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Bovine Rumen Metabolome Database



Showing metabocard for L-Fucose (RMDB00174)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:44
Accession Number RMDB00174
Common Name L-Fucose
Description Fucose is a hexose sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian and plant cell surface. Fucose is secreted in urine when the liver is damaged. Alpha1->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.
Synonyms
  1. (-)-Fucose
  2. (-)-L-Fucose
  3. 6-Deoxy-D-galactopyranose
  4. 6-Deoxy-L-beta-galactose
  5. 6-Deoxy-L-galactopyranose
  6. 6-Deoxy-L-galactose
  7. 6-Deoxy-beta-galactose
  8. 6-Desoxygalactose
  9. 6-methyltetrahydropyran-2,3,4,5-tetraol
  10. Fucose
  11. L-(-)-Fucose
  12. L-Fucose
  13. L-Galactomethylose
  14. Rhodeose
  15. 6-Deoxy-delta-galactopyranose
  16. isodulcit
  17. L-fucopyranose
  18. D-threo-Aldose
  19. 6-methyloxane-2,3,4,5-tetrol
Chemical IUPAC Name (3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
Chemical Formula C6H12O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Monosaccharides
Family
  • Mammalian_Metabolite
Species
  • hemiacetal; secondary alcohol; 1,2-diol; heterocyclic compound
Biofunction
  • Component of Fructose and mannose metabolism
Application
Source
  • Endogenous
Average Molecular Weight 164.156
Monoisotopic Molecular Weight 164.068481
Isomeric SMILES C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O
Canonical SMILES CC1OC(O)C(O)C(O)C1O
KEGG Compound ID C01019 Link Image
BioCyc ID L-FUCOSE Link Image
BiGG ID 36636 Link Image
Wikipedia Link L-Fucose Link Image
METLIN ID 268 Link Image
PubChem Compound 17106 Link Image
PubChem Substance 4264 Link Image
ChEBI ID 18287 Link Image
CAS Registry Number 2438-80-4
InChI Identifier InChI=1/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6?/m0/s1
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.
Melting Point (Experimental) 140 oC
Experimental Water Solubility 985 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 679.0 mg/mL [MEYLAN,WM et al. (1996)]; 827.00006 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.39 [Predicted by ALOGPS]; -1.4 [Predicted by PubChem via XLOGP]; -1.56 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID 1AH1 Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
  • Extracellular
  • lysosome
Biofluid Location
  • Rumen
Tissue Location
Concentrations (Normal)
Biofluid Rumen
Value 763.813 +/- 751.731 uM
Age N/A
Sex N/A
Condition Normal
Breed Not Available
Experimental Condition Not Available
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Beta-1,3-N-acetylglucosaminyltransferase lunatic fringe
  2. Tissue alpha-L-fucosidase
Enzyme 1 [top]
Enzyme 1 ID 633
Enzyme 1 Name Beta-1,3-N-acetylglucosaminyltransferase lunatic fringe
Enzyme 1 Synonyms
  1. O-fucosylpeptide 3-beta-N-acetylglucosaminyltransferase
