Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:10 UTC
HMDB IDHMDB0000174
Secondary Accession Numbers
  • HMDB00174
  • HMDB0059624
  • HMDB59624
Metabolite Identification
Common NameL-Fucose
DescriptionFucose (CAS: 2438-80-4) is a hexose deoxy sugar with the chemical formula C6H12O5. L-Fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells. It is the fundamental subunit of the fucoidan polysaccharide. As a free sugar, L-fucose is normally found at very low levels in mammals. It is unique in that it is the only levorotatory sugar synthesized and utilized by mammals. Fucose polymers are synthesized by fucosyltransferases. All fucosyltransferases utilize a nucleotide-activated form of fucose, GDP-fucose, as a fucose donor in the construction of fucosylated oligosaccharides. The ABO blood group antigens are among the most well known fucosylated glycans. The alpha-1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. Fucose is metabolized by an enzyme called alpha-fucosidase. Fucose is secreted in urine when the liver is damaged. Free L-fucose in serum and urine can be used as a marker for cancer, cirrhosis, alcoholic liver disease and gastric ulcers (PMID: 2311216 , 8488966 ). Elevated levels of serum fucose have been reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes, and cardiovascular disease. It has been shown that feeding rats a diet high in L-fucose induces neuropathy similar to that seen in diabetics.
Structure
Data?1600223512
Synonyms
ValueSource
alpha-L-FucChEBI
alpha-L-FucpChEBI
a-L-FucGenerator
α-L-FucGenerator
a-L-FucoseGenerator
α-L-fucoseGenerator
a-L-FucpGenerator
α-L-fucpGenerator
6-Deoxy-L-galactopyranoseHMDB
6-Deoxy-L-galactoseHMDB
6-Deoxy-alpha-L-galactopyranoseHMDB
6-Deoxy-alpha-L-galactoseHMDB
6-Deoxy-α-L-galactopyranoseHMDB
6-Deoxy-α-L-galactoseHMDB
alpha-L-FucopyranoseHMDB
alpha-L-FucoseHMDB
α-L-FucopyranoseHMDB
α-L-FucoseHMDB
(-)-FucoseHMDB
6-DesoxygalactoseHMDB
FucoseHMDB
L-(-)-FucoseHMDB
L-FucoseHMDB
L-GalactomethyloseHMDB
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
Traditional Nameα-L-fucose
CAS Registry Number6696-41-9
SMILES
C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier
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
InChI KeySHZGCJCMOBCMKK-SXUWKVJYSA-N
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
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility985 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility827 g/LALOGPS
logP-2.4ALOGPS
logP-1.9ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+139.98130932474
DeepCCS[M-H]-137.65930932474
DeepCCS[M-2H]-172.37730932474
DeepCCS[M+Na]+146.61830932474
AllCCS[M+H]+138.032859911
AllCCS[M+H-H2O]+133.632859911
AllCCS[M+NH4]+142.232859911
AllCCS[M+Na]+143.332859911
AllCCS[M-H]-129.532859911
AllCCS[M+Na-2H]-130.832859911
AllCCS[M+HCOO]-132.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-FucoseC[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O3109.0Standard polar33892256
L-FucoseC[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O1503.5Standard non polar33892256
L-FucoseC[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O1434.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Fucose,1TMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O1458.1Semi standard non polar33892256
L-Fucose,1TMS,isomer #2C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O1468.2Semi standard non polar33892256
L-Fucose,1TMS,isomer #3C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O1481.0Semi standard non polar33892256
L-Fucose,1TMS,isomer #4C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C1496.0Semi standard non polar33892256
L-Fucose,2TMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O1495.4Semi standard non polar33892256
L-Fucose,2TMS,isomer #2C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O1529.5Semi standard non polar33892256
L-Fucose,2TMS,isomer #3C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C1514.2Semi standard non polar33892256
L-Fucose,2TMS,isomer #4C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O1523.2Semi standard non polar33892256
L-Fucose,2TMS,isomer #5C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C1544.2Semi standard non polar33892256
L-Fucose,2TMS,isomer #6C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1504.2Semi standard non polar33892256
L-Fucose,3TMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O1572.7Semi standard non polar33892256
L-Fucose,3TMS,isomer #2C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C1582.5Semi standard non polar33892256
