Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:31 UTC
Update Date2023-02-21 17:16:32 UTC
HMDB IDHMDB0003081
Secondary Accession Numbers
  • HMDB03081
Metabolite Identification
Common Namebeta-D-Fucose
Descriptionbeta-D-Fucose, also known as b-D-fuc, 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. beta-D-Fucose has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make beta-D-fucose a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on beta-D-Fucose.
Structure
Data?1676999792
Synonyms
ValueSource
beta-D-FucChEBI
WURCS=2.0/1,1,0/[a2112m-1b_1-5]/1/ChEBI
b-D-FucGenerator
Β-D-fucGenerator
b-D-FucoseGenerator
Β-D-fucoseGenerator
6-Deoxy-beta-D-galactopyranoseHMDB
6-Deoxy-beta-delta-galactopyranoseHMDB
b-D-FucopyranoseHMDB
beta-D-FucopyranoseHMDB
beta-delta-FucHMDB
beta-delta-FucopyranoseHMDB
FCBHMDB
6-Deoxy-beta-D-galactoseHMDB
6-Deoxy-β-D-galactopyranoseHMDB
6-Deoxy-β-D-galactoseHMDB
beta-D-FucoseHMDB
β-D-FucopyranoseHMDB
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(2R,3R,4S,5R,6R)-6-methyloxane-2,3,4,5-tetrol
Traditional Nameβ-D-fucose
CAS Registry Number28161-52-6
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-/m1/s1
InChI KeySHZGCJCMOBCMKK-FPRJBGLDSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
Polarizability15.28 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
DarkChem[M+H]+137.60131661259
DarkChem[M-H]-134.61231661259
DeepCCS[M+H]+139.1130932474
DeepCCS[M-H]-136.77430932474
DeepCCS[M-2H]-171.3230932474
DeepCCS[M+Na]+145.57630932474
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
beta-D-FucoseC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O3109.0Standard polar33892256
beta-D-FucoseC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O1503.5Standard non polar33892256
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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
beta-D-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 - beta-D-Fucose EI-B (Non-derivatized)splash10-014i-0920000000-5b075e8c757a442fb54b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-D-Fucose EI-B (Non-derivatized)splash10-014i-0920000000-7c01738b0df3e68efc9d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-D-Fucose EI-B (Non-derivatized)splash10-014i-0920000000-5b075e8c757a442fb54b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-D-Fucose EI-B (Non-derivatized)splash10-014i-0920000000-7c01738b0df3e68efc9d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-D-Fucose GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a71-9300000000-58709e6800d01fa794ab2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-D-Fucose GC-MS (4 TMS) - 70eV, Positivesplash10-002r-9346400000-7524daf3b04caf0c441a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-D-Fucose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 10V, Positive-QTOFsplash10-014i-1900000000-04506e2fa3c1371dff282017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 20V, Positive-QTOFsplash10-00kb-2900000000-1d1ccb65a0c5c37cc4ec2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 40V, Positive-QTOFsplash10-0a4r-9000000000-e8a063be68714f958e832017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 10V, Negative-QTOFsplash10-03di-4900000000-f7a6ce4690afa04fd7a92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 20V, Negative-QTOFsplash10-03dj-7900000000-2c2df196269f093c8ec12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 40V, Negative-QTOFsplash10-0a4l-9000000000-bccf2eed4e06ffb85d572017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 10V, Negative-QTOFsplash10-03di-2900000000-39b12ef61b5dc955b65a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 20V, Negative-QTOFsplash10-052f-9200000000-b035b501120515e5ba702021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 40V, Negative-QTOFsplash10-0a4i-9000000000-b4e3f8e66eccd71547b02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 10V, Positive-QTOFsplash10-016s-0900000000-1b35b25727b8097815572021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 20V, Positive-QTOFsplash10-0002-9400000000-d296c72cacbcd6d61db12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-D-Fucose 40V, Positive-QTOFsplash10-0a4j-9000000000-daa4eb13673f38090d732021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04062
Phenol Explorer Compound IDNot Available
FooDB IDFDB023106
KNApSAcK IDNot Available
Chemspider ID388721
KEGG Compound IDC02095
BioCyc IDCPD-13293
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3284
PubChem Compound439650
PDB IDNot Available
ChEBI ID27442
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wiederschain GYa, Beyer EM, Klyashchitsky BA, Shashkov AS: Specificity patterns of different types of human fucosidase. Recognition of a certain region of the pyranose ring in sugars by the enzymes. Biochim Biophys Acta. 1981 Jun 15;659(2):434-44. [PubMed:6789883 ]