Enzyme 1 Gene Name LFNG
Enzyme 1 Protein Sequence >Beta-1,3-N-acetylglucosaminyltransferase lunatic fringe
MLKRCGRRLLLALAGALLACLLVLTADPPPPPVPAERGRRALRSLAGPSGVATAPGLEAA
AAAAPGAPVREVHSLSEYFSLLTRSRRDVGPPPGGAPRPADGPPRPLAEPLAPRDVFIAV
KTTKKFHRARLDLLLETWISRHEEMTFIFTDGEDEALARRTGHVVNTNCSAAHSRQALSC
KMAVEYDRFIESGRKWFCHVDDDNYVNVRALLRLLGSYPHTQDVYLGKPSLDRPIQATER
VSENKVRPVHFWFATGGAGFCISRGLALKMSPWASGGHFMSTAERIRLPDDCTIGYIVEA
LLGVPLVRCGLFHSHLENLQQVPASELHEQVTLSYGMFENKRNSVHIKGPFSVEADPSRF
RSVHCHLYPDTSWCPRSAIF
Enzyme 1 Number of Residues 380
Enzyme 1 Molecular Weight 41846.6
Enzyme 1 Theoretical pI 8.84
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Involved in O-fucosylpeptide 3-beta-N-acetylglucosaminy
Enzyme 1 Specific Function Glycosyltransferase that initiates the elongation of O- linked fucose residues attached to EGF-like repeats in the extracellular domain of Notch molecules. Decreases the binding of JAGGED1 to NOTCH2 but not that of DELTA1. Essential mediator of somite segmentation and patterning
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • 9-29
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 86821726 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q2KJ92 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name LFNG_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1143 bp
ATGCTCAAGCGCTGCGGCCGCCGCCTGCTGCTGGCGCTGGCGGGCGCACTGCTTGCCTGC
CTACTGGTGCTCACGGCCGACCCGCCGCCGCCCCCGGTGCCCGCTGAACGCGGTCGGCGC
GCGCTGCGCAGCCTGGCGGGCCCCTCGGGGGTGGCCACGGCCCCTGGACTGGAGGCGGCG
GCGGCGGCGGCGCCCGGGGCGCCCGTCCGCGAGGTGCACAGTCTGTCCGAGTACTTCAGC
CTGCTCACCCGCTCTCGCAGAGACGTGGGCCCACCTCCCGGGGGCGCCCCCCGCCCCGCT
GACGGTCCTCCGCGGCCCCTGGCCGAGCCGCTGGCCCCACGCGACGTCTTCATCGCGGTG
AAGACCACCAAAAAGTTTCATCGCGCGCGTCTCGACTTGCTTCTGGAGACATGGATCTCG
CGCCACGAGGAGATGACGTTCATTTTCACGGACGGGGAAGACGAGGCACTGGCCAGGCGC
ACGGGCCACGTGGTCAACACCAACTGCTCGGCAGCCCACAGCCGCCAGGCACTGTCCTGC
AAGATGGCCGTGGAGTACGACCGCTTTATCGAGTCGGGGAGGAAGTGGTTCTGCCACGTG
GATGACGATAACTACGTGAATGTGCGGGCCCTGCTGAGGCTGCTGGGCAGTTACCCGCAC
ACGCAGGACGTCTACCTGGGCAAGCCCAGCCTGGACAGGCCCATCCAGGCCACGGAGCGG
GTCAGCGAAAACAAAGTGCGTCCTGTCCACTTCTGGTTTGCCACTGGCGGGGCTGGCTTC
TGCATCAGCCGAGGACTGGCCCTGAAGATGAGCCCCTGGGCCAGCGGAGGCCACTTCATG
AGCACGGCCGAGCGGATCCGGCTGCCTGACGACTGTACCATTGGCTACATCGTGGAGGCG
CTGCTGGGCGTGCCCCTCGTGCGCTGCGGGCTCTTCCACTCCCACCTGGAGAACCTGCAG
CAGGTGCCCGCCTCCGAGCTCCATGAGCAGGTGACCCTGAGCTACGGCATGTTTGAAAAC
AAGCGCAACTCCGTCCACATTAAGGGGCCCTTCTCGGTGGAGGCTGACCCGTCAAGGTTC
CGTTCCGTCCACTGCCACCTGTACCCGGACACGTCCTGGTGCCCCCGCTCTGCCATCTTC
TAG
Enzyme 1 GenBank Gene ID BC105463 Link Image
Enzyme 1 GeneCard ID LFNG Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:7
Enzyme 1 Locus 7p22.2
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 634
Enzyme 2 Name Tissue alpha-L-fucosidase
Enzyme 2 Synonyms
  1. Alpha-L-fucoside fucohydrolase
  2. Alpha-L-fucosidase I
Enzyme 2 Gene Name FUCA1
