Human Metabolome Database Version 3.5

Showing metabocard for Xylulose 5-phosphate (HMDB00868)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:29:26 -0600
HMDB ID HMDB00868
Secondary Accession Numbers
  • HMDB06212
Metabolite Identification
Common Name Xylulose 5-phosphate
Description Xylulose 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. D-Xylulose 5-phosphate
  2. D-Xylulose 5-PO4
  3. D-Xylulose-5-P
  4. D-Xylulose-5-phosphate
  5. Xu-5-P
  6. Xylulose 5-phosphate
  7. Xylulose-P
  8. Xylulose-phosphate
Chemical Formula C5H11O8P
Average Molecular Weight 230.1098
Monoisotopic Molecular Weight 230.01915384
IUPAC Name {[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
Traditional IUPAC Name [(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxyphosphonic acid
CAS Registry Number 4212-65-1
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 Key FNZLKVNUWIIPSJ-RFZPGFLSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Pentoses
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monosaccharide Phosphates
  • ribulose 5-phosphate(ChEBI)
Substituents
  • 1,2 Diol
  • Acyloin
  • Alpha Ketoaldehyde
  • Beta Ketoaldehyde
  • Ketone
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Pentoses
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 26.1 g/L ALOGPS
LogP -1.81 ALOGPS
LogP -2.8 ChemAxon
LogS -0.95 ALOGPS
pKa (strongest acidic) 1.48 ChemAxon
pKa (strongest basic) -3.3 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 144.52 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 42.47 ChemAxon
Polarizability 18.08 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Cellular Cytoplasm
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pentose Phosphate Pathway SMP00031 map00030 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cellular Cytoplasm Detected and Quantified
0.43 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022290
KNApSAcK ID Not Available
Chemspider ID 388330 Link_out
KEGG Compound ID C00231 Link_out
BioCyc ID XYLULOSE-5-PHOSPHATE Link_out
BiGG ID 34329 Link_out
Wikipedia Link Xylulose 5-phosphate Link_out
NuGOwiki Link HMDB00868 Link_out
Metagene Link HMDB00868 Link_out
METLIN ID 5829 Link_out
PubChem Compound 439190 Link_out
PDB ID 5SP Link_out
ChEBI ID 16332 Link_out
References
Synthesis Reference Shaeri, Jobin; Wohlgemuth, Roland; Woodley, John M. Semiquantitative Process Screening for the Biocatalytic Synthesis of D-Xylulose-5-phosphate. Organic Process Research & Development (2006), 10(3), 605-610.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Sanchez B, Champomier-Verges MC, Anglade P, Baraige F, de Los Reyes-Gavilan CG, Margolles A, Zagorec M: Proteomic analysis of global changes in protein expression during bile salt exposure of Bifidobacterium longum NCIMB 8809. J Bacteriol. 2005 Aug;187(16):5799-808. Pubmed: 16077128 Link_out
  2. Williams DG: Effect of added xylulose-5-phosphate on the assay of erythrocyte transketolase. Clin Chem. 1977 Jul;23(7):1368. Pubmed: 872397 Link_out
  3. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454 Link_out
  4. Himmo SD, Thomson M, Gubler CJ: Isolation of transketolase from human erythrocytes. Prep Biochem. 1988;18(3):261-76. Pubmed: 3237644 Link_out
  5. Veech RL: A humble hexose monophosphate pathway metabolite regulates short- and long-term control of lipogenesis. Proc Natl Acad Sci U S A. 2003 May 13;100(10):5578-80. Epub 2003 Apr 29. Pubmed: 12721358 Link_out

Enzymes
Name: Transketolase-like protein 1
Reactions:
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Ribose 5-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Ribose 5-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Gene Name: TKTL1
Uniprot ID: P51854 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase
Reactions:
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Ribose 5-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Ribose 5-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Gene Name: TKT
Uniprot ID: P29401 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Xylulose kinase
Reactions:
Adenosine triphosphate + D-Xylulose unknown ADP + Xylulose 5-phosphate details
Gene Name: XYLB
Uniprot ID: O75191 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative uncharacterized protein RPE
Reactions: Not Available
Gene Name: RPE
Uniprot ID: Q53TV9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ribulose-phosphate 3-epimerase
Reactions:
D-Ribulose 5-phosphate unknown Xylulose 5-phosphate details
Gene Name: RPE
Uniprot ID: Q96AT9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Transketolase-like protein 2
Reactions:
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Ribose 5-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Ribose 5-phosphate + Xylulose 5-phosphate details
Beta-D-Fructose 6-phosphate + D-Glyceraldehyde 3-phosphate unknown D-Erythrose 4-phosphate + Xylulose 5-phosphate details
Gene Name: TKTL2
Uniprot ID: Q9H0I9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA