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Human Metabolome Database Version 2.5

 

Showing metabocard for Fucose 1-phosphate (HMDB01265)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:58:38
Accession Number HMDB01265
Secondary Accession Numbers Not Available
Common Name Fucose 1-phosphate
Description Fucose-1-phosphate is an intermediate in the reversible synthesis of GDP-L-fucose, in a reaction catalyzed by the enzyme guanosine triphosphate fucose pyrophosphorylase (GFPP, E.C. 2.7.7.30) . The reversible reaction is magnesium-dependent, although the enzyme is partially active when cobalt or manganese is substituted. The reaction is unusual in that, of the four canonical nucleoside triphosphates, only guanosine can be utilized efficiently to form a nucleotide-sugar. Free cytosolic fucose is phosphorylated by L-fucokinase (EC 2.7.1.52) to form fucose-1-phosphate in the salvage pathway of GDP-L-fucose. (PMID: 16185085, 14686921)
Synonyms
  1. (3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxyphosphonate
  2. (3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxyphosphonic acid
  3. 6-Deoxy-L-galactose 1-phosphate
  4. 6-deoxy-L-Galactopyranose 1-(dihydrogen phosphate)
  5. Fuculose 1-phosphate
  6. L-Fucose 1-phosphate
  7. L-Fucose 1-phosphic acid
  8. beta-L-fucose 1-phosphate
  9. b-L-fucose 1-phosphate
  10. beta-L-fucose-1-phosphate
  11. b-L-fucose-1-phosphate
Chemical IUPAC Name (3,4,5-trihydroxy-6-methyl-oxan-2-yl)oxyphosphonic acid
Chemical Formula C6H13O8P
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Sugar Phosphates
Sub Class
  • Monosaccharide phosphates
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • 1,2-diol
  • phosphoric acid ester
  • heterocyclic compound
Biofunction
  • Component of Fructose and mannose metabolism
Application
—
Source
  • Endogenous
Average Molecular Weight 244.136
Monoisotopic Molecular Weight 244.034805
Isomeric SMILES C[C@@H]1OC(OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O
Canonical SMILES CC1OC(OP(O)(O)=O)C(O)C(O)C1O
KEGG Compound ID C02985 Link Image
BioCyc ID CPD-488 Link Image
BiGG ID 40955 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB01265 Link Image
Metagene Link HMDB01265 Link Image
METLIN ID 6120 Link Image
PubChem Compound 439871 Link Image
PubChem Substance 841981 Link Image
ChEBI ID 28319 Link Image
CAS Registry Number 16562-58-6
