Adenine

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. The shape of adenine is complementary to either thymine in DNA or uracil in RNA.

Not to be confused with Adenosine or Adrenaline.
Adenine
Names
Preferred IUPAC name
9H-Purin-6-amine
Other names
6-Aminopurine
Identifiers
3D model (JSmol)
608603
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.724
EC Number
  • 200-796-1
3903
KEGG
RTECS number
  • AU6125000
UNII
  • InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10) Y
    Key: GFFGJBXGBJISGV-UHFFFAOYSA-N Y
  • 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
  • NC1=NC=NC2=C1N=CN2
  • Nc1c2ncNc2ncn1
Properties
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
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)
Thermochemistry
147.0 J/(K·mol)
96.9 kJ/mol
Hazards
Lethal dose or concentration (LD, LC):
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).
Y verify (what is YN ?)
Infobox references

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.

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