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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:12 UTC

Update Date

2023-02-21 17:16:28 UTC

HMDB ID

HMDB0002818

Secondary Accession Numbers

HMDB02818

Metabolite Identification

Common Name

Alloxan

Description

Alloxan 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,4,5,6(1H,3H)-Pyrimidinetetrone	ChEBI
2,4,5,6-Pyrimidinetetrone	ChEBI
2,4,5,6-Tetraoxohexahydropyrimidine	ChEBI
5,6-Dioxouracil	ChEBI
5-Oxobarbituric acid	ChEBI
Alloxane	ChEBI
Mesoxalylcarbamide	ChEBI
Mesoxalylurea	ChEBI
NSC 7169	ChEBI
Pyrimidinetetrone	ChEBI
5-Oxobarbitate	Generator
5-Oxobarbitic acid	Generator
2,4,5,6-Pyrimidintetron	HMDB
2,4,5,6-Pyrimidintetrone	HMDB
5-oxo-Barbiturate	HMDB
5-oxo-Barbituric acid	HMDB
Alloxan 7169	HMDB
Alloxan tetrahydrat	HMDB
Mesoxalyl-urea	HMDB

Chemical Formula

C₄H₂N₂O₄

Average Molecular Weight

142.0697

Monoisotopic Molecular Weight

142.001456562

IUPAC Name

1,3-diazinane-2,4,5,6-tetrone

Traditional Name

alloxan

CAS Registry Number

50-71-5

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 Key

HIMXGTXNXJYFGB-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Pyrimidones

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pyrimidone (CHEBI:76451 )
an amine (CPD-3684 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0002818)

Tissue

Epithelium

Epidermis (HMDB: HMDB0002818)

Organ

Pancreas (HMDB: HMDB0002818)

Cell

Hematocyte

Platelet (HMDB: HMDB0002818)

Source

Endogenous

Endogenous (HMDB: HMDB0002818)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	256 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.84	BIOBYTE (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.2 g/L	ALOGPS
logP	-0.85	ALOGPS
logP	-0.91	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.34 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	26.77 m³·mol⁻¹	ChemAxon
Polarizability	10.3 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.146	31661259
DarkChem	[M-H]-	126.104	31661259
DeepCCS	[M+H]+	130.521	30932474
DeepCCS	[M-H]-	126.886	30932474
DeepCCS	[M-2H]-	164.455	30932474
DeepCCS	[M+Na]+	139.59	30932474
AllCCS	[M+H]+	129.2	32859911
AllCCS	[M+H-H2O]+	124.6	32859911
AllCCS	[M+NH4]+	133.6	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	120.6	32859911
AllCCS	[M+Na-2H]-	122.2	32859911
AllCCS	[M+HCOO]-	124.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alloxan	O=C1NC(=O)C(=O)C(=O)N1	2936.4	Standard polar	33892256
Alloxan	O=C1NC(=O)C(=O)C(=O)N1	1523.4	Standard non polar	33892256
Alloxan	O=C1NC(=O)C(=O)C(=O)N1	1762.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alloxan,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(=O)C(=O)C1=O	1606.7	Semi standard non polar	33892256
Alloxan,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(=O)C(=O)C1=O	1667.9	Standard non polar	33892256
Alloxan,1TMS,isomer #1	C[Si](C)(C)N1C(=O)NC(=O)C(=O)C1=O	3486.8	Standard polar	33892256
Alloxan,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)C(=O)N([Si](C)(C)C)C1=O	1559.2	Semi standard non polar	33892256
Alloxan,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)C(=O)N([Si](C)(C)C)C1=O	1647.3	Standard non polar	33892256
Alloxan,2TMS,isomer #1	C[Si](C)(C)N1C(=O)C(=O)C(=O)N([Si](C)(C)C)C1=O	2584.3	Standard polar	33892256
Alloxan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C(=O)C1=O	1879.2	Semi standard non polar	33892256
Alloxan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C(=O)C1=O	1949.2	Standard non polar	33892256
Alloxan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)NC(=O)C(=O)C1=O	3545.9	Standard polar	33892256
Alloxan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2064.8	Semi standard non polar	33892256
Alloxan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2114.9	Standard non polar	33892256
Alloxan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)C(=O)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2526.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alloxan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-d176d0d6fcffbf493496	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alloxan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alloxan Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-9400000000-4493e387c163fd19672e	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alloxan Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-056r-9000000000-ebb9b8d2b3db01ac1b30	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alloxan Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-01ox-9000000000-e390f807cb6126c81a8e	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 10V, Positive-QTOF	splash10-0006-1900000000-5b8617c49e887cf6346c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 20V, Positive-QTOF	splash10-00di-9400000000-2cc94355c95e93b2971f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 40V, Positive-QTOF	splash10-00ku-9000000000-dd466f209ed4ed32dfc6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 10V, Negative-QTOF	splash10-0006-6900000000-4c1a6e3cf8a058b034cf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 20V, Negative-QTOF	splash10-0006-9000000000-ae29c061699f170b84a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 40V, Negative-QTOF	splash10-0006-9000000000-1d9fa304c38627a77f7d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 10V, Negative-QTOF	splash10-0006-4900000000-af3b61eae6a9fbb8e9a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 20V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 10V, Positive-QTOF	splash10-0006-3900000000-7554f9bede8cd74601d8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 20V, Positive-QTOF	splash10-0006-9200000000-2e8e42582aa24cbd48bc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloxan 40V, Positive-QTOF	splash10-014l-9000000000-87926f5a9b3025440357	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Epidermis
Pancreas
Platelet

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Alloxan

METLIN ID

252

PubChem Compound

5781

PDB ID

Not Available

ChEBI ID

76451

Food Biomarker Ontology

Not Available

VMH ID

CE0074

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Kamilli I, Gresser U: Allopurinol and oxypurinol in human breast milk. Clin Investig. 1993 Feb;71(2):161-4. [PubMed:8461629 ]
Murrell GA, Rapeport WG: Clinical pharmacokinetics of allopurinol. Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53. [PubMed:3536254 ]
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 ]
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 ]
Hande K, Reed E, Chabner B: Allopurinol kinetics. Clin Pharmacol Ther. 1978 May;23(5):598-605. [PubMed:639435 ]

Showing metabocard for Alloxan (HMDB0002818)

MOL for HMDB0002818 (Alloxan)

3D MOL for HMDB0002818 (Alloxan)

3D SDF for HMDB0002818 (Alloxan)

3D-SDF for HMDB0002818 (Alloxan)

PDB for HMDB0002818 (Alloxan)

3D PDB for HMDB0002818 (Alloxan)

SMILES for HMDB0002818 (Alloxan)

INCHI for HMDB0002818 (Alloxan)

Structure for HMDB0002818 (Alloxan)

3D Structure for HMDB0002818 (Alloxan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra