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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:40:10 UTC

HMDB ID

HMDB0000174

Secondary Accession Numbers

HMDB00174
HMDB0059624
HMDB59624

Metabolite Identification

Common Name

L-Fucose

Description

Fucose (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

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-L-Fuc	ChEBI
alpha-L-Fucp	ChEBI
a-L-Fuc	Generator
α-L-Fuc	Generator
a-L-Fucose	Generator
α-L-fucose	Generator
a-L-Fucp	Generator
α-L-fucp	Generator
6-Deoxy-L-galactopyranose	HMDB
6-Deoxy-L-galactose	HMDB
6-Deoxy-alpha-L-galactopyranose	HMDB
6-Deoxy-alpha-L-galactose	HMDB
6-Deoxy-α-L-galactopyranose	HMDB
6-Deoxy-α-L-galactose	HMDB
alpha-L-Fucopyranose	HMDB
alpha-L-Fucose	HMDB
α-L-Fucopyranose	HMDB
α-L-Fucose	HMDB
(-)-Fucose	HMDB
6-Desoxygalactose	HMDB
Fucose	HMDB
L-(-)-Fucose	HMDB
L-Fucose	HMDB
L-Galactomethylose	HMDB

Chemical Formula

C₆H₁₂O₅

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

IUPAC Name

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

Traditional Name

α-L-fucose

CAS Registry Number

6696-41-9

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 Key

SHZGCJCMOBCMKK-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.

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:42548 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	140 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	985 mg/mL	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	15.21 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
DeepCCS	[M+H]+	139.981	30932474
DeepCCS	[M-H]-	137.659	30932474
DeepCCS	[M-2H]-	172.377	30932474
DeepCCS	[M+Na]+	146.618	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
L-Fucose	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O	3109.0	Standard polar	33892256
L-Fucose	C[C@@H]1O[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O	1503.5	Standard non polar	33892256
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Experimental GC-MS	GC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-ff79aee2e9ac3a4f53c8	2020-09-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-23d1bd654495aefbf615	2020-09-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-ff79aee2e9ac3a4f53c8	2020-09-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-Fucose GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-23d1bd654495aefbf615	2020-09-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Fucose GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Fucose Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0uxr-1900000000-78487d681dfa23efe227	2020-09-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Fucose Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-9000000000-c8f3e40cfff39fe7c419	2020-09-16	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-Fucose Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-9000000000-6752b85bef2dc57dfb8e	2020-09-16	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 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 - 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 - 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 - 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 - 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 - 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 - L-Fucose 10V, Negative-QTOF	splash10-03di-2900000000-39b12ef61b5dc955b65a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Fucose 20V, Negative-QTOF	splash10-052f-9200000000-b035b501120515e5ba70	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Fucose 40V, Negative-QTOF	splash10-0a4i-9000000000-b4e3f8e66eccd71547b0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Fucose 10V, Positive-QTOF	splash10-016s-0900000000-1b35b25727b809781557	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Fucose 20V, Positive-QTOF	splash10-0002-9400000000-d296c72cacbcd6d61db1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Fucose 40V, Positive-QTOF	splash10-0a4j-9000000000-daa4eb13673f38090d73	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2020-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2020-09-16	Wishart Lab	View 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

Name	SMPDB/PathBank	KEGG
Fructose and mannose metabolism	Not Available
Fructosuria		Not Available
Fructose intolerance, hereditary		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Breast Milk	Detected and Quantified	182 +/- 135 uM	Adult (>18 years old)	Female	Normal	24027187	details
Breast Milk	Detected and Quantified	50.8908566 uM	Adult (>18 years old)	Female	Normal	11787731	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected and Quantified	112.06 +/- 87.04 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details
Urine	Detected and Quantified	11.8 (6.7-26.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	9.6 (6.38-16.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	15.722 +/- 16.37 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	15.0 (0.0-30.0) uM	Adult (>18 years old)	Both	Cancer - assorted types	2311216	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	16.162 +/- 12.201 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Thyroid cancer
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
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 ] 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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB04473

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Fucose

METLIN ID

Not Available

PubChem Compound

439554

PDB ID

Not Available

ChEBI ID

42548

Food Biomarker Ontology

Not Available

VMH ID

FUC_L

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Xu, 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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Fleischer M, Przondo-Mordarska A: [Adhesins of Acinetobacter strains]. Med Dosw Mikrobiol. 1998;50(3-4):229-37. [PubMed:10222738 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Quirk S, Seley KL: Substrate discrimination by the human GTP fucose pyrophosphorylase. Biochemistry. 2005 Aug 16;44(32):10854-63. [PubMed:16086588 ]
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 ]
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 ]
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 ]
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 ]
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

Enzyme Details

1. L-fucose kinase

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-phosphate	details

Enzyme Details

2. Acetylcholinesterase

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

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 ]
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 ]
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 ]

Enzyme Details

3. Tissue alpha-L-fucosidase

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 alcohol	details

Enzyme Details

4. Plasma alpha-L-fucosidase

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 alcohol	details

Enzyme Details

5. 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 L-Fucose (HMDB0000174)

MOL for HMDB0000174 (L-Fucose)

3D MOL for HMDB0000174 (L-Fucose)

3D SDF for HMDB0000174 (L-Fucose)

3D-SDF for HMDB0000174 (L-Fucose)

PDB for HMDB0000174 (L-Fucose)

3D PDB for HMDB0000174 (L-Fucose)

SMILES for HMDB0000174 (L-Fucose)

INCHI for HMDB0000174 (L-Fucose)

Structure for HMDB0000174 (L-Fucose)

3D Structure for HMDB0000174 (L-Fucose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

References

Reactions

Reactions

Reactions