InChI Identifier InChI=1/C6H13O8P/c1-2-3(7)4(8)5(9)6(13-2)14-15(10,11)12/h2-9H,1H3,(H2,10,11,12)/t2-,3+,4+,5-,6?/m0/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 34.2 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.53 [Predicted by ALOGPS]; -2.9 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
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
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 Link Image map00051 Link Image
General References Not Available
Metabolic Enzymes
  1. Fucose-1-phosphate guanylyltransferase
  2. L-fucose kinase
Enzyme 1 [top]
Enzyme 1 ID 5486
Enzyme 1 Name Fucose-1-phosphate guanylyltransferase
Enzyme 1 Synonyms
  1. GDP-L-fucose pyrophosphorylase
  2. GDP-L-fucose diphosphorylase
Enzyme 1 Gene Name FPGT
Enzyme 1 Protein Sequence >Fucose-1-phosphate guanylyltransferase 
MAAARDPPEVSLREATQRKLRRFSELRGKLVARGEFWDIVAITAADEKQELAYNQQLSEK
LKRKELPLGVQYHVFVDPAGAKIGNGGSTLCALQCLEKLYGDKWNSFTILLIHSGGYSQR
LPNASALGKIFTALPLGNPIYQMLELKLAMYIDFPLNMNPGILVTCADDIELYSIGEFEF
IRFDKPGFTALAHPSSLTIGTTHGVFVLDPFDDLKHRDLEYRSCHRFLHKPSIEKMYQFN
AVCRPGNFCQQDFAGGDIADLKLDSDYVYTDSLFYMDHKSAKMLLAFYEKIGTLSCEIDA
YGDFLQALGPGATVEYTRNTSNVIKEESELVEMRQRIFHLLKGTSLNVVVLNNSKFYHIG
TTEEYLFYFTSDNSLKSELGLQSITFSIFPDIPECSGKTSCIIQSILDSRCSVAPGSVVE
YSRLGPDVSVGENCIISGSYILTKAALPAHSFVCSLSLKMNRCLKYATMAFGVQDNLKKS
VKTLSDIKLLQFFGVCFLSCLDVWNLKVTEELFSGNKTCLSLWTARIFPVCSSLSDSVIT
SLKMLNAVKNKSAFSLNSYKLLSIEEMLIYKDVEDMITYREQIFLEISLKSSLM
Enzyme 1 Number of Residues 594
Enzyme 1 Molecular Weight 66600
Enzyme 1 Theoretical pI 6.44
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Catalyzes the formation of GDP-L-fucose from GTP and L- fucose-1-phosphate. Functions as a salvage pathway to reutilize L- fucose arising from the turnover of glycoproteins and glycolipids
Enzyme 1 Pathways
Enzyme 1 Reactions
  • GTP + beta-L-fucose 1-phosphate = diphosphate + GDP-L-fucose
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 2582185 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID O14772 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name FPGT_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1785 bp 
ATGGCAGCTGCTAGGGACCCTCCGGAAGTATCGCTGCGAGAAGCCACCCAGCGAAAATTG
CGGAGGTTTTCCGAGCTAAGAGGCAAACTTGTAGCACGTGGAGAATTCTGGGACATAGTT
GCAATAACAGCGGCTGATGAAAAACAGGAACTTGCTTACAACCAACAGCTGTCAGAAAAG
CTGAAAAGAAAGGAGTTACCCCTTGGAGTTCAATATCACGTTTTTGTGGATCCTGCTGGA
GCCAAAATTGGAAATGGAGGATCAACACTTTGTGCCCTTCAATGTTTGGAAAAGCTATAT
GGAGATAAATGGAATTCTTTTACCATCTTATTAATTCACTCTGGTGGCTACAGTCAACGA
CTTCCAAATGCAAGTGCTCTGGGAAAAATTTTCACTGCTTTACCTCTTGGTAACCCCATT
TATCAGATGCTAGAATTAAAGCTAGCCATGTACATTGATTTCCCCTTAAATATGAATCCT
GGAATTCTGGTTACCTGTGCAGATGATATTGAACTTTATAGTATTGGAGAATTTGAGTTT
