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CHEBI:16335 - adenosine

ChEBI IDCHEBI:16335
ChEBI Nameadenosine
Stars
DefinitionA ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a β‒N9-glycosidic bond.
Secondary ChEBI IDsCHEBI:2472, CHEBI:13734, CHEBI:22237, CHEBI:40558, CHEBI:40825, CHEBI:40906, CHEBI:40911
Last Modified29 November 2024
DownloadsMolfile
FormulaC10H13N5O4
Net Charge0
Average Mass267.245
Monoisotopic Mass267.09675
SMILESNc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChIInChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
InChIKeyOIRDTQYFTABQOQ-KQYNXXCUSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Cordyceps sinensis (ncbitaxon:72228) mycelium (BTO:0001436) PubMed (21848266) Ethanolic extract of dried mycelia
Daphnia magna (ncbitaxon:35525) - Article (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)
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Roles Classification
Biological Roles:
fundamental metabolite  Any metabolite produced by all living cells.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
Applications:
vasodilator agent  A drug used to cause dilation of the blood vessels.
anti-arrhythmia drug  A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
adenosine (CHEBI:16335) has functional parent adenine (CHEBI:16708)
adenosine (CHEBI:16335) has role analgesic (CHEBI:35480)
adenosine (CHEBI:16335) has role anti-arrhythmia drug (CHEBI:38070)
adenosine (CHEBI:16335) has role fundamental metabolite (CHEBI:78675)
adenosine (CHEBI:16335) has role human metabolite (CHEBI:77746)
adenosine (CHEBI:16335) has role vasodilator agent (CHEBI:35620)
adenosine (CHEBI:16335) is a adenosines (CHEBI:22260)
adenosine (CHEBI:16335) is a purines D-ribonucleoside (CHEBI:142355)
Incoming Relation(s)
(−)-N6-(2-phenylisopropyl)adenosine (CHEBI:192091) has functional parent adenosine (CHEBI:16335)
N-[(9-β-D-ribofuranosyl-2-methylthiopurin-6-yl)carbamoyl]threonine (CHEBI:21457) has functional parent adenosine (CHEBI:16335)
N-[(9-β-D-ribofuranosylpurin-6-yl)carbamoyl]threonine (CHEBI:21440) has functional parent adenosine (CHEBI:16335)
N-ethyl-5'-carboxamidoadenosine (CHEBI:73284) has functional parent adenosine (CHEBI:16335)
N6-(Δ2-isopentenyl)adenosine (CHEBI:62881) has functional parent adenosine (CHEBI:16335)
N6,N6-dimethyladenosine (CHEBI:28284) has functional parent adenosine (CHEBI:16335)
N6,2'-O-dimethyladenosine (CHEBI:229469) has functional parent adenosine (CHEBI:16335)
L-adenosylselenohomocysteine (CHEBI:77028) has functional parent adenosine (CHEBI:16335)
1-methyladenosine (CHEBI:16020) has functional parent adenosine (CHEBI:16335)
1-tuberculosinyladenosine(1+) (CHEBI:85603) has functional parent adenosine (CHEBI:16335)
1,N6-ethenoadenosine (CHEBI:233185) has functional parent adenosine (CHEBI:16335)
2-methylthio-N6-(cis-4-hydroxy-Δ2-isopentenyl)adenosine (CHEBI:62879) has functional parent adenosine (CHEBI:16335)
2-methylthio-N6-(Δ2-isopentenyl)adenosine (CHEBI:62875) has functional parent adenosine (CHEBI:16335)
2-thio-N6-(Δ2-isopentenyl)adenosine (CHEBI:73551) has functional parent adenosine (CHEBI:16335)
