Record Information
Version1.0
Creation date2015-10-09 22:29:02 UTC
Update date2017-01-19 02:36:15 UTC
FoodComEx IDPC000174
FoodDB RecordFDB021894
Chemical Information
NameDeoxyadenosine
DescriptionDeoxyadenosine, 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 Number958-09-8
Structure
Thumb
Synonyms
SynonymSource
(2R,3S,5R)-5-(6-amino-9H-Purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-olChEBI
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-b-D-Ribofuranosehmdb
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-D-Ribofuranosehmdb
1-(6-amino-9H-purin-9-yl)-1,2-dideoxy-beta-delta-Ribofuranosehmdb
2-Deoxyadenosinehmdb
2'-Deoxyadenosinehmdb
5-(6-amino-PURIN-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-olChEBI
9-(2-deoxy-b-D-erythro-pentofuranosyl)-9H-Purin-6-aminehmdb
9-(2-Deoxy-b-D-erythro-pentofuranosyl)adeninehmdb
9-(2-deoxy-b-D-ribofuranosyl)-9H-Purin-6-aminehmdb
9-(2-deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-aminehmdb
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adeninehmdb
9-(2-deoxy-beta-D-ribofuranosyl)-9H-Purin-6-aminehmdb
9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9H-Purin-6-aminehmdb
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)adeninehmdb
9-(2-deoxy-beta-delta-ribofuranosyl)-9H-Purin-6-aminehmdb
9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenineGenerator
9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amineGenerator
Adenine deoxyribonucleosidehmdb
Adenine deoxyribosehmdb
adenine-9 2-deoxy-b-D-erythro-Pentofuranosidehmdb
adenine-9 2-deoxy-beta-D-erythro-Pentofuranosidehmdb
adenine-9 2-deoxy-beta-delta-erythro-Pentofuranosidehmdb
Adenyldeoxyribosidehmdb
DAhmdb
Deoxyadenosinehmdb
Desoxyadenosinehmdb
Chemical FormulaC10H13N5O3
IUPAC name(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
InChI IdentifierInChI=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 KeyOLXZPDWKRNYJJZ-RRKCRQDMSA-N
Isomeric SMILESNC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](CO)O1
Average Molecular Weight251.2419
Monoisotopic Molecular Weight251.101839307
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 2'-deoxyribonucleosides
Direct ParentPurine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci J90387
AKSci K731
MetaSci HMDB0000101
Sigma-Aldrich HMDB0000101
Toronto Research Chemicals D239583