ATTAGGTTTGACAAACCTGGCTTTACTGCTTTAGCTCATCCTTCTAGTTTGACGATAGGT
ACCACACATGGAGTATTTGTCTTAGATCCTTTTGATGATTTAAAACATAGAGACCTTGAA
TACAGGTCTTGCCATCGTTTCCTTCATAAGCCCAGCATAGAAAAGATGTATCAGTTTAAT
GCTGTGTGTAGACCTGGAAATTTTTGTCAACAGGACTTTGCTGGGGGTGACATTGCCGAT
CTTAAATTAGACTCTGACTATGTCTACACAGATAGCCTATTTTATATGGATCATAAATCA
GCAAAAATGTTACTTGCTTTTTATGAAAAAATAGGCACACTGAGCTGTGAAATAGATGCC
TATGGTGACTTTCTGCAGGCTTTGGGACCTGGAGCAACTGTGGAGTACACCAGAAACACA
TCACATGTCATTAAAGAAGAGTCAGAGTTGGTAGAAATGAGGCAGAGAATATTTCATCTT
CTTAAAGGAACATCACTAAATGTTGTTGTTCTTAATAACTCCAAATTTTATCACATTGGA
ACAACCGAAGAATATTTGTTTTACTTTACCTCAGATAACAGTTTAAAGTCAGAGCTCGGC
TTACAGTCCATAACTTTTAGTATCTTTCCAGATATACCAGAATGCTCTGGCAAAACATCC
TGTATCATTCAAAGCATACTGGATTCAAGATGTTCTGTGGCACCTGGCTCAGTTGTGGAG
TATTCCAGATTGGGGCCTGATGTTTCAGTTGGGGAAAACTGCATTATTAGTGGTTCTTAC
ATCCTAACAAAAGCTGCCCTCCCCGCACATTCTTTTGTATGTTCCTTAAGCTTAAAGATG
AATAGATGCTTAAAGTATGCAACTATGGCATTTGGAGTGCAAGACAACTTGAAAAAGAGT
GTGAAAACATTGTCAGATATAAAGTTACTTCAATTCTTTGGAGTCTGTTTCCTGTCATGC
TTAGATGTTTGGAATCTTAAAGTTACAGAGGAACTGTTCTCTGGTAACAAGACATGTCTG
AGTTTGTGGACTGCACGCATTTTCCCAGTTTGTTCTTCTTTGAGTGACTCAGTTATAACA
TCCCTAAAGATGTTAAATGCTGTTAAGAACAAGTCAGCATTCAGCCTGAATAGCTATAAG
TTGCTGTCCATTGAAGAAATGCTTATCTACAAAGATGTAGAAGATATGATAACTTACAGG
GAACAAATTTTTCTAGAAATCAGTTTAAAAAGCAGTTTGATGTAG
Enzyme 1 GenBank Gene ID AF017445 Link Image
Enzyme 1 GeneCard ID FPGT Link Image
Enzyme 1 GenAtlas ID FPGT Link Image
Enzyme 1 HGNC ID HGNC:3825 Link Image
Enzyme 1 Chromosome Location 1
Enzyme 1 Locus 1p31.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Pastuszak I, Ketchum C, Hermanson G, Sjoberg EJ, Drake R, Elbein AD: GDP-L-fucose pyrophosphorylase. Purification, cDNA cloning, and properties of the enzyme. J Biol Chem. 1998 Nov 13;273(46):30165-74. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 5487
Enzyme 2 Name L-fucose kinase
Enzyme 2 Synonyms
  1. Fucokinase
Enzyme 2 Gene Name FUK
Enzyme 2 Protein Sequence >L-fucose kinase 
MEQPKGVDWTVIILTCQYKDSVQVFQRELEVRQKREQIPAGTLLLAVEDPEKRVGSGGAT
LNALLVAAEHLSARAGFTVVTSDVLHSAWILILHMGRDFPFDDCGRAFTCLPVENPEAPV
EALVCNLDCLLDIMTYRLGPGSPPGVWVCSTDMLLSVPANPGISWDSFRGARVIALPGSP
AYAQNHGVYLTDPQGLVLDIYYQGTEAEIQRCVRPDGRVPLVSGVVFFSVETAERLLATH
VSPPLDACTYLGLDSGARPVQLSLFFDILHCMAENVTREDFLVGRPPELGQGDADVAGYL
QSARAQLWRELRDQPLTMAYVSSGSYSYMTSSASEFLLSLTLPGAPGAQIVHSQVEEQQL
LAAGSSVVSCLLEGPVQLGPGSVLQHCHLQGPIHIGAGCLVTGLDTAHSKALHGRELRDL
VLQGHHTRLHGSPGHAFTLVGRLDSWERQGAGTYLNVPWSEFFKRTGVRAWDLWDPETLP
AEYCLPSARLFPVLHPSRELGPQDLLWMLDHQEDGGEALRAWRASWRLSWEQLQPCLDRA
ATLASRRDLFFRQALHKARHVLEARQDLSLRPLIWAAVREGCPGPLLATLDQVAAGAGDP
