adenosine (CHEBI:16335)

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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	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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Marvin 12170711313D

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Marvin 12170711313D

32 34 0 0 1 0 999 V2000

3.7355 3.0487 -0.7823 N 0 0 0 0 0 0 0 0 0 0 0 0

2.6607 2.4920 -0.2878 C 0 0 0 0 0 0 0 0 0 0 0 0

2.0323 3.0660 0.7802 N 0 0 0 0 0 0 0 0 0 0 0 0

0.9031 2.5594 1.3584 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3933 1.4139 0.8201 N 0 0 0 0 0 0 0 0 0 0 0 0

0.9791 0.7905 -0.2442 C 0 0 0 0 0 0 0 0 0 0 0 0

2.1358 1.3046 -0.8402 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5045 0.5143 -1.8531 N 0 0 0 0 0 0 0 0 0 0 0 0

1.5924 -0.4739 -1.8837 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6536 -0.3329 -0.9179 N 0 0 0 0 0 0 0 0 0 0 0 0

-0.4671 -1.2113 -0.6864 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.6962 -0.4824 -0.7894 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.7285 -1.2800 -0.1991 C 0 0 2 0 0 0 0 0 0 0 0 0

-3.9441 -0.4019 0.1551 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.4685 0.2879 -0.9715 O 0 0 0 0 0 0 0 0 0 0 0 0

-2.0566 -1.9695 1.0123 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.5145 -3.3125 1.1558 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5439 -1.8584 0.7158 C 0 0 1 0 0 0 0 0 0 0 0 0

0.1480 -3.1033 0.7587 O 0 0 0 0 0 0 0 0 0 0 0 0

4.1001 3.8961 -0.3711 H 0 0 0 0 0 0 0 0 0 0 0 0

4.2010 2.6314 -1.5756 H 0 0 0 0 0 0 0 0 0 0 0 0

0.4302 3.0472 2.2108 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6118 -1.2911 -2.6048 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.3278 -1.9341 -1.4902 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.0908 -2.0110 -0.9220 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.7493 -1.0660 0.4691 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.5968 0.3870 0.8223 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.6502 1.1997 -0.7324 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3316 -1.5797 1.9924 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3011 -3.4413 0.6209 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0047 -1.3359 1.4995 H 0 0 0 0 0 0 0 0 0 0 0 0

0.6550 -3.1597 1.5719 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

2 3 4 0 0 0 0

2 7 4 0 0 0 0

3 4 4 0 0 0 0

4 5 4 0 0 0 0

5 6 4 0 0 0 0

6 7 4 0 0 0 0

6 10 4 0 0 0 0

7 8 4 0 0 0 0

8 9 4 0 0 0 0

9 10 4 0 0 0 0

11 10 1 0 0 0 0

11 12 1 0 0 0 0

11 18 1 0 0 0 0

12 13 1 0 0 0 0

13 14 1 0 0 0 0

13 16 1 0 0 0 0

14 15 1 0 0 0 0

16 17 1 0 0 0 0

16 18 1 0 0 0 0

18 19 1 0 0 0 0

1 20 1 0 0 0 0

1 21 1 0 0 0 0

4 22 1 0 0 0 0

9 23 1 0 0 0 0

11 24 1 0 0 0 0

13 25 1 0 0 0 0

14 26 1 0 0 0 0

14 27 1 0 0 0 0

15 28 1 0 0 0 0

16 29 1 0 0 0 0

17 30 1 0 0 0 0

18 31 1 0 0 0 0

19 32 1 0 0 0 0

M END): 18 ms

reading 32 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

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Wikipedia	License
Adenosine (symbol A) is an organic compound that occurs widely in nature in the form of diverse derivatives. The molecule consists of an adenine attached to a ribose via a β-N9-glycosidic bond. Adenosine is one of the four nucleoside building blocks of RNA (and its derivative deoxyadenosine is a building block of DNA), which are essential for all life on Earth. Its derivatives include the energy carriers adenosine mono-, di-, and triphosphate, also known as AMP/ADP/ATP. Cyclic adenosine monophosphate (cAMP) is pervasive in signal transduction. Adenosine is used as an intravenous medication for some cardiac arrhythmias. Adenosyl (abbreviated Ado or 5'-dAdo) is the chemical group formed by removal of the 5′-hydroxy (OH) group. It is found in adenosylcobalamin (an active form of vitamin B12) and as a radical in the radical SAM enzymes.
Read full article at Wikipedia

Formula

C10H13N5O4

Net Charge

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

Forman MB, Jackson EK (2007)
Importance of tissue perfusion in ST segment elevation myocardial infarction patients undergoing reperfusion strategies: role of adenosine.
Clinical cardiology 30, 583-585 [PubMed:18000974]
[show Abstract]

Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)
A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human.
Physiological genomics 29, 99-108 [PubMed:17190852]
[show Abstract]

Roman J, Rivera HN, Roser-Page S, Sitaraman SV, Ritzenthaler JD (2006)
Adenosine induces fibronectin expression in lung epithelial cells: implications for airway remodeling.
American journal of physiology. Lung cellular and molecular physiology 290, L317-25 [PubMed:16183671]
[show Abstract]

Ernens I, Rouy D, Velot E, Devaux Y, Wagner DR (2006)
Adenosine inhibits matrix metalloproteinase-9 secretion by neutrophils: implication of A2a receptor and cAMP/PKA/Ca2+ pathway.
Circulation research 99, 590-597 [PubMed:16917093]
[show Abstract]

MacKenzie WM, Hoskin DW, Blay J (2002)
Adenosine suppresses alpha(4)beta(7) integrin-mediated adhesion of T lymphocytes to colon adenocarcinoma cells.
Experimental cell research 276, 90-100 [PubMed:11978011]
[show Abstract]

Blardi P, de Lalla A, Volpi L, Auteri A, Di Perri T (2002)
Increase of adenosine plasma levels after oral trimetazidine: a pharmacological preconditioning?
Pharmacological research 45, 69-72 [PubMed:11820865]
[show Abstract]

Pasini FL, Capecchi PL, Perri TD (2000)
Adenosine and chronic ischemia of the lower limbs.
Vascular medicine (London, England) 5, 243-250 [PubMed:11213237]
[show Abstract]

Politz SM, Glitz DG (1977)
Ribosome structure: localization of N6,N6-dimethyladenosine by electron microscopy of a ribosome-antibody complex.
Proceedings of the National Academy of Sciences of the United States of America 74, 1468-1472 [PubMed:323854]
[show Abstract]

Last Modified

29 November 2024

CHEBI:16335 - adenosine

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