L-Fucose,3TMS,isomer #3C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1589.1Semi standard non polar33892256
L-Fucose,3TMS,isomer #4C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1581.2Semi standard non polar33892256
L-Fucose,4TMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1681.3Semi standard non polar33892256
L-Fucose,1TBDMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O1720.3Semi standard non polar33892256
L-Fucose,1TBDMS,isomer #2C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O1741.2Semi standard non polar33892256
L-Fucose,1TBDMS,isomer #3C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O1741.1Semi standard non polar33892256
L-Fucose,1TBDMS,isomer #4C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C1757.7Semi standard non polar33892256
L-Fucose,2TBDMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O1987.4Semi standard non polar33892256
L-Fucose,2TBDMS,isomer #2C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2014.5Semi standard non polar33892256
L-Fucose,2TBDMS,isomer #3C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2016.9Semi standard non polar33892256
L-Fucose,2TBDMS,isomer #4C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2008.0Semi standard non polar33892256
L-Fucose,2TBDMS,isomer #5C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2029.2Semi standard non polar33892256
L-Fucose,2TBDMS,isomer #6C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2003.6Semi standard non polar33892256
L-Fucose,3TBDMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2255.5Semi standard non polar33892256
L-Fucose,3TBDMS,isomer #2C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2271.2Semi standard non polar33892256
L-Fucose,3TBDMS,isomer #3C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2269.8Semi standard non polar33892256
L-Fucose,3TBDMS,isomer #4C[C@@H]1O[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2274.9Semi standard non polar33892256
L-Fucose,4TBDMS,isomer #1C[C@@H]1O[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2479.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-ff79aee2e9ac3a4f53c82020-09-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-23d1bd654495aefbf6152020-09-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-ff79aee2e9ac3a4f53c82020-09-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-23d1bd654495aefbf6152020-09-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TMS_4_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Fucose Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0uxr-1900000000-78487d681dfa23efe2272020-09-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Fucose Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-9000000000-c8f3e40cfff39fe7c4192020-09-16HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - L-Fucose Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-9000000000-6752b85bef2dc57dfb8e2020-09-16HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 10V, Positive-QTOFsplash10-014i-1900000000-73abedcfedce730de9242015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 20V, Positive-QTOFsplash10-014j-1900000000-5f2bd8fc908e0f2d17d82015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 40V, Positive-QTOFsplash10-0a4s-9000000000-4ae8072a5651434f44b42015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 10V, Negative-QTOFsplash10-03di-3900000000-e7a20de995c932bdb5d12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 20V, Negative-QTOFsplash10-03dj-6900000000-03f10dd2373a0985cc0e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 40V, Negative-QTOFsplash10-0a4i-9000000000-1ef6b887ff1a4477de1f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 10V, Negative-QTOFsplash10-03di-2900000000-39b12ef61b5dc955b65a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 20V, Negative-QTOFsplash10-052f-9200000000-b035b501120515e5ba702021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 40V, Negative-QTOFsplash10-0a4i-9000000000-b4e3f8e66eccd71547b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 10V, Positive-QTOFsplash10-016s-0900000000-1b35b25727b8097815572021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 20V, Positive-QTOFsplash10-0002-9400000000-d296c72cacbcd6d61db12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Fucose 40V, Positive-QTOFsplash10-0a4j-9000000000-daa4eb13673f38090d732021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2020-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2020-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
Biospecimen Locations
  • Blood
