FComEx: Adenosine (PC000029)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:32 UTC

Update date

2017-01-19 02:36:10 UTC

FoodComEx ID

PC000029

FoodDB Record

FDB003554

Chemical Information

Name

Adenosine

Description

Adenosine, also known as adenocard or ade-rib, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. Adenosine is a drug which is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (pvst), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (svt). also used as an adjunct to thallous chloride ti 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex svt. Adenosine is a strong basic compound (based on its pKa). Adenosine exists in all living species, ranging from bacteria to humans. Within humans, adenosine participates in a number of enzymatic reactions. In particular, adenosine can be converted into inosine; which is mediated by the enzyme adenosine deaminase. In addition, adenosine can be converted into adenine and ribose 1-phosphate; which is mediated by the enzyme purine nucleoside phosphorylase. In humans, adenosine is involved in thioguanine action pathway. Outside of the human body, Adenosine is found, on average, in the highest concentration within beers and milk (cow). Adenosine has also been detected, but not quantified in, several different foods, such as capers, new zealand spinachs, welsh onions, hickory nuts, and pepper (spice). This could make adenosine a potential biomarker for the consumption of these foods. Adenosine is a potentially toxic compound.

CAS Number

58-61-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol	ChEBI
1-(6-amino-9H-Purin-9-yl)-1-deoxy-beta-D-ribofuranose	HMDB
1-(6-amino-9H-Purin-9-yl)-1-deoxy-beta-delta-ribofuranose	HMDB
4-Aminopyrazolo[3,4-d]pyrimidine ribonucleoside	biospider
6-amino-9-b-D-Ribofuranosyl-9H-purine	Generator
6-Amino-9-beta-D-ribofuranosyl-9H-purine	biospider
6-amino-9-β-D-ribofuranosyl-9H-purine	Generator
6-Amino-9β-D-ribofuranosyl-9H-purine	biospider
6-amino-9beta-D-Ribofuranosyl-9H-purine	HMDB
6-amino-9beta-delta-Ribofuranosyl-9H-purine	HMDB
9-β-D-Ribofuranosidoadenine	biospider
9-β-D-Ribofuranosyl-9H-purin-6-amine	biospider
9-β-d-Ribofuranosyladenine	biospider
9-b-D-Ribofuranosidoadenine	Generator
9-b-D-Ribofuranosyl-9H-purin-6-amine	Generator
9-beta-D-Arabinofuranosyladenine	HMDB
9-beta-D-Ribofuranosidoadenine	biospider
9-beta-D-Ribofuranosyl-9H-purin-6-amine	biospider
9-beta-d-ribofuranosyladenine	biospider
9-beta-delta-Arabinofuranosyladenine	HMDB
9-beta-delta-Ribofuranosidoadenine	biospider
9-beta-delta-Ribofuranosyl-9H-purin-6-amine	biospider
9-beta-delta-Ribofuranosyladenine	biospider
9-β-D-ribofuranosidoadenine	Generator
9-β-D-ribofuranosyl-9H-purin-6-amine	Generator
9beta-D-ribofuranosyl-9H-Purin-6-amine	biospider
9beta-D-Ribofuranosyladenine	biospider
9beta-delta-ribofuranosyl-9H-Purin-6-amine	biospider
9beta-delta-Ribofuranosyladenine	biospider
9H-Purin-6-amine, 9β-D-ribofuranosyl-	biospider
9H-Purin-6-amine, 9beta-D-ribofuranosyl-	biospider
Ade-rib	ChEBI
Adenine nucleoside	HMDB
Adenine riboside	HMDB
Adenine-9-beta-D-ribofuranoside	biospider
Adenine-9beta-D-ribofuranoside	HMDB
Adenine-9beta-delta-ribofuranoside	HMDB
Adenine-d-ribose	biospider
Adenocard	ChEBI
Adenocor	ChEBI
Adenoscan	ChEBI
Adenosin	ChEBI
Ado	ChEBI
b-D-Adenosine	Generator
Beta-adenosine	biospider
Beta-d-adenosine	biospider
beta-D-Ribofuranoside, adenine-9	biospider
Beta-delta-adenosine	biospider
Boniton	HMDB
Myocol	HMDB
Nucleocardyl	HMDB
Sandesin	HMDB
β-D-adenosine	Generator

Chemical Formula

C10H13N5O4

IUPAC name

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

InChI Identifier

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

InChI Key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Isomeric SMILES

NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1

Average Molecular Weight

267.2413

Monoisotopic Molecular Weight

267.096753929

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents