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Pyrimidine information


Pyrimidine
Pyrimidine molecule
Pyrimidine molecule
Names
Preferred IUPAC name
Pyrimidine[1]
Systematic IUPAC name
1,3-Diazabenzene
Other names
1,3-Diazine
m-Diazine
Identifiers
CAS Number
  • 289-95-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16898 checkY
ChEMBL
  • ChEMBL15562 checkY
ChemSpider
  • 8903 checkY
ECHA InfoCard 100.005.479 Edit this at Wikidata
KEGG
  • C00396 checkY
MeSH pyrimidine
PubChem CID
  • 9260
UNII
  • K8CXK5Q32L checkY
CompTox Dashboard (EPA)
  • DTXSID1051228 Edit this at Wikidata
InChI
  • InChI=1S/C4H4N2/c1-2-5-4-6-3-1/h1-4H checkY
    Key: CZPWVGJYEJSRLH-UHFFFAOYSA-N checkY
  • InChI=1/C4H4N2/c1-2-5-4-6-3-1/h1-4H
    Key: CZPWVGJYEJSRLH-UHFFFAOYAT
SMILES
  • n1cnccc1
Properties
Chemical formula
C4H4N2
Molar mass 80.088 g mol−1
Density 1.016 g cm−3
Melting point 20 to 22 °C (68 to 72 °F; 293 to 295 K)
Boiling point 123 to 124 °C (253 to 255 °F; 396 to 397 K)
Solubility in water
Miscible (25°C)
Acidity (pKa) 1.10[2] (protonated pyrimidine)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pyrimidine (C4H4N2; /pɪˈrɪ.mɪˌdn, pˈrɪ.mɪˌdn/) is an aromatic, heterocyclic, organic compound similar to pyridine (C5H5N).[3] One of the three diazines (six-membered heterocyclics with two nitrogen atoms in the ring), it has nitrogen atoms at positions 1 and 3 in the ring.[4]: 250  The other diazines are pyrazine (nitrogen atoms at the 1 and 4 positions) and pyridazine (nitrogen atoms at the 1 and 2 positions).

In nucleic acids, three types of nucleobases are pyrimidine derivatives: cytosine (C), thymine (T), and uracil (U).

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 141. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Brown, H. C.; et al. (1955). Baude, E. A.; F. C., Nachod (eds.). Determination of Organic Structures by Physical Methods. New York, NY: Academic Press.
  3. ^ Gilchrist, Thomas Lonsdale (1997). Heterocyclic chemistry. New York: Longman. ISBN 978-0-582-27843-1.
  4. ^ Joule, John A.; Mills, Keith, eds. (2010). Heterocyclic Chemistry (5th ed.). Oxford: Wiley. ISBN 978-1-405-13300-5.

and 26 Related for: Pyrimidine information

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Pyrimidine

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Pyrimidine (C4H4N2; /pɪˈrɪ.mɪˌdiːn, paɪˈrɪ.mɪˌdiːn/) is an aromatic, heterocyclic, organic compound similar to pyridine (C5H5N). One of the three diazines...

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Pyrimidine dimer

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Pyrimidine dimers represent molecular lesions originating from thymine or cytosine bases within DNA, resulting from photochemical reactions. These lesions...

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Nucleotide

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The purine bases adenine and guanine and pyrimidine base cytosine occur in both DNA and RNA, while the pyrimidine bases thymine (in DNA) and uracil (in RNA)...

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Pyrimidine metabolism

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Pyrimidine biosynthesis occurs both in the body and through organic synthesis. De Novo biosynthesis of a pyrimidine is catalyzed by three gene products...

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Nucleobase

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of cytosine, uracil, and thymine is derived of pyrimidine, so those three bases are called the pyrimidine bases. Each of the base pairs in a typical double-helix...

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Pyrimidine analogue

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Pyrimidine analogues are antimetabolites which mimic the structure of metabolic pyrimidines. Nucleobase analogues Fluorouracil (5FU), which inhibits thymidylate...