GVAARALACVADVLGCMAEGRGGLRSGPAANPEWMRPFSYLECGDLAAGVEALAQERDKW
LSRPALLVRAARHYEGAGQILIRQAVMSAQHFVSTEQVELPGPGQWVVAECPARVDFSGG
WSDTPPLAYELGGAVLGLAVRVDGRRPIGARARRIPEPELWLAVGPRQDEMTVKIVCRCL
ADLRDYCQPHAPGALLKAAFICAGIVHVHSELQLSEQLLRTFGGGFELHTWSELPHGSGL
GTSSILAGTALAALQRAAGRVVGTEALIHAVLHLEQVLTTGGGWQDQVGGLMPGIKVGRS
RAQLPLKVEVEEVTVPEGFVQKLNDHLLLVYTGKTRLARNLLQDVLRSWYARLPAVVQNA
HSLVRQTEECAEGFRQGSLPLLGQCLTSYWEQKKLMAPGCEPLTVRRMMDVLAPHVHGQS
LAGAGGGGFLYLLTKEPQQKEALEAVLAKTEGLGNYSIHLVEVDTQGLSLKLLGTEASTC
CPFP
Enzyme 2 Number of Residues 1084
Enzyme 2 Molecular Weight 117624
Enzyme 2 Theoretical pI 6.21
Enzyme 2 GO Classification
Function
  • ATP binding
  • adenyl nucleotide binding
  • binding
  • catalytic activity
  • kinase activity
  • nucleotide binding
  • phosphotransferase activity, alcohol group as acceptor
  • purine nucleotide binding
  • transferase activity
  • transferase activity, transferring phosphorus-containing groups
Process
  • cellular metabolism
  • metabolism
  • phosphate metabolism
  • phosphorus metabolism
  • phosphorylation
  • physiological process
Component
  • cell
  • cytoplasm
  • intracellular
Enzyme 2 General Function Not Available
Enzyme 2 Specific Function Takes part in the salvage pathway for reutilization of fucose from the degradation of oligosaccharides
Enzyme 2 Pathways
Enzyme 2 Reactions
  • ATP + L-fucose = ADP + beta-L-fucose 1-phosphate
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 21212956 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q8N0W3 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name FUK_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >2973 bp 
ATGGGTCGAGACTTCCCCTTTGATGACTGTGGCAGGGCTTTCACCTGCCTCCCCGTGGAG
AACCCCGAGGCCCCCGTGGAAGCCTTGGTCTGCAACCTGGACTGCCTGCTGGACATCATG
ACCTATCGGCTGGGCCCGGGCTCCCCGCCAGGCGTGTGGGTCTGCAGCACCGACATGCTG
CTGTCTGTTCCTGCAAATCCTGGTATCAGCTGGGACAGCTTCCGGGGAGCCAGAGTGATC
GCCCTCCCAGGGAGCCCGGCCTACGCTCAGAATCATGGCGTCTACCTAACTGACCCCCAG
GGCCTTGTTTTGGACATTTACTACCAGGGCACTGAGGCAGAGATTCAGCGGTGTGTCAGG
CCTGATGGGCGGGTGCCACTGGTCTCTGGGGTTGTCTTCTTCTCTGTGGAGACTGCCGAG
CGCCTCCTAGCCACCCACGTGAGCCCGCCCCTGGATGCCTGCACCTACCTAGGCTTGGAC
TCCGGAGCCCGGCCTGTCCAGCTGTCTCTGTTTTTTGACATTCTCCACTGCATGGCTGAG
AACGTGACCAGGGAGGACTTCCTGGTGGGGAGGCCCCCAGAGTTGGGGCAAGGCGATGCA
GATGTAGCGGGTTATCTGCAGAGCGCCCGGGCCCAGCTGTGGAGGGAGCTTCGCGATCAG
CCCCTTACCATGGCCTATGTCTCCAGCGGCAGCTACAGCTACATGACCTCCTCAGCCAGT
GAGTTCCTGCTCAGCCTCACACTCCCCGGGGCTCCTGGGGCCCAGATTGTGCACTCCCAG
GTGGAGGAGCAGCAGCTTCTGGCGGCCGGGAGCTCTGTGGTCAGCTGCCTGCTGGAGGGC
CCTGTCCAGCTGGGTCCTGGGAGCGTCCTGCAGCACTGCCACCTGCAGGGCCCCATTCAC
