ContaminantDB: 2,8-Dihydroxyadenine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:16:17 UTC

Update Date

2016-11-09 01:21:12 UTC

Accession Number

CHEM034846

Identification

Common Name

2,8-Dihydroxyadenine

Class

Small Molecule

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 calculi and arthritis, and is identified in Adenine phosphoribosyltransferase deficiency (APRT, OMIM 102600). (PMID 16613999) In APRT, 2,8-dihydroxyadenine (DHA) accumulates in crystals within the tubular 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) [HMDB]

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6R)-2,6-2,8-Dihydroxyadenine	HMDB
2,8-Dioxyadenine	HMDB
6-Amino-1H-purine-2,8(3H,7H)-dione	HMDB
6-Amino-2,8-dihydroxypurine	HMDB
6-Amino-7H-purine-2,8-diol	HMDB
6-Amino-purine-2,8-diol	HMDB
Dimethyloctanoate	HMDB
Dimethyloctanoic acid	HMDB
2,8-Dihydroxyadenine	MeSH

Chemical Formula

C₅H₅N₅O₂

Average Molecular Mass

167.126 g/mol

Monoisotopic Mass

167.044 g/mol

CAS Registry Number

30377-37-8

IUPAC Name

6-amino-7H-purine-2,8-diol

Traditional Name

6-amino-2,8-dihydroxypurine

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

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
Pyrimidone
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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	7.11 g/L	ALOGPS
logP	-0.7	ALOGPS
logP	0.18	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	8.78	ChemAxon
pKa (Strongest Basic)	0.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.94 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.6 m³·mol⁻¹	ChemAxon
Polarizability	14.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-2900000000-2a6ad00e5a61874dafba	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-006t-5590000000-9a6615b1bb6baa991e39	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-992c36bf805d3bd5b77c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-0900000000-b0d2a41d5894b75e61ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc3-9500000000-094a0ab08df4cb8d66d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-73c402f938cd3d00ebbb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-2900000000-dfacf0b01ba05bd293a8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-56660a79cc117195f3ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-f1c385fcdecbeefa0015	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1900000000-926ad02fad1950acf99d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-a310374a286696bca445	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-2907e7cb009d3747cf21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1900000000-623b79f0acf731c6831f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-9200000000-2c1cb7961f2587587a7a	Spectrum