)C2405.7Semi standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C(C)(C)C2308.2Standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=NC2=NC=NC(N)=C2N1[Si](C)(C)C(C)(C)C2855.3Standard polar33892256
8-Hydroxyadenine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C(C)(C)C2530.3Semi standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C(C)(C)C2435.1Standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1[NH]C(O)=N2)[Si](C)(C)C(C)(C)C2765.7Standard polar33892256
8-Hydroxyadenine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N22450.0Semi standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N22290.8Standard non polar33892256
8-Hydroxyadenine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C(O)=N22798.5Standard polar33892256
8-Hydroxyadenine,3TBDMS,isomer #1CC(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]12538.3Semi standard non polar33892256
8-Hydroxyadenine,3TBDMS,isomer #1CC(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]12607.2Standard non polar33892256
8-Hydroxyadenine,3TBDMS,isomer #1CC(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]12766.1Standard polar33892256
8-Hydroxyadenine,3TBDMS,isomer #2CC(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)=N22574.3Semi standard non polar33892256
8-Hydroxyadenine,3TBDMS,isomer #2CC(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)=N22544.5Standard non polar33892256
8-Hydroxyadenine,3TBDMS,isomer #2CC(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)=N22808.3Standard polar33892256
8-Hydroxyadenine,3TBDMS,isomer #3CC(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)C2625.0Semi standard non polar33892256
8-Hydroxyadenine,3TBDMS,isomer #3CC(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)C2601.2Standard non polar33892256
8-Hydroxyadenine,3TBDMS,isomer #3CC(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)C2634.4Standard polar33892256
8-Hydroxyadenine,4TBDMS,isomer #1CC(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)C2744.7Semi standard non polar33892256
8-Hydroxyadenine,4TBDMS,isomer #1CC(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)C2828.5Standard non polar33892256
8-Hydroxyadenine,4TBDMS,isomer #1CC(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)C2685.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zmi-2900000000-15799f7dfde6b61d5e9d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-5930000000-e3d510cf39e85c0d6c202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxyadenine GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 10V, Positive-QTOFsplash10-0udi-0900000000-d209f35bcb47000991e22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Positive-QTOFsplash10-0udi-0900000000-ccfafe3d723f793a566c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Positive-QTOFsplash10-0kai-9500000000-8441670cd85efff4fc682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 10V, Negative-QTOFsplash10-0udi-0900000000-7396c5f39ca266e16ca22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Negative-QTOFsplash10-0udi-0900000000-fcac70e143de08e16c172017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Negative-QTOFsplash10-0006-9100000000-c317d7036a3bfb98fedb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 10V, Positive-QTOFsplash10-0udi-0900000000-361a2474138028086bb32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Positive-QTOFsplash10-0udi-0900000000-50d8e77d9b1fbd7cf4b12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Positive-QTOFsplash10-05ai-7900000000-40365895919344706a262021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 10V, Negative-QTOFsplash10-0udi-0900000000-062eb4a75a9800bdbe072021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 20V, Negative-QTOFsplash10-0ul0-0900000000-6b703dbbb8530abc96532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxyadenine 40V, Negative-QTOFsplash10-014l-9200000000-5a08d4210b257200ae712021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022105
KNApSAcK IDC00043227
Chemspider ID4511108
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5527
PubChem Compound95215
PDB IDNot Available
ChEBI ID134104
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMakarieva, 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
  1. Bartlett GR: Metabolism by man of intravenously administered adenine. Transfusion. 1977 Jul-Aug;17(4):367-73. [PubMed:878002 ]
  2. 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 ]
  3. 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 ]
  4. Webb AL, Singh RH, Kennedy MJ, Elsas LJ: Verbal dyspraxia and galactosemia. Pediatr Res. 2003 Mar;53(3):396-402. [PubMed:12595586 ]
  5. 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 ]
  6. 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 ]
  7. Markesbery WR, Lovell MA: DNA oxidation in Alzheimer's disease. Antioxid Redox Signal. 2006 Nov-Dec;8(11-12):2039-45. [PubMed:17034348 ]