  • Breast Milk
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Breast MilkDetected and Quantified182 +/- 135 uMAdult (>18 years old)Female
Normal
details
Breast MilkDetected and Quantified50.8908566 uMAdult (>18 years old)FemaleNormal details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not AvailableNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified112.06 +/- 87.04 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified11.8 (6.7-26.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified9.6 (6.38-16.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified15.722 +/- 16.37 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified15.0 (0.0-30.0) uMAdult (>18 years old)BothCancer - assorted types details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
UrineDetected and Quantified16.162 +/- 12.201 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
Associated Disorders and Diseases
Disease References
Thyroid cancer
  1. Sakai T, Yamamoto K, Yokota H, Hakozaki-Usui K, Hino F, Kato I: Rapid, simple enzymatic assay of free L-fucose in serum and urine, and its use as a marker for cancer, cirrhosis, and gastric ulcers. Clin Chem. 1990 Mar;36(3):474-6. [PubMed:2311216 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB04473
Phenol Explorer Compound IDNot Available
FooDB IDFDB020543
KNApSAcK IDC00035100
Chemspider ID388645
KEGG Compound IDC01019
BioCyc IDL-FUCOSE
BiGG IDNot Available
Wikipedia LinkFucose
METLIN IDNot Available
PubChem Compound439554
PDB IDNot Available
ChEBI ID42548
Food Biomarker OntologyNot Available
VMH IDFUC_L
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceXu, Zuhong; Zhao, Zengqin; Zhang, Quanbin; Niu, Xizhen; Zhang, Hong; Li, Zhien. Method for preparing L-fucose from laminaria japonica. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  2. Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. [PubMed:3757018 ]
  3. Condaminet B, Peguet-Navarro J, Stahl PD, Dalbiez-Gauthier C, Schmitt D, Berthier-Vergnes O: Human epidermal Langerhans cells express the mannose-fucose binding receptor. Eur J Immunol. 1998 Nov;28(11):3541-51. [PubMed:9842897 ]
  4. Havenaar EC, Hoff RC, van den Eijnden DH, van Dijk W: Sialyl Lewis(x) epitopes do not occur on acute phase proteins in mice: relationship to the absence of alpha3-fucosyltransferase in the liver. Glycoconj J. 1998 Apr;15(4):389-95. [PubMed:9613826 ]
  5. Roelfzema H, van Erp PE: Studies on the plasma membrane of normal and psoriatic keratinocytes. 6. Cell surface and shed glycoproteins. J Invest Dermatol. 1983 Jan;80(1):24-6. [PubMed:6184420 ]
  6. Wiese TJ, Dunlap JA, Yorek MA: Effect of L-fucose and D-glucose concentration on L-fucoprotein metabolism in human Hep G2 cells and changes in fucosyltransferase and alpha-L-fucosidase activity in liver of diabetic rats. Biochim Biophys Acta. 1997 Apr 17;1335(1-2):61-72. [PubMed:9133643 ]
  7. Isnard N, Fodil-Bourahla I, Robert AM, Robert L: Pharmacology of skin aging. Stimulation of glycosaminoglycan biosynthesis by L-fucose and fucose-rich polysaccharides, effect of in vitro aging of fibroblasts. Biomed Pharmacother. 2004 Apr;58(3):202-4. [PubMed:15082343 ]
  8. Rizzi M, Tonetti M, Vigevani P, Sturla L, Bisso A, Flora AD, Bordo D, Bolognesi M: GDP-4-keto-6-deoxy-D-mannose epimerase/reductase from Escherichia coli, a key enzyme in the biosynthesis of GDP-L-fucose, displays the structural characteristics of the RED protein homology superfamily. Structure. 1998 Nov 15;6(11):1453-65. [PubMed:9817848 ]
  9. Gheri G, Sgambati E, Thyrion GD, Vichi D, Orlandini GE: The oligosaccharidic content of the glycoconjugates of the prepubertal descended and undescended testis: lectin histochemical study. Ital J Anat Embryol. 2004 Apr-Jun;109(2):69-84. [PubMed:15481156 ]
  10. Fediv OI, Kolomoiets' MIu: [Role of cytokines in the metabolism of the extracellular matrix carbohydrate-protein components in patients of various ages with gastroduodenal ulcer]. Lik Sprava. 2001 Jul-Aug;(4):181-2. [PubMed:11692712 ]
  11. Hutchinson WL, Du MQ, Johnson PJ, Williams R: Fucosyltransferases: differential plasma and tissue alterations in hepatocellular carcinoma and cirrhosis. Hepatology. 1991 Apr;13(4):683-8. [PubMed:1849114 ]
  12. Fleischer M, Przondo-Mordarska A: [Adhesins of Acinetobacter strains]. Med Dosw Mikrobiol. 1998;50(3-4):229-37. [PubMed:10222738 ]
  13. Gohlke M, Baude G, Nuck R, Grunow D, Kannicht C, Bringmann P, Donner P, Reutter W: O-linked L-fucose is present in Desmodus rotundus salivary plasminogen activator. J Biol Chem. 1996 Mar 29;271(13):7381-6. [PubMed:8631761 ]