3-iodo-4-aminobenzyl-5'-N-methylcarboxamidoadenosine (CHEBI:73285) has functional parent adenosine (CHEBI:16335)
3-iodobenzyl-5'-N-methylcarboxamidoadenosine (CHEBI:73286) has functional parent adenosine (CHEBI:16335)
3'-O-salicyl-AMP (CHEBI:60351) has functional parent adenosine (CHEBI:16335)
3'-phosphoadenylyl selenate (CHEBI:28450) has functional parent adenosine (CHEBI:16335)
5'-O-sulfamoyladenosine (CHEBI:43716) has functional parent adenosine (CHEBI:16335)
5'-S-methyl-5'-thioadenosine (CHEBI:17509) has functional parent adenosine (CHEBI:16335)
5'-chloro-5'-deoxyadenosine (CHEBI:47133) has functional parent adenosine (CHEBI:16335)
5'-deoxyadenosine (CHEBI:17319) has functional parent adenosine (CHEBI:16335)
5'-ethylthioadenosine (CHEBI:74046) has functional parent adenosine (CHEBI:16335)
9-ribosyl-trans-zeatin (CHEBI:71693) has functional parent adenosine (CHEBI:16335)
adenosine phosphate (CHEBI:22256) has functional parent adenosine (CHEBI:16335)
adenylyl selenate (CHEBI:2485) has functional parent adenosine (CHEBI:16335)
aspartyl adenylate β-ketophosphonate isostere (CHEBI:74089) has functional parent adenosine (CHEBI:16335)
CGS-21680 (CHEBI:73283) has functional parent adenosine (CHEBI:16335)
cordysinin B (CHEBI:69426) has functional parent adenosine (CHEBI:16335)
diadenosyl diphosphate (CHEBI:64369) has functional parent adenosine (CHEBI:16335)
diadenosyl hexaphosphate (CHEBI:63736) has functional parent adenosine (CHEBI:16335)
diadenosyl pentaphosphate (CHEBI:63737) has functional parent adenosine (CHEBI:16335)
diadenosyl tetraphosphate (CHEBI:63738) has functional parent adenosine (CHEBI:16335)
diadenosyl triphosphate (CHEBI:63739) has functional parent adenosine (CHEBI:16335)
nucleocidin (CHEBI:166872) has functional parent adenosine (CHEBI:16335)
propionyl adenylate (CHEBI:74517) has functional parent adenosine (CHEBI:16335)
sangivamycin (CHEBI:85997) has functional parent adenosine (CHEBI:16335)
succinyladenosine (CHEBI:71169) has functional parent adenosine (CHEBI:16335)
thioadenosine (CHEBI:26953) has functional parent adenosine (CHEBI:16335)
α-N-(9-β-D-ribofuranosylpurin-6-yl)glycinamide (CHEBI:77005) has functional parent adenosine (CHEBI:16335)
adenosine residue (CHEBI:62885) is substituent group from adenosine (CHEBI:16335)
IUPAC Name 
adenosine
Synonyms  Source
(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diolDrugBank
6-Amino-9-beta-D-ribofuranosyl-9H-purineChemIDplus
9-beta-D-RibofuranosidoadenineChemIDplus
9-beta-D-Ribofuranosyl-9H-purin-6-amineChemIDplus
9-β-D-ribofuranosyl-9H-purin-6-amineChEBI
9-β-D-ribofuranosyladenineHMDB
Brand Names  Source
AdenocardDrugBank
AdenocorDrugBank
AdenoscanDrugBank
UniProt Name  Source
adenosineUniProt
Manual XrefsDatabases
90DrugCentral
AdenosineWikipedia
ADENOSINEMetaCyc
ADNPDBeChem
ArF00PDBeChem
ArS00PDBeChem
C00007444KNApSAcK
C00212KEGG COMPOUND
D00045KEGG DRUG
DB00640DrugBank
ECMDB00050ECMDB
HMDB0000050HMDB
LSM-28568LINCS
YMDB00058YMDB
Registry NumbersSources
Gmelin:53385Gmelin
Reaxys:93029Reaxys
CAS:58-61-7ChemIDplus
CAS:58-61-7NIST Chemistry WebBook
CAS:58-61-7KEGG COMPOUND
Citations