Common NameD-xylulose 5-phosphate
DescriptionXylulose 5-phosphate (Xu-5-P) is a metabolite of the hexose monophosphate pathway that activates protein phosphatase 2A to mediate the acute effects of carbohydrate feeding on the glycolytic pathway, as well as the coordinate long-term control of the enzymes required for fatty acid and triglyceride synthesis. Xu-5-P is the signal for the coordinated control of lipogenesis. Feeding carbohydrate causes levels of liver glucose, Glucose-6-phosphate (Glc-6-P), and Fructose-6-phosphate (Fru-6-P) to rise. Elevation of Fru-6-P leads to elevation of Xu-5-P in reactions catalyzed by the near-equilibrium isomerases of the nonoxidative portion of the hexose monophosphate pathway (ribulose 5-phosphate (Ru5P) epimerase [EC 5.1.3.1], ribose 5-phosphate (Rib5P) isomerase [EC 5.3.1.6], transaldolase [EC 2.2.1.2], and transketolase [EC 2.2.1.1]). The elevation of Xu-5-P is the coordinating signal that both acutely activates phosphofructokinase [PFK; EC 2.7.1.11] in glycolysis and promotes the action of the transcription factor carbohydrate responsive element binding protein (ChREBP) to increase transcription of the genes for the enzymes of lipogenesis, the hexose monophosphate shunt, and glycolysis, all of which are required for the de novo synthesis of fat. (PMID 12721358 ).
Structure
Molecular FormulaC5H11O8P
Average Mass230.10980
Monoisotopic Mass230.01915
IUPAC Name{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
Traditional Name[(2r,3s)-2,3,5-trihydroxy-4-oxopentyl]oxyphosphonic acid
CAS Registry Number4212-65-1
SMILESO=C(CO)[C@@H](O)[C@H](O)COP(=O)([O-])[O-]
InChI IdentifierInChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1
InChI KeyFNZLKVNUWIIPSJ-RFZPGFLSSA-N
CHEBI IDCHEBI:57737
HMDB IDHMDB0000868
Pathways
NameSMPDB/PathBank
pentose phosphate pathway
Glucose-6-phosphate dehydrogenase deficiency
Ribose-5-phosphate isomerase deficiency
Transaldolase deficiency
Warburg Effect
StateSolid
Water Solubility2.61e+01 g/l
logP-1.81
logS-0.95
pKa (Strongest Acidic)1.48
pKa (Strongest Basic)-3.33
Hydrogen Acceptor Count7
Hydrogen Donor Count5
Polar Surface Area144.52 Ų
Rotatable Bond Count6
Physiological Charge-2
Formal Charge0
Refractivity42.47 m³·mol⁻¹
Polarizability18.08

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