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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-08 14:59:26 UTC

Update Date

2023-02-21 17:18:40 UTC

HMDB ID

HMDB0029196

Secondary Accession Numbers

HMDB29196

Metabolite Identification

Common Name

D-Fucose

Description

D-Fucose, also known as alpha-D-fuc or α-D-fucp, 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. Based on a literature review a significant number of articles have been published on D-Fucose.

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-D-Fuc	ChEBI
alpha-D-Fucp	ChEBI
WURCS=2.0/1,1,0/[a2112m-1a_1-5]/1/	ChEBI
a-D-Fuc	Generator
Α-D-fuc	Generator
a-D-Fucp	Generator
Α-D-fucp	Generator
6-Deoxy-D-galactopyranose	HMDB
6-Deoxy-D-galactose	HMDB
D-Fucopyranose	HMDB
a-D-Fucose	HMDB
Α-D-fucose	HMDB
6-Deoxy-alpha-D-galactopyranose	HMDB
6-Deoxy-alpha-D-galactose	HMDB
6-Deoxy-α-D-galactopyranose	HMDB
6-Deoxy-α-D-galactose	HMDB
alpha-D-Fucopyranose	HMDB
alpha-D-Fucose	HMDB
Α-D-fucopyranose	HMDB

Chemical Formula

C₆H₁₂O₅

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

IUPAC Name

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

Traditional Name

α-d-fucose

CAS Registry Number

6189-71-5

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 Key

SHZGCJCMOBCMKK-PHYPRBDBSA-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

D-fucopyranose (CHEBI:42564 )

Ontology

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	15.18 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]+	137.779	31661259
DarkChem	[M-H]-	133.237	31661259
DeepCCS	[M+H]+	139.011	30932474
DeepCCS	[M-H]-	136.671	30932474
DeepCCS	[M-2H]-	171.181	30932474
DeepCCS	[M+Na]+	145.441	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
D-Fucose	C[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O	3109.0	Standard polar	33892256
D-Fucose	C[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O	1503.5	Standard non polar	33892256
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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
D-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 - D-Fucose GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a71-9300000000-58709e6800d01fa794ab	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-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 - D-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 - D-Fucose 10V, Positive-QTOF	splash10-014i-1900000000-04506e2fa3c1371dff28	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 20V, Positive-QTOF	splash10-00kb-2900000000-1d1ccb65a0c5c37cc4ec	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 40V, Positive-QTOF	splash10-0a4r-9000000000-e8a063be68714f958e83	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 10V, Negative-QTOF	splash10-03di-4900000000-f7a6ce4690afa04fd7a9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 20V, Negative-QTOF	splash10-03dj-7900000000-2c2df196269f093c8ec1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 40V, Negative-QTOF	splash10-0a4l-9000000000-bccf2eed4e06ffb85d57	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 10V, Negative-QTOF	splash10-03di-2900000000-39b12ef61b5dc955b65a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 20V, Negative-QTOF	splash10-052f-9200000000-b035b501120515e5ba70	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 40V, Negative-QTOF	splash10-0a4i-9000000000-b4e3f8e66eccd71547b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 10V, Positive-QTOF	splash10-016s-0900000000-1b35b25727b809781557	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 20V, Positive-QTOF	splash10-0002-9400000000-d296c72cacbcd6d61db1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fucose 40V, Positive-QTOF	splash10-0a4j-9000000000-daa4eb13673f38090d73	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03485

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001118

Chemspider ID

392189

KEGG Compound ID

C01018

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fucose

METLIN ID

Not Available

PubChem Compound

444200

PDB ID

Not Available

ChEBI ID

42564

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

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 ]

Showing metabocard for D-Fucose (HMDB0029196)

MOL for HMDB0029196 (D-Fucose)

3D MOL for HMDB0029196 (D-Fucose)

3D SDF for HMDB0029196 (D-Fucose)

3D-SDF for HMDB0029196 (D-Fucose)

PDB for HMDB0029196 (D-Fucose)

3D PDB for HMDB0029196 (D-Fucose)

SMILES for HMDB0029196 (D-Fucose)

INCHI for HMDB0029196 (D-Fucose)

Structure for HMDB0029196 (D-Fucose)

3D Structure for HMDB0029196 (D-Fucose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra