Xanthine (ECMDB00292) (M2MDB000121)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:25:46 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Xanthine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Xanthine is an intermediate in the degradation of adenosine monophosphate to uric acid, being formed by oxidation of hypoxanthine. The methylated xanthine compounds caffeine, theobromine, and theophylline and their derivatives are used in medicine for their bronchodilator effects. (Dorland, 28th ed.) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C5H4N4O2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 152.1109 Monoisotopic: 152.033425392 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | LRFVTYWOQMYALW-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C5H4N4O2/c10-4-2-3(7-1-6-2)8-5(11)9-4/h1H,(H3,6,7,8,9,10,11) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 69-89-6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 2,3,6,7-tetrahydro-1H-purine-2,6-dione | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | xanthine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | O=C1NC2=C(NC=N2)C(=O)N1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Imidazopyrimidines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purines and purine derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Xanthines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | >300 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + NAD + Xanthine <> Hydrogen ion + NADH + Uric acid Water + Xanthosine > Ribose + Xanthine Phosphoribosyl pyrophosphate + Xanthine <> Pyrophosphate + Xanthylic acid Phosphate + Xanthosine <> Ribose-1-phosphate + Xanthine Guanine + Hydrogen ion + Water > Ammonium + Xanthine Guanine + Water <> Xanthine + Ammonia Hypoxanthine + NAD + Water <> Xanthine + NADH + Hydrogen ion Xanthylic acid + Pyrophosphate <> Xanthine + Phosphoribosyl pyrophosphate Xanthosine + Phosphate <> Xanthine + alpha-D-Ribose 1-phosphate isoguanine + Water > Xanthine + Ammonia Water + Guanine > Ammonia + Xanthine Xanthosine + Water > D-ribose + Xanthine Xanthine + NAD + Water > Uric acid + NADH + Hydrogen ion Xanthylic acid + Pyrophosphate < Xanthine + Phosphoribosyl pyrophosphate Xanthosine + Phosphate > Ribose-1-phosphate + Xanthine Xanthine + NAD + Water > Uric acid + NADH Hypoxanthine + NAD + Water > Xanthine + NADH Xanthylic acid + Pyrophosphate > Phosphoribosyl pyrophosphate + Xanthine Xanthine + Phosphoribosyl pyrophosphate > Xanthylic acid + Pyrophosphate Guanine + Water <> Xanthine + Ammonia Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Procedure for the production of xanthine and xanthine-like materials. Fr. (1967), 4 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in hypoxanthine phosphoribosyltransferase activity
- Specific function:
- This enzyme acts exclusively on hypoxanthine; it does not act on guanine
- Gene Name:
- hpt
- Uniprot ID:
- P0A9M2
- Molecular weight:
- 20115
Reactions
IMP + diphosphate = hypoxanthine + 5-phospho-alpha-D-ribose 1-diphosphate. |
- General function:
- Involved in nucleoside metabolic process
- Specific function:
- Acts on guanine, xanthine and to a lesser extent hypoxanthine
- Gene Name:
- gpt
- Uniprot ID:
- P0A9M5
- Molecular weight:
- 16971
Reactions
XMP + diphosphate = 5-phospho-alpha-D-ribose 1-diphosphate + xanthine. |
- General function:
- Involved in purine-nucleoside phosphorylase activity
- Specific function:
- Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
- Gene Name:
- deoD
- Uniprot ID:
- P0ABP8
- Molecular weight:
- 25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate. |
- General function:
- Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
- Specific function:
- Hydrolyzes both purine and pyrimidine ribonucleosides with a broad-substrate specificity with decreasing activity in the order uridine, xanthosine, inosine, adenosine, cytidine, guanosine
- Gene Name:
- rihC
- Uniprot ID:
- P22564
- Molecular weight:
- 32560
- General function:
- Involved in hydrolase activity
- Specific function:
- Catalyzes the hydrolytic deamination of guanine, producing xanthine and ammonia
- Gene Name:
- guaD
- Uniprot ID:
- P76641
- Molecular weight:
- 50244
Reactions
Guanine + H(2)O = xanthine + NH(3). |
- General function:
- Involved in flavin adenine dinucleotide binding
- Specific function:
- Xanthine + NAD(+) + H(2)O = urate + NADH
- Gene Name:
- yagS
- Uniprot ID:
- P77324
- Molecular weight:
- 33858
Reactions
Xanthine + NAD(+) + H(2)O = urate + NADH. |
Hypoxanthine + NAD(+) + H(2)O = xanthine + NADH. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Xanthine + NAD(+) + H(2)O = urate + NADH
- Gene Name:
- yagR
- Uniprot ID:
- P77489
- Molecular weight:
- 78088
Reactions
Xanthine + NAD(+) + H(2)O = urate + NADH. |
Hypoxanthine + NAD(+) + H(2)O = xanthine + NADH. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Presumed to be a dehydrogenase, but possibly an oxidase. Participates in limited purine salvage (requires aspartate) but does not support aerobic growth on purines as the sole carbon source (purine catabolism). Deletion results in increased adenine sensitivity, suggesting that this protein contributes to the conversion of adenine to guanine nucleotides during purine salvage
- Gene Name:
- xdhA
- Uniprot ID:
- Q46799
- Molecular weight:
- 81320
Reactions
Xanthine + NAD(+) + H(2)O = urate + NADH. |
Hypoxanthine + NAD(+) + H(2)O = xanthine + NADH. |
- General function:
- Involved in flavin adenine dinucleotide binding
- Specific function:
- Presumed to be a dehydrogenase, but possibly an oxidase. Participates in limited purine salvage (requires aspartate) but does not support aerobic growth on purines as the sole carbon source (purine catabolism)
- Gene Name:
- xdhB
- Uniprot ID:
- Q46800
- Molecular weight:
- 31557
Reactions
Xanthine + NAD(+) + H(2)O = urate + NADH. |
Hypoxanthine + NAD(+) + H(2)O = xanthine + NADH. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Iron-sulfur subunit of the xanthine dehydrogenase complex
- Gene Name:
- xdhC
- Uniprot ID:
- Q46801
- Molecular weight:
- 16922
- General function:
- Involved in purine-nucleoside phosphorylase activity
- Specific function:
- The nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the nucleoside molecule, with the formation of the corresponding free bases and pentose-1-phosphate. This protein can degrade all purine nucleosides except adenosine and deoxyadenosine
- Gene Name:
- xapA
- Uniprot ID:
- P45563
- Molecular weight:
- 29834
- General function:
- Not Available
- Specific function:
- Not Available
- Gene Name:
- paoA
- Uniprot ID:
- P77165
- Molecular weight:
- Not Available
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Specific, proton motive force-dependent high-affinity transporter for xanthine
- Gene Name:
- xanP
- Uniprot ID:
- P0AGM9
- Molecular weight:
- 48868
- General function:
- Involved in transporter activity
- Specific function:
- Specific, proton motive force-dependent high-affinity transporter for xanthine
- Gene Name:
- xanQ
- Uniprot ID:
- P67444
- Molecular weight:
- 49108
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368