Milk Composition Database: Showing metabocard for Uric acid (BMDB0000289)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:52 UTC

Update Date

2020-06-04 20:51:39 UTC

MCDB ID

BMDB0000289

Secondary Accession Numbers

BMDB00289

Metabolite Identification

Common Name

Uric acid

Description

Uric acid, also known as urate or acid, uric, 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. Uric acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Uric acid exists in all living species, ranging from bacteria to humans. Uric acid is a potentially toxic compound. Uric acid has been found to be associated with several diseases known as fanconi syndrome, impaired glucose tolerance, and d-lactic acidosis; also uric acid has been linked to several inborn metabolic disorders including atic deficiency and lesch-nyhan syndrome.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	> 300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.06 mg/mL	Not Available
LogP	-2.17	NAHUM,A & HORVATH,C (1980)

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	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	Deposition Date	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	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-052f-0603900000-8c1224738bed2608c262	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0g59-5917000000-4b28946431495667844b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0537-0913400000-bd24364053510c462ade	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-052f-0603900000-8c1224738bed2608c262	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0g59-5917000000-4b28946431495667844b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-052g-0902500000-05851611f4bbf0745b81	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00os-4900000000-54b6de73b60ab2faad65	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-0525c12dc3951f55a2c8	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-006w-9500000000-fe10d491ad634ca46332	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0gbd-9100000000-d48a3e7919c385949313	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-01c0-3900000000-b3b3f0a20aaac71095d7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0f6x-0900000000-a6699ab18f69b21b3823	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-9000000000-ed929369da80ee084e89	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-dae78aaa83fc4120e56f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00r7-9500000000-120c639f57df45d23153	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-96d2ee50d279f8056671	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00xr-4900000000-1d613278865ada2e6457	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-2900000000-a8460af7fe6f1d23fbfe	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0btc-9000000000-d9b1f657e4c7e43bd776	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-02na-9500000000-7dddbc2120455b19bba9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-01c0-3900000000-95ebf9c951d7085b85e3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-1900000000-029e9b2adfbb2e0d26d8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-88f140dfad19d2f058f6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0gcc-6900000000-d9540bd8f38fac1e92b0	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-9200000000-80997201350d0752fbbf	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-971b5c8c5d975d306fed	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016r-1900000000-72edb3607fe9beb9b805	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-9500000000-753be769a0b48fc2960b	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-a4f5b18495486c5a1d5a	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-1900000000-bc9e45f168dafb0d874c	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-e01e386869d687364c61	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-e82d2b9a4cad815cef76	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-002f-9200000000-e5abb655836214cc56b3	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-22	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	199 uM	PMID: 6539345	details
Detected and Quantified	56 +/- 12 uM	PMID: 7962859	details
Detected and Quantified	53 - 142 uM	PMID: 15084094	details
Detected and Quantified	122 +/- 1 uM	Carbohydrate Poly...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details

External Links

HMDB ID

HMDB0000289

DrugBank ID

DB08844

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

1175

PDB ID

Not Available

ChEBI ID

17775

References

Synthesis Reference

Brenner-Holzach, O.; Leuthardt, F. Uric acid formation from glucose carbon in Drosophila melanogaster. Preliminary report. Helvetica Chimica Acta (1963), 46(4), 1426-8.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2. [PubMed:6539345 ]
Giesecke D, Ehrentreich L, Stangassinger M, Ahrens F: Mammary and renal excretion of purine metabolites in relation to energy intake and milk yield in dairy cows. J Dairy Sci. 1994 Aug;77(8):2376-81. doi: 10.3168/jds.S0022-0302(94)77180-0. [PubMed:7962859 ]
Indyk HE, Woollard DC: Determination of orotic acid, uric acid, and creatinine in milk by liquid chromatography. J AOAC Int. 2004 Jan-Feb;87(1):116-22. [PubMed:15084094 ]
I.M.P.L.V.O Ferreira, A.M.P Gomes, M.A Ferreira (1998). Carbohydrate Polymers 37 (1998) 225-229. Carbohydrate Polymers.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.

Showing metabocard for Uric acid (BMDB0000289)

Structure for BMDB0000289 (Uric acid)