adenine

Also known as Adenin, Ade, 7H-purin-6-amine, 3,6-Dihydro-6-iminopurine, 6-Amino-1H-purine, 6-Amino-Purine, 9H-Purin-6-ylamine, Vitamin B4

Adenine (symbol A, or Ade) is a purine nucleotide base that is found in DNA, RNA, and ATP. Usually a white crystalline subtance. The shape of adenine is complementary and pairs to either thymine in DNA or uracil in RNA. In cells adenine, as an independent molecule, is rare. It is almost always covalently bound to become a part of a larger biomolecule.

AI overview

Adenine is a chemical building block found in DNA, RNA, and ATP—key molecules that store and use genetic information and energy in cells. It pairs with thymine in DNA or uracil in RNA, and while adenine itself is rarely found alone, it's almost always bonded into larger molecules where it plays an essential role in life's basic functions.

AI-generated from the Wikipedia summary — may contain errors.

Chemical data

Formula: C5H5N5
Molecular weight: 135.13 g/mol
IUPAC name: 7H-purin-6-amine
SMILES: C1=NC2=NC=NC(=C2N1)N
InChIKey: GFFGJBXGBJISGV-UHFFFAOYSA-N
XLogP: -0.1
Polar surface area: 80.5 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

97,964 papers

On the evolution of protein-adenine binding.Proceedings of the National Academy of Sciences of the United States of America · 2020Narunsky A, Kessel A, Solan R et al.DOI: 10.1073/pnas.1911349117
Novel derivatives of brincidofovir and (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine inhibit orthopoxviruses and human adenoviruses more potently than brincidofovir.Signal transduction and targeted therapy · 2025Zhang Y, Wan Y, Guo C et al.DOI: 10.1038/s41392-025-02207-w
[Adenine phosphoribosyltransferase (APRT)].ReviewNihon rinsho. Japanese journal of clinical medicine · 2003Taniguchi A
A new method for sequencing DNA.Proceedings of the National Academy of Sciences of the United States of America · 1977Maxam AM, Gilbert WDOI: 10.1073/pnas.74.2.560
Adenine suppresses inflammatory response in vascular smooth muscle cells via modulating AMPK/p53/NF-κB cascade.European journal of pharmacology · 2025Lin CM, Peng YH, Chen HM et al.DOI: 10.1016/j.ejphar.2025.178239
Adenine N6-methylation in diverse fungi.Nature genetics · 2017Seidl MFDOI: 10.1038/ng.3873
Efficient in vivo base editing via single adeno-associated viruses with size-optimized genomes encoding compact adenine base editors.Nature biomedical engineering · 2022Davis JR, Wang X, Witte IP et al.DOI: 10.1038/s41551-022-00911-4
[Adenine phosphoribosyltransferase (APRT) deficiency].ReviewRyoikibetsu shokogun shirizu · 1998Taniguchi A

via PubMed

Wikidata facts

Mass: 135.054

Show 5 more facts

Commons category: Adenine
chemical formula: C₅H₅N₅
canonical SMILES: C1=NC2=C(N1)C(=NC=N2)N
melting point: 360
density: 1.6

Sources (6)

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~5 min read

Article

7 sections

Contents

Structure
Biosynthesis
Function
History
Notes
References
External links

Adenine has a central role in cellular respiration. It is part of adenosine triphosphate which provides the energy that drives and supports most activities in living cells, such as protein synthesis, chemical synthesis, muscle contraction, and nerve impulse propagation. In respiration it also participates as part of the cofactors nicotinamide adenine dinucleotide, flavin adenine dinucleotide, and Coenzyme A.