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 | 2021-06-29 00:46:54 UTC |
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NP-MRD ID | NP0000450 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Allose |
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Description | Allose is an aldohexose sugar. Allose is a C-3 epimer of glucose. D-allose is a rare sugar found in nature and, because of its very limited amount and of the high cost associated with its synthesis, its physiological functions remain virtually unknown (PMID 16080505 ). It is believed to have inhibitory effect on cancer cell proliferation (PMID 16142305 ), protective effects against ischemia reperfusion injury (PMID 14605979 , 16716947 ), immunosuppressant on allogenic orthotopic liver transplantation (PMID 11120048 ), neuroprotective effects against retinal ischemia (PMID 16565406 ), suppress development of salt-induced hypertension (PMID 16148613 ) and an inhibitory effect on human ovarian carcinoma cells (PMID 16080505 ). It is a rare monosaccharide that has been isolated from the leaves of the African shrub Protea rubropilosa. It is soluble in water and practically insoluble in methanol. |
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Structure | [H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m0/s1 |
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Synonyms | Value | Source |
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WURCS=2.0/1,1,0/[a1111h-1x_1-5]/1/ | ChEBI | beta-D-Allopyranose | HMDB | beta-D-Allose | HMDB | beta-delta-Allopyranose | HMDB | beta-delta-Allose | HMDB | D-Allose | HMDB | delta-Allose | HMDB | DL-Allose | HMDB |
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Chemical Formula | C6H12O6 |
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Average Mass | 180.1559 Da |
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Monoisotopic Mass | 180.06339 Da |
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IUPAC Name | (3S,4S,5R,6S)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol |
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Traditional Name | (D)-allose |
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CAS Registry Number | 6038-51-3 |
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SMILES | [H][C@@]1(CO)OC(O)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O |
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InChI Identifier | InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m0/s1 |
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InChI Key | WQZGKKKJIJFFOK-HOWGCPQDSA-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 | 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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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. |
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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 | Hexoses |
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Alternative Parents | |
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Substituents | - Hexose monosaccharide
- Oxane
- 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 | |
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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 | 128.0 - 128.5 °C | 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 | - Sui L, Dong Y, Watanabe Y, Yamaguchi F, Hatano N, Izumori K, Tokuda M: Growth inhibitory effect of D-allose on human ovarian carcinoma cells in vitro. Anticancer Res. 2005 Jul-Aug;25(4):2639-44. [PubMed:16080505 ]
- Sui L, Dong Y, Watanabe Y, Yamaguchi F, Hatano N, Tsukamoto I, Izumori K, Tokuda M: The inhibitory effect and possible mechanisms of D-allose on cancer cell proliferation. Int J Oncol. 2005 Oct;27(4):907-12. [PubMed:16142305 ]
- Hossain MA, Izuishi K, Maeta H: Protective effects of D-allose against ischemia reperfusion injury of the rat liver. J Hepatobiliary Pancreat Surg. 2003;10(3):218-25. [PubMed:14605979 ]
- Hossain MA, Wakabayashi H, Izuishi K, Okano K, Yachida S, Tokuda M, Izumori K, Maeta H: Improved microcirculatory effect of D-allose on hepatic ischemia reperfusion following partial hepatectomy in cirrhotic rat liver. J Biosci Bioeng. 2006 Apr;101(4):369-71. [PubMed:16716947 ]
- Hossain MA, Wakabayashi H, Goda F, Kobayashi S, Maeba T, Maeta H: Effect of the immunosuppressants FK506 and D-allose on allogenic orthotopic liver transplantation in rats. Transplant Proc. 2000 Nov;32(7):2021-3. [PubMed:11120048 ]
- Hirooka K, Miyamoto O, Jinming P, Du Y, Itano T, Baba T, Tokuda M, Shiraga F: Neuroprotective effects of D-allose against retinal ischemia-reperfusion injury. Invest Ophthalmol Vis Sci. 2006 Apr;47(4):1653-7. [PubMed:16565406 ]
- Kimura S, Zhang GX, Nishiyama A, Nagai Y, Nakagawa T, Miyanaka H, Fujisawa Y, Miyatake A, Nagai T, Tokuda M, Abe Y: D-allose, an all-cis aldo-hexose, suppresses development of salt-induced hypertension in Dahl rats. J Hypertens. 2005 Oct;23(10):1887-94. [PubMed:16148613 ]
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