Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 18:26:10 UTC |
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Updated at | 2022-02-10 15:50:21 UTC |
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NP-MRD ID | NP0002654 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | L-(+)-Arabinose |
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Provided By | BMRB |
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Description | L-Arabinose, also known as BETA-L-arabinose or L-arabinopyranose, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. L-Arabinose is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. L-Arabinose, with regard to humans, has been found to be associated with several diseases such as colorectal cancer and eosinophilic esophagitis; L-arabinose has also been linked to the inborn metabolic disorder ribose-5-phosphate isomerase deficiency. It was first documented in 2004 (PMID: 14988808). Based on a literature review a significant number of articles have been published on L-Arabinose (PMID: 17984079) (PMID: 34543107) (PMID: 34541742) (PMID: 34531843) (PMID: 34515844) (PMID: 34507733). |
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Structure | O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5-/m0/s1 |
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Synonyms | Value | Source |
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BETA-L-ARABINOSE | ChEBI | WURCS=2.0/1,1,0/[a211h-1b_1-5]/1/ | ChEBI | b-L-ARABINOSE | Generator | Β-L-arabinose | Generator | b-L-Arabinopyranose | HMDB | Β-L-arabinopyranose | HMDB | L-Arabinopyranose | HMDB | Pectinose | HMDB | beta-L-Arabinopyranose | HMDB | Arabinopyranose | HMDB | Arabinose | HMDB | L-Arabinose | HMDB |
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Chemical Formula | C5H10O5 |
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Average Mass | 150.1299 Da |
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Monoisotopic Mass | 150.05282 Da |
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IUPAC Name | (2S,3R,4S,5S)-oxane-2,3,4,5-tetrol |
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Traditional Name | β-L-arabinopyranose |
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CAS Registry Number | Not Available |
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SMILES | O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5-/m0/s1 |
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InChI Key | SRBFZHDQGSBBOR-KLVWXMOXSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-02-10 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, experimental) | Ahselim | | | 2022-02-10 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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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
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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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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General References | - 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 ]
- Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Marghani D, Ma Z, Centone AJ, Huang W, Malik M, Bakshi CS: An AraC/XylS Family Transcriptional Regulator Modulates the Oxidative Stress Response of Francisella tularensis. J Bacteriol. 2021 Nov 5;203(23):e0018521. doi: 10.1128/JB.00185-21. Epub 2021 Sep 20. [PubMed:34543107 ]
- De Doncker M, De Graeve C, Franceus J, Beerens K, Kren V, Pelantova H, Vercauteren R, Desmet T: Exploration of GH94 Sequence Space for Enzyme Discovery Reveals a Novel Glucosylgalactose Phosphorylase Specificity. Chembiochem. 2021 Dec 2;22(23):3319-3325. doi: 10.1002/cbic.202100401. Epub 2021 Oct 7. [PubMed:34541742 ]
- Jeannot K, Hagart K, Dortet L, Kostrzewa M, Filloux A, Plesiat P, Larrouy-Maumus G: Detection of Colistin Resistance in Pseudomonas aeruginosa Using the MALDIxin Test on the Routine MALDI Biotyper Sirius Mass Spectrometer. Front Microbiol. 2021 Aug 31;12:725383. doi: 10.3389/fmicb.2021.725383. eCollection 2021. [PubMed:34531843 ]
- Chen Q, Xu W, Wu H, Guang C, Zhang W, Mu W: An overview of D-galactose utilization through microbial fermentation and enzyme-catalyzed conversion. Appl Microbiol Biotechnol. 2021 Oct;105(19):7161-7170. doi: 10.1007/s00253-021-11568-5. Epub 2021 Sep 13. [PubMed:34515844 ]
- Wen M, Cui Y, Dong CX, Zhang L: Quantitative changes in monosaccharides of Keemun black tea and qualitative analysis of theaflavins-glucose adducts during processing. Food Res Int. 2021 Oct;148:110588. doi: 10.1016/j.foodres.2021.110588. Epub 2021 Jul 3. [PubMed:34507733 ]
- Malan AK, Tuleski T, Catalan AI, de Souza EM, Batista S: Herbaspirillum seropedicae expresses non-phosphorylative pathways for D-xylose catabolism. Appl Microbiol Biotechnol. 2021 Oct;105(19):7339-7352. doi: 10.1007/s00253-021-11507-4. Epub 2021 Sep 9. [PubMed:34499201 ]
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