| Common Name |
2-Hydroxyadenine
| Description |
2-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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
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
IsoguanineHMDB
2-OH-AdeMeSH
CrotonosideMeSH
| Chemical Formlia |
C5H5N5O
| Average Molecliar Weight |
151.1261
| Monoisotopic Molecliar Weight |
151.049409807
| IUPAC Name |
6-amino-7H-purin-2-ol
| Traditional Name |
2-hydroxy-6-aminopurine
| CAS Registry Number |
3373-53-3
| 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 Key |
DRAVOWXCEBXPTN-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Imidazopyrimidines
| Direct Parent |
6-aminopurines
| Alternative Parents |
Hydroxypyrimidines
Aminopyrimidines and derivatives
Primary aromatic amines
Imidolactams
Imidazoles
Heteroaromatic compounds
Azacyclic compounds
Organopnictogen compounds
Organooxygen compounds
Hydrocarbon derivatives
| Substituents |
6-aminopurine
Aminopyrimidine
Hydroxypyrimidine
Primary aromatic amine
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
oxopurine (CHEBI:62462 )
a small moleclie (CPD0-2461 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point> 360 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0625 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0900000000-42af2345f291c0931747View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-053r-2900000000-20dc64d93a8160bc7cbaView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0kai-9200000000-dd4e5a7f42bbde9a7362View in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
UrineDetected and Quantified<1 nmol/mmol creatinineAdlit (>18 years old)BothNormal
19309105
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022019
| KNApSAcK ID |
Not Available
| Chemspider ID |
69351
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
isoguanine
| NuGOwiki Link |
HMDB00403
| Metagene Link |
HMDB00403
| METLIN ID |
5392
| PubChem Compound |
76900
| PDB ID |
IGA
| ChEBI ID |
62462
Product: GDC-0834 (S-enantiomer)
References |
| Synthesis Reference |
Hayashi, Taketo; Tamato, Toyomochi. Preparation of isoguanine. Jpn. Kokai Tokkyo Koho (1994), 3 pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- 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. [PubMed:1324197 ]
- 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. [PubMed:9726022 ]
|
PMID: 26396196