Livestock Metabolome Database: Showing metabocard for Uric acid (LMDB00128)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:58 UTC

Update Date

2016-09-23 18:44:44 UTC

Lmdb

LMDB00128

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Uric acid

Description

Uric acid is a heterocyclic purine derivative that is the final oxidation product of purine metabolism. It is produced by the enzyme xanthine oxidase, which oxidizes oxypurines such as xanthine into uric acid. In most mammals, except animals and higher primates, the enzyme uricase further oxidizes uric acid to allantoin. Uric acid is also the end product of nitrogen metabolism in birds and reptiles. In such species, it is excreted in feces as a dry mass. Humans produce only small quantities of uric acid with excess accumulation leading to a type of arthritis known as gout. The loss of uricase in higher primates parallels the similar loss of the ability to synthesize ascorbic acid vitamin C. This may be because in higher primates uric acid partially replaces ascorbic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,6,8-Trioxopurine	ChEBI
2,6,8-Trioxypurine	ChEBI
Purine-2,6,8(1H,3H,9H)-trione	ChEBI
Urate	ChEBI
1H-Purine-2,6,8-triol	HMDB
2,6,8-Trihydroxypurine	HMDB
Lithate	HMDB
Lithic acid	HMDB
Acid urate, ammonium	HMDB
Ammonium acid urate	HMDB
Monohydrate, sodium urate	HMDB
Urate, ammonium acid	HMDB
Urate, monosodium	HMDB
Acid, uric	HMDB
Monosodium urate monohydrate	HMDB
Sodium acid urate	HMDB
Sodium urate	HMDB
Trioxopurine	HMDB
Urate, sodium acid	HMDB
Monohydrate, monosodium urate	HMDB
Monosodium urate	HMDB
Potassium urate	HMDB
Sodium acid urate monohydrate	HMDB
Urate monohydrate, sodium	HMDB
Acid urate, sodium	HMDB
Sodium urate monohydrate	HMDB
Urate monohydrate, monosodium	HMDB
Urate, potassium	HMDB
Urate, sodium	HMDB

Chemical Formula

C₅H₄N₄O₃

Average Molecular Weight

168.1103

Monoisotopic Molecular Weight

168.028340014

IUPAC Name

2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

Traditional Name

uric acid

CAS Registry Number

69-93-2

SMILES

O=C1NC2=C(N1)C(=O)NC(=O)N2

InChI Identifier

InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)

InChI Key

LEHOTFFKMJEONL-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
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

uric acid (CHEBI:17775 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.1	ALOGPS
logP	-1.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.25	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.63 m³·mol⁻¹	ChemAxon
Polarizability	13.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0537-0913400000-bd24364053510c462ade	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-052f-0603900000-8c1224738bed2608c262	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0g59-5917000000-4b28946431495667844b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0537-0913400000-bd24364053510c462ade	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-052f-0603900000-8c1224738bed2608c262	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0g59-5917000000-4b28946431495667844b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052g-0902500000-05851611f4bbf0745b81	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00os-4900000000-54b6de73b60ab2faad65	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 (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-0525c12dc3951f55a2c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-006w-9500000000-fe10d491ad634ca46332	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0gbd-9100000000-d48a3e7919c385949313	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-01c0-3900000000-b3b3f0a20aaac71095d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0f6x-0900000000-a6699ab18f69b21b3823	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-9000000000-ed929369da80ee084e89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-dae78aaa83fc4120e56f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00r7-9500000000-120c639f57df45d23153	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-96d2ee50d279f8056671	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-4900000000-1d613278865ada2e6457	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-2900000000-a8460af7fe6f1d23fbfe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0btc-9000000000-d9b1f657e4c7e43bd776	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-02na-9500000000-7dddbc2120455b19bba9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-01c0-3900000000-95ebf9c951d7085b85e3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-1900000000-029e9b2adfbb2e0d26d8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-88f140dfad19d2f058f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0gcc-6900000000-d9540bd8f38fac1e92b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-9200000000-80997201350d0752fbbf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-971b5c8c5d975d306fed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016r-1900000000-72edb3607fe9beb9b805	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-9500000000-753be769a0b48fc2960b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-a4f5b18495486c5a1d5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-1900000000-bc9e45f168dafb0d874c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e01e386869d687364c61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-e82d2b9a4cad815cef76	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9200000000-e5abb655836214cc56b3	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Milk
Plasma
Serum
Whole blood

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	5.948 +/- 0 uM	Not Available	Porcine	183842	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	Kurt J. Boudonck,...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25828073	details
Serum	Detected and Quantified	4.759 +/- 3.569 uM	Not Available	Porcine	183842	details
Whole blood	Detected and Quantified	91.0117-191.541 uM	Not Available	Bovine	Arthur K. Anderso...	details