Showing Metabocard for alpha-D-ribose 1-phosphate (BASm0002911)

Common NameAlpha-d-ribose 1-phosphate
DescriptionRibose 1-phosphate is an intermediate in the metabolism of Pyrimidine and the metabolism of Nicotinate and nicotinamide. It is a substrate for Uridine phosphorylase 2, Phosphoglucomutase, Purine nucleoside phosphorylase and Uridine phosphorylase 1. Ribose 1-phosphate can be formed from guanosine through the action of purine nucleoside phosphorylase. Ribose 1-phosphate can also act as a ribose donor in the synthesis of xanthosine as catalyzed by the same enzyme (purine nucleoside phosphorylase). The presence of guanase, which irreversibly converts guanine to xanthine, affects the overall process of guanosine transformation. As a result of this purine pathway, guanosine is converted into xanthosine, thus overcoming the lack of guanosine deaminase in mammals. The activated ribose moiety in Ribose 1-phosphate which stems from the catabolism of purine nucleosides can be transferred to uracil and, in the presence of ATP, used for the synthesis of pyrimidine nucleotides; therefore, purine nucleosides can act as ribose donors for the salvage of pyrimidine bases. (PMID: 9133638 ).
Structure
Molecular FormulaC5H11O8P
Average Mass230.10980
Monoisotopic Mass230.01915
IUPAC Name{[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}phosphonic acid
Traditional Name[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxyphosphonic acid
CAS Registry Number14075-00-4
SMILESO=P([O-])([O-])O[C@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI IdentifierInChI=1S/C5H11O8P/c6-1-2-3(7)4(8)5(12-2)13-14(9,10)11/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5-/m1/s1
InChI KeyYXJDFQJKERBOBM-TXICZTDVSA-N
CHEBI IDCHEBI:57720
HMDB IDHMDB0001489
Pathways
NameSMPDB/PathBank
pentose phosphate pathway
Purine metabolism
Pyrimidine metabolism
Nicotinate and nicotinamide metabolism
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
AICA-Ribosiduria
Beta Ureidopropionase Deficiency
Dihydropyrimidinase Deficiency
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)
Molybdenum Cofactor Deficiency
Purine Nucleoside Phosphorylase Deficiency
UMP Synthase Deficiency (Orotic Aciduria)
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
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
StateSolid
Water Solubility3.52e+01 g/l
logP-2.04
logS-0.82
pKa (Strongest Acidic)1.16
pKa (Strongest Basic)-2.98
Hydrogen Acceptor Count7
Hydrogen Donor Count5
Polar Surface Area136.68 Ų
Rotatable Bond Count3
Physiological Charge-2
Formal Charge0
Refractivity40.83 m³·mol⁻¹
Polarizability18.27

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