Uracil (ECMDB00300) (M2MDB000126)
Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 10:26:02 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-13 12:56:07 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Uracil | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Uracil is a common naturally occurring pyrimidine found in RNA, it base pairs with adenine and is replaced by thymine in DNA. Methylation of uracil produces thymine. Uracil serves as allosteric regulator and coenzyme for many important biochemical reactions. Uracil is also involved in the biosynthesis of polysaccharides and the transportation of sugars containing aldehydes. In E. coli, uracil catabolism is regulated by the amount of metabolically available nitrogen. (PMID: 4567228) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C4H4N2O2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 112.0868 Monoisotopic: 112.027277382 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | ISAKRJDGNUQOIC-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 66-22-8 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 1,2,3,4-tetrahydropyrimidine-2,4-dione | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | uracil | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | O=C1NC=CC(=O)N1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 |
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Molecular Framework | Aromatic heteromonocyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | 330 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Hydrogen ion + NADH + Oxygen + Uracil > NAD + Ureidoacrylate peracid Dihydrouracil + NAD <> Hydrogen ion + NADH + Uracil Water + Uridine > Ribose + Uracil Deoxyuridine + Phosphate <> Deoxyribose 1-phosphate + Uracil Cytosine + Hydrogen ion + Water > Ammonium + Uracil Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate Phosphate + Uridine <> Ribose-1-phosphate + Uracil Uridine 5'-monophosphate + Pyrophosphate <> Uracil + Phosphoribosyl pyrophosphate Cytosine + Water <> Uracil + Ammonia Uridine + Phosphate <> Uracil + alpha-D-Ribose 1-phosphate + Ribose-1-phosphate Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin Mononucleotide Deoxyuridine + Phosphate <> deoxyribose-1-phosphate + Uracil Water + Cytosine > Ammonia + Uracil D-Ribose-5-phosphate + Uracil <> Water + Pseudouridine 5'-phosphate Uracil + Oxygen + FMNH > Hydrogen ion + Ureidoacrylate peracid + Flavin Mononucleotide Pyrophosphate + Uridine 5'-monophosphate < Phosphoribosyl pyrophosphate + Uracil Uridine + Water > D-ribose + Uracil Dihydrouracil + NAD > Uracil + NADH Pseudouridine 5'-phosphate + Water > Uracil + D-Ribose-5-phosphate Uracil + FMNH(2) + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Water Uridine + Inorganic phosphate > Uracil + Ribose-1-phosphate Uridine 5'-monophosphate + Pyrophosphate > Uracil + Phosphoribosyl pyrophosphate Dihydrouracil + NAD + Dihydrothymine <> Uracil + NADH + Hydrogen ion + Thymine Uracil + FMNH + Oxygen + Thymine <> Ureidoacrylate peracid + Flavin Mononucleotide + (Z)-2-Methyl-ureidoacrylate peracid Pseudouridine 5'-phosphate + Water > Uracil + D-ribofuranose 5-phosphate + D-ribofuranose 5-phosphate Uracil + FMNH2 + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion + Peroxyaminoacrylate More...Uridine + Phosphate > Uracil + Ribose-1-phosphate Deoxyuridine + Phosphate > Uracil + Deoxyribose 1-phosphate Cytosine + Water <> Uracil + Ammonia Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate Cytosine + Water <> Uracil + Ammonia Phosphoribosyl pyrophosphate + Uracil <> Pyrophosphate + Uridine 5'-monophosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Burckhalter, J. H.; Scarborough, Homer C. The synthesis of uracils as anticonvulsants. Journal of the American Pharmaceutical Association (1912-1977) (1955), 44 545-50. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in transferase activity, transferring glycosyl groups
- Specific function:
- The enzymes which catalyze the reversible phosphorolysis of pyrimidine nucleosides are involved in the degradation of these compounds and in their utilization as carbon and energy sources, or in the rescue of pyrimidine bases for nucleotide synthesis
- Gene Name:
- deoA
- Uniprot ID:
- P07650
- Molecular weight:
- 47207
Reactions
Thymidine + phosphate = thymine + 2-deoxy-alpha-D-ribose 1-phosphate. |
- General function:
- Involved in nucleoside metabolic process
- Specific function:
- Catalyzes the conversion of uracil and 5-phospho-alpha- D-ribose 1-diphosphate (PRPP) to UMP and diphosphate
- Gene Name:
- upp
- Uniprot ID:
- P0A8F0
- Molecular weight:
- 22533
Reactions
UMP + diphosphate = uracil + 5-phospho-alpha-D-ribose 1-diphosphate. |
- 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 transferase activity, transferring pentosyl groups
- Specific function:
- Catalyzes the reversible phosphorylytic cleavage of uridine and deoxyuridine to uracil and ribose- or deoxyribose-1- phosphate. The produced molecules are then utilized as carbon and energy sources or in the rescue of pyrimidine bases for nucleotide synthesis
- Gene Name:
- udp
- Uniprot ID:
- P12758
- Molecular weight:
- 27159
Reactions
Uridine + phosphate = uracil + 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, acting on carbon-nitrogen (but not peptide) bonds
- Specific function:
- Cytosine + H(2)O = uracil + NH(3)
- Gene Name:
- codA
- Uniprot ID:
- P25524
- Molecular weight:
- 47591
Reactions
Cytosine + H(2)O = uracil + 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 hydrolase activity, hydrolyzing N-glycosyl compounds
- Specific function:
- Hydrolyzes with equal efficiency cytidine or uridine to ribose and cytosine or uracil, respectively
- Gene Name:
- rihA
- Uniprot ID:
- P41409
- Molecular weight:
- 33823
- General function:
- Involved in FMN binding
- Specific function:
- Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
- Gene Name:
- rutF
- Uniprot ID:
- P75893
- Molecular weight:
- 17749
Reactions
FMNH(2) + NAD(+) = FMN + NADH. |
- General function:
- Involved in iron-sulfur cluster binding
- Specific function:
- Specific function unknown
- Gene Name:
- yeiA
- Uniprot ID:
- P25889
- Molecular weight:
- 45069
Reactions
5,6-dihydrouracil + NAD(+) = uracil + NADH. |
5,6-dihydrothymine + NAD(+) = thymine + NADH. |
- General function:
- Involved in oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
- Specific function:
- Part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
- Gene Name:
- rutA
- Uniprot ID:
- P75898
- Molecular weight:
- 42219
Reactions
Uracil + FMNH(2) + O(2) = (Z)-3-ureidoacrylate peracid + FMN + H(2)O. |
Thymine + FMNH(2) + O(2) = (Z)-2-methylureidoacrylate peracid + FMN + H(2)O. |
- General function:
- Involved in oxidoreductase activity
- Specific function:
- Specific function unknown
- Gene Name:
- yeiT
- Uniprot ID:
- P76440
- Molecular weight:
- 44329
Reactions
5,6-dihydrouracil + NAD(+) = uracil + NADH. |
5,6-dihydrothymine + NAD(+) = thymine + NADH. |
Transporters
- General function:
- Involved in transporter activity
- Specific function:
- Transport of uracil in the cell
- Gene Name:
- uraA
- Uniprot ID:
- P0AGM7
- Molecular weight:
- 45060
- General function:
- Involved in transporter activity
- Specific function:
- Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
- Gene Name:
- rutG
- Uniprot ID:
- P75892
- Molecular weight:
- 45557
- 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