Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:43:01 UTC
Update Date2022-08-31 17:18:48 UTC
Metabolite IDMMDBc0029819
Metabolite Identification
Common NameXylulose 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 carbohydrates to cells causes levels of 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 will 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
Synonyms
ValueSource
5-O-Phosphono-D-threo-pentos-2-uloseChEBI
5-O-Phosphono-D-xyluloseChEBI
D-Xylulose-5-phosphateChEBI
D-Xylulose-5-phosphoric acidGenerator
Xylulose 5-phosphoric acidGenerator
D-Xylulose 5-phosphateHMDB
D-Xylulose 5-PO4HMDB
D-Xylulose-5-PHMDB
Xu-5-PHMDB
Xylulose-PHMDB
Xylulose-phosphateHMDB
Xylulose-5-phosphateMeSH, HMDB
Xylulose-5-phosphate, (D)-isomerMeSH, HMDB
Xylulose 5-phosphateHMDB
keto-D-Xylulose 5-phosphateHMDB
Molecular FormulaC5H11O8P
Average Mass230.1098
Monoisotopic Mass230.01915384
IUPAC Name{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
Traditional Nameribulose-5-phosphate
CAS Registry Number4212-65-1
SMILES
OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O
InChI Identifier
InChI=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