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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-17 17:19:54 UTC
HMDB IDHMDB0000868
Secondary Accession Numbers
  • HMDB0006212
  • HMDB00868
  • HMDB06212
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 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
Data?1592414394
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-phosphateHMDB
Xylulose-5-phosphate, (D)-isomerHMDB
Xylulose 5-phosphateHMDB
keto-D-Xylulose 5-phosphateHMDB
Chemical FormulaC5H11O8P
Average Molecular Weight230.1098
Monoisotopic Molecular Weight230.01915384
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
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility26.1 g/LALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity42.47 m³·mol⁻¹ChemAxon
Polarizability18.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0592-9800000000-d336b0e2eff1402939d8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-9023200000-1dd7d8e1f64921beb234Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, negativesplash10-004j-9170000000-997b74cb48ace33cccd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, negativesplash10-004j-9000000000-6bc02f4fe0074c9abd68Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, negativesplash10-004j-9000000000-bdadc167eb24a88aac33Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, negativesplash10-004j-9000000000-93d31d83892e88720b87Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, negativesplash10-004i-9000000000-10cd88e85162e6269751Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, negativesplash10-004i-9000000000-e9f2bf02f0d01a879d20Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, negativesplash10-004i-9000000000-732cd41f406b617c64a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, negativesplash10-004i-9000000000-25a5607c50f3e9bb5a14Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, negativesplash10-004i-9000000000-ea506b9429ed926c5f93Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, negativesplash10-0002-9120000000-1172898b831a36b0afcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 25V, negativesplash10-0002-9110000000-132340cd62e8e4a0ccd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 27V, negativesplash10-0002-9110000000-297d4c6907686258e552Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, negativesplash10-0002-9100000000-1cce49f995c912b1cc94Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 33V, negativesplash10-0002-9100000000-8bba2d7511cc9829eb36Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, negativesplash10-0002-9100000000-89b3b4fdcb0326bfa0e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, negativesplash10-0002-9100000000-91e850ff1cd255a2f7fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 45V, negativesplash10-002b-9100000000-9c43f84a30add3ebce50Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, negativesplash10-0002-9000000000-75847d481a06c31fa479Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 16V, negativesplash10-004i-0091000000-0af17cfb2eb7eab94967Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-3790000000-6f5913e9948fa7667e41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btd-9710000000-3724bb9f611bbdc1fe11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-8bc9cecb2dddad8ca5e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9520000000-c36fdbcc1d3b19b2fafdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-b67b8ea484aa4ddb40e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-82b17cf4f5a8c927fe64Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Cellular Cytoplasm
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cellular CytoplasmDetected and Quantified0.43 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04034
Phenol Explorer Compound IDNot Available
FooDB IDFDB030802
KNApSAcK IDC00019693
Chemspider ID388330
KEGG Compound IDC00231
BioCyc IDXYLULOSE-5-PHOSPHATE
BiGG ID34329
Wikipedia LinkXylulose 5-phosphate
METLIN ID5829
PubChem Compound439190
PDB IDNot Available
ChEBI ID16332
Food Biomarker OntologyNot Available
VMH IDXU5P_D
MarkerDB ID
References
Synthesis ReferenceShaeri, 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 ]
  2. Williams DG: Effect of added xylulose-5-phosphate on the assay of erythrocyte transketolase. Clin Chem. 1977 Jul;23(7):1368. [PubMed:872397 ]
  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;2:18. [PubMed:15882454 ]
  4. Himmo SD, Thomson M, Gubler CJ: Isolation of transketolase from human erythrocytes. Prep Biochem. 1988;18(3):261-76. [PubMed:3237644 ]
  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 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate (By similarity).
Gene Name:
TKTL1
Uniprot ID:
P51854
Molecular weight:
59302.195
Reactions
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
P29401
Molecular weight:
67876.95
Reactions
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Not Available
Gene Name:
XYLB
Uniprot ID:
O75191
Molecular weight:
58381.695
Reactions
Adenosine triphosphate + D-Xylulose → ADP + Xylulose 5-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
RPE
Uniprot ID:
Q53TV9
Molecular weight:
19537.4
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reversible epimerization of D-ribulose 5-phosphate to D-xylulose 5-phosphate.
Gene Name:
RPE
Uniprot ID:
Q96AT9
Molecular weight:
19537.385
Reactions
D-Ribulose 5-phosphate → Xylulose 5-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Plays an essential role in total transketolase activity and cell proliferation in cancer cells; after transfection with anti-TKTL1 siRNA, total transketolase activity dramatically decreases and proliferation was significantly inhibited in cancer cells. Plays a pivotal role in carcinogenesis.
Gene Name:
TKTL2
Uniprot ID:
Q9H0I9
Molecular weight:
67876.625
Reactions
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails
D-Sedoheptulose 7-phosphate + Glyceraldehyde 3-phosphate → D-Ribose 5-phosphate + Xylulose 5-phosphatedetails
Beta-D-Fructose 6-phosphate + Glyceraldehyde 3-phosphate → D-Erythrose 4-phosphate + Xylulose 5-phosphatedetails