| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2021-10-07 20:39:45 UTC |
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| NP-MRD ID | NP0000808 |
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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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| Description | L-Arabinose (CAS: 5328-37-0) Belongs to the class of compounds known as aldopentoses. An aldopentose is a monosaccharide containing five carbon atoms, including an aldehyde (CHO) functional group. Arabinose gets its name from gum arabic, from which it was first isolate. Most saccharides found in nature are in the "D"-form, however, L-arabinose is in fact more common than D-arabinose. L-arabinose is found in nature as a component of biopolymers such as hemicellulose and pectin. L-arabinose is found in all organisms from bacteria to plants to animals. Arabinose is the second most abundant pentose in lignocellulosic biomass after xylose. There are two different arabinose utilization pathways in nature: Bacterial and fungal. The bacterial pathway converts arabinose into xylulose-5-P via ribulose-5-P using three enzymes (L-arabinose isomerase, L-ribulokinase, and L-ribulose-5-P 4-epimerase) after which it enters the pentose phosphate pathway for ethanol production. The fungal pathway converts arabinose into L-arabinitol by aldose reductase (AR) or XR, L-xylulose by L-arabinitol 4-dehydrogenase (LAD), xylitol by L-xylulose reductase (LXR), D-xylulose by xylulose dehydrogenase (XDH), and D-xylulose-5-P by xylulose kinase (XK), and lastly enters the nonoxidative pentose phosphate pathway for further metabolism. Arabinose has a sweet taste and is one of the most abundant components released by complete hydrolysis of non-starch polysaccharides (NSP) of vegetable origin. Although widely present in nature, L-arabinose is rarely used in food production or food flavoring, and its physiological effects in vivo have received little attention. L-arabinose is known to selectively inhibit intestinal sucrase activity in a non-competitive manner. Sucrase is the enzyme that breaks down sucrose into glucose and fructose in the small intestine. As a result, L-arabinose suppresses plasma glucose increase due to sucrose ingestion. The presence of arabinose in urine may indicate overgrowth of intestinal yeast such as Candida albicans or other yeast/fungus species. L-arabinose is also a microbial metabolite found in, and produced by, Mycobacterium (PMID: 16232643 ). In a rare case of two autistic brothers that were not associated with any known metabolic disease, it was found the median value for L-arabinose in their urine samples was 179 umol/mmol creatinine, nearly six times greater than normal children (PMID: 11238761 , 8931641 , 1390604 , 7628083 ). |
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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 | 5328-37-0 |
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| SMILES | O[C@H]1COC(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-HWQSCIPKSA-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, 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 | |
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| Species Where Detected | |
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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 | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 158 - 160 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 500 mg/mL | Not Available | | LogP | -3.02 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - Onkenhout W, Groener JE, Verhoeven NM, Yin C, Laan LA: L-Arabinosuria: a new defect in human pentose metabolism. Mol Genet Metab. 2002 Sep-Oct;77(1-2):80-5. [PubMed:12359133 ]
- Lobley RW, Burrows PC, Warwick R, Dawson DJ, Holmes R: Simultaneous assessment of intestinal permeability and lactose tolerance with orally administered raffinose, lactose and L-arabinose. Clin Sci (Lond). 1990 Aug;79(2):175-83. [PubMed:2167807 ]
- Osaki S, Kimura T, Sugimoto T, Hizukuri S, Iritani N: L-arabinose feeding prevents increases due to dietary sucrose in lipogenic enzymes and triacylglycerol levels in rats. J Nutr. 2001 Mar;131(3):796-9. [PubMed:11238761 ]
- Seri K, Sanai K, Matsuo N, Kawakubo K, Xue C, Inoue S: L-arabinose selectively inhibits intestinal sucrase in an uncompetitive manner and suppresses glycemic response after sucrose ingestion in animals. Metabolism. 1996 Nov;45(11):1368-74. [PubMed:8931641 ]
- Schutte JB, de Jong J, van Weerden EJ, Tamminga S: Nutritional implications of L-arabinose in pigs. Br J Nutr. 1992 Jul;68(1):195-207. [PubMed:1390604 ]
- Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. [PubMed:7628083 ]
- Ahmed Z, Shimonishi T, Bhuiyan SH, Utamura M, Takada G, Izumori K: Biochemical preparation of L-ribose and L-arabinose from ribitol: a new approach. J Biosci Bioeng. 1999;88(4):444-8. doi: 10.1016/s1389-1723(99)80225-4. [PubMed:16232643 ]
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