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Record Information
Version	2.0
Creation Date	2012-10-10 12:17:04 -0600
Update Date	2015-06-03 17:25:57 -0600
Secondary Accession Numbers	ECMDB23110
Identification
Name:	5-Hydroxyisourate
Description	5-Hydroxyisourate is involved in purine degradation. It is a substrate of the enzyme hydroxyisourate hydrolase which catalyzes the reaction 5-hydroxyisourate + H2O <=> 5-hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate. In most organisms, including some bacteria (such as E. coli), plants, and certain animals, urate is metabolized via a common pathway, producing the stereospecific form S-allantoin as the final product. In the first step of the pathway factor-independent urate hydroxylase catalyzes the conversion of urate to 5-hydroxyisourate.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xabab3a78> Close
Synonyms:	5-Hydroxy-2,6-dioxo-2,5,6,7-tetrahydro-1H-purin-8-olate 5-Hydroxy-2,6-dioxo-2,5,6,7-tetrahydro-1H-purin-8-olic acid 5-hydroxy-3,7-dihydropurine-2,6,8-trione 5-Hydroxy-5,7-dihydro-1H-purin-2,6,8(3H)-trion 5-hydroxy-5,7-dihydro-1H-purine-2,6,8(9H)-trione 5-Hydroxyisoate 5-Hydroxyisoic acid 5-Hydroxyisouric acid
Chemical Formula:	C5H4N4O4
Weight:	Average: 184.1097 Monoisotopic: 184.023254636
InChI Key:	LTQYPAVLAYVKTK-UHFFFAOYSA-N
InChI:	InChI=1S/C5H4N4O4/c10-2-5(13)1(6-3(11)8-2)7-4(12)9-5/h13H,(H3,6,7,8,9,10,11,12)
CAS number:	Not Available
IUPAC Name:	5-hydroxy-2,3,5,6,7,8-hexahydro-1H-purine-2,6,8-trione
Traditional IUPAC Name:	5-hydroxyisourate
SMILES:	OC12NC(=O)N=C1NC(=O)NC2=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Imidazopyrimidines
Sub Class	Purines and purine derivatives
Direct Parent	Xanthines
Alternative Parents	Purinones Alpha amino acids and derivatives Alkaloids and derivatives Pyrimidones N-acyl ureas Diazinanes Imidazolines Dicarboximides Propargyl-type 1,3-dipolar organic compounds Alkanolamines Carboximidamides Carboxamidines Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds
Substituents	Xanthine Alpha-amino acid or derivatives Purinone Alkaloid or derivatives N-acyl urea Pyrimidone Ureide 1,3-diazinane Pyrimidine Dicarboximide 3-imidazoline Carbonic acid derivative Urea Organic 1,3-dipolar compound Propargyl-type 1,3-dipolar organic compound Amidine Carboxylic acid amidine Carboxylic acid derivative Carboximidamide Azacycle Alkanolamine Organic nitrogen compound Carbonyl group Organic oxygen compound Hydrocarbon derivative Organonitrogen compound Organooxygen compound Organopnictogen compound Organic oxide Aliphatic heteropolycyclic compound
Molecular Framework	Aliphatic heteropolycyclic compounds
External Descriptors	oxopurine (CHEBI:18072 ) a small molecule (5-HYDROXYISOURATE )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 10.6 g/L ALOGPS logP -1.5 ALOGPS logP -2.1 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 9.01 ChemAxon pKa (Strongest Basic) -1.2 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 119.89 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 35.59 m³·mol⁻¹ ChemAxon Polarizability 14.17 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	5-Hydroxyisourate + Water + 5-Hydroxyisourate <> 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate + 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate 5-Hydroxyisourate + Water > 5-Hydroxy-2-oxo-4-ureido-2,5-dihydro-1H-imidazole-5-carboxylate
SMPDB Pathways:	Not Available
KEGG Pathways:	Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120 Purine metabolism ec00230
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-03di-3900000000-9b1ae81006075657af68 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-02p3-9650000000-825c5f18d73a46374e67 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0900000000-8943d9513d56a0d37995 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0900000000-bacca7a51ca984e98e8d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0006-9300000000-31f89414751f8acd2682 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001l-2900000000-6239a44eb8a55c6e1a17 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0006-9400000000-c4edb92f0fb9241b2770 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0006-9000000000-90e2feee28cabb16c73c View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 18072 HMDB ID HMDB30097 Pubchem Compound ID 250388 Kegg ID C11821 ChemSpider ID 219288 Wikipedia 5-Hydroxyisourate BioCyc ID Not Available

Enzymes