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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:
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.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
fundamental metabolite  Any metabolite produced by all living cells.
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