Adenine

Adenine
Adenine.svg
Adenine-3D-balls.png
Adenine-3D-vdW.png
Names
IUPAC name
9H-purin-6-amine
Other names
6-aminopurine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.724
EC Number200-796-1
KEGG
RTECS numberAU6125000
UNII
Properties
C5H5N5
Molar mass135.13 g/mol
Appearancewhite to light yellow, crystalline
Density1.6 g/cm3 (calculated)
Melting point 360 to 365 °C (680 to 689 °F; 633 to 638 K) decomposes
0.103 g/100 mL
Solubilitynegligible in ethanol
Acidity (pKa)4.15 (secondary), 9.80 (primary)[1]
Thermochemistry
147.0 J/(K·mol)
96.9 kJ/mol
Hazards
Safety data sheetMSDS
Lethal dose or concentration (LD, LC):
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).
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Infobox references

Adenine n/ (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.[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, so removing the hydrogen. The remaining structure rachod 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.

Structure

Adenine structure, with standard numbering of positions in red.

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.[3][4]

Other Languages
العربية: أدينين
azərbaycanca: Adenin
تۆرکجه: آدنین
Bân-lâm-gú: Adenin
беларуская: Адэнін
български: Аденин
bosanski: Adenin
brezhoneg: Adenin
català: Adenina
čeština: Adenin
dansk: Adenin
Deutsch: Adenin
eesti: Adeniin
Ελληνικά: Αδενίνη
español: Adenina
Esperanto: Adenino
euskara: Adenina
فارسی: آدنین
français: Adénine
Gaeilge: Adainín
galego: Adenina
한국어: 아데닌
Հայերեն: Ադենին
हिन्दी: एडेनिन
hrvatski: Adenin
Ido: Adenino
Bahasa Indonesia: Adenina
interlingua: Adenine
italiano: Adenina
עברית: אדנין
Basa Jawa: Adenin
ქართული: ადენინი
қазақша: Аденин
kurdî: Adenîn
Кыргызча: Аденин
latviešu: Adenīns
lietuvių: Adeninas
magyar: Adenin
македонски: Аденин
മലയാളം: അഡിനിൻ
Bahasa Melayu: Adenina
Nederlands: Adenine
日本語: アデニン
norsk: Adenin
occitan: Adenina
polski: Adenina
português: Adenina
română: Adenină
русиньскый: Аденин
русский: Аденин
Scots: Adenine
Simple English: Adenine
slovenčina: Adenín
slovenščina: Adenin
српски / srpski: Аденин
srpskohrvatski / српскохрватски: Adenin
suomi: Adeniini
svenska: Adenin
Tagalog: Adenine
தமிழ்: அடினின்
Türkçe: Adenin
українська: Аденін
اردو: ادینین
Tiếng Việt: Adenine
吴语: 腺嘌呤
中文: 腺嘌呤
Lingua Franca Nova: Adenina