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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 | 2020-10-09 20:59:44 UTC |
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HMDB ID | HMDB0000568 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Arabitol |
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Description | D-Arabitol is a polyol. Polyols are sugar alcohols linked to the pentose phosphate pathway (PPP). They are classified on the basis of the number of carbon atoms. Polyols occur in body fluids. A patient with leukoencephalopathy and peripheral neuropathy has been identified as suffering from ribose-5-phosphate isomerase (RPI) deficiency, a defect in the PPP. In this disorder, highly elevated concentrations of the C5 polyols such as D-arabitol are found in body fluids. In addition, transaldolase deficiency, another defect in the PPP, has been diagnosed in a patient with mainly liver problems among others. This patient had increased concentrations of polyols, mainly D-arabitol. So far, the pathophysiological role of polyols is relatively unknown. It is thought that D-arabitol is a metabolic end-product in humans. The strong brain-CSF-plasma gradient of polyols in the patient with RPI deficiency suggested a primary metabolic disorder. The mechanisms of brain and neuronal damage in RPI deficiency remain to be elucidated. A neurotoxic effect due to the accumulation of the polyols may play a role. D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the pentose and glucuronate interconversion pathway (PMID: 16435225 , J Inherit Metab Dis. 2005;28(6):1181-3). D-Arabitol has also been found to be a fungal metabolite, urinary D-Arabinitol is a marker for invasive candidiasis or infection by Candida fungal species (PMID: 15183861 ; PMID: 10647119 ). It can also a metabolite in Debaryomyces, Pichia and Zygosaccharomyces (PMID: 25809659 ). |
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Structure | |
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Synonyms | Value | Source |
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D-Arabinol | ChEBI | D-Lyxitol | ChEBI | D-Arabinitol | Kegg | Arabitol, (D)-isomer | HMDB | Arabitol | HMDB | D-(+)-Arabitol | HMDB | (+--)-Arabitol | HMDB | DL-Arabitol | HMDB | Arabino-pentitol | HMDB | Lyxitol | HMDB | D-Arabitol | ChEBI |
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Chemical Formula | C5H12O5 |
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Average Molecular Weight | 152.1458 |
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Monoisotopic Molecular Weight | 152.068473494 |
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IUPAC Name | (2R,4R)-pentane-1,2,3,4,5-pentol |
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Traditional Name | arabitol |
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CAS Registry Number | 488-82-4 |
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SMILES | OC[C@@H](O)C(O)[C@H](O)CO |
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InChI Identifier | InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1 |
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InChI Key | HEBKCHPVOIAQTA-QWWZWVQMSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. |
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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 | Sugar alcohols |
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Alternative Parents | |
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Substituents | - Sugar alcohol
- Monosaccharide
- Secondary alcohol
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: 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 | 101 - 104 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 729 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0gb9-0982000000-4e5007f03273cea8b23e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-01ba-9500000000-67233150807800e941f0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-01b9-9000000000-1ff17a8b87bbab9a3622 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-044i-9000000000-e0e330c8a899be718f60 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-00m0-2900000000-c6b1101b88fa522fabd0 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0zmr-9500000000-164d598431954fc1aeae | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-0uki-9600000000-b90e9cee04cd0631b599 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-00e9-2900000000-75413a29e8c6b3d9a6a1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0900000000-c5cc931b9156365c4ca7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a5a-0900000000-94cf956e3f47a633d572 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-03k9-0900000000-f0634d5b1d1f523b3caa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-1900000000-4f856d537cc8252ecc47 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9300000000-403bacad5117a30582df | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9000000000-eb879b27e7b182cfe7c0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udu-9400000000-3db6454ab3e2315aa744 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0btl-9200000000-b84c400427c7e44eb4dd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-c37624fb31a8cb33b163 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-01vo-9000000000-f065454e8412613f8ecd | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 3 (0-5) uM | Adolescent (13-18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 0 uM | Not Specified | Not Specified | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 19.0 +/- 6.3 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 9.0-39.0 uM | Adolescent (13-18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 19.0 +/- 6.3 uM | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 16-89 umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 19.0 +/- 6.0 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 53.153 +/- 16.798 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 23 (8-36) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 115 (32 - 198) uM | Adolescent (13-18 years old) | Male | Ribose-5-Phosphate Isomerase Deficiency | | details | Blood | Detected and Quantified | 39.4 (0.7-788) uM | Adult (>18 years old) | Both | Invasive candidiasis | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 3342-5535 uM | Adolescent (13-18 years old) | Both | Ribose-5-Phosphate Isomerase Deficiency | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected and Quantified | 1021 - 1612 umol/mmol creatinine | Adult (>18 years old) | Both | Ribose-5-Phosphate Isomerase Deficiency | | details | Urine | Detected and Quantified | 63.837 +/- 87.775 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | 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 ]
| Invasive candidiasis |
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- Kiehn TE, Bernard EM, Gold JW, Armstrong D: Candidiasis: detection by gas-liquid chromatography of D-arabinitol, a fungal metabolite, in human serum. Science. 1979 Nov 2;206(4418):577-80. [PubMed:493963 ]
| Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | - 608611 (Ribose-5-phosphate isomerase deficiency)
- 114500 (Colorectal cancer)
- 610247 (Eosinophilic esophagitis)
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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 | FDB001475 |
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KNApSAcK ID | C00001156 |
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Chemspider ID | 84971 |
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KEGG Compound ID | C01904 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | D-arabinitol |
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METLIN ID | 5551 |
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PubChem Compound | 94154 |
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PDB ID | Not Available |
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ChEBI ID | 18333 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000189 |
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References |
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Synthesis Reference | Delobeau, Didier; Moine, Didier. Process for the preparation of d-arabitol from lactose. Eur. Pat. Appl. (1997), 9 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Kiehn TE, Bernard EM, Gold JW, Armstrong D: Candidiasis: detection by gas-liquid chromatography of D-arabinitol, a fungal metabolite, in human serum. Science. 1979 Nov 2;206(4418):577-80. [PubMed:493963 ]
- Klusmann A, Fleischer W, Waldhaus A, Siebler M, Mayatepek E: Influence of D-arabitol and ribitol on neuronal network activity. J Inherit Metab Dis. 2005;28(6):1181-3. [PubMed:16435225 ]
- Hui M, Cheung SW, Chin ML, Chu KC, Chan RC, Cheng AF: Development and application of a rapid diagnostic method for invasive Candidiasis by the detection of D-/L-arabinitol using gas chromatography/mass spectrometry. Diagn Microbiol Infect Dis. 2004 Jun;49(2):117-23. doi: 10.1016/j.diagmicrobio.2004.02.006. [PubMed:15183861 ]
- Christensson B, Sigmundsdottir G, Larsson L: D-arabinitol--a marker for invasive candidiasis. Med Mycol. 1999 Dec;37(6):391-6. [PubMed:10647119 ]
- Kordowska-Wiater M: Production of arabitol by yeasts: current status and future prospects. J Appl Microbiol. 2015 Aug;119(2):303-14. doi: 10.1111/jam.12807. Epub 2015 Apr 8. [PubMed:25809659 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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