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Record Information
Version	2.0
Creation Date	2012-05-31 14:04:10 -0600
Update Date	2015-10-15 16:14:30 -0600
Secondary Accession Numbers	ECMDB04069
Identification
Name:	L-Fuculose
Description	L-fuculose is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Fuculose or 6-deoxy-tagatose is a ketohexose deoxy sugar. (WikiPedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xace9bb30> Close
Synonyms:	6-Deoxy-L-lyxo-hex-2-ulose 6-Deoxy-L-tagatose Fuculose
Chemical Formula:	C6H12O5
Weight:	Average: 164.157 Monoisotopic: 164.068473486
InChI Key:	QZNPNKJXABGCRC-UHFFFAOYSA-N
InChI:	InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3
CAS number:	2438-80-4
IUPAC Name:	(3R,4R,5S)-1,3,4,5-tetrahydroxyhexan-2-one
Traditional IUPAC Name:	L-fuculose
SMILES:	CC(O)C(O)C(O)C(=O)CO
Chemical Taxonomy
Description	belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Fatty Acyls
Sub Class	Fatty alcohols
Direct Parent	Fatty alcohols
Alternative Parents	Monosaccharides Beta-hydroxy ketones Acyloins Alpha-hydroxy ketones Secondary alcohols Polyols Primary alcohols Organic oxides Hydrocarbon derivatives
Substituents	Fatty alcohol Acyloin Beta-hydroxy ketone Monosaccharide Alpha-hydroxy ketone Ketone Secondary alcohol Polyol Primary alcohol Organooxygen compound Organic oxygen compound Carbonyl group Alcohol Hydrocarbon derivative Organic oxide Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	deoxyketohexose (CHEBI:17617 )
Physical Properties
State:	Not Available
Charge:	0
Melting point:	150 - 153
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 388 g/L ALOGPS logP -1.8 ALOGPS logP -2.2 ChemAxon logS 0.37 ALOGPS pKa (Strongest Acidic) 10.47 ChemAxon pKa (Strongest Basic) -3.1 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 97.99 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 36.02 m³·mol⁻¹ ChemAxon Polarizability 15.48 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	L-Fucose <> L-Fuculose Adenosine triphosphate + L-Fuculose <> ADP + L-Fuculose 1-phosphate + Hydrogen ion Adenosine triphosphate + L-Fuculose <> ADP + L-Fuculose 1-phosphate L-fucose <> L-Fuculose L-Fuculose + Adenosine triphosphate > Hydrogen ion + L-Fuculose 1-phosphate + ADP L-Fucose > L-Fuculose Adenosine triphosphate + L-Fuculose > ADP + L-Fuculose 1-phosphate
SMPDB Pathways:	Not Available
KEGG Pathways:	Fructose and mannose metabolism ec00051 Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:	fucose degradation FUCCAT-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0a4i-9100000000-cf8e670799ffd3eba856 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive splash10-0fhi-5926400000-84b8394b0979399eb91c View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014j-2900000000-4fea56d8ac6e1f9c39f5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a6r-9200000000-1970754062af802fdcc1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-c31c6727c566e780cfc0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0k9i-9600000000-e099358e8071a9159c2f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0abi-9200000000-df6af27b57ded6f02536 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-70d5c6dd38db6d9ac9ab View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-3900000000-2afa12a48ce45199190c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4i-9000000000-588d79f5053524d63f63 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0007-9000000000-27d8b5b47307b9601e16 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-9300000000-771b9637362d29b99550 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-9000000000-4b8c3982888760ed6a16 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-21cd1cdbd105ca2d1adb View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View 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:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17617 HMDB ID HMDB0060267 Pubchem Compound ID 6857362 Kegg ID C01721 ChemSpider ID 5256704 Wikipedia ID Fuculose BioCyc ID L-FUCULOSE EcoCyc ID L-FUCULOSE

Enzymes

Transporters