Showing metabocard for Deoxyadenosine (BMDB0000101)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:19:38 UTC
Update Date2020-05-21 16:28:54 UTC
BMDB IDBMDB0000101
Secondary Accession Numbers
  • BMDB00101
Metabolite 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 exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Deoxyadenosine exists in all living species, ranging from bacteria to humans. Deoxyadenosine is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight251.2419
Monoisotopic Molecular Weight251.101839307
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
  • Nucleus
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
  • Nucleus
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000101
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021894
KNApSAcK IDC00019281
Chemspider ID13135
KEGG Compound IDC00559
BioCyc IDDEOXYADENOSINE
BiGG ID35352
Wikipedia LinkDeoxyadenosine
METLIN ID3382
PubChem Compound13730
PDB IDNot Available
ChEBI ID17256
References
Synthesis ReferenceAnderson, Charles D.; Goodman, Leon; Baker, B. R. Potential anticancer agents. XIX. Synthesis of 2-deoxyadenosine. Journal of the American Chemical Society (1959), 81 3967-74.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  2. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]

Enzymes

Enzyme Details
1. Cytosolic purine 5'-nucleotidase
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:
O46411
Molecular weight:
64841.0
Reactions
Deoxyadenosine monophosphate + Water → Deoxyadenosine + Hydrogen phosphatedetails
Enzyme Details
2. Purine nucleoside phosphorylase
General function:
Nucleotide transport and metabolism
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:
P55859
Molecular weight:
32037.0
Reactions
Deoxyadenosine + Hydrogen phosphate → Adenine + Deoxyribose 1-phosphatedetails
Enzyme Details
3. Adenosine deaminase
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine (By similarity). Plays an important role in purine metabolism and in adenosine homeostasis (By similarity). Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events (By similarity). Acts as a positive regulator of T-cell coactivation, by binding DPP4 (By similarity). Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion (By similarity). Enhances dendritic cell immunogenicity by affecting dendritic cell costimulatory molecule expression and cytokines and chemokines secretion (PubMed:23240012). Enhances CD4+ T-cell differentiation and proliferation (By similarity). Acts as a positive modulator of adenosine receptors ADORA1 and ADORA2A, by enhancing their ligand affinity via conformational change (By similarity). Stimulates plasminogen activation (By similarity). Plays a role in male fertility (By similarity). Plays a protective role in early postimplantation embryonic development (By similarity).
Gene Name:
ADA
Uniprot ID:
P56658
Molecular weight:
40919.0
Reactions
Deoxyadenosine + Water → Deoxyinosine + Ammoniadetails