Showing metabocard for Deoxyguanosine (BMDB0000085)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:19:27 UTC
Update Date2020-05-21 16:28:52 UTC
BMDB IDBMDB0000085
Secondary Accession Numbers
  • BMDB00085
Metabolite Identification
Common NameDeoxyguanosine
DescriptionDeoxyguanosine, also known as dG, 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. Deoxyguanosine is an extremely weak basic (essentially neutral) compound (based on its pKa). Deoxyguanosine exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-9H-purin-6-olChEBI
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-guanineChEBI
dGChEBI
Guanine deoxy nucleosideChEBI
2'-DeoxyguanosineKegg
2-Amino-9-(2-deoxy-9-b-D-ribofuranosyl)-9H-purin-6-olGenerator
2-Amino-9-(2-deoxy-9-β-D-ribofuranosyl)-9H-purin-6-olGenerator
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-guanineGenerator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanineGenerator
2'-Deoxy-guanosineHMDB
2-DeoxyguanosineHMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanineHMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-guanineHMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanineHMDB
DesoxyguanosineHMDB
Guanine deoxyribosideHMDB
DeoxyguanosineChEBI
Chemical FormulaC10H13N5O4
Average Molecular Weight267.2413
Monoisotopic Molecular Weight267.096753929
IUPAC Name2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
Traditional Name2-deoxyguanosine
CAS Registry Number961-07-9
SMILES
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1
InChI Identifier
InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1
InChI KeyYKBGVTZYEHREMT-KVQBGUIXSA-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-oxopurine
  • Hypoxanthine
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.3BALZARINI,JM ET AL. (1989)
Predicted Properties
PropertyValueSource
logP-1.8ALOGPS
logP-1.8ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)10.16ChemAxon
pKa (Strongest Basic)0.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.11 m³·mol⁻¹ChemAxon
Polarizability25.24 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
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000085
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012064
KNApSAcK IDNot Available
Chemspider ID163230
KEGG Compound IDC00330
BioCyc IDDEOXYGUANOSINE
BiGG ID34637
Wikipedia LinkDeoxyguanosine
METLIN ID3395
PubChem Compound187790
PDB IDNot Available
ChEBI ID17172
References
Synthesis ReferenceNoguchi, Toshitada; Hamamoto, Tomoki; Okuyama, Kiyoshi; Shibuya, Susumu. Process for producing 2'-deoxyguanosine. PCT Int. Appl. (2003), 31 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + 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
Deoxyguanosine + Hydrogen phosphate → Guanine + Deoxyribose 1-phosphatedetails
Enzyme Details
3. Deoxycytidine kinase
General function:
Nucleotide transport and metabolism
Specific function:
Phosphorylates the deoxyribonucleosides deoxycytidine, deoxyguanosine and deoxyadenosine.
Gene Name:
DCK
Uniprot ID:
Q3MHR2
Molecular weight:
30329.0
Reactions
Adenosine triphosphate + Deoxyguanosine → ADP + 2'-Deoxyguanosine 5'-monophosphatedetails