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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:12 UTC
Update Date2019-01-11 19:17:14 UTC
HMDB IDHMDB0002818
Secondary Accession Numbers
  • HMDB02818
Metabolite Identification
Common NameAlloxan
DescriptionAlloxan or mesoxalylurea is an organic compound based on a pyrimidine heterocyclic skeleton. This compound has a high affinity for water and therefore exists as the monohydrate. The compound was discovered by Justus von Liebig and Friedrich Wohler following the discovery of urea in 1828 and is one of the oldest named organic compounds that exist. The name is derived from allantoin, a product of uric acid excreted by the fetus into the allantois and oxaluric acid derived from oxalic acid and urea, found in urine. The original recipe for Alloxan was by oxidation of uric acid by nitric acid. Alloxan is a strong oxidizing agent and it forms a hemiacetal with its reduced reaction product dialuric acid (in which a carbonyl group is reduced to a hydroxyl group) which is called alloxantin. -- Wikipedia; Alloxane is a raw material for the production of the purple dye Murexide. Carl Wilhelm Scheele discovered the dye in 1776. Murexide is the product of the complex in-situ multistep reaction of alloxantin and gaseous ammonia. Murexide results from the condensation of the unisolated intermdiate uramil with alloxan, liberated during the course of the reaction. Scheele sourced uric acid from human calculi (such as kidney stones) and called the compound lithic acid. William Prout investigated the compound in 1818 and he used boa constrictor excrement with up to 90% ammonium acid urate. Liebig and Wohler in the nineteenth century coined the name murexide for the dye after the Trunculus Murex which is the source of the Tyrian purple of antiquity. Primo Levi in his world famous novel The Periodic Table in chapter Nitrogen considers pythons as a source for alloxane on behalf of a lipstick producer but he is turned down by the director of the Turin zoo because the zoo already has lucrative contracts with cosmetics companies (his attempts with chicken dung end in misery). -- Wikipedia.
Structure
Data?1547234234
Synonyms
ValueSource
2,4,5,6(1H,3H)-PyrimidinetetroneChEBI
2,4,5,6-PyrimidinetetroneChEBI
2,4,5,6-TetraoxohexahydropyrimidineChEBI
5,6-DioxouracilChEBI
5-Oxobarbituric acidChEBI
AlloxaneChEBI
MesoxalylcarbamideChEBI
MesoxalylureaChEBI
NSC 7169ChEBI
PyrimidinetetroneChEBI
5-OxobarbitateGenerator
5-Oxobarbitic acidGenerator
2,4,5,6-PyrimidintetronHMDB
2,4,5,6-PyrimidintetroneHMDB
5-oxo-BarbiturateHMDB
5-oxo-Barbituric acidHMDB
Alloxan 7169HMDB
Alloxan tetrahydratHMDB
Mesoxalyl-ureaHMDB
Chemical FormulaC4H2N2O4
Average Molecular Weight142.0697
Monoisotopic Molecular Weight142.001456562
IUPAC Name1,3-diazinane-2,4,5,6-tetrone
Traditional Namealloxan
CAS Registry Number50-71-5
SMILES
O=C1NC(=O)C(=O)C(=O)N1
InChI Identifier
InChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10)
InChI KeyHIMXGTXNXJYFGB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidones. Pyrimidones are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentPyrimidones
Alternative Parents
Substituents
  • Pyrimidone
  • Hydropyrimidine
  • 2,5-dihydropyrimidine
  • Ketone
  • Carbonic acid derivative
  • Cyclic ketone
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point256 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.84BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility10.2 g/LALOGPS
logP-0.85ALOGPS
logP-0.91ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.34 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.77 m³·mol⁻¹ChemAxon
Polarizability10.3 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-d176d0d6fcffbf493496JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9400000000-4493e387c163fd19672eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-056r-9000000000-ebb9b8d2b3db01ac1b30JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01ox-9000000000-e390f807cb6126c81a8eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-5b8617c49e887cf6346cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9400000000-2cc94355c95e93b2971fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9000000000-dd466f209ed4ed32dfc6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-6900000000-4c1a6e3cf8a058b034cfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-ae29c061699f170b84a2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1d9fa304c38627a77f7dJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Epidermis
  • Pancreas
  • Platelet
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023068
KNApSAcK IDNot Available
Chemspider ID5577
KEGG Compound IDC07599
BioCyc IDCPD-3684
BiGG IDNot Available
Wikipedia LinkAlloxan
METLIN ID252
PubChem Compound5781
PDB IDNot Available
ChEBI ID76451
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mashima R, Nakanishi-Ueda T, Yamamoto Y: Simultaneous determination of methionine sulfoxide and methionine in blood plasma using gas chromatography-mass spectrometry. Anal Biochem. 2003 Feb 1;313(1):28-33. [PubMed:12576054 ]
  2. Dixon JL, Stoops JD, Parker JL, Laughlin MH, Weisman GA, Sturek M: Dyslipidemia and vascular dysfunction in diabetic pigs fed an atherogenic diet. Arterioscler Thromb Vasc Biol. 1999 Dec;19(12):2981-92. [PubMed:10591679 ]
  3. Sakai S, Endo Y, Ozawa N, Sugawara T, Kusaka A, Sayo T, Tagami H, Inoue S: Characteristics of the epidermis and stratum corneum of hairless mice with experimentally induced diabetes mellitus. J Invest Dermatol. 2003 Jan;120(1):79-85. [PubMed:12535201 ]
  4. Rayat GR, Rajotte RV, Ao Z, Korbutt GS: Microencapsulation of neonatal porcine islets: protection from human antibody/complement-mediated cytolysis in vitro and long-term reversal of diabetes in nude mice. Transplantation. 2000 Mar 27;69(6):1084-90. [PubMed:10762211 ]
  5. Otton R, Carvalho CR, Mendonca JR, Curi R: Low proliferation capacity of lymphocytes from alloxan-diabetic rats: involvement of high glucose and tyrosine phosphorylation of Shc and IRS-1. Life Sci. 2002 Oct 25;71(23):2759-71. [PubMed:12383882 ]
  6. Murata M, Imada M, Inoue S, Kawanishi S: Metal-mediated DNA damage induced by diabetogenic alloxan in the presence of NADH. Free Radic Biol Med. 1998 Sep;25(4-5):586-95. [PubMed:9741596 ]
  7. Kamilli I, Gresser U: Allopurinol and oxypurinol in human breast milk. Clin Investig. 1993 Feb;71(2):161-4. [PubMed:8461629 ]
  8. Murrell GA, Rapeport WG: Clinical pharmacokinetics of allopurinol. Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53. [PubMed:3536254 ]
  9. Vaughan LM, Gottehrer A: Effect of xanthine-related compounds on a theophylline assay using theophylline oxidase. Ann Pharmacother. 1992 Dec;26(12):1576-9. [PubMed:1482815 ]
  10. Luca VC, Mocanu V: [The history of experimental diabetes in Iasi ]. Rev Med Chir Soc Med Nat Iasi. 2003 Jan-Mar;107(1):227-31. [PubMed:14756003 ]
  11. Hande K, Reed E, Chabner B: Allopurinol kinetics. Clin Pharmacol Ther. 1978 May;23(5):598-605. [PubMed:639435 ]