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Uracil

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demethylated form of thymine. Uracil is a common and naturally occurring pyrimidine derivative. The name "uracil" was coined in 1885 by the German chemist...

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Nucleic acid metabolism

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nitrogenous base. The bases found in nucleic acids are either purines or pyrimidines. In the more complex multicellular animals, they are both primarily produced...

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Purine

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a heterocyclic aromatic organic compound that consists of two rings (pyrimidine and imidazole) fused together. It is water-soluble. Purine also gives...

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Nucleoside deoxyribosyltransferase

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nucleoside:purine(pyrimidine) deoxy-D-ribosyltransferase. Other names in common use include purine(pyrimidine) nucleoside:purine(pyrimidine) deoxyribosyl...

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Cytosine

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RNA, along with adenine, guanine, and thymine (uracil in RNA). It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached...

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Ribosylpyrimidine nucleosidase

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pyrimidine nucleoside + H2O ⇌ {\displaystyle \rightleftharpoons } D-ribose + a pyrimidine base Thus, the two substrates of this enzyme are pyrimidine...

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Photolyase

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is called photoreactivation. They mainly convert pyrimidine dimers into a normal pair of pyrimidine bases. Photo reactivation, the first DNA repair mechanism...

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Pyrimidine phosphorylase

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Pyrimidine phosphorylase may refer to: Thymidine phosphorylase Uridine phosphorylase This article includes a list of related items that share the same...

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Deoxyribodipyrimidine endonucleosidase

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endonucleosidase (EC 3.2.2.17, pyrimidine dimer DNA-glycosylase, endonuclease V, deoxyribonucleate pyrimidine dimer glycosidase, pyrimidine dimer DNA glycosylase...

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Nucleoside

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linked through a glycosidic bond to the N9 of a purine or the N1 of a pyrimidine. Nucleotides are the molecular building blocks of DNA and RNA. This list...

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Orotic aciduria

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decreased ability to synthesize pyrimidines. It was the first described enzyme deficiency of the de novo pyrimidine synthesis pathway. Orotic aciduria...

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Orotic acid

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orotidine-5'-monophosphate (OMP). A distinguishing characteristic of pyrimidine synthesis is that the pyrimidine ring is fully synthesized before being attached to the...

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Pyrimidine oxygenase

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Pyrimidine oxygenase (EC 1.14.99.46, RutA) is an enzyme with systematic name uracil,FMNH2:oxygen oxidoreductase (uracil hydroxylating, ring-opening). This...

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Thymine

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adenine, guanine, and cytosine. Thymine is also known as 5-methyluracil, a pyrimidine nucleobase. In RNA, thymine is replaced by the nucleobase uracil. Thymine...

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Polynucleotide

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governed by physico-chemical processes. RNA is composed of purine and pyrimidine nucleotides, both of which are necessary for reliable information transfer...

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Nucleotide salvage

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to nucleotide salvage in particular, in which nucleotides (purine and pyrimidine) are synthesized from intermediates in their degradative pathway. Nucleotide...

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Orotate phosphoribosyltransferase

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(OPRTase) or orotic acid phosphoribosyltransferase is an enzyme involved in pyrimidine biosynthesis. It catalyzes the formation of orotidine 5'-monophosphate...

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Base pair

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single-ringed chemical structures called pyrimidines. Purines are complementary only with pyrimidines: pyrimidinepyrimidine pairings are energetically unfavorable...

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DNA

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divided into two groups, the single-ringed pyrimidines and the double-ringed purines. In DNA, the pyrimidines are thymine and cytosine; the purines are...

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Diaminohydroxyphosphoribosylaminopyrimidine deaminase

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the chemical reaction 2,5-diamino-6-hydroxy-4-(5-phosphoribosylamino)pyrimidine + H2O ⇌ {\displaystyle \rightleftharpoons } 5-amino-6-(5-phosphoribosylamino)uracil...

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