L-Arabinose (PAMDB000164)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000164
Identification
Name: L-Arabinose
Description:L-Arabinose is a pentose with a sweet taste. In Pseudomonas aeruginosa, 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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 150.1299
Monoisotopic Molecular Weight: 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:(2R,3S,4S)-2,3,4,5-tetrahydroxypentanal
Traditional IUPAC Name: L-arabinose
SMILES:O[C@H]1COC(O)[C@H](O)[C@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Monosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic 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 Solubility380.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.9ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)11.87ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.38 m3·mol-1ChemAxon
Polarizability13.42 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Water + L-Arabinose > ADP + L-Arabinose + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + L-Arabinose > ADP + L-Arabinose + Hydrogen ion + Phosphate
L-Arabinose <> L-Ribulose
-->-->
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-f8b9c6d77ac7485b2a13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-c381cba09705c9d22367View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-157eda9875c5cd43b332View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-8bb17d4c0bc5362b2610View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-9200000000-f20b8cc45d0196859991View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-83841c4e2cbd5aa6df09View in MoNA
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

Transporters

Protein Details
• Sugar efflux transporter
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
Locus Tag:
PA4113
Molecular weight:
41.8 kDa