ATAGGCGCTGGCTGCTTGGTGACTGGCCTGGATACAGCCCACTCCAAGGCCCTGCATGGC
CGGGAGCTGCGTGACCTTGTCCTGCAGGGACACCACACGCGGCTACACGGCTCCCCGGGC
CACGCCTTCACCCTCGTTGGCCGTCTGGACAGCTGGGAGAGACAGGGGGCAGGCACATAT
CTCAACGTGCCCTGGAGTGAATTCTTCAAGAGGACAGGTGTTCGAGCCTGGGACCTGTGG
GACCCCGAGACGCTGCCCGCAGAGTACTGCCTTCCCAGCGCCCGCCTCTTTCCTGTGCTC
CACCCCTCGAGGGAGCTGGGACCCCAGGACCTGCTGTGGATGCTGGACCACCAGGAGGAT
GGGGGCGAGGCCCTGCGAGCCTGGCGGGCCTCCTGGCGCCTGTCCTGGGAGCAGCTGCAG
CCGTGCCTGGATCGGGCTGCCACGCTGGCCTCTCGCCGGGACCTGTTCTTCCGCCAGGCC
CTGCATAAGGCGCGGCACGTGCTGGAGGCCCGGCAGGACCTCAGCCTGCGCCCGCTGATC
TGGGCTGCTGTCCGCGAGGGCTGCCCCGGGCCCCTGCTGGCCACGCTGGACCAGGTTGCA
GCTGGGGCAGGAGACCCTGGTGTGGCGGCACGGGCACTGGCCTGTGTGGCGGACGTCCTG
GGCTGCATGGCAGAGGGCCGTGGGGGCTTGCGGAGCGGGCCAGCTGCCAACCCTGAGTGG
ATGCGGCCCTTCTCATACCTGGAGTGTGGAGACCTGGCAGCGGGCGTGGAGGCGCTTGCC
CAGGAGAGGGACAAGTGGCTAAGCAGGCCAGCCTTGCTGGTGCGAGCGGCCCGCCACTAT
GAGGGGGCTGGTCAGATCCTGATCCGCCAGGCTGTGATGTCAGCCCAGCACTTTGTCTCC
ACAGAGCAGGTGGAACTGCCGGGACCTGGGCAGTGGGTGGTGGCTGAGTGCCCGGCCCGT
GTGGATTTCTCTGGGGGCTGGAGTGACACGCCACCCCTTGCCTATGAGCTTGGCGGGGCT
GTGCTGGGCCTGGCTGTGCGAGTGGACGGCCGCCGGCCCATCGGAGCCAGGGCACGCCGC
ATCCCGGAGCCTGAGCTGTGGCTGGCGGTGGGGCCTCGGCAGGATGAGATGACTGTGAAG
ATAGTGTGCCGGTGCCTGGCTGACCTGCGGGACTACTGCCAGCCTCATGCCCCAGGGGCC
CTGCTGAAGGCGGCCTTCATCTGTGCAGGGATCGTGCATGTCCACTCGGAACTCCAGCTG
AGTGAGCAGCTGCTCCGCACCTTCGGGGGCGGCTTTGAGCTGCACACCTGGTCTGAGCTG
CCCCACGGCTCTGGCCTGGGCACCAGCAGCATCCTGGCAGGCACTGCCCTGGCTGCCTTG
CAGCGAGCCGCAGGCCGGGTGGTGGGCACGGAAGCCCTGATCCACGCAGTGCTGCACCTG
GAGCAGGTGCTCACCACTGGAGGTGGCTGGCAGGACCAAGTAGGTGGCCTAATGCCTGGC
ATCAAGGTGGGGCGCTCCCGGGCTCAGCTGCCACTGAAGGTGGAGGTAGAAGAGGTCACG
GTGCCTGAGGGCTTTGTCCAGAAGCTCAATGACCACCTGCTCTTGGTGTACACTGGCAAG
ACCCGCCTGGCTCGGAACCTGCTGCAGGATGTGCTGAGGAGCTGGTATGCCCGACTTCCT
GCTGTGGTGCAGAATGCCCACAGCCTGGTACGGCAAACTGAGGAGTGTGCTGAAGGCTTC
CGCCAAGGAAGCCTGCCTCTGCTGGGCCAGTGCCTGACCTCGTACTGGGAGCAGAAGAAG
CTCATGGCTCCAGGCTGTGAGCCCCTGACTGTGCGGCGTATGATGGATGTCCTGGCCCCC
CACGTGCATGGCCAGAGCCTGGCTGGGGCAGGCGGTGGAGGCTTTCTCTATCTGTTGACC
AAGGAGCCACAGCAAAAGGAGGCCTTGGAGGCGGTGCTGGCCAAGACCGAGGGCCTTGGG
AATTACAGCATCCACCTGGTTGAAGTGGACACTCAGGGCCTGAGCCTGAAGCTGCTGGGG
ACCGAGGCCTCAACCTGTTGCCCTTTCCCATGA
Enzyme 2 GenBank Gene ID AJ441184 Link Image
Enzyme 2 GeneCard ID FUK Link Image
Enzyme 2 GenAtlas ID FUK Link Image
Enzyme 2 HGNC ID HGNC:29500 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Hinderlich S, Berger M, Blume A, Chen H, Ghaderi D, Bauer C: Identification of human L-fucose kinase amino acid sequence. Biochem Biophys Res Commun. 2002 Jun 14;294(3):650-4. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available