Adenine

Adenine

Names
IUPAC name 9H-purin-6-amine
Other names 6-aminopurine
Identifiers
CAS Number	73-24-5 Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:16708 Y
ChEMBL	ChEMBL226345 Y
ChemSpider	185 Y
DrugBank	DB00173 Y
ECHA InfoCard	100.000.724
EC Number	200-796-1
IUPHAR/BPS	4788
KEGG	D00034 Y
PubChem	190
RTECS number	AU6125000
UNII	JAC85A2161 Y
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=C[N]2 Nc1ncnc2[nH]cnc12
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
Acidity (pKa)	4.15 (secondary), 9.80 (primary)
Thermochemistry
Specific heat capacity (C)	147.0 J/(K·mol)
Std enthalpy of formation (ΔfHo298)	96.9 kJ/mol
Hazards
Safety data sheet	MSDS
Lethal dose or concentration (LD, LC):
LD50 (median dose)	227 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Adenine /ˈædᵻnᵻn/ (A, Ade) is a nucleobase (a purine derivative). Its derivatives have a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD). 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.

The image on the right shows pure adenine, as an independent molecule. When connected into DNA, a covalent bond is formed between deoxyribose sugar and the bottom left nitrogen, so removing the hydrogen. 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 adenine attached to deoxyribose, as is used to form DNA.

Adenine forms several tautomers, compounds that can be rapidly interconverted and are often considered equivalent. However, in isolated conditions, i.e. in an inert gas matrix and in the gas phase, mainly the 9H-adenine tautomer is found.