Alloxan (CHEM020914)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 02:34:36 UTC
Update Date2016-10-28 10:01:27 UTC
Accession NumberCHEM020914
Identification
Common NameAlloxan
ClassSmall Molecule
DescriptionA member of the class of pyrimidones, the structure of which is that of perhydropyrimidine substituted at C-2, -4, -5 and -6 by oxo groups.
Contaminant Sources
  • Disinfection Byproducts
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass142.070 g/mol
Monoisotopic Mass142.001 g/mol
CAS Registry NumberNot Available
IUPAC Name1,3-diazinane-2,4,5,6-tetrone
Traditional Namealloxan
SMILESO=C1NC(=O)C(=O)C(=O)N1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-d176d0d6fcffbf493496Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9400000000-4493e387c163fd19672eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-056r-9000000000-ebb9b8d2b3db01ac1b30Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01ox-9000000000-e390f807cb6126c81a8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-5b8617c49e887cf6346cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9400000000-2cc94355c95e93b2971fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ku-9000000000-dd466f209ed4ed32dfc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-6900000000-4c1a6e3cf8a058b034cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-ae29c061699f170b84a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1d9fa304c38627a77f7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4900000000-af3b61eae6a9fbb8e9a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c5299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3900000000-7554f9bede8cd74601d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9200000000-2e8e42582aa24cbd48bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-87926f5a9b3025440357Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002818
FooDB IDFDB023068
Phenol Explorer IDNot Available
KNApSAcK IDC00019778
BiGG IDNot Available
BioCyc IDCPD-3684
METLIN ID252
PDB IDNot Available
Wikipedia LinkAlloxan
Chemspider ID5577
ChEBI ID76451
PubChem Compound ID5781
Kegg Compound IDC07599
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21344938
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23408741
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23473942
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23658878
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23667864
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23762986
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24129090
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24374440
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. Kamilli I, Gresser U: Allopurinol and oxypurinol in human breast milk. Clin Investig. 1993 Feb;71(2):161-4.
15. Murrell GA, Rapeport WG: Clinical pharmacokinetics of allopurinol. Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53.
16. 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.
17. Vaughan LM, Gottehrer A: Effect of xanthine-related compounds on a theophylline assay using theophylline oxidase. Ann Pharmacother. 1992 Dec;26(12):1576-9.
18. 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.
19. Hande K, Reed E, Chabner B: Allopurinol kinetics. Clin Pharmacol Ther. 1978 May;23(5):598-605.