FComEx: Deoxyadenosine (PC000174)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:02 UTC

Update date

2017-01-19 02:36:15 UTC

FoodComEx ID

PC000174

FoodDB Record

FDB021894

Chemical Information

Name

Deoxyadenosine

Description

Deoxyadenosine, also known as dA, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. Deoxyadenosine is a strong basic compound (based on its pKa). Deoxyadenosine exists in all living species, ranging from bacteria to humans. Within humans, deoxyadenosine participates in a number of enzymatic reactions. In particular, deoxyadenosine can be converted into adenine and deoxyribose 1-phosphate through its interaction with the enzyme purine nucleoside phosphorylase. In addition, deoxyadenosine can be converted into deoxyinosine through its interaction with the enzyme adenosine deaminase. A purine 2'-deoxyribonucleoside having adenine as the nucleobase. In humans, deoxyadenosine is involved in mercaptopurine action pathway. Outside of the human body, Deoxyadenosine is found, on average, in the highest concentration within beers. Deoxyadenosine has also been detected, but not quantified in, milk (cow). This could make deoxyadenosine a potential biomarker for the consumption of these foods. Deoxyadenosine is a potentially toxic compound. Deoxyadenosine, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and eosinophilic esophagitis; deoxyadenosine has also been linked to several inborn metabolic disorders including adenosine deaminase deficiency and adenylosuccinate lyase deficiency.

CAS Number

958-09-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2R,3S,5R)-5-(6-amino-9H-Purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol	ChEBI
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-b-D-Ribofuranose	hmdb
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-Ribofuranose	hmdb
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-Ribofuranose	hmdb
2-Deoxyadenosine	hmdb
2'-Deoxyadenosine	hmdb
5-(6-amino-PURIN-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol	ChEBI
9-(2-deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-amine	hmdb
9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenine	hmdb
9-(2-deoxy-b-D-ribofuranosyl)-9H-Purin-6-amine	hmdb
9-(2-deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-amine	hmdb
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine	hmdb
9-(2-deoxy-beta-D-ribofuranosyl)-9H-Purin-6-amine	hmdb
9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9H-Purin-6-amine	hmdb
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adenine	hmdb
9-(2-deoxy-beta-delta-ribofuranosyl)-9H-Purin-6-amine	hmdb
9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenine	Generator
9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amine	Generator
Adenine deoxyribonucleoside	hmdb
Adenine deoxyribose	hmdb
adenine-9 2-deoxy-b-D-erythro-Pentofuranoside	hmdb
adenine-9 2-deoxy-beta-D-erythro-Pentofuranoside	hmdb
adenine-9 2-deoxy-beta-delta-erythro-Pentofuranoside	hmdb
Adenyldeoxyriboside	hmdb
DA	hmdb
Deoxyadenosine	hmdb
Desoxyadenosine	hmdb

Chemical Formula

C10H13N5O3

IUPAC name

(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

InChI Identifier

InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1

InChI Key

OLXZPDWKRNYJJZ-RRKCRQDMSA-N

Isomeric SMILES

NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1

Average Molecular Weight

251.2419

Monoisotopic Molecular Weight

251.101839307

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2'-deoxyribonucleosides

Direct Parent

Purine 2'-deoxyribonucleosides

Alternative Parents