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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-06-15 17:04:51 UTC |
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HMDB ID | HMDB0000751 |
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Secondary Accession Numbers | - HMDB0002245
- HMDB00751
- HMDB02245
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Metabolite Identification |
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Common Name | L-Xylulose |
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Description | L-Xylulose, also known as L-lyxulose or L-threo-pentulose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Xylulose is a ketopentose, a monosaccharide containing five carbon atoms, and including a ketone functional group. L-Xylulose accumulates in the urine in patients with pentosuria, due to a deficiency in L-xylulose reductase. L-Xylulose is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Xylulose, with regard to humans, has been found to be associated with the diseases such as leukoencephalopathy; L-xylulose has also been linked to the inborn metabolic disorder ribose-5-phosphate isomerase deficiency. It has the chemical formula C5H10O5. In nature, it occurs in both the L- and D-enantiomers. Since L-xylulose is a reducing sugar like D-glucose, pentosuria patients have been wrongly diagnosed in the past to be diabetic. |
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Structure | |
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Synonyms | Value | Source |
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L-Lyxulose | HMDB | L-Threo-pentulose | HMDB | L-Threo-2-pentulose | HMDB | Xylulose | HMDB | beta-L-Threo-pentulofuranose | HMDB | beta-L-Threo-2-pentulofuranose | HMDB | Β-L-threo-pentulofuranose | HMDB | Β-L-threo-2-pentulofuranose | HMDB | L-Xylulose | HMDB |
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Chemical Formula | C5H10O5 |
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Average Molecular Weight | 150.13 |
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Monoisotopic Molecular Weight | 150.052823422 |
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IUPAC Name | (2S,3R,4S)-2-(hydroxymethyl)oxolane-2,3,4-triol |
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Traditional Name | (2S,3R,4S)-2-(hydroxymethyl)oxolane-2,3,4-triol |
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CAS Registry Number | 1932596-80-9 |
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SMILES | OC[C@]1(O)OC[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C5H10O5/c6-2-5(9)4(8)3(7)1-10-5/h3-4,6-9H,1-2H2/t3-,4+,5-/m0/s1 |
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InChI Key | LQXVFWRQNMEDEE-LMVFSUKVSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Pentoses |
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Alternative Parents | |
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Substituents | - Pentose monosaccharide
- Oxolane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Not Available |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 9.0 +/- 12.0 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | < 5.0 uM | Children (1-13 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0-0.5 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 5.0 (0.0-10.0) uM | Adult (>18 years old) | Both | Ribose-5-phosphate isomerase deficiency | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 254.0 (88.0-166.0) uM | Adult (>18 years old) | Both | Leukoencephalopathy and peripheral neuropathy | | details |
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Associated Disorders and Diseases |
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Disease References | Ribose-5-phosphate isomerase deficiency |
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- 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 ]
| Leukoencephalopathy |
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- 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 ]
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Associated OMIM IDs | - 608611 (Ribose-5-phosphate isomerase deficiency)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022223 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 61612021 |
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KEGG Compound ID | C00312 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Xylulose |
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METLIN ID | Not Available |
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PubChem Compound | 89810215 |
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PDB ID | Not Available |
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ChEBI ID | 17399 |
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Food Biomarker Ontology | Not Available |
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VMH ID | XYLU_L |
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MarkerDB ID | |
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References |
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Synthesis Reference | Ashwell, Gilbert; Kanfer, Julian; Burns, J. J. Mechanism of L-xylulose formation by kidney enzymes. Journal of Biological Chemistry (1959), 234 472-5. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Oka H, Suzuki S, Suzuki H, Oda T: Increased urinary excretion of L-xylulose in patients with liver cirrhosis. Clin Chim Acta. 1976 Mar 1;67(2):131-6. [PubMed:1248150 ]
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