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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:38 UTC
HMDB IDHMDB00403
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxyadenine
Description2-Hydroxyadenine (2-OH-Ade) is formed by hydroxyl radical attack on DNA bases and shows a genotoxicity in human, being the source of the mutations induced by reactive oxygen species. 2-OH-Ade in DNA is miscoding and elicits various mutations, and is a mutagenic in bacterial and mammalian cells. (Recent Research Developments in Biochemistry (2000)2:41-50).
Structure
Thumb
Synonyms
ValueSource
2-HydroxyadenineChEBI
2-OxoadenineChEBI
6-amino-1,3-dihydro-2H-Purin-2-oneChEBI
6-amino-3,7-dihydro-Purin-2-oneChEBI
6-amino-3,9-dihydro-2H-Purin-2-oneChEBI
6-amino-7H-Purin-2-olChEBI
6-amino-9H-Purin-2-olChEBI
2-Hydroxy-6-aminopurineHMDB
2-OxyadenineHMDB
6-amino-2-HydroxypurineHMDB
6-amino-3,7(9)-dihydro-Purin-2-oneHMDB
Chemical FormulaC5H5N5O
Average Molecular Weight151.1261
Monoisotopic Molecular Weight151.049409807
IUPAC Name6-amino-7H-purin-2-ol
Traditional Name2-hydroxy-6-aminopurine
CAS Registry Number3373-53-3
SMILES
NC1=NC(O)=NC2=C1NC=N2
InChI Identifier
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyInChIKey=DRAVOWXCEBXPTN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. 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 Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Hydroxypyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0625 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.06 mg/mLALOGPS
logP-0.65ALOGPS
logP-0.2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.78ChemAxon
pKa (Strongest Basic)2.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.71 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.15 m3·mol-1ChemAxon
Polarizability13.36 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-42af2345f291c0931747View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-2900000000-20dc64d93a8160bc7cbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kai-9200000000-dd4e5a7f42bbde9a7362View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified<1 nmol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022019
KNApSAcK IDNot Available
Chemspider ID69351
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Linkisoguanine
NuGOwiki LinkHMDB00403
Metagene LinkHMDB00403
METLIN ID5392
PubChem Compound76900
PDB IDIGA
ChEBI ID62462
References
Synthesis ReferenceHayashi, Taketo; Tamato, Toyomochi. Preparation of isoguanine. Jpn. Kokai Tokkyo Koho (1994), 3 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Olinski R, Zastawny T, Budzbon J, Skokowski J, Zegarski W, Dizdaroglu M: DNA base modifications in chromatin of human cancerous tissues. FEBS Lett. 1992 Sep 7;309(2):193-8. [1324197 ]
  2. Arashidani K, Iwamoto-Tanaka N, Muraoka M, Kasai H: Genotoxicity of ribo- and deoxyribonucleosides of 8-hydroxyguanine, 5-hydroxycytosine, and 2-hydroxyadenine: induction of SCE in human lymphocytes and mutagenicity in Salmonella typhimurium TA 100. Mutat Res. 1998 Jul 17;403(1-2):223-7. [9726022 ]