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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 15:00:32 UTC
Update Date2021-09-14 15:44:43 UTC
HMDB IDHMDB0006534
Secondary Accession Numbers
  • HMDB06534
Metabolite Identification
Common NameD-Xylulose 1-phosphate
DescriptionD-Xylulose 1-phosphate is produced in the hepatocytes and is the product of fructokinase (ketohexokinase, EC 2.7.1.3) phosphorylation of D-xylulose. The cleavage of D-xylulose-1-phosphate glycolaldehyde by aldolase (fructose-bisphosphate aldolase, EC 4.1.2.13) produces glycolaldehyde which is an oxalate precursor. The distribution of both enzymes in human tissues indicates that this reaction sequence occurs mainly in the liver, to a lesser extent in the kidney, and very little in heart, brain and muscle. The kinetic properties of fructokinase show that this enzyme can phosphorylate D-xylulose as readily as D-fructose (PMID: 6458298 , 13898172 , 6284103 , 2996495 ).
Structure
Data?1586456045
Synonyms
ValueSource
D-Xylulose 1-phosphoric acidGenerator
L-Threo-pentulose 1-phosphateHMDB
Xylulose-1-phosphateHMDB
D-Xylulose-1-phosphateHMDB
D-Xylulose 1-phosphateHMDB
Chemical FormulaC5H11O8P
Average Molecular Weight230.109
Monoisotopic Molecular Weight230.019154312
IUPAC Name{[(3S,4R)-3,4,5-trihydroxy-2-oxopentyl]oxy}phosphonic acid
Traditional Name[(3S,4R)-3,4,5-trihydroxy-2-oxopentyl]oxyphosphonic acid
CAS Registry Number63323-91-1
SMILES
OC[C@@H](O)[C@H](O)C(=O)COP(O)(O)=O
InChI Identifier
InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h3,5-7,9H,1-2H2,(H2,10,11,12)/t3-,5+/m1/s1
InChI KeyNBOCCPQHBPGYCX-WUJLRWPWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Beta-hydroxy ketone
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023963
KNApSAcK IDNot Available
Chemspider ID133112
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151020
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDXU1P_D
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceGhalambor, Mohammad Ali; Heath, Edward C. Metabolism of L-fucose. II. The enzymic cleavage of 1-fuculose 1-phosphate. Journal of Biological Chemistry (1962), 237 2427-33.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barngrover DA, Stevens HC, Dills WL Jr: D-Xylulose-1-phosphate: enzymatic assay and production in isolated rat hepatocytes. Biochem Biophys Res Commun. 1981 Sep 16;102(1):75-80. [PubMed:6458298 ]
  2. GHALAMBOR MA, HEATH EC: The metabolism of L-fucose. II. The enzymatic cleavage of L-fuculose 1-phosphate. J Biol Chem. 1962 Aug;237:2427-33. [PubMed:13898172 ]
  3. James HM, Bais R, Edwards JB, Rofe AM, Conyers AJ: Models for the metabolic production of oxalate from xylitol in humans: a role for fructokinase and aldolase. Aust J Exp Biol Med Sci. 1982 Feb;60(Pt 1):117-22. [PubMed:6284103 ]
  4. Bais R, James HM, Rofe AM, Conyers RA: The purification and properties of human liver ketohexokinase. A role for ketohexokinase and fructose-bisphosphate aldolase in the metabolic production of oxalate from xylitol. Biochem J. 1985 Aug 15;230(1):53-60. [PubMed:2996495 ]

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
KHK
Uniprot ID:
P50053
Molecular weight:
32730.055