CHEBI:16335 - adenosine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name adenosine
ChEBI ID CHEBI:16335
Definition A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a β‒N9-glycosidic bond.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2472, CHEBI:40558, CHEBI:40825, CHEBI:40906, CHEBI:40911, CHEBI:13734, CHEBI:22237
Supplier Information
Save molfile Download Molfile
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C10H13N5O4
Net Charge 0
Average Mass 267.24152
Monoisotopic Mass 267.097
InChI InChI=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
InChIKey OIRDTQYFTABQOQ-KQYNXXCUSA-N
SMILES Nc1ncnc2n(cnc12)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:3055) See: PubMed
Daphnia magna (NCBI:35525) 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:4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Cordyceps sinensis (NCBI:72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Biological Role(s): 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.
Application(s): 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.
vasodilator agent
A drug used to cause dilation of the blood vessels.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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)
Incoming α-N-(9-β-D-ribofuranosylpurin-6-yl)glycinamide (CHEBI:77005) 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)
2-methylthio-N6-(Δ2-isopentenyl)adenosine (CHEBI:62875) has functional parent adenosine (CHEBI:16335)
2-methylthio-N6-(cis-4-hydroxy-Δ2-isopentenyl)adenosine (CHEBI:62879) has functional parent adenosine (CHEBI:16335)
2-thio-N6-(Δ2-isopentenyl)adenosine (CHEBI:73551) 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)
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)
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)
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,N6-dimethyladenosine (CHEBI:28284) has functional parent adenosine (CHEBI:16335)
N6-(Δ2-isopentenyl)adenosine (CHEBI:62881) has functional parent adenosine (CHEBI:16335)
L-adenosylselenohomocysteine (CHEBI:77028) 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)
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)
adenosine residue (CHEBI:62885) is substituent group from adenosine (CHEBI:16335)
IUPAC Name
adenosine
Synonyms Sources
(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol DrugBank
6-Amino-9-beta-D-ribofuranosyl-9H-purine ChemIDplus
9-beta-D-Ribofuranosidoadenine ChemIDplus
9-β-D-ribofuranosyl-9H-purin-6-amine ChEBI
9-beta-D-Ribofuranosyl-9H-purin-6-amine ChemIDplus
Ade-Rib CBN
Adenine Deoxyribonucleoside DrugBank
Adenosin ChEBI
ADENOSINE PDBeChem
Adenosine KEGG COMPOUND
adenosine UniProt
Adenyldeoxyriboside DrugBank
Ado CBN
beta-D-Adenosine ChemIDplus
Deoxyadenosine DrugBank
Desoxyadenosine DrugBank
Brand Names Sources
Adenocard DrugBank
Adenocor DrugBank
Adenoscan DrugBank
Database Links Databases
Adenosine Wikipedia
ADENOSINE MetaCyc
ADN PDBeChem
C00007444 KNApSAcK
C00212 KEGG COMPOUND
D00045 KEGG DRUG
DB00640 DrugBank
ECMDB00050 ECMDB
HMDB00050 HMDB
LSM-28568 LINCS
YMDB00058 YMDB
View more database links
Registry Numbers Types Sources
53385 Gmelin Registry Number Gmelin
58-61-7 CAS Registry Number KEGG COMPOUND
58-61-7 CAS Registry Number NIST Chemistry WebBook
58-61-7 CAS Registry Number ChemIDplus
93029 Beilstein Registry Number Beilstein
93029 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11213237 PubMed citation CiteXplore
11820865 PubMed citation CiteXplore
11978011 PubMed citation CiteXplore
16183671 PubMed citation CiteXplore
16917093 PubMed citation CiteXplore
17190852 PubMed citation CiteXplore
18000974 PubMed citation CiteXplore
323854 PubMed citation CiteXplore
Last Modified
21 April 2016