ContaminantDB: Uric acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:47:26 UTC

Update Date

2026-03-31 17:39:28 UTC

Accession Number

CHEM003115

Identification

Common Name

Uric acid

Class

Small Molecule

Description

Uric acid is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. 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 humans 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.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Food Toxin
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical 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 Mass

168.110 g/mol

Monoisotopic Mass

168.028 g/mol

CAS Registry Number

69-93-2

IUPAC Name

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

Traditional Name

uric acid

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Bladder
Brain
Epidermis
Erythrocyte
Intestine
Kidney
Liver
Muscle
Placenta
Platelet
Prostate
Spleen

Pathways

Name	SMPDB Link	KEGG Link
Purine Metabolism	SMP00050	map00230
Gout or Kelley-Seegmiller Syndrome	SMP00365	Not Available
Lesch-Nyhan Syndrome (LNS)	SMP00364	Not Available
Methylmalonic Aciduria	SMP00200	Not Available
Methylmalonic Aciduria Due to Cobalamin-Related Disorders	SMP00201	Not Available
Purine Nucleoside Phosphorylase Deficiency	SMP00210	Not Available
Xanthine Dehydrogenase Deficiency (Xanthinuria)	SMP00220	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	> 300°C
Boiling Point	Not Available
Solubility	0.06 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	1.76 g/L	ALOGPS
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	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
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

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as uric acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (4). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (5).

Metabolism

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.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous).

Minimum Risk Level

>450 uM in serum

Health Effects

Excess serum accumulation of uric acid in the blood can lead to a type of arthritis known as gout. This painful condition is the result of needle-like crystals of uric acid precipitating in joints, capillaries, skin, and other tissues. Kidney stones can also form through the process of formation and deposition of sodium urate microcrystals. Although uric acid can act as an antioxidant, excess serum accumulation is often associated with cardiovascular disease. High uric acid in the blood may cause kidney stones, which may advance to a more severe condition called chronic kidney failure. High serum uric acid is associated with higher risk of type 2 diabetes, independent of obesity, dyslipidemia, and hypertension. Chronically high levels of uric acid are associated with at least 6 inborn errors of metabolism including: Gout or Kelley-Seegmiller Syndrome, Lesch-Nyhan Syndrome, Methylmalonic Aciduria, Methylmalonic Aciduria Due to Cobalamin-Related Disorders, Purine nucleoside phosphorylase deficiency and Xanthinuria.

Symptoms

As a uremic toxin, uric acid can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.

Concentrations

Not Available

External Links

DrugBank ID

DB08844

HMDB ID

HMDB0000289

FooDB ID

FDB015350

Phenol Explorer ID

Not Available

KNApSAcK ID