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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-30 10:32:48 UTC

Update Date

2022-03-07 03:17:34 UTC

HMDB ID

HMDB0059625

Secondary Accession Numbers

HMDB59625

Metabolite Identification

Common Name

beta-L-Fucose

Description

beta-L-Fucose, also known as β-L-fuc or beta-L-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-L-Fucose is an extremely weak basic (essentially neutral) compound (based on its pKa). beta-L-Fucose exists in all living organisms, ranging from bacteria to humans. A L-fucopyranose with a beta-configuration at the anomeric position.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
beta-L-Fuc	ChEBI
b-L-Fuc	Generator
Β-L-fuc	Generator
b-L-Fucose	Generator
Β-L-fucose	Generator
6-Deoxy-L-galactopyranose	HMDB
6-Deoxy-L-galactose	HMDB
6-Deoxy-beta-L-galactopyranose	HMDB
6-Deoxy-beta-L-galactose	HMDB
6-Deoxy-β-L-galactopyranose	HMDB
6-Deoxy-β-L-galactose	HMDB
beta-L-Fucopyranose	HMDB
Β-L-fucopyranose	HMDB
beta-L-Fucose	HMDB

Chemical Formula

C₆H₁₂O₅

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

IUPAC Name

(2S,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol

Traditional Name

β-l-fucose

CAS Registry Number

13224-93-6

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-/m0/s1

InChI Key

SHZGCJCMOBCMKK-KGJVWPDLSA-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

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:42589 )