Enzyme 2 Protein Sequence >Tissue alpha-L-fucosidase
MRSWVVGARLLLLLQLVLVLGAVRLPPCTDPRHCTDPPRYTPDWPSLDSRPLPAWFDEAK
FGVFVHWGVFSVPAWGSEWFWWHWQGEKLPQYESFMKENYPPDFSYADFGPRFTARFFNP
DSWADLFKAAGAKYVVLTTKHHEGYTNWPSPVSWNWNSKDVGPHRDLVGELGTAIRKRNI
RYGLYHSLLEWFHPLYLRDKKNGFKTQYFVNAKTMPELYDLVNRYKPDLIWSDGEWECPD
TYWNSTDFLAWLYNDSPVKDEVVVNDRWGQNCSCHHGGYYNCKDKFQPETLPDHKWEMCT
SIDQRSWGYRRDMEMADITNESTIISELVQTVSLGGNYLLNVGPTKDGLIVPIFQERLLA
VGKWLSINGEAIYASKPWRVQSEKNSVWYTSKGLAVYAILLHWPEYGILSLISPIATSTT
KVTMLGIQKDLKWSLNPSGKGLLVFLPQLPPAALPTEFAWTIKLTGVK
Enzyme 2 Number of Residues 468
Enzyme 2 Molecular Weight 54088.4
Enzyme 2 Theoretical pI 7.34
Enzyme 2 GO Classification
Function
Process
Component
Enzyme 2 General Function Carbohydrate transport and metabolism
Enzyme 2 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
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • 1-22
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 86827599 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q2KIM0 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name FUCO_BOVIN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >1407 bp
ATGAGGTCGTGGGTGGTCGGCGCCCGGCTGCTGCTTTTGCTGCAGCTGGTGCTGGTGCTC
GGAGCGGTGCGGCTCCCACCCTGCACCGACCCTCGGCACTGCACCGACCCTCCGCGCTAT
ACCCCGGACTGGCCTAGTCTGGACTCCCGGCCGCTGCCGGCCTGGTTCGATGAAGCCAAA
TTCGGGGTGTTCGTGCACTGGGGCGTGTTTTCGGTGCCCGCCTGGGGCAGCGAGTGGTTC
TGGTGGCACTGGCAGGGCGAGAAGCTGCCACAGTACGAGAGCTTCATGAAAGAGAACTAC
CCGCCGGATTTCAGCTACGCCGACTTCGGGCCAAGGTTCACGGCGCGCTTCTTCAACCCC
GACAGCTGGGCTGACCTCTTCAAGGCCGCTGGGGCCAAGTATGTAGTCCTGACGACAAAG
CATCACGAAGGCTACACAAACTGGCCAAGCCCTGTGTCTTGGAACTGGAACTCTAAGGAT
GTGGGGCCCCATCGTGATTTGGTTGGTGAGTTGGGAACAGCCATCCGGAAGAGGAACATA
CGCTATGGACTGTATCACTCACTTTTAGAATGGTTCCATCCTCTCTACCTACGTGATAAG
AAAAATGGCTTTAAAACCCAGTACTTCGTCAATGCAAAAACAATGCCAGAGCTCTATGAC
CTTGTTAACAGGTATAAACCTGACTTGATTTGGTCTGATGGAGAGTGGGAATGTCCTGAC
ACTTACTGGAACTCTACAGATTTTCTTGCTTGGCTCTACAATGATAGCCCAGTTAAGGAT
GAGGTCGTAGTGAATGACCGATGGGGTCAGAACTGCTCCTGTCATCATGGAGGATACTAC
AACTGTAAAGATAAATTCCAGCCAGAGACCTTGCCAGATCACAAGTGGGAGATGTGCACC
TCCATAGACCAGCGGTCCTGGGGCTACCGTCGAGACATGGAGATGGCTGACATCACAAAC
GAATCCACGATCATTTCGGAACTGGTTCAGACAGTAAGTTTGGGAGGCAACTATCTTCTC
AACGTCGGACCAACCAAAGACGGACTGATCGTTCCCATCTTCCAAGAAAGGCTACTTGCT
GTTGGGAAGTGGCTGAGCATCAATGGAGAGGCTATCTATGCCTCCAAACCATGGAGAGTA
CAATCTGAGAAGAACTCTGTATGGTATACGTCTAAAGGATTAGCTGTTTATGCCATTTTA
CTGCACTGGCCAGAATATGGAATCTTAAGCCTTATATCCCCTATAGCTACTTCAACCACA
AAGGTAACAATGCTGGGAATCCAAAAGGATCTGAAGTGGTCCCTAAATCCCTCAGGTAAA
GGTCTCCTCGTGTTCCTGCCCCAGTTACCACCCGCTGCTCTTCCAACTGAGTTTGCTTGG
ACCATAAAGCTGACAGGAGTGAAGTGA
Enzyme 2 GenBank Gene ID BC112588 Link Image
Enzyme 2 GeneCard ID FUCA1 Link Image
Enzyme 2 GenAtlas ID Not Available
Enzyme 2 HGNC ID Not Available
Enzyme 2 Chromosome Location Chromosome:1
Enzyme 2 Locus 1p34
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References Not Available
Enzyme 2 Metabolite References Not Available