CHEBI:16708 - adenine

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ChEBI Name adenine
ChEBI ID CHEBI:16708
Definition The parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40579, CHEBI:2470, CHEBI:13733, CHEBI:22236
Supplier Information ChemicalBook:CB3259991, eMolecules:476391, eMolecules:27515804, ZINC000000968256
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Amantadine, sold under the brand name Gocovri among others, is a medication used to treat dyskinesia associated with parkinsonism and influenza caused by type A influenzavirus, though its use for the latter is no longer recommended because of widespread drug resistance. It is also used for a variety of other uses. The drug is taken by mouth. Amantadine has a mild side-effect profile. Common neurological side effects include drowsiness, lightheadedness, dizziness, and confusion. Because of its effects on the central nervous system (CNS), it should be combined cautiously with additional CNS stimulants or anticholinergic drugs. Given that it is cleared by the kidneys, amantadine is contraindicated in persons with end-stage kidney disease. Due to its anticholinergic effects, it should be taken with caution by those with enlarged prostates or glaucoma. The pharmacology of amantadine is complex. It acts as a sigma σ1 receptor agonist, nicotinic acetylcholine receptor negative allosteric modulator, dopaminergic agent, and weak NMDA receptor antagonist, among other actions. The precise mechanism of action of its therapeutic effects in the treatment of CNS disorders is unclear. The antiviral mechanism of action is inhibition of the influenza virus A M2 proton channel, which prevents endosomal escape (i.e., the release of viral genetic material into the host cytoplasm). Amantadine is an adamantane derivative and is related to memantine and rimantadine. Amantadine was first used for the treatment of influenza A. After its antiviral properties were initially reported in 1963, amantadine received approval for prophylaxis against the influenza virus A in 1966. In 1968, its antiparkinsonian effects were serendipitously discovered. In 1973, the Food and Drug Administration (FDA) approved amantadine for use in the treatment of pharmacology. In 2020, the agonist was approved for use in the treatment of nicotinic acetylcholine receptor negative allosteric modulator.
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Formula C5H5N5
Net Charge 0
Average Mass 135.12690
Monoisotopic Mass 135.05450
InChI InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
InChIKey GFFGJBXGBJISGV-UHFFFAOYSA-N
SMILES Nc1ncnc2[nH]cnc12
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Daphnia magna (NCBI:txid35525) See: Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
Saccharomyces cerevisiae (NCBI:txid4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing adenine (CHEBI:16708) has parent hydride 9H-purine (CHEBI:35589)
adenine (CHEBI:16708) has role Daphnia magna metabolite (CHEBI:83056)
adenine (CHEBI:16708) has role Escherichia coli metabolite (CHEBI:76971)
adenine (CHEBI:16708) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
adenine (CHEBI:16708) has role human metabolite (CHEBI:77746)
adenine (CHEBI:16708) has role mouse metabolite (CHEBI:75771)
adenine (CHEBI:16708) is a 6-aminopurines (CHEBI:20706)
adenine (CHEBI:16708) is a purine nucleobase (CHEBI:26386)
Incoming (3S,4R,5R)-5-(adenin-9-yl)-4-hydroxytetrahydrofuran-3-yl dihydrogen phosphate (CHEBI:42413) has functional parent adenine (CHEBI:16708)
1H-imidazo[2,1-i]purine (CHEBI:29146) has functional parent adenine (CHEBI:16708)
2,8-dihydroxyadenine (CHEBI:183641) has functional parent adenine (CHEBI:16708)
