Record Information
Version2.0
Creation Date2012-05-31 10:28:12 -0600
Update Date2015-10-23 17:32:16 -0600
Secondary Accession Numbers
  • ECMDB00646
Identification
Name:L-Arabinose
DescriptionL-Arabinose is a pentose with a sweet taste. In E coli, it is involved in the catabolism of arabinose, a process directed by the L-arabinose operon. This process is activated in the presence of arabinose and the absence of glucose. (Wikipedia)
Structure
Thumb
Synonyms:
  • α-L-arabinose
  • a-L-Arabinopyranose
  • a-L-Arabinose
  • Alpha-L-Arabinopyranose
  • Alpha-L-Arabinose
  • Arabinose
  • L-(+)-Arabinose
  • L-Arabinopyranose
  • α-L-Arabinopyranose
  • α-L-Arabinose
Chemical Formula:C5H10O5
Weight:Average: 150.1299
Monoisotopic: 150.05282343
InChI Key:SRBFZHDQGSBBOR-HWQSCIPKSA-N
InChI:InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1
CAS number:5328-37-0
IUPAC Name:(3R,4S,5S)-oxane-2,3,4,5-tetrol
Traditional IUPAC Name:L-arabinopyranose
SMILES:O[C@H]1COC(O)[C@H](O)[C@H]1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:158-160 °C
Experimental Properties:
PropertyValueSource
Water Solubility:500.0 mg/mL [MERCK INDEX (1989)]PhysProp
LogP:-3.02 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1220 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.91ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.38 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:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05al-9300000000-73d0d716ea47fc77a7aeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00g0-9256300000-ae2d57025e3828494249View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1900000000-07783f4be8db8a14f6f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-1900000000-510acee1186ebf4c526bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07s1-9100000000-ff1e6f260ccdb7260dedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2900000000-f624316a77fb9d1bc74fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-4900000000-768143fc08314c41644fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-13182c55ee979014fcfaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D 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
  • Osaki, S., Kimura, T., Sugimoto, T., Hizukuri, S., Iritani, N. (2001). "L-arabinose feeding prevents increases due to dietary sucrose in lipogenic enzymes and triacylglycerol levels in rats." J Nutr 131:796-799. Pubmed: 11238761
  • 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
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • 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:Whistler, Roy L.; Schweiger, Richard. Preparation of D-arabinose from D-glucose with hypochlorite. Journal of the American Chemical Society (1959), 81 5190-2.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17535
HMDB IDHMDB00646
Pubchem Compound ID439195
Kegg IDC00259
ChemSpider ID388335
WikipediaArabinose
BioCyc IDARABINOSE
EcoCyc IDARABINOSE
Ligand ExpoLAI

Enzymes

General function:
Involved in L-fucose isomerase activity
Specific function:
Catalyzes the conversion of L-arabinose to L-ribulose
Gene Name:
araA
Uniprot ID:
P08202
Molecular weight:
56074
Reactions
L-arabinose = L-ribulose.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex AraFGH involved in arabinose import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
araG
Uniprot ID:
P0AAF3
Molecular weight:
55018
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 for L-arabinose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
araH
Uniprot ID:
P0AE26
Molecular weight:
34211
General function:
Carbohydrate transport and metabolism
Specific function:
Involved in the high-affinity L-arabinose membrane transport system. Binds with high affinity to arabinose, but can also bind D-galactose (approximately 2-fold reduction) and D- fucose (approximately 40-fold reduction)
Gene Name:
araF
Uniprot ID:
P02924
Molecular weight:
35541

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex AraFGH involved in arabinose import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
araG
Uniprot ID:
P0AAF3
Molecular weight:
55018
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 transmembrane transporter activity
Specific function:
Uptake of arabinose across the boundary membrane with the concomitant transport of protons into the cell (symport system)
Gene Name:
araE
Uniprot ID:
P0AE24
Molecular weight:
51684
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for L-arabinose. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
araH
Uniprot ID:
P0AE26
Molecular weight:
34211
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the reduction of the intracellular concentration of toxic sugars or sugar metabolites. Transports L-arabinose and to a lesser extent IPTG. Seems to contribute to the control of the arabinose regulon
Gene Name:
sotB
Uniprot ID:
P31122
Molecular weight:
42538
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:
Carbohydrate transport and metabolism
Specific function:
Involved in the high-affinity L-arabinose membrane transport system. Binds with high affinity to arabinose, but can also bind D-galactose (approximately 2-fold reduction) and D- fucose (approximately 40-fold reduction)
Gene Name:
araF
Uniprot ID:
P02924
Molecular weight:
35541
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