Record Information
Version1.0
Creation date2011-09-21 00:04:45 UTC
Update date2020-09-17 15:38:19 UTC
Primary IDFDB021894
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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
5-(6-AMINO-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-olChEBI
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenineChEBI
9-(2-Deoxy-beta-D-ribofuranosyl)-9H-purin-6-amineChEBI
Adenine deoxyribonucleosideChEBI
AdenyldeoxyribosideChEBI
dAChEBI
2'-DeoxyadenosineKegg
9-(2-Deoxy-b-D-erythro-pentofuranosyl)adenineGenerator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)adenineGenerator
9-(2-Deoxy-b-D-ribofuranosyl)-9H-purin-6-amineGenerator
9-(2-Deoxy-β-D-ribofuranosyl)-9H-purin-6-amineGenerator
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
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-amineHMDB
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-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
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
DesoxyadenosineHMDB
DeoxyadenosineChEBI
(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
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-ribofuranosyl)-9H-Purin-6-aminehmdb
9-(2-deoxy-beta-D-erythro-pentofuranosyl)-9H-Purin-6-aminehmdb
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-ribofuranosyl)-9H-Purin-6-aminehmdb
adenine-9 2-deoxy-b-D-erythro-Pentofuranosidehmdb
adenine-9 2-deoxy-beta-D-erythro-Pentofuranosidehmdb
adenine-9 2-deoxy-beta-delta-erythro-Pentofuranosidehmdb
DAhmdb
Predicted Properties
PropertyValueSource
Water Solubility10.7 g/LALOGPS
logP-0.95ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)3.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.68 m³·mol⁻¹ChemAxon
Polarizability24.24 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Indirect biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDeoxyadenosine, 3 TMS, GC-MS Spectrumsplash10-0pbc-1950000000-892b755b10f34bcfa1c7Spectrum
GC-MSDeoxyadenosine, 3 TMS, GC-MS Spectrumsplash10-05fr-9750000000-34ebf7e59598c6551f52Spectrum
GC-MSDeoxyadenosine, 3 TMS, GC-MS Spectrumsplash10-0pbc-2950000000-9d52e7dcd83de5a30aefSpectrum
GC-MSDeoxyadenosine, non-derivatized, GC-MS Spectrumsplash10-0pbc-1950000000-892b755b10f34bcfa1c7Spectrum
GC-MSDeoxyadenosine, non-derivatized, GC-MS Spectrumsplash10-05fr-9750000000-34ebf7e59598c6551f52Spectrum
GC-MSDeoxyadenosine, non-derivatized, GC-MS Spectrumsplash10-0pbc-2950000000-9d52e7dcd83de5a30aefSpectrum
Predicted GC-MSDeoxyadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000x-9550000000-219c39ab05ecbebb53eeSpectrum
Predicted GC-MSDeoxyadenosine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ge9-6917000000-51808985bdc9abeb3cb3Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udr-1790000000-c0d4c0cc085cab7c2dcfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-e2abd19062db64ff67beSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-2900000000-1b8d5c847c2b1955056eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-5900000000-845c20e0f6bd5494b6dcSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004r-8900000000-484d9f08e4e28fab1f70Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-e852451e7253e0de72beSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0390000000-fba17d1430b371138db2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-0930000000-931c7b084c33f9122af4Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0900000000-66ae7ac8bd510a173402Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0900000000-c71d67857e2136dc7666Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-1790000000-cfbdf2e3950e7987b94bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-a3c367588a28d36cf5f0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-1b8d5c847c2b1955056eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-5900000000-f950493ce420caae6a66Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004r-8900000000-61ed5b4b3e748a449803Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-31d03c242f14d91a718cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-fba17d1430b371138db2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0930000000-931c7b084c33f9122af4Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-81ac782a59b2ca52f52bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920000000-2e897a458cf4c7af381cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f52b5322fde2e3722903Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-fcb0a5032b8607fd8b11Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-bec96a9658c683fa0d9bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0910000000-b504aa725d20d6213b20Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-d09551db93d558a5aed7Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID13135
ChEMBL IDCHEMBL449329
KEGG Compound IDC00559
Pubchem Compound ID13730
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00101
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35352
KNApSAcK IDNot Available
HET ID3D1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDeoxyadenosine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Adenosine deaminaseADAP00813
Purine nucleoside phosphorylasePNPP00491
Cytosolic 5'-nucleotidase 3NT5C3Q9H0P0
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference