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Bovine Rumen Metabolome Database



Showing metabocard for Allose (RMDB01151)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:31
Accession Number RMDB01151
Common Name Allose
Description 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) Allose is an aldohexose sugar. 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. Allose is a C-3 epimer of glucose. [edit] References * Merck Index, 11th Edition, 279. [wikipedia]
Synonyms
  1. ALLOSE
  2. D-allose
  3. beta-D-Allopyranose
  4. beta-D-allose
  5. dl-Allose
  6. delta-allose
  7. beta-delta-Allopyranose
  8. beta-delta-allose
Chemical IUPAC Name 6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Chemical Formula C6H12O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Monosaccharides
Family
  • Microbial_Metabolite
Species
  • hemiacetal; primary alcohol; secondary alcohol; 1,2-diol; heterocyclic compound
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 180.156
Monoisotopic Molecular Weight 180.063385
Isomeric SMILES OC[C@@H]1OC(O)[C@@H](O)[C@@H](O)[C@H]1O
Canonical SMILES OCC1OC(O)C(O)C(O)C1O
KEGG Compound ID C01487 Link Image
BioCyc ID D-ALLOSE-6-PHOSPHATE Link Image
BiGG ID Not Available
Wikipedia Link Allose Link Image
METLIN ID 348 Link Image
PubChem Compound 102288 Link Image
PubChem Substance 428708 Link Image
ChEBI ID 17393 Link Image
CAS Registry Number 6038-51-3
InChI Identifier InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m0/s1
Synthesis Reference Menavuvu Buetusiwa Thomas; Poonperm Wayoon; Leang Khim; Noguchi Naoki; Okada Hiromi; Morimoto Kenji; Granstrom Tom Birger; Takada Goro; Izumori Ken Efficient biosynthesis of D-allose from D-psicose by cross-linked recombinant L-rhamnose isomerase: separation of product by ethanol crystallization. Journal of bioscience and bioengineering (2006), 101(4), 340-5.
Melting Point (Experimental) 128.0-128.5oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 782.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.57 [Predicted by ALOGPS]; -3.3 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1A47 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
Download File
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 763.813 +/- 751.731 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image