Showing Metabocard for 2'-deoxyinosine (BASm0001649)

Common Name2'-deoxyinosine
DescriptionDeoxyinosine is a nucleoside that is formed when hypoxanthine is attached to a deoxyribose ring (also known as a ribofuranose) via a beta-N9-glycosidic bond. Deoxyinosine is found in DNA while inosine is found in RNA. Inosine is a nucleic acid important for RNA editing. Adenosine deaminase (ADA) catalyzes the conversion of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively. ADA-deficient individuals suffer from severe combined immunodeficiency (SCID) and are unable to produce significant numbers of mature T or B lymphocytes. This occurs as a consequence of the accumulation of ADA substrates or their metabolites. Inosine is also an intermediate in a chain of purine nucleotides reactions required for muscle movements. Moreover, deoxyinosine is found to be associated with purine nucleoside phosphorylase (PNP) deficiency, which is an inborn error of metabolism.
Structure
Molecular FormulaC10H12N4O4
Average Mass252.23000
Monoisotopic Mass252.08585
IUPAC Name9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-ol
Traditional Name9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-ol
CAS Registry Number890-38-0
SMILESO=c1[nH]cnc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1
InChI IdentifierInChI=1S/C10H12N4O4/c15-2-6-5(16)1-7(18-6)14-4-13-8-9(14)11-3-12-10(8)17/h3-7,15-16H,1-2H2,(H,11,12,17)/t5-,6+,7+/m0/s1
InChI KeyVGONTNSXDCQUGY-RRKCRQDMSA-N
CHEBI IDCHEBI:28997
HMDB IDHMDB0000071
Pathways
NameSMPDB/PathBank
Purine metabolism
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway
Xanthinuria type I
Xanthinuria type II
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
StateNot Available
Water Solubility1.87e+01 g/l
logP-1.62
logS-1.13
pKa (Strongest Acidic)11.68
pKa (Strongest Basic)0.08
Hydrogen Acceptor Count7
Hydrogen Donor Count3
Polar Surface Area113.52 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity58.97 m³·mol⁻¹
Polarizability23.69

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