Record Information
Version1.0
Created at2020-04-17 18:38:10 UTC
Updated at2020-12-07 19:10:58 UTC
CannabisDB IDCDB004801
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. Deoxyadenosine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC10H13N5O3
Average Molecular Weight251.24
Monoisotopic Molecular Weight251.1018
IUPAC Name(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Traditional Name2-deoxyadenosine
CAS Registry Number958-09-8
SMILES
NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC=N1
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 KeyOLXZPDWKRNYJJZ-RRKCRQDMSA-N
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
Ontology
Disposition

Source:

Biological location:

Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP-0.55HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
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
Predicted GC-MSDeoxyadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDeoxyadenosine, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udr-1790000000-c0d4c0cc085cab7c2dcf2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-e2abd19062db64ff67be2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000i-2900000000-1b8d5c847c2b1955056e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000i-5900000000-845c20e0f6bd5494b6dc2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004r-8900000000-484d9f08e4e28fab1f702012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-e852451e7253e0de72be2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0390000000-fba17d1430b371138db22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-000i-0930000000-931c7b084c33f9122af42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0900000000-66ae7ac8bd510a1734022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0900000000-c71d67857e2136dc76662017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-1790000000-cfbdf2e3950e7987b94b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-a3c367588a28d36cf5f02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-1b8d5c847c2b1955056e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-5900000000-f950493ce420caae6a662017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004r-8900000000-61ed5b4b3e748a4498032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-0900000000-31d03c242f14d91a718c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0390000000-fba17d1430b371138db22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0930000000-931c7b084c33f9122af42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-81ac782a59b2ca52f52b2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0920000000-2e897a458cf4c7af381c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f52b5322fde2e37229032016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-fcb0a5032b8607fd8b112016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-bec96a9658c683fa0d9b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0910000000-b504aa725d20d6213b202016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-d09551db93d558a5aed72016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Adenosine deaminaseADA20q13.12P00813 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Purine nucleoside phosphorylasePNP14q13.1P00491 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
5'-nucleotidaseNT5E6q14-q21P21589 details
Cytosolic 5'-nucleotidase 1BNT5C1B2p24.2Q96P26 details
Cytosolic 5'-nucleotidase 1ANT5C1A1p34.3-p33Q9BXI3 details
5'(3')-deoxyribonucleotidase, cytosolic typeNT5CQ8TCD5 details
5'(3')-deoxyribonucleotidase, mitochondrialNT5MQ9NPB1 details
Adenosine deaminaseADA20q13.12P00813 details
Cytosolic 5'-nucleotidase 3NT5C37p14.3Q9H0P0 details
Cytosolic purine 5'-nucleotidaseNT5C210q24.32P49902 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Adenosine deaminaseADA20q13.12P00813 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000101
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021894
KNApSAcK IDC00019281
Chemspider ID13135
KEGG Compound IDC00559
BioCyc IDDEOXYADENOSINE
BiGG ID35352
Wikipedia LinkDeoxyadenosine
METLIN ID3382
PubChem Compound13730
PDB IDNot Available
ChEBI ID17256
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:
NT5E
Uniprot ID:
P21589
Molecular weight:
57948.125
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:
NT5C1B
Uniprot ID:
Q96P26
Molecular weight:
68803.055
General function:
Involved in nucleotide binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:
NT5C1A
Uniprot ID:
Q9BXI3
Molecular weight:
41020.145
General function:
Involved in metal ion binding
Specific function:
Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:
NT5C
Uniprot ID:
Q8TCD5
Molecular weight:
Not Available
General function:
Involved in phosphatase activity
Specific function:
Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:
NT5M
Uniprot ID:
Q9NPB1
Molecular weight:
Not Available
General function:
Involved in deaminase activity
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
Gene Name:
ADA
Uniprot ID:
P00813
Molecular weight:
40764.13
General function:
Involved in magnesium ion binding
Specific function:
Can act both as nucleotidase and as phosphotransferase.
Gene Name:
NT5C3
Uniprot ID:
Q9H0P0
Molecular weight:
33914.91
General function:
Involved in 5'-nucleotidase activity
Specific function:
May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:
NT5C2
Uniprot ID:
P49902
Molecular weight:
64969.2
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Molecular weight:
32117.69

Only showing the first 10 proteins. There are 18 proteins in total.