Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 14:36:06 -0600
Update Date	2015-06-03 17:19:40 -0600
Secondary Accession Numbers	ECMDB20264
Identification
Name:	alpha-L-Fucose
Description	Fucose is a hexose sugar with the chemical formula C6H12O5. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa45e51b0> Close
Synonyms:	α-L-fucopyranose (-)-fucose (-)-L-fucose 6-Deoxy-b-galactose 6-Deoxy-beta-galactose 6-Deoxy-D-galactopyranose 6-Deoxy-delta-galactopyranose 6-Deoxy-L-b-galactose 6-Deoxy-L-beta-galactose 6-Deoxy-L-galactopyranose 6-Deoxy-L-galactose 6-Deoxy-L-β-galactose 6-Deoxy-β-galactose 6-Deoxy-δ-galactopyranose 6-Desoxygalactose 6-Methyloxane-2,3,4,5-tetrol 6-Methyltetrahydropyran-2,3,4,5-tetraol a-L-Fucopyranose a-L-Fucose Alpha-L-Fucopyranose D-Threo-aldose F2252_SIGMA FUC Fucopyranose, L- (7CI) Fucose Isodulcit L-Fucose α-L-Fucopyranose α-L-Fucose
Chemical Formula:	C6H12O5
Weight:	Average: 164.1565 Monoisotopic: 164.068473494
InChI Key:	SHZGCJCMOBCMKK-SXUWKVJYSA-N
InChI:	InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1
CAS number:	2438-80-4
IUPAC Name:	(2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional IUPAC Name:	α-L-fucose
SMILES:	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O
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.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Hexoses
Alternative Parents	Oxanes Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Hydrocarbon derivatives
Substituents	Hexose monosaccharide Oxane Secondary alcohol Hemiacetal Oxacycle Organoheterocyclic compound Polyol Hydrocarbon derivative Alcohol Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	L-fucopyranose (CHEBI:42548 )
Physical Properties
State:	Solid
Charge:	0
Melting point:	140 °C
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 827 g/L ALOGPS logP -2.4 ALOGPS logP -1.9 ChemAxon logS 0.7 ALOGPS pKa (Strongest Acidic) 11.3 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 90.15 Ų ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 34.38 m³·mol⁻¹ ChemAxon Polarizability 15.21 ų ChemAxon Number of Rings 1 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:	alpha-L-Fucose > beta-L-fucose alpha-L-Fucose > keto-L-rhamnulose β-L-fucopyranose > alpha-L-Fucose
SMPDB Pathways:	fucose and rhamnose degradation PW000826
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520 Fructose and mannose metabolism ec00051
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-0900000000-ff79aee2e9ac3a4f53c8 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-0900000000-23d1bd654495aefbf615 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-0900000000-ff79aee2e9ac3a4f53c8 View in MoNA GC-MS GC-MS Spectrum - GC-EI-TOF (Non-derivatized) splash10-014i-0900000000-23d1bd654495aefbf615 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_4_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-0uxr-1900000000-78487d681dfa23efe227 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-014i-9000000000-c8f3e40cfff39fe7c419 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) splash10-014i-9000000000-6752b85bef2dc57dfb8e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-1900000000-73abedcfedce730de924 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014j-1900000000-5f2bd8fc908e0f2d17d8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4s-9000000000-4ae8072a5651434f44b4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-3900000000-e7a20de995c932bdb5d1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03dj-6900000000-03f10dd2373a0985cc0e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-1ef6b887ff1a4477de1f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-2900000000-39b12ef61b5dc955b65a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052f-9200000000-b035b501120515e5ba70 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-b4e3f8e66eccd71547b0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-016s-0900000000-1b35b25727b809781557 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0002-9400000000-d296c72cacbcd6d61db1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4j-9000000000-daa4eb13673f38090d73 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 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,1H] 2D NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 18287 HMDB ID HMDB0000174 Pubchem Compound ID 17106 Kegg ID C01019 ChemSpider ID 817 Wikipedia ID Fucose BioCyc ID CPD-10329 EcoCyc ID CPD-10329 Ligand Expo FUC

Enzymes

Transporters