| Common Name |
2,8-Dihydroxyadenine
| Description |
2,8-Dihydroxyadenine is a Purine metabolite usually not detectable in biofluids of normal individuals; this insoluble metabolite (at physiological urinary pH) cause urinary tract calclii and arthritis, and is identified in Adenine phosphoribosyltransferase deficiency (APRT, OMIM 102600 ). (PMID 16613999 ) In APRT, 2,8-dihydroxyadenine (DHA) accumliates in crystals within the tubliar lumens (a feature of many kidney stone diseases) creating crystal-induced injury in human kidney epithelial cells. (PMID 16374038 ) Urinary DHA crystals are easily recognized under a microscope, and effective treatment can be offered and therefore the prognosis depends upon the renal function at diagnosis; treatment consists of adequate fluid intake, a low-purine diet and administration of allopurinol. (PMID 15764278 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(6R)-2,6-2,8-DihydroxyadenineHMDB
2,8-DioxyadenineHMDB
6-amino-1H-Purine-2,8(3H,7H)-dioneHMDB
6-amino-2,8-DihydroxypurineHMDB
6-amino-7H-Purine-2,8-diolHMDB
6-amino-Purine-2,8-diolHMDB
DimethyloctanoateHMDB
Dimethyloctanoic acidHMDB
| Chemical Formlia |
C5H5N5O2
| Average Molecliar Weight |
167.1255
| Monoisotopic Molecliar Weight |
167.044324429
| IUPAC Name |
6-amino-7H-purine-2,8-diol
| Traditional Name |
6-amino-2,8-dihydroxypurine
| CAS Registry Number |
30377-37-8
| SMILES |
NC1=NC(O)=NC2=C1NC(O)=N2
| InChI Identifier |
InChI=1S/C5H5N5O2/c6-2-1-3(9-4(11)7-1)10-5(12)8-2/h(H5,6,7,8,9,10,11,12)
| InChI Key |
XFBOJHLYDJZYSP-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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 |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Imidazopyrimidines
| Direct Parent |
Purinones
| Alternative Parents |
6-aminopurines
Pyrimidones
Aminopyrimidines and derivatives
Primary aromatic amines
Imidazoles
Heteroaromatic compounds
Ureas
Azacyclic compounds
Organopnictogen compounds
Organooxygen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
6-aminopurine
Purinone
Aminopyrimidine
Pyrimidone
Primary aromatic amine
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.002 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility7.11 mg/mLALOGPS
logP-0.7ALOGPS
logP0.18ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.78ChemAxon
pKa (Strongest Basic)0.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.94 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.6 m3·mol-1ChemAxon
Polarizability14.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| 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
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022018
| KNApSAcK ID |
Not Available
| Chemspider ID |
83302
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
2,8-Dihydroxyadenine
| NuGOwiki Link |
HMDB00401
| Metagene Link |
HMDB00401
| METLIN ID |
5390
| PubChem Compound |
92268
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: PNU-282987 (S enantiomer free base)
References |
| Synthesis Reference |
Stevens, Marcus A.; Smith, Herman W.; Brown, George Bosworth. Purine N-oxides. VII. Reaction of aminopurine 1-N-oxides with acetic anhydride. Journal of the American Chemical Society (1960), 82 1148-52. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Hartmann S, Okun JG, Schmidt C, Langhans CD, Garbade SF, Burgard P, Haas D, Sass JO, Nyhan WL, Hoffmann GF: Comprehensive detection of disorders of purine and pyrimidine metabolism by HPLC with electrospray ionization tandem mass spectrometry. Clin Chem. 2006 Jun;52(6):1127-37. Epub 2006 Apr 13. [PubMed:16613999 ]
- Roth GJ, Moore GL, Kline WE, Poskitt TR: The renal effect of intravenous adenine in humans. Transfusion. 1975 Mar-Apr;15(2):116-23. [PubMed:1091029 ]
- Peck CC, Bailey FJ, Moore GL: Enhanced solubility of 2,8 dihydroxyadenine (DOA) in human urine. Transfusion. 1977 Jul-Aug;17(4):383-90. [PubMed:17934 ]
- Bartlett GR: Metabolism by man of intravenously administered adenine. Transfusion. 1977 Jul-Aug;17(4):367-73. [PubMed:878002 ]
- Liang L, Chen J, Vittal R, Selvanayagam ZE, McAteer JA, Deng L, Tischfield J, Chin KV, Sahota A: Expression profiling of crystal-induced injury in human kidney epithelial cells. Nephron Physiol. 2006;103(1):p53-62. Epub 2005 Dec 21. [PubMed:16374038 ]
- Arnadottir M, Laxdal T, Halldorsdottir B: 2,8-dihydroxyadeninuria: are there no cases in Scandinavia? Scand J Urol Nephrol. 2005;39(1):82-6. [PubMed:15764278 ]
|
PMID: 26552848