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Adenine information


Adenine
Names
Preferred IUPAC name
9H-Purin-6-amine
Other names
6-Aminopurine
Identifiers
CAS Number
  • 73-24-5 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
Beilstein Reference
608603
ChEBI
  • CHEBI:16708 checkY
ChEMBL
  • ChEMBL226345 checkY
ChemSpider
  • 185 checkY
DrugBank
  • DB00173 checkY
ECHA InfoCard 100.000.724 Edit this at Wikidata
EC Number
  • 200-796-1
Gmelin Reference
3903
IUPHAR/BPS
  • 4788
KEGG
  • D00034 checkY
PubChem CID
  • 190
RTECS number
  • AU6125000
UNII
  • JAC85A2161 checkY
CompTox Dashboard (EPA)
  • DTXSID6022557 Edit this at Wikidata
InChI
  • InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) checkY
    Key: GFFGJBXGBJISGV-UHFFFAOYSA-N checkY
  • InChI=1/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
    Key: GFFGJBXGBJISGV-UHFFFAOYAT
SMILES
  • NC1=NC=NC2=C1N=CN2
  • Nc1c2ncNc2ncn1
Properties
Chemical formula
C5H5N5
Molar mass 135.13 g/mol
Appearance white to light yellow, crystalline
Density 1.6 g/cm3 (calculated)
Melting point 360 to 365 °C (680 to 689 °F; 633 to 638 K) decomposes
Solubility in water
0.103 g/100 mL
Solubility negligible in ethanol, soluble in hot water and/or aqua ammonia
Acidity (pKa) 4.15 (secondary), 9.80 (primary)[1]
Thermochemistry
Heat capacity (C)
147.0 J/(K·mol)
Std enthalpy of
formation fH298)
96.9 kJ/mol
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)
227 mg/kg (rat, oral)
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Adenine (/ˈædɪnɪn/) (symbol A or Ade) is a purine nucleobase. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine (G), cytosine (C), and thymine (T). Adenine derivatives have various roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD), flavin adenine dinucleotide (FAD) and Coenzyme A. It also has functions in protein synthesis and as a chemical component of DNA and RNA.[2] The shape of adenine is complementary to either thymine in DNA or uracil in RNA.

The adjacent image shows pure adenine, as an independent molecule. When connected into DNA, a covalent bond is formed between deoxyribose sugar and the bottom left nitrogen (thereby removing the existing hydrogen atom). The remaining structure is called an adenine residue, as part of a larger molecule. Adenosine is adenine reacted with ribose, as used in RNA and ATP; Deoxyadenosine is adenine attached to deoxyribose, as used to form DNA.

  1. ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  2. ^ "MedlinePlus: Genetics". medlineplus.gov. Retrieved 2022-12-23.

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Adenine

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Adenine (/ˈædɪnɪn/) (symbol A or Ade) is a purine nucleobase. It is one of the four nucleobases in the nucleic acids of DNA, the other three being guanine...

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Nicotinamide adenine dinucleotide

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Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists...

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Nicotinamide adenine dinucleotide phosphate

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Nicotinamide adenine dinucleotide phosphate, abbreviated NADP+ or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic...

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Adenine deaminase

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In enzymology, an adenine deaminase (EC 3.5.4.2) is an enzyme that catalyzes the chemical reaction adenine + H2O ⇌ {\displaystyle \rightleftharpoons }...

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Purine

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the two groups of nucleotide bases. The purine bases are guanine (G) and adenine (A) which form corresponding nucleosides-deoxyribonucleosides (deoxyguanosine...

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Adenine phosphoribosyltransferase

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Adenine phosphoribosyltransferase (APRTase) is an enzyme encoded by the APRT gene, found in humans on chromosome 16. It is part of the Type I PRTase family...

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Nucleobase

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aminoadenine (Z) instead of adenine. It differs in having an extra amine group, creating a more stable bond to thymine. Adenine and guanine have a fused-ring...

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Flavin adenine dinucleotide

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In biochemistry, flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic...

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Adenine nucleotide translocator

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Adenine nucleotide translocator (ANT), also known as the ADP/ATP translocase (ANT), ADP/ATP carrier protein (AAC) or mitochondrial ADP/ATP carrier, exchanges...

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DNA adenine methylase

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DNA adenine methylase, (Dam) (also site-specific DNA-methyltransferase (adenine-specific), EC 2.1.1.72, modification methylase, restriction-modification...

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DNA methylation

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have been found on which natural, enzymatic DNA methylation takes place: adenine and cytosine. The modified bases are N6-methyladenine, 5-methylcytosine...

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Adenosine

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nature in the form of diverse derivatives. The molecule consists of an adenine attached to a ribose via a β-N9-glycosidic bond. Adenosine is one of the...

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Flavin mononucleotide

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as well as jams, milk products, and sweets and sugar products. Flavin adenine dinucleotide Tsibris, John C. M.; McCormick, Donald B.; Wright, Lemuel...

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Guanine

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main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine (uracil in RNA). In DNA, guanine is paired with...

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DNA adenine methyltransferase identification

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DNA adenine methyltransferase identification, often abbreviated DamID, is a molecular biology protocol used to map the binding sites of DNA- and chromatin-binding...

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DNA methyltransferase

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methyltransferases (N-6 adenine-specific DNA methylase) (A-Mtase) are enzymes that specifically methylate the amino group at the C-6 position of adenines in DNA. They...

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Vidarabine

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Furthermore, replacement of adenine with 2-fluoroadenine in the enzymatic transglycosylation reaction from ara-U to the 9-position of adenine made it bring about...

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Hypoxanthine

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spontaneous deamination product of adenine. Because of its resemblance to guanine, the spontaneous deamination of adenine can lead to an error in DNA...

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Purine metabolism

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particular as ribotides, i.e. bases attached to ribose 5-phosphate. Both adenine and guanine are derived from the nucleotide inosine monophosphate (IMP)...

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Biochemistry

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acid. Adenine binds with thymine and uracil, thymine binds only with adenine, and cytosine and guanine can bind only with one another. Adenine, thymine...

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Genome editing

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Genome editing, or genome engineering, or gene editing, is a type of genetic engineering in which DNA is inserted, deleted, modified or replaced in the...

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Nucleotide

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consisting of one to three phosphates. The four nucleobases in DNA are guanine, adenine, cytosine, and thymine; in RNA, uracil is used in place of thymine. Nucleotides...

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Polyadenylation

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adenosine monophosphates; in other words, it is a stretch of RNA that has only adenine bases. In eukaryotes, polyadenylation is part of the process that produces...

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DNA

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one of four nitrogen-containing nucleobases (cytosine [C], guanine [G], adenine [A] or thymine [T]), a sugar called deoxyribose, and a phosphate group...

Word Count : 17845

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