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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
Cordyceps sinensis (ncbitaxon:72228) mycelium (BTO:0001436) PubMed (21848266) Ethanolic extract of dried mycelia
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
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)
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Saccharomyces cerevisiae (ncbitaxon:4932) - PubMed (24678285) Source: yeast.sf.net
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
fundamental metabolite  Any metabolite produced by all living cells.
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:
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.
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.
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
AdenosineKEGG COMPOUND
9-β-D-ribofuranosyl-9H-purin-6-amineChEBI
AdoIUBMB
ADENOSINEPDBeChem
Ade-RibIUBMB
AdenosinChEBI
Brand Names  Source
AdenocardDrugBank
AdenocorDrugBank
AdenoscanDrugBank
UniProt Name  Source
adenosineUniProt
Manual XrefsDatabases
C00212KEGG COMPOUND
ADNPDBeChem
ArF00PDBeChem
ArS00PDBeChem
D00045KEGG DRUG
DB00640DrugBank
HMDB0000050HMDB
ADENOSINEMetaCyc
AdenosineWikipedia
C00007444KNApSAcK
YMDB00058YMDB
ECMDB00050ECMDB
LSM-28568LINCS
90DrugCentral
Registry NumbersSources
Gmelin:53385Gmelin
Reaxys:93029Reaxys
CAS:58-61-7KEGG COMPOUND
CAS:58-61-7ChemIDplus
CAS:58-61-7NIST Chemistry WebBook
Citations