Hypoxanthine (ECMDB00157) (M2MDB000059)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:22:08 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 15:53:19 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Hypoxanthine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Hypoxanthine is a naturally occurring purine derivative and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway. Hypoxanthine is also a spontaneous deamination product of adenine. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C5H4N4O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 136.1115 Monoisotopic: 136.03851077 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | FDGQSTZJBFJUBT-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 68-94-0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 7H-purin-6-ol | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 6-hydroxypurine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | OC1=NC=NC2=C1NC=N2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organoheterocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Imidazopyrimidines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Purines and purine derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Hypoxanthines | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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: | 150 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Hypoxanthine + Phosphoribosyl pyrophosphate <> Inosinic acid + Pyrophosphate Deoxyinosine + Phosphate <> Deoxyribose 1-phosphate + Hypoxanthine Inosine + Phosphate <> Hypoxanthine + Ribose-1-phosphate Water + Hypoxanthine + NAD > Hydrogen ion + NADH + Xanthine Water + Inosine > Hypoxanthine + Ribose Adenine + Hydrogen ion + Water > Hypoxanthine + Ammonium Inosinic acid + Pyrophosphate <> Hypoxanthine + Phosphoribosyl pyrophosphate Adenine + Water <> Hypoxanthine + Ammonia Hypoxanthine + NAD + Water <> Xanthine + NADH + Hydrogen ion Inosine + Water <> Hypoxanthine + Ribose Inosine + Phosphate <> Hypoxanthine + alpha-D-Ribose 1-phosphate Water + Adenine > Ammonia + Hypoxanthine Deoxyinosine + Phosphate <> deoxyribose-1-phosphate + Hypoxanthine Pyrophosphate + Inosinic acid < Phosphoribosyl pyrophosphate + Hypoxanthine Inosine + Water > D-ribose + Hypoxanthine Inosinic acid + Pyrophosphate > Hypoxanthine + Phosphoribosyl pyrophosphate Hypoxanthine + NAD + Water > Xanthine + NADH Inosine + Phosphate > Ribose-1-phosphate + Hypoxanthine Hypoxanthine + Phosphoribosyl pyrophosphate > Inosinic acid + Pyrophosphate 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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Shaw, Elliott.New synthesis of the purines adenine, hypoxanthine, xanthine, and isoguanine. Journal of Biological Chemistry (1950), 185 439-47. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 adenine deaminase activity
- Specific function:
- Adenine + H(2)O = hypoxanthine + NH(3)
- Gene Name:
- ade
- Uniprot ID:
- P31441
- Molecular weight:
- 63739
Reactions
Adenine + H(2)O = hypoxanthine + NH(3). |
- General function:
- Involved in hydrolase activity, hydrolyzing N-glycosyl compounds
- Specific function:
- Hydrolyzes cytidine or uridine to ribose and cytosine or uracil, respectively. Has a clear preference for cytidine over uridine. Strictly specific for ribonucleosides. Has a low but significant activity for the purine nucleoside xanthosine
- Gene Name:
- rihB
- Uniprot ID:
- P33022
- Molecular weight:
- 33748
Reactions
A pyrimidine nucleoside + H(2)O = D-ribose + a pyrimidine base. |
- 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:
- 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