Ontology

Not Available

Exogenous (HMDB: HMDB0059625)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	34.38 m³·mol⁻¹	ChemAxon
Polarizability	15.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.808	31661259
DarkChem	[M-H]-	133.53	31661259
DeepCCS	[M+H]+	139.996	30932474
DeepCCS	[M-H]-	137.662	30932474
DeepCCS	[M-2H]-	172.335	30932474
DeepCCS	[M+Na]+	146.59	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	133.6	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.3	32859911
AllCCS	[M-H]-	129.5	32859911
AllCCS	[M+Na-2H]-	130.8	32859911
AllCCS	[M+HCOO]-	132.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-L-Fucose	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O)[C@@H]1O	3109.0	Standard polar	33892256
beta-L-Fucose	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O)[C@@H]1O	1503.5	Standard non polar	33892256
beta-L-Fucose	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O)[C@@H]1O	1434.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-L-Fucose,1TMS,isomer #1	C[C@@H]1O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O	1458.1	Semi standard non polar	33892256
beta-L-Fucose,1TMS,isomer #2	C[C@@H]1O[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O	1468.2	Semi standard non polar	33892256
beta-L-Fucose,1TMS,isomer #3	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O	1481.0	Semi standard non polar	33892256
beta-L-Fucose,1TMS,isomer #4	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C	1496.0	Semi standard non polar	33892256
beta-L-Fucose,2TMS,isomer #1	C[C@@H]1O[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O	1495.4	Semi standard non polar	33892256
beta-L-Fucose,2TMS,isomer #2	C[C@@H]1O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O	1529.5	Semi standard non polar	33892256
beta-L-Fucose,2TMS,isomer #3	C[C@@H]1O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C	1514.2	Semi standard non polar	33892256
beta-L-Fucose,2TMS,isomer #4	C[C@@H]1O[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O	1523.2	Semi standard non polar	33892256
beta-L-Fucose,2TMS,isomer #5	C[C@@H]1O[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C	1544.2	Semi standard non polar	33892256
beta-L-Fucose,2TMS,isomer #6	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1504.2	Semi standard non polar	33892256
beta-L-Fucose,3TMS,isomer #1	C[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	1572.7	Semi standard non polar	33892256
beta-L-Fucose,3TMS,isomer #2	C[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)C	1582.5	Semi standard non polar	33892256
beta-L-Fucose,3TMS,isomer #3	C[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)C	1589.1	Semi standard non polar	33892256
beta-L-Fucose,3TMS,isomer #4	C[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)C	1581.2	Semi standard non polar	33892256
beta-L-Fucose,4TMS,isomer #1	C[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)C	1681.3	Semi standard non polar	33892256
beta-L-Fucose,1TBDMS,isomer #1	C[C@@H]1O[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@@H]1O	1720.3	Semi standard non polar	33892256
beta-L-Fucose,1TBDMS,isomer #2	C[C@@H]1O[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O	1741.2	Semi standard non polar	33892256
beta-L-Fucose,1TBDMS,isomer #3	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	1741.1	Semi standard non polar	33892256
beta-L-Fucose,1TBDMS,isomer #4	C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	1757.7	Semi standard non polar	33892256
beta-L-Fucose,2TBDMS,isomer #1	C[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	1987.4	Semi standard non polar	33892256
beta-L-Fucose,2TBDMS,isomer #2	C[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	2014.5	Semi standard non polar	33892256
beta-L-Fucose,2TBDMS,isomer #3	C[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)C	2016.9	Semi standard non polar	33892256
beta-L-Fucose,2TBDMS,isomer #4	C[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	2008.0	Semi standard non polar	33892256
beta-L-Fucose,2TBDMS,isomer #5	C[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)C	2029.2	Semi standard non polar	33892256
beta-L-Fucose,2TBDMS,isomer #6	C[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)C	2003.6	Semi standard non polar	33892256
beta-L-Fucose,3TBDMS,isomer #1	C[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	2255.5	Semi standard non polar	33892256
beta-L-Fucose,3TBDMS,isomer #2	C[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)C	2271.2	Semi standard non polar	33892256
beta-L-Fucose,3TBDMS,isomer #3	C[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)C	2269.8	Semi standard non polar	33892256
beta-L-Fucose,3TBDMS,isomer #4	C[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)C	2274.9	Semi standard non polar	33892256
beta-L-Fucose,4TBDMS,isomer #1	C[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)C	2479.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-L-Fucose GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9500000000-cfa9e0d8f1f20b29e5d8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-L-Fucose GC-MS (4 TMS) - 70eV, Positive	splash10-002r-9346400000-7524daf3b04caf0c441a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-L-Fucose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 10V, Positive-QTOF	splash10-014i-1900000000-73abedcfedce730de924	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 20V, Positive-QTOF	splash10-014j-1900000000-5f2bd8fc908e0f2d17d8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 40V, Positive-QTOF	splash10-0a4s-9000000000-4ae8072a5651434f44b4	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 10V, Negative-QTOF	splash10-03di-3900000000-e7a20de995c932bdb5d1	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 20V, Negative-QTOF	splash10-03dj-6900000000-03f10dd2373a0985cc0e	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 40V, Negative-QTOF	splash10-0a4i-9000000000-1ef6b887ff1a4477de1f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 10V, Negative-QTOF	splash10-03di-2900000000-39b12ef61b5dc955b65a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 20V, Negative-QTOF	splash10-052f-9200000000-b035b501120515e5ba70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 40V, Negative-QTOF	splash10-0a4i-9000000000-b4e3f8e66eccd71547b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 10V, Positive-QTOF	splash10-016s-0900000000-1b35b25727b809781557	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 20V, Positive-QTOF	splash10-0002-9400000000-d296c72cacbcd6d61db1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-L-Fucose 40V, Positive-QTOF	splash10-0a4j-9000000000-daa4eb13673f38090d73	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03283

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

392667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

444863

PDB ID

Not Available

ChEBI ID

42589

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Fucose mutarotase

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-Fucose	details

Showing metabocard for beta-L-Fucose (HMDB0059625)

MOL for HMDB0059625 (beta-L-Fucose)

3D MOL for HMDB0059625 (beta-L-Fucose)

3D SDF for HMDB0059625 (beta-L-Fucose)

3D-SDF for HMDB0059625 (beta-L-Fucose)

PDB for HMDB0059625 (beta-L-Fucose)

3D PDB for HMDB0059625 (beta-L-Fucose)

SMILES for HMDB0059625 (beta-L-Fucose)

INCHI for HMDB0059625 (beta-L-Fucose)

Structure for HMDB0059625 (beta-L-Fucose)

3D Structure for HMDB0059625 (beta-L-Fucose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions