MiMeDB: Showing metabocard for 5-Hydroxyisourate (MMDBc0031761)

Plant

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:48:16 UTC

Update Date

2022-08-31 18:24:26 UTC

Metabolite ID

MMDBc0031761

Metabolite Identification

Common 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

MOL SDF PDB SMILES InChI


  Mrv1652303082006202D          

 13 14  0  0  0  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    0.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  1 12  1  0  0  0  0
  6 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031761

> <DATABASE_NAME>
MIME

> <SMILES>
OC12NC(=O)N=C1NC(=O)NC2=O

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
LTQYPAVLAYVKTK-UHFFFAOYSA-N

> <FORMULA>
C5H4N4O4

> <MOLECULAR_WEIGHT>
184.1097

> <EXACT_MASS>
184.023254636

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.166023939273785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-2,3,5,6,7,8-hexahydro-1H-purine-2,6,8-trione

> <ALOGPS_LOGP>
-1.48

> <JCHEM_LOGP>
-2.0658222776666664

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.609775593458831

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.010594873632646

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1773185839455471

> <JCHEM_POLAR_SURFACE_AREA>
119.89

> <JCHEM_REFRACTIVITY>
35.5905

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxyisourate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.530   1.777   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       1.036   0.999   0.000  0.00  0.00           O+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    1    7   13                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    1                                                       
CONECT   13    6                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Synonyms

Value	Source
5-Hydroxyisouric acid	Generator
5-Hydroxy-2,6-dioxo-2,5,6,7-tetrahydro-1H-purin-8-olate	HMDB
5-Hydroxy-5,7-dihydro-1H-purine-2,6,8(9H)-trione	HMDB

Molecular Formula

C₅H₄N₄O₄

Average Mass

184.1097

Monoisotopic Mass

184.023254636

IUPAC Name

5-hydroxy-2,3,5,6,7,8-hexahydro-1H-purine-2,6,8-trione

Traditional Name

5-hydroxyisourate

CAS Registry Number

Not Available

SMILES

OC12NC(=O)N=C1NC(=O)NC2=O

InChI Identifier

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)

InChI Key

LTQYPAVLAYVKTK-UHFFFAOYSA-N

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.59 m³·mol⁻¹	ChemAxon
Polarizability	14.17 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	61	Human feces; Human ; Human feces; pleural fluid plaque; bal; Human sputum; Pig	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	117	Human feces; Human	Metabolic reconstruction
Bacteria	Actinobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	1		Metabolic reconstruction
Bacteria	Bacteroidetes	43	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	13	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1	Human feces	Metabolic reconstruction
Bacteria/NULL	Actinobacteria	1	Human feces; Human	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	4	Human feces
Archaea/Archaea	Euryarchaeota	2	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	1
Bacteria	Deinococcus-Thermus	1

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0030097

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

5-Hydroxyisourate

METLIN ID

Not Available

PubChem Compound

250388

PDB ID

Not Available

ChEBI ID

18072

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 5-Hydroxyisourate (MMDBc0031761)

MOL for #<Metabolite:0x0000560be27eff10>

3D MOL for #<Metabolite:0x0000560be27eff10>

3D SDF for #<Metabolite:0x0000560be27eff10>

3D-SDF for #<Metabolite:0x0000560be27eff10>

PDB for #<Metabolite:0x0000560be27eff10>

3D PDB for #<Metabolite:0x0000560be27eff10>

SMILES for #<Metabolite:0x0000560be27eff10>

INCHI for #<Metabolite:0x0000560be27eff10>

Structure for #<Metabolite:0x0000560be27eff10>

3D Structure for #<Metabolite:0x0000560be27eff10>