Record Information
Version2.0
Creation Date2012-05-31 13:46:27 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01151
Identification
Name:D-Allose
DescriptionAllose is an aldohexose sugar. It is a rare monosaccharide that can be used by E. coli as a carbon source. Allose is a C-3 epimer of glucose. It is soluble in water and practically insoluble in methanol. It is transported into E. coli by the D-allose periplasmic binding protein. It is a substrate for D-allose kinase.
Structure
Thumb
Synonyms:
  • β-D-allose
  • ALLOSE
  • b-D-Allopyranose
  • B-D-Allose
  • b-delta-Allopyranose
  • b-delta-Allose
  • b-δ-Allopyranose
  • b-δ-Allose
  • Beta-D-Allopyranose
  • Beta-D-Allose
  • Beta-delta-Allopyranose
  • Beta-delta-Allose
  • D-Allose
  • Delta-Allose
  • Dl-Allose
  • β-D-Allopyranose
  • β-D-Allose
  • β-δ-Allopyranose
  • β-δ-Allose
  • δ-Allose
Chemical Formula:C6H12O6
Weight:Average: 180.1559
Monoisotopic: 180.063388116
InChI Key:WQZGKKKJIJFFOK-IVMDWMLBSA-N
InChI:InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4-,5-,6?/m1/s1
CAS number:6038-51-3
IUPAC Name:(3R,4R,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name:D-allopyranose
SMILES:[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@@]([H])(O)[C@@]1([H])O
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:128.0-128.5°C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility782 g/LALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-066s-0931000000-f283886e60a0fc2d142cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0931000000-bee54bd8f09322c97184View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b09944a9fb6b31e38cc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-00cc1bba57550100b44aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9300000000-886f06847a343d9a59b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-273df9b1216e7fc46777View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-d2d6f261629cd06b8248View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-88a02c20e38a5ca6b91cView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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: separa
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17393
HMDB IDHMDB01151
Pubchem Compound ID102288
Kegg IDC01487
ChemSpider ID13076841
WikipediaAllose
BioCyc IDALLOSE
EcoCyc IDALLOSE

Enzymes

General function:
Transcription
Specific function:
Catalyzes the phosphorylation of D-allose to D-allose 6- P. Has also low level glucokinase activity in vitro
Gene Name:
alsK
Uniprot ID:
P32718
Molecular weight:
33821
Reactions
ATP + D-allose = ADP + D-allose 6-phosphate.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex AlsBAC involved in D-allose import. Probably responsible for energy coupling to the transport system
Gene Name:
alsA
Uniprot ID:
P32721
Molecular weight:
56744
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system AlsBAC for D-allose; probably responsible for the translocation of the substrate across the membrane
Gene Name:
alsC
Uniprot ID:
P32720
Molecular weight:
34315
General function:
Carbohydrate transport and metabolism
Specific function:
Part of the binding-protein-dependent transport system AlsBAC for D-allose
Gene Name:
alsB
Uniprot ID:
P39265
Molecular weight:
32910

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex AlsBAC involved in D-allose import. Probably responsible for energy coupling to the transport system
Gene Name:
alsA
Uniprot ID:
P32721
Molecular weight:
56744
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system AlsBAC for D-allose; probably responsible for the translocation of the substrate across the membrane
Gene Name:
alsC
Uniprot ID:
P32720
Molecular weight:
34315
General function:
Carbohydrate transport and metabolism
Specific function:
Part of the binding-protein-dependent transport system AlsBAC for D-allose
Gene Name:
alsB
Uniprot ID:
P39265
Molecular weight:
32910
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368