Showing Metabocard for 5-phospho-alpha-D-ribose 1-diphosphate (BASm0003137)

Common Name5-phospho-alpha-d-ribose 1-diphosphate
DescriptionPhosphoribosyl pyrophosphate, also known as PRPP or PRib-PP, 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. Phosphoribosyl pyrophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Phosphoribosyl pyrophosphate exists in all living species, ranging from bacteria to humans. Within humans, phosphoribosyl pyrophosphate participates in a number of enzymatic reactions. In particular, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate through its interaction with the enzyme adenine phosphoribosyltransferase. In addition, guanine and phosphoribosyl pyrophosphate can be biosynthesized from guanosine monophosphate; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, phosphoribosyl pyrophosphate is involved in adenosine deaminase deficiency. Phosphoribosyl pyrophosphate is a pentosephosphate and it is the key substance in the biosynthesis of histidine, tryptophan, and purine and pyrimidine nucleotides. It is formed from ribose 5-phosphate by the enzyme ribose-phosphate diphosphokinase. It plays a role in transferring phosphate groups in several reactions.
Structure
Molecular FormulaC5H13O14P3
Average Mass390.06960
Monoisotopic Mass389.95181
IUPAC Name{[(2R,3S,4R,5R)-3,4-dihydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2r,3s,4r,5r)-3,4-dihydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number7540-64-9
SMILESO=P([O-])([O-])OC[C@H]1O[C@H](OP(=O)([O-])OP(=O)([O-])[O-])[C@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C5H13O14P3/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13)/t2-,3-,4-,5-/m1/s1
InChI KeyPQGCEDQWHSBAJP-TXICZTDVSA-N
CHEBI IDCHEBI:58017
HMDB IDHMDB0000280
Pathways
NameSMPDB/PathBank
Pyrimidine metabolism
Purine metabolism
pentose phosphate pathway
Nicotinate and nicotinamide metabolism
Glutamate Metabolism
2-Hydroxyglutric Aciduria (D And L Form)
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)
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
Lesch-Nyhan Syndrome (LNS)
Gout or Kelley-Seegmiller Syndrome
Homocarnosinosis
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
Succinic semialdehyde dehydrogenase deficiency
Mercaptopurine Metabolism Pathway
Thioguanine Metabolism Pathway
StateSolid
Water Solubility1.16e+01 g/l
logP-0.74
logS-1.53
pKa (Strongest Acidic)1.09
pKa (Strongest Basic)-3.68
Hydrogen Acceptor Count11
Hydrogen Donor Count7
Polar Surface Area229.74 Ų
Rotatable Bond Count7
Physiological Charge-4
Formal Charge0
Refractivity62.58 m³·mol⁻¹
Polarizability27.11

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