2,8-dioxoadenine (CHEBI:179632) has functional parent adenine (CHEBI:16708)
2-amino-6-hydroxyaminopurine (CHEBI:78685) has functional parent adenine (CHEBI:16708)
2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (CHEBI:47311) has functional parent adenine (CHEBI:16708)
6-alkylaminopurine (CHEBI:17524) has functional parent adenine (CHEBI:16708)
6-hydroxymethyladenine (CHEBI:142766) has functional parent adenine (CHEBI:16708)
6-isopentenylaminopurine (CHEBI:38643) has functional parent adenine (CHEBI:16708)
8-(2-chloro-3,4,5-trimethoxybenzyl)-2-fluoro-9-pent-4-yn-1-yl-9H-purin-6-amine (CHEBI:47628) has functional parent adenine (CHEBI:16708)
8-hydroxyadenine (CHEBI:134105) has functional parent adenine (CHEBI:16708)
8-oxoadenine (CHEBI:134104) has functional parent adenine (CHEBI:16708)
9-β-D-erythrofuranosyladenine (CHEBI:41421) has functional parent adenine (CHEBI:16708)
9-β-D-xylofuranosyladenine (CHEBI:46515) has functional parent adenine (CHEBI:16708)
9-(tetrahydrofuryl)adenine (CHEBI:90232) has functional parent adenine (CHEBI:16708)
9-riburonosyladenine (CHEBI:16009) has functional parent adenine (CHEBI:16708)
9-{2,5-anhydro-4-[(phosphonooxy)methyl]-α-L-lyxofuranosyl}-9H-purin-6-amine (CHEBI:43791) has functional parent adenine (CHEBI:16708)
9H-purine-2,6-diamine (CHEBI:40235) has functional parent adenine (CHEBI:16708)
N-benzyl-9-(α-D-glucosyl)adenine (CHEBI:72604) has functional parent adenine (CHEBI:16708)
N-benzyladenine (CHEBI:29022) has functional parent adenine (CHEBI:16708)
N6,N6-dimethyladenine (CHEBI:60281) has functional parent adenine (CHEBI:16708)
N6-carbamoylmethyl-2'-deoxyadenosine (CHEBI:102719) has functional parent adenine (CHEBI:16708)
N6-carbamoylmethyladenine (CHEBI:102525) has functional parent adenine (CHEBI:16708)
N6-hydroxyadenine (CHEBI:78235) has functional parent adenine (CHEBI:16708)
adefovir (CHEBI:2469) has functional parent adenine (CHEBI:16708)
adenine arabinoside (CHEBI:45327) has functional parent adenine (CHEBI:16708)
adenosine (CHEBI:16335) has functional parent adenine (CHEBI:16708)
adenosines (CHEBI:22260) has functional parent adenine (CHEBI:16708)
hypoxanthine (CHEBI:17368) has functional parent adenine (CHEBI:16708)
M3Ade (CHEBI:233180) has functional parent adenine (CHEBI:16708)
methyladenine (CHEBI:25272) has functional parent adenine (CHEBI:16708)
oxetanocin A (CHEBI:86012) has functional parent adenine (CHEBI:16708)
tenofovir alafenamide (CHEBI:90926) has functional parent adenine (CHEBI:16708)
EHNA (CHEBI:63057) has parent hydride adenine (CHEBI:16708)
adenin-9-yl group (CHEBI:30756) is substituent group from adenine (CHEBI:16708)
IUPAC Name
9H-purin-6-amine
Synonyms Sources
6-Aminopurine KEGG COMPOUND
A ChEBI
Ade CBN
Adenin NIST Chemistry WebBook
Adenine KEGG COMPOUND
ADENINE PDBeChem
adenine UniProt
Manual Xrefs Databases
89 DrugCentral
ADE PDBeChem
Adenine Wikipedia
ADENINE MetaCyc
C00001490 KNApSAcK
C00147 KEGG COMPOUND
D00034 KEGG DRUG
DB00173 DrugBank
HMDB0000034 HMDB
View more database links
Registry Numbers Types Sources
3903 Gmelin Registry Number Gmelin
608603 Reaxys Registry Number Reaxys
73-24-5 CAS Registry Number KEGG COMPOUND
73-24-5 CAS Registry Number NIST Chemistry WebBook
73-24-5 CAS Registry Number ChemIDplus
Citations Types Sources
11985597 PubMed citation Europe PMC
12829005 PubMed citation Europe PMC
12951489 PubMed citation Europe PMC
15063338 PubMed citation Europe PMC
15715490 PubMed citation Europe PMC
17439666 PubMed citation Europe PMC
8070089 PubMed citation Europe PMC
Last Modified
11 November 2021
General Comment
2010-12-21 A component of DNA and RNA, it also plays biochemical roles in cellular respiration and protein synthesis.