CHEBI:16335 - adenosine

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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 ChemicalBook:CB7159905, eMolecules:539941, ZINC000004623738
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Leukotriene B4 (LTB4) is a leukotriene involved in inflammation. It has been shown to promote insulin resistance in obese mice.
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Formula C10H13N5O4
Net Charge 0
Average Mass 267.24152
Monoisotopic Mass 267.09675
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:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055) 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
Cordyceps sinensis (NCBI:txid72228) Found in mycelium (BTO:0001436). Ethanolic extract of dried mycelia See: PubMed
Homo sapiens (NCBI:txid9606) 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)
adenosine (CHEBI:16335) is a purines D-ribonucleoside (CHEBI:142355)
Incoming α-N-(9-β-D-ribofuranosylpurin-6-yl)glycinamide (CHEBI:77005) has functional parent adenosine (CHEBI:16335)
(−)-N6-(2-phenylisopropyl)adenosine (CHEBI:192091) has functional parent adenosine (CHEBI:16335)
1,N6-ethenoadenosine (CHEBI:233185) 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)
N6,2'-O-dimethyladenosine (CHEBI:229469) 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)
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)
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
9-β-D-ribofuranosyladenine HMDB
Ade-Rib CBN
adenine riboside HMDB
Adenosin ChEBI
ADENOSINE PDBeChem
Adenosine KEGG COMPOUND
adenosine UniProt
Ado CBN
β-D-adenosine ChemIDplus
Brand Names Sources
Adenocard DrugBank
Adenocor DrugBank
Adenoscan DrugBank
Manual Xrefs Databases
90 DrugCentral
Adenosine Wikipedia
ADENOSINE MetaCyc
ADN PDBeChem
ArF00 PDBeChem
ArS00 PDBeChem
C00007444 KNApSAcK
C00212 KEGG COMPOUND
D00045 KEGG DRUG
DB00640 DrugBank
ECMDB00050 ECMDB
HMDB0000050 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 ChemIDplus
58-61-7 CAS Registry Number NIST Chemistry WebBook
93029 Reaxys Registry Number Reaxys
Citations Types Sources
11213237 PubMed citation Europe PMC
11820865 PubMed citation Europe PMC
11978011 PubMed citation Europe PMC
16183671 PubMed citation Europe PMC
16917093 PubMed citation Europe PMC
17190852 PubMed citation Europe PMC
18000974 PubMed citation Europe PMC
323854 PubMed citation Europe PMC
Last Modified
29 November 2024