L-Fuculose 1-phosphate (ECMDB20165) (M2MDB001012)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (195)
Record Information
Version2.0
Creation Date2012-05-31 14:30:57 -0600
Update Date2015-09-17 15:42:02 -0600
Secondary Accession Numbers
  • ECMDB20165
Identification
Name:L-Fuculose 1-phosphate
DescriptionL-fuculose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Collectively, the data suggest that L-fuculose-1-phosphate plays a role in the regulation of ribose usage as a carbon source by E. Collectively, the data suggest that L-fuculose-1-phosphate plays a role in the regulation of ribose usage as a carbon source by E. Collectively, the data suggest that L-fuculose-1-phosphate plays a role in the regulation of ribose usage as a carbon source by E. (PMID 17709419)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 6-Deoxy-1-O-phosphono-L-tagatose
  • 6-Deoxy-L-lyxo-hex-2-ulose 1-(dihydrogen phosphate)
  • 6-Deoxy-L-lyxo-hex-2-ulose 1-(dihydrogen phosphoric acid)
  • 6-Deoxy-L-tagatose 1-(dihydrogen phosphate)
  • 6-Deoxy-L-tagatose 1-(dihydrogen phosphoric acid)
  • Fuculose-1-P
  • Fuculose-1-phosphate
  • Fuculose-1-phosphoric acid
  • Fuculose1P
  • L-Fuculose 1-phosphoric acid
  • L-Fuculose-1-P
  • Rhamnulose 1-phosphate
  • Rhamnulose 1-phosphoric acid
Chemical Formula:C6H11O8P
Weight:Average: 242.121
Monoisotopic: 242.020251472
InChI Key:KNYGWWDTPGSEPD-UHFFFAOYSA-L
InChI:InChI=1S/C6H13O8P/c1-3(7)5(9)6(10)4(8)2-14-15(11,12)13/h3,5-7,9-10H,2H2,1H3,(H2,11,12,13)/p-2
CAS number:92418-41-2
IUPAC Name:{[(3R,4R,5S)-3,4,5-trihydroxy-2-oxohexyl]oxy}phosphonic acid
Traditional IUPAC Name:L-fuculose 1-phosphate
SMILES:CC(O)C(O)C(O)C(=O)COP([O-])([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Octose monosaccharide
  • Monosaccharide phosphate
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Sugar acid
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility24.9 g/LALOGPS
logP-1.9ALOGPS
logP-2.3ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.89 m³·mol⁻¹ChemAxon
Polarizability20.05 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde + (S)-Lactaldehyde
Adenosine triphosphate + L-Fuculose <> ADP + L-Fuculose 1-phosphate + Hydrogen ion
L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde
Adenosine triphosphate + L-Fuculose <> ADP + L-Fuculose 1-phosphate
L-Fuculose + Adenosine triphosphate > Hydrogen ion + L-Fuculose 1-phosphate + ADP
L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + Lactaldehyde
Adenosine triphosphate + L-Fuculose > ADP + L-Fuculose 1-phosphate
L-fuculose 1-phosphate + L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde
Adenosine triphosphate + keto-L-rhamnulose > L-fuculose 1-phosphate + Adenosine diphosphate + Hydrogen ion + L-Fuculose 1-phosphate + ADP
SMPDB Pathways:
fucose and rhamnose degradationPW000826 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-4690000000-17d50e11374f92e3400bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0570-4920000000-9ae486510db3f7669f8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9400000000-f5b1483aaa2a22aee511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fvi-9820000000-96d11cb52700915d345fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-748c93e00b37e4e87981View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-17db9f9872cd5d9166e0View in MoNA
References
References:
  • Autieri, S. M., Lins, J. J., Leatham, M. P., Laux, D. C., Conway, T., Cohen, P. S. (2007). "L-fucose stimulates utilization of D-ribose by Escherichia coli MG1655 DeltafucAO and E. coli Nissle 1917 DeltafucAO mutants in the mouse intestine and in M9 minimal medium." Infect Immun 75:5465-5475. Pubmed: 17709419
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16647
HMDB IDNot Available
Pubchem Compound ID6857415
Kegg IDC01099
ChemSpider ID5256754
Wikipedia IDNot Available
BioCyc IDFUCULOSE-1P
EcoCyc IDFUCULOSE-1P

Enzymes

Protein Details
1. L-fuculose phosphate aldolase
General function:
Involved in metal ion binding
Specific function:
L-fuculose 1-phosphate = glycerone phosphate + (S)-lactaldehyde
Gene Name:
fucA
Uniprot ID:
P0AB87
Molecular weight:
23775
Reactions
L-fuculose 1-phosphate = glycerone phosphate + (S)-lactaldehyde.
Protein Details
2. L-fuculokinase
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + L-fuculose = ADP + L-fuculose 1- phosphate
Gene Name:
fucK
Uniprot ID:
P11553
Molecular weight:
53235
Reactions
ATP + L-fuculose = ADP + L-fuculose 1-phosphate.
Protein Details
3. Putative aldolase class 2 protein ygbL
General function:
Involved in metal ion binding
Specific function:
Specific function unknown
Gene Name:
ygbL
Uniprot ID:
Q46890
Molecular weight:
23222