Showing Metabocard for D-ribose 5-phosphate (BASm0006472)

Common NameD-ribose 5-phosphate
DescriptionD-Ribose 5-phosphate (CAS: 4300-28-1), also known as R-5-P, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-Ribose 5-phosphate exists in all living species, ranging from bacteria to humans. Within humans, D-ribose 5-phosphate participates in a number of enzymatic reactions. In particular, D-ribose 5-phosphate can be biosynthesized from D-ribulose 5-phosphate; which is mediated by the enzyme ribose-5-phosphate isomerase. In addition, D-ribose 5-phosphate can be biosynthesized from D-ribose; which is catalyzed by the enzyme ribokinase. Outside of the human body, D-ribose 5-phosphate has been detected, but not quantified in cow milk and rices. D-Ribose 5-phosphate is both a product and an intermediate of the pentose phosphate pathway. The last step of the oxidative reactions in the pentose phosphate pathway is the production of ribulose 5-phosphate. D-Ribose 5-phosphate is an important intermediate metabolite in the pentose phosphate pathway and in the purine metabolism pathway. The intracellular ribose 5-phosphate concentration is an important determinant of the rate of de novo purine synthesis (PMID:6699001 ).
Structure
Molecular FormulaC5H11O8P
Average Mass230.10980
Monoisotopic Mass230.01915
IUPAC Name{[(2R,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r)-3,4,5-trihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number34980-65-9
SMILESO=P([O-])([O-])OC[C@H]1OC(O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C5H11O8P/c6-3-2(1-12-14(9,10)11)13-5(8)4(3)7/h2-8H,1H2,(H2,9,10,11)/t2-,3-,4-,5+/m1/s1
InChI KeyKTVPXOYAKDPRHY-AIHAYLRMSA-N
CHEBI IDCHEBI:78346
HMDB IDHMDB0001548
Pathways
NameSMPDB/PathBank
Purine metabolism
pentose phosphate pathway
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
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Adenine phosphoribosyltransferase deficiency (APRT)
Mitochondrial DNA depletion syndrome
Myoadenylate deaminase deficiency
Warburg Effect
StateSolid
Water Solubility3.36e+01 g/l
logP-2.07
logS-0.84
pKa (Strongest Acidic)1.22
pKa (Strongest Basic)-3.68
Hydrogen Acceptor Count7
Hydrogen Donor Count5
Polar Surface Area136.68 Ų
Rotatable Bond Count3
Physiological Charge-2
Formal Charge0
Refractivity40.83 m³·mol⁻¹
Polarizability18.35

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