Adenine

Adenine

Names
Preferred IUPAC name 9H-Purin-6-amine
Other names 6-Aminopurine
Identifiers
CAS Number	73-24-5 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	608603
ChEBI	CHEBI:16708 Y
ChEMBL	ChEMBL226345 Y
ChemSpider	185 Y
DrugBank	DB00173 Y
ECHA InfoCard	100.000.724
EC Number	200-796-1
Gmelin Reference	3903
IUPHAR/BPS	4788
KEGG	D00034 Y
PubChem CID	190
RTECS number	AU6125000
UNII	JAC85A2161 Y
CompTox Dashboard (EPA)	DTXSID6022557
InChI 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
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 (ΔfH⦵298)	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). Y verify (what is YN ?) Infobox references

Adenine (/ˈædɪnɪn/) (symbol A or Ade) is a purine nucleotide base. 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.