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Record Information
Version2.0
Creation Date2012-07-30 14:54:59 -0600
Update Date2015-06-03 17:20:55 -0600
Secondary Accession Numbers
  • ECMDB21219
Identification
Name:GDP-4-Oxo-L-fucose
DescriptionGDP-4-oxo-L-fucose is a member of the chemical class known as Purine Nucleotide Sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Structure
Thumb
Synonyms:
  • GDP-4-Oxo-L-fucose
  • Guanosine 5'-[3-(6-deoxy-L-xylo-hexopyranosyl-4-ulose) dihydrogen diphosphate]
  • Guanosine 5'-[3-(6-deoxy-L-xylo-hexopyranosyl-4-ulose) dihydrogen diphosphoric acid]
Chemical Formula:C16H21N5O15P2
Weight:Average: 585.31
Monoisotopic: 585.050938051
InChI Key:PNHLMHWWFOPQLK-WAMCPPDZSA-L
InChI:InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/p-2/t4-,5+,8+,9+,10+,11-,14+,15?/m0/s1
CAS number:Not Available
IUPAC Name:[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxy}phosphonate
Traditional IUPAC Name:[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(3S,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl phosphonato]oxyphosphonate
SMILES:[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])OP([O-])(=O)OP([O-])(=O)OC2([H])O[C@]([H])(C(=O)[C@@]([H])(O[H])[C@]2([H])O[H])C([H])([H])[H])[C@@]1([H])O[H])N1C([H])=NC2=C1N([H])C(=NC2=O)N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Aminopyrimidine
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.83 g/LALOGPS
logP-0.95ALOGPS
logP-4.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.54ChemAxon
pKa (Strongest Basic)1.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area309.7 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity113.52 m³·mol⁻¹ChemAxon
Polarizability48.39 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0200090000-63731f453f9fe730872dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0121090000-ce0277aca6d4031f71c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-0c3578e30354ce3381d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3200090000-3d8eb9f14992876ae999View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-8710090000-7174b0a35c72a2bdae67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0avi-9200000000-48d202975eff6b7c9db4View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28530
HMDB IDNot Available
Pubchem Compound ID46173240
Kegg IDC05389
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2128
EcoCyc IDCPD0-2128

Enzymes

General function:
Involved in catalytic activity
Specific function:
Two step NADP-dependent conversion of GDP-4-dehydro-6- deoxy-D-mannose to GDP-fucose, involving an epimerase and a reductase reaction
Gene Name:
fcl
Uniprot ID:
P32055
Molecular weight:
36141
Reactions
GDP-L-fucose + NADP(+) = GDP-4-dehydro-6-deoxy-D-mannose + NADPH.