Alloxan
PubChem CID: 5781
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| Compound Synonyms | Alloxan, 50-71-5, 2,4,5,6(1H,3H)-Pyrimidinetetrone, Mesoxalylurea, Pyrimidine-2,4,5,6(1H,3H)-tetraone, Mesoxalylcarbamide, ALLOXANE, 1,3-diazinane-2,4,5,6-tetrone, Alloxan 7169, Urea, mesoxalyl-, Pyrimidinetetrone, 2,4,5,6-Tetraoxohexahydropyrimidine, Barbituric acid, 5-oxo-, NSC 7169, 5,6-dioxouracil, pyrimidine-2,4,5,6(1H,3H)-tetrone, 2,4,5,6-Pyrimidintetron, UNII-6SW5YHA5NG, 6SW5YHA5NG, EINECS 200-062-0, ALLOXANUM, CCRIS 9509, CHEBI:76451, AI3-15282, HSDB 7493, NSC-7169, 2,4,5,6-Pyrimidintetrone, 2,4,5,6-pyrimidinetetrone, DTXSID5044946, 5-Oxobarbituric acid, 2,4,5,6-Pyrimidintetron [Czech], mesoxalyl-Urea, 2xgm, 5-oxo-barbiturate, Alloxan tetrahydrat, hexahydropyrimidine-2,4,5,6-tetrone, 5-oxo-barbituric acid, Spectrum_001080, SpecPlus_000865, ALLOXAN [HSDB], WLN: T6MVMVVVJ, 2,5,6-Pyrimidintetron, ALLOXAN [MI], ALLOXANUM [HPUS], Spectrum2_000531, Spectrum3_000615, Spectrum4_000606, Spectrum5_001490, SCHEMBL64547, BSPBio_002150, KBioGR_001132, KBioSS_001560, DivK1c_006961, SPECTRUM1500802, SPBio_000541, SCHEMBL9652639, CHEMBL1096009, DTXCID3024946, KBio1_001905, KBio2_001560, KBio2_004128, KBio2_006696, KBio3_001650, NSC7169, 2,5,6-Tetraoxohexahydropyrimidine, 2,5,6(1H,3H)-Pyrimidinetetrone, 6-hydroxy-2,4,5-triketopyrimidine, BBL002915, CCG-39561, STK378289, AKOS005448465, 2,4,5,6(1H,3H) Pyrimidinetetrone, SB55621, NCGC00095912-01, NCGC00095912-02, VS-01259, DB-019799, A0216, NS00014786, EN300-21254, AB00052179-03, 5,5-dihydroxy-hexahydro-pyrimidine-2,4,6-trione, A828261, AE-562/40299936, Q417701, F8881-2259, Z104494840, InChI=1/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10, 200-062-0, LXN |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 92.3 |
| Hydrogen Bond Donor Count | 2.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC1CC(C)C(C)C(C)C1 |
| Deep Smiles | O=CNC=O)C=O)C=O)N6 |
| Heavy Atom Count | 10.0 |
| Classyfire Class | Diazines |
| 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 [HMDB] |
| Scaffold Graph Node Level | OC1NC(O)C(O)C(O)N1 |
| Classyfire Subclass | Pyrimidines and pyrimidine derivatives |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 222.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;imppat_phytochem;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Iupac Name | 1,3-diazinane-2,4,5,6-tetrone |
| Class | Diazines |
| Veber Rule | True |
| Classyfire Superclass | Organoheterocyclic compounds |
| Xlogp | -1.0 |
| Superclass | Organoheterocyclic compounds |
| Subclass | Pyrimidines and pyrimidine derivatives |
| Gsk 4 400 Rule | True |
| Molecular Formula | C4H2N2O4 |
| Scaffold Graph Node Bond Level | O=C1NC(=O)C(=O)C(=O)N1 |
| Inchi Key | HIMXGTXNXJYFGB-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 0.0 |
| State | Solid |
| Synonyms | 2,4,5,6-Pyrimidinetetrone, 2,4,5,6-Pyrimidintetron, 2,4,5,6-Pyrimidintetrone, 2,4,5,6-Tetraoxohexahydropyrimidine, 2,4,5,6(1H,3H)-Pyrimidinetetrone, 5-oxo-barbiturate, 5-oxo-barbituric acid, 5-Oxobarbitate, 5-Oxobarbitic acid, 5-Oxobarbituric acid, 5,6-Dioxouracil, alloxan, Alloxan 7169, Alloxan tetrahydrat, Alloxane, mesoxalyl-Urea, Mesoxalylcarbamide, Mesoxalylurea, NSC 7169, Pyrimidinetetrone, 5-oxo-Barbiturate, 5-oxo-Barbituric acid, Mesoxalyl-urea |
| Substituent Name | Barbiturate, Ureide, 1,3-diazinane, Cyclic ketone, Urea, Ketone, Carboxamide group, Azacycle, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Organonitrogen compound, Carbonyl group, Aliphatic heteromonocyclic compound |
| Esol Class | Highly soluble |
| Functional Groups | O=C1NC(=O)C(=O)C(=O)N1 |
| Compound Name | Alloxan |
| Kingdom | Organic compounds |
| Exact Mass | 142.001 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 142.001 |
| Hydrogen Bond Acceptor Count | 4.0 |
| Molecular Weight | 142.07 |
| Gi Absorption | False |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| Lipinski Rule Of 5 | True |
| Inchi | InChI=1S/C4H2N2O4/c7-1-2(8)5-4(10)6-3(1)9/h(H2,5,6,8,9,10) |
| Smiles | C1(=O)C(=O)NC(=O)NC1=O |
| Np Classifier Biosynthetic Pathway | Alkaloids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | False |
| Taxonomy Direct Parent | Pyrimidones |
| Np Classifier Superclass | Pseudoalkaloids |
- 1. Outgoing r'ship
FOUND_INto/from Allium Ascalonicum (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/4435106 - 2. Outgoing r'ship
FOUND_INto/from Allium Cepa (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/4435106 - 3. Outgoing r'ship
FOUND_INto/from Catharanthus Roseus (Plant) Rel Props:Reference:https://doi.org/10.1093/database/bav075 - 4. Outgoing r'ship
FOUND_INto/from Euphorbia Hirta (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/21218075 - 5. Outgoing r'ship
FOUND_INto/from Phaseolus Vulgaris (Plant) Rel Props:Reference:https://www.ncbi.nlm.nih.gov/pubmed/18338641