uracil

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's use in the body is to help carry out the synthesis of many enzymes necessary for cell function through bonding with riboses and phosphates. Uracil serves as allosteric regulator and coenzyme for many important biochemical reactions.

5,6-Dihydrouracil (5,6-Dihydrouracil) is an intermediate breakdown product of uracil.

2-Thiouracil (Deracil) is a thiolated uracil derivative that is a known anti-hyperthyroid agent.

1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside), isolated from the Caribbean sponge [Tectitethya crypta], is a methoxyadenosine derivative with anti-inflammatory activity, analgesic, and vasodilation properties.

5,6-Dihydro-5-methyluracil (Dihydrothymine) is an intermediate breakdown product of thymine.

5-Bromouracil disrupts nucleosome positioning by inducing A-form-like DNA.

6-Methyluracil, also known as Pseudothymine, is a metabolite derived from Uracil. It serves as an indicator for the accumulation of acetoacetyl-CoA (AACoA). Additionally, 6-Methyluracil has been observed to possess antiradiation properties in vivo.

5-(Hydroxymethyl)uracil is a product of oxidative DNA damage and is capable of enhancing or inhibiting potential epigenetic markers for transcription by bacterial RNA polymerases.

3-Methyluracil exhibits extremely weak inhibitory activity against uridine phosphorylase 1 and is widely used in biochemical experiments and drug synthesis research.

2'-Deoxyuridine (2-deoxyuridine). An antimetabolite that is converted to deoxyuridine triphosphate during DNA synthesis. Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies.

2,4-Dihydroxypyrimidine-5-carboxylic acid (Isoorotic acid) has been obtained from 5-formyluracil by the action of enzyme, thymine 7-hydroxylase. 2,4-Dihydroxypyrimidine-5-carboxylic acid has been used to synthesize N1-alkylated uracil derivatives.

5'-Uridylic acid. A uracil nucleotide containing one phosphate group esterified to the sugar moiety in the 2', 3' or 5' position. Uridine 5'-monophosphate (Uridylic acid) is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil.

Pyrimidine (Metadiazine)s are heterocyclic, six-membered, nitrogen-containing carbon ring structures, with uracil, cytosine and thymine being the basal structures of ribose-containing nucleosides (uridine, cytidine, and thymidine respectively), or deoxyribose-containing deoxynucleosides, and their corresponding ribonucleotides or deoxyribonucleotides. Pyrimidines serve essential functions in human metabolism as ribonucleotide bases in RNA (uracil and cytosine), and as deoxyribonucleotide bases in DNA (cytosine and thymine), and are linked by phosphodiester bridges to purine nucleotides in double-stranded DNA, in both the nucleus and the mitochondria. Pyrimidine activated sugars are also involved in polysaccharide and phospholipid synthesis, glucuronidation in detoxification processes, glycosylation of proteins and lipids and in the recently identified novel endothelium-derived vasoactive dinucleotides.

Cylindrospermopsin, a tricyclic uracil derivative, is a cyanobacterial toxin that was first discovered in an algal bloom contaminating a local drinking supply on Palm Island in Queensland, Australia after an outbreak of a mysterious disease. Cylindrospermopsin targets protein and glutathione synthesis in hepatocytes (IC50s = 1.3 and 2.4 µM, respectively), leading to cell death. [1] It has been shown to inhibit the activity of the uridine monophosphate synthase complex with a Ki value of 10 µM.[2] Cylindrospermopsin is genotoxic, inducing DNA damage as evidenced by double strand breaks and reducing cell viability in HepG2 cells at 0.1-0.5 µg ml.[3]

Ureidopropionic acid (3-Ureidopropionic acid) is an intermediate in uracil metabolism, produced from dihydrouracil by the enzyme dihydropyrimidase and further decomposed to beta-alanine by beta-ureidopropionase. It is a urea derivative of beta-alanine. High levels of Ureidopropionic acid are found in individuals with beta-ureidopropionase (UP) deficiency. Enzyme deficiencies in pyrimidine metabolism are associated with severe toxicity to the antineoplastic agent 5-fluorouracil.

Tsugaric acid A significantly inhibits superoxide anion formation in fMLP CB-stimulated rat neutrophils and protects human keratinocytes against damage induced by ultraviolet B (UV B) light, indicating that tsugaric acid A can safeguard keratinocytes from photodamage.