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Record Information
Version4.0
Creation Date2005-11-20 22:13:13 UTC
Update Date2017-10-03 20:09:19 UTC
HMDB IDHMDB0001644
Secondary Accession Numbers
  • HMDB00654
  • HMDB01644
Metabolite Identification
Common NameD-Xylulose
DescriptionD-xylulose is a monosaccharide containing five carbon atoms. D-xylulose is converted from xylitol by the enzyme NAD+-linked xylitol dehydrogenase (EC 1.1.1.9) in the glucuronate pathway, the most important xylitol-handling metabolic pathway in mammals. This activity has been described in human erythrocytes. Most likely, D-xylulose (as well as D-arabinose or D-ribulose) is a precursor of the pentiol D-arabitol, since pentitols are derived from their corresponding pentose phosphate precursors via pentoses. This pathway can play a role in inherited metabolic disorders underlying the accumulation of pentitols e.g., ribose 5-phosphate isomerase deficiency and transaldolase deficiency. Although pentitols are present in all living organisms, knowledge concerning their metabolism is limited. (PMID: 15234337 , Mol Genet Metab. 2004 Jul;82(3):231-7.).
Structure
Thumb
Synonyms
ValueSource
D-LyxuloseChEBI
D-threo-PentuloseChEBI
D-XulChEBI
Chemical FormulaC5H10O5
Average Molecular Weight150.1299
Monoisotopic Molecular Weight150.05282343
IUPAC Name(3S,4R)-1,3,4,5-tetrahydroxypentan-2-one
Traditional NameD-xylulose
CAS Registry Number551-84-8
SMILES
OC[C@@H](O)[C@H](O)C(=O)CO
InChI Identifier
InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5+/m1/s1
InChI KeyZAQJHHRNXZUBTE-WUJLRWPWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

    Cell:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point15 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility678 g/LALOGPS
logP-2.2ALOGPS
logP-2.6ChemAxon
logS0.65ALOGPS
pKa (Strongest Acidic)10.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.6 m³·mol⁻¹ChemAxon
Polarizability13.53 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0930000000-c3a525ee2ad524114f0dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9100000000-1304cf35b8860cd7a456View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positivesplash10-00g3-9127300000-b6aed5448276d0184bc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014r-4900000000-0a4d51584b79dc230edbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-2131da3ca52caffed55fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-305f431957b24a5b888aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-3e1ebc07944b3d190ec8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-9be7fcf2c9ec6f8829c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-931753afec5aa068bca8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-1c39b6f316e1745d355cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-9100000000-095c1d8c10895109ecb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-5ea417513158cb617f30View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.5 (0.0-5.0) uMAdolescent (13-18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0 - 5.0 uMAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified19.7 (6.4-32.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0 - 5.0 umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.5 (5.0-10.0) uMAdolescent (13-18 years old)BothRibose-5-phosphate isomerase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified88 - 166 uMAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
UrineDetected and Quantified1096.00 (438.00-1753.7) umol/mmol creatinineChildren (1-13 years old)BothPentosuria details
UrineDetected and Quantified39 - 52 umol/mmol creatinineAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  1. Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [PubMed:14988808 ]
Pentosuria
    MetaGene
Associated OMIM IDs
DrugBank IDDB03947
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022698
KNApSAcK IDNot Available
Chemspider ID4451524
KEGG Compound IDC00310
BioCyc IDD-XYLULOSE
BiGG ID34575
Wikipedia LinkXylulose
METLIN ID6333
PubChem Compound5289590
PDB IDXUL
ChEBI ID17140
References
Synthesis ReferenceTakeuchi, Sonoko; Tonouchi, Naoto; Yokozeki, Kenzo. Production of xylitol or D-xylulose by fermentation of glucose with Gluconobacter, Acetobacter, and Frateuria. Eur. Pat. Appl. (2000), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Huck JH, Roos B, Jakobs C, van der Knaap MS, Verhoeven NM: Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism. Mol Genet Metab. 2004 Jul;82(3):231-7. [PubMed:15234337 ]

Enzymes

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