Record Information
Version2.0
Creation Date2012-05-31 14:29:30 -0600
Update Date2015-06-03 17:19:23 -0600
Secondary Accession Numbers
  • ECMDB20138
Identification
Name:D-Fructuronate
Description:D-fructuronate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. One of the most divergent members of this superfamily, uronate isomerase from Escherichia coli, catalyzes the isomerization of d-glucuronate to d-fructuronate and d-galacturonate to d-tagaturonate and is the only uronate isomerase in this organism. (PMID 18171028)
Structure
Thumb
Synonyms:
  • D-Fructofuranuronic aicd
  • D-Fructuronic acid
  • D-Lyxo-hex-5-ulofuranosonate
  • D-Lyxo-hex-5-ulofuranosonic acid
  • Fructuronate
  • Fructuronic acid
Chemical Formula:C6H10O7
Weight:Average: 194.1394
Monoisotopic: 194.042652674
InChI Key:PTCIWUZVDIQTOW-XDJBDKDSSA-N
InChI:InChI=1S/C6H10O7/c7-1-6(12)4(9)2(8)3(13-6)5(10)11/h2-4,7-9,12H,1H2,(H,10,11)/t2-,3+,4+,6?/m1/s1
CAS number:669-90-9
IUPAC Name:(2S,3S,4S)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolane-2-carboxylic acid
Traditional IUPAC Name:D-fructuronate
SMILES:[H][C@]1(O)[C@]([H])(O)C(O)(CO)O[C@]1([H])C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Pentose monosaccharide
  • Beta-hydroxy acid
  • Sugar acid
  • Hydroxy acid
  • Monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Polyol
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Primary alcohol
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility637.0 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.4ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.23 m3·mol-1ChemAxon
Polarizability16.4 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
hexuronide and hexuronate degradationPW000834 Pw000834Pw000834 greyscalePw000834 simple
inner membrane transportPW000786 Pw000786Pw000786 greyscalePw000786 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-1900000000-2b8f975dd22a7e399465View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-3900000000-860690fdebac0a9e90bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9200000000-53984abf2627b85ee328View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3900000000-3d96c33887e1f346e941View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002e-3900000000-aeddfeb0da00a9d7627cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-e2a89f0dd9d53ec01f14View in MoNA
References
References:
  • 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
  • Nguyen, T. T., Brown, S., Fedorov, A. A., Fedorov, E. V., Babbitt, P. C., Almo, S. C., Raushel, F. M. (2008). "At the periphery of the amidohydrolase superfamily: Bh0493 from Bacillus halodurans catalyzes the isomerization of D-galacturonate to D-tagaturonate." Biochemistry 47:1194-1206. Pubmed: 18171028
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16849
HMDB IDNot Available
Pubchem Compound ID439343
Kegg IDC00905
ChemSpider ID388470
Wikipedia IDNot Available
BioCyc IDFRUCTURONATE
EcoCyc IDFRUCTURONATE

Enzymes

General function:
Involved in glucuronate isomerase activity
Specific function:
D-glucuronate = D-fructuronate
Gene Name:
uxaC
Uniprot ID:
P0A8G3
Molecular weight:
53987
Reactions
D-glucuronate = D-fructuronate.
D-galacturonate = D-tagaturonate.
General function:
Involved in oxidation-reduction process
Specific function:
D-mannonate + NAD(+) = D-fructuronate + NADH
Gene Name:
uxuB
Uniprot ID:
P39160
Molecular weight:
53580
Reactions
D-mannonate + NAD(+) = D-fructuronate + NADH.
General function:
zinc ion binding
Specific function:
Not known; probable catabolic enzyme.
Gene Name:
rspB
Uniprot ID:
P38105
Molecular weight:
36563
Reactions
=

Transporters

General function:
Involved in gluconate transmembrane transporter activity
Specific function:
High-affinity gluconate transporter with fairly broad specificity, including low affinity for glucuronate, several disaccharides, and some hexoses, but not glucose
Gene Name:
gntP
Uniprot ID:
P0AC94
Molecular weight:
47137
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368