  14. Chien CM, Cheng JL, Chang WT, Tien MH, Tsao CM, Chang YH, Chang HY, Hsieh JF, Wong CH, Chen ST: Polysaccharides of Ganoderma lucidum alter cell immunophenotypic expression and enhance CD56+ NK-cell cytotoxicity in cord blood. Bioorg Med Chem. 2004 Nov 1;12(21):5603-9. [PubMed:15465338 ]
  15. Hanisch FG, Heimbuchel G, Baldus SE, Uhlenbruck G, Schmits R, Pfreundschuh M, Schwonzen M, Vierbuchen M, Bara J, Peter-Katalinic J: Monoclonal antibody FW6 defines an epitope on alpha 3/4-monofucosylated polylactosaminoglycans expressed by fetal and colon carcinoma-associated mucins. Cancer Res. 1993 Sep 15;53(18):4367-75. [PubMed:8364932 ]
  16. Tonetti M, Sturla L, Bisso A, Zanardi D, Benatti U, De Flora A: The metabolism of 6-deoxyhexoses in bacterial and animal cells. Biochimie. 1998 Nov;80(11):923-31. [PubMed:9893952 ]
  17. Sato T, Sato M, Kiyohara K, Sogabe M, Shikanai T, Kikuchi N, Togayachi A, Ishida H, Ito H, Kameyama A, Gotoh M, Narimatsu H: Molecular cloning and characterization of a novel human beta1,3-glucosyltransferase, which is localized at the endoplasmic reticulum and glucosylates O-linked fucosylglycan on thrombospondin type 1 repeat domain. Glycobiology. 2006 Dec;16(12):1194-206. Epub 2006 Aug 9. [PubMed:16899492 ]
  18. Coyne MJ, Reinap B, Lee MM, Comstock LE: Human symbionts use a host-like pathway for surface fucosylation. Science. 2005 Mar 18;307(5716):1778-81. [PubMed:15774760 ]
  19. Quirk S, Seley KL: Substrate discrimination by the human GTP fucose pyrophosphorylase. Biochemistry. 2005 Aug 16;44(32):10854-63. [PubMed:16086588 ]
  20. Bathi RJ, Nandimath K, Kannan N, Shetty P: Evaluation of glycoproteins as prognosticators in head and neck malignancy. Indian J Dent Res. 2001 Apr-Jun;12(2):93-9. [PubMed:11665403 ]
  21. Sakai T, Yamamoto K, Yokota H, Hakozaki-Usui K, Hino F, Kato I: Rapid, simple enzymatic assay of free L-fucose in serum and urine, and its use as a marker for cancer, cirrhosis, and gastric ulcers. Clin Chem. 1990 Mar;36(3):474-6. [PubMed:2311216 ]
  22. Yamauchi M, Kimura K, Maezawa Y, Ohata M, Mizuhara Y, Hirakawa J, Nakajima H, Toda G: Urinary level of L-fucose as a marker of alcoholic liver disease. Alcohol Clin Exp Res. 1993 Apr;17(2):268-71. [PubMed:8488966 ]
  23. Chang TW, Gorbach SL, Bartlett JG: Inhibition of binding of Clostridium difficile toxin by steroids. J Infect Dis. 1980 Jul;142(1):113. [PubMed:6772711 ]
  24. Neethling FA, Koren E, Ye Y, Richards SV, Kujundzic M, Oriol R, Cooper DK: Protection of pig kidney (PK15) cells from the cytotoxic effect of anti-pig antibodies by alpha-galactosyl oligosaccharides. Transplantation. 1994 Mar 27;57(6):959-63. [PubMed:8154046 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Takes part in the salvage pathway for reutilization of fucose from the degradation of oligosaccharides.
Gene Name:
FUK
Uniprot ID:
Q8N0W3
Molecular weight:
117621.795
Reactions
Adenosine triphosphate + L-Fucose → ADP + Fucose 1-phosphatedetails
General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in alpha-L-fucosidase activity
Specific function:
Alpha-L-fucosidase is responsible for hydrolyzing the alpha-1,6-linked fucose joined to the reducing-end N-acetylglucosamine of the carbohydrate moieties of glycoproteins.
Gene Name:
FUCA1
Uniprot ID:
P04066
Molecular weight:
53688.475
Reactions
An alpha-L-fucoside + Water → L-Fucose + an alcoholdetails
General function:
Involved in alpha-L-fucosidase activity
Specific function:
Alpha-L-fucosidase is responsible for hydrolyzing the alpha-1,6-linked fucose joined to the reducing-end N-acetylglucosamine of the carbohydrate moieties of glycoproteins.
Gene Name:
FUCA2
Uniprot ID:
Q9BTY2
Molecular weight:
54066.31
Reactions
An alpha-L-fucoside + Water → L-Fucose + an alcoholdetails
General function:
Not Available
Specific function:
Involved in the interconversion between alpha- and beta-L-fucoses. L-Fucose (6-deoxy-L-galactose) exists as alpha-L-fucose (29.5%) and beta-L-fucose (70.5%), the beta-form is metabolized through the salvage pathway. GDP-L-fucose formed either by the de novo or salvage pathways is transported into the endoplasmic reticulum, where it serves as a substrate for N- and O-glycosylations by fucosyltransferases. Fucosylated structures expressed on cell surfaces or secreted in biological fluids are believed to play a critical role in cell-cell adhesion and recognition processes.
Gene Name:
FUOM
Uniprot ID:
A2VDF0
Molecular weight:
16764.555
Reactions
L-Fucose → beta-L-Fucosedetails