| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:27:56 UTC |
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| Update Date | 2020-06-04 20:46:39 UTC |
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| BMDB ID | BMDB0000292 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Xanthine |
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| Description | Xanthine, also known as Xan or 2,6-dioxopurine, 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. Xanthine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Xanthine exists in all living species, ranging from bacteria to humans. Xanthine is a potentially toxic compound. Xanthine has been found to be associated with several diseases known as crohn's disease, colorectal cancer, degenerative disc disease, and cystic fibrosis; also xanthine has been linked to the inborn metabolic disorders including lesch-nyhan syndrome. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2,6-Dihydroxypurine | ChEBI | | 2,6-Dioxo-1,2,3,6-tetrahydropurine | ChEBI | | 9H-Purine-2,6-(1H,3H)-dione | ChEBI | | Purine-2(3H),6(1H)-dione | ChEBI | | Xan | ChEBI | | 1H-Purine-2,6-diol | HMDB | | 2,6(1,3)-Purinedion | HMDB | | 2,6-Dioxopurine | HMDB | | 3,7-Dihydro-1H-purine-2,6-dione | HMDB | | 3,7-Dihydropurine-2,6-dione | HMDB | | 9H-Purine-2,6(1H,3H)-dione | HMDB | | 9H-Purine-2,6-diol | HMDB | | Dioxopurine | HMDB | | Isoxanthine | HMDB | | Pseudoxanthine | HMDB | | Purine-2,6(1H,3H)-dione | HMDB | | Purine-2,6-diol | HMDB | | Xanthic oxide | HMDB | | Xanthin | HMDB |
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| Chemical Formula | C5H4N4O2 |
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| Average Molecular Weight | 152.1109 |
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| Monoisotopic Molecular Weight | 152.033425392 |
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| IUPAC Name | 2,3,6,7-tetrahydro-1H-purine-2,6-dione |
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| Traditional Name | xanthine |
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| CAS Registry Number | 69-89-6 |
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| SMILES | O=C1NC2=C(NC=N2)C(=O)N1 |
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| InChI Identifier | InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11) |
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| InChI Key | LRFVTYWOQMYALW-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Imidazopyrimidines |
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| Sub Class | Purines and purine derivatives |
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| Direct Parent | Xanthines |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | > 300 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.069 mg/mL at 16 °C; 9.5 mg/mL (sodium salt) | MERCK INDEX (1996); Human Metabolome Project (salt) | | LogP | -0.73 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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