Record Information
Version2.0
Creation Date2012-05-31 14:29:36 -0600
Update Date2015-06-03 17:19:23 -0600
Secondary Accession Numbers
  • ECMDB20140
Identification
Name:D-Galactonate
Description:D-galactonate is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. The gluconic acid is produced by direct extracellular oxidation of glucose by a glucose dehydrogenase equipped with pyrroloquinoline quinone (PQQ) as a cofactor. (PMID 14756528) Glucuronate is converted to l-gulonate by aldehyde reductase, an enzyme of the aldo-keto reductase superfamily. l-Gulonate is converted to l-gulonolactone by a lactonase identified as SMP30 or regucalcin, whose absence in mice leads to vitamin C deficiency. (PMID 17222174)
Structure
Thumb
Synonyms:
  • (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoate
  • (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
  • 2,3,4,5,6-Pentahydroxyhexanoate
  • 2,3,4,5,6-Pentahydroxyhexanoic acid
  • Altronate
  • Altronic acid
  • D-Altronate
  • D-Altronic acid
  • D-Galactonate
  • D-Galactonic acid
  • D-Gluco-hexonate
  • D-Gluco-hexonic acid
  • D-Gluconate
  • D-Gluconic acid
  • D-Mannonate
  • D-Mannonic acid
  • Galactonate
  • Galactonic acid
  • Gluconate
  • Gluconate, technical
  • Gluconic acid
  • Gluconic acid, technical
  • Gulonate
  • Gulonic acid
  • Hexonate
  • Hexonic acid
  • L-Galactonate
  • L-Galactonic acid
  • L-Gulonate
  • L-Gulonic acid
  • L-Idonate
  • L-Idonic acid
  • Mannonate
  • Mannonic acid
Chemical Formula:C6H12O7
Weight:Average: 196.1553
Monoisotopic: 196.058302738
InChI Key:RGHNJXZEOKUKBD-UHFFFAOYSA-N
InChI:InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)
CAS number:133-42-6
IUPAC Name:2,3,4,5,6-pentahydroxyhexanoic acid
Traditional IUPAC Name:magnesium gluconate anhydrous
SMILES:OCC(O)C(O)C(O)C(O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassHydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility159.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.27 m3·mol-1ChemAxon
Polarizability16.83 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-2e0c26c445c5561e064cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9500000000-08150b4c43e2fcfe6007View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9100000000-8da11e6efabcbf705943View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ic-9800000000-4dc890f0b0119480c820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9400000000-d470360cffa908b2cb78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-a7d8afb4037ece167045View 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
  • Kim, C. H., Han, S. H., Kim, K. Y., Cho, B. H., Kim, Y. H., Koo, B. S., Kim, Y. C. (2003). "Cloning and expression of pyrroloquinoline quinone (PQQ) genes from a phosphate-solubilizing bacterium Enterobacter intermedium." Curr Microbiol 47:457-461. Pubmed: 14756528
  • Linster, C. L., Van Schaftingen, E. (2007). "Vitamin C. Biosynthesis, recycling and degradation in mammals." FEBS J 274:1-22. Pubmed: 17222174
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID12931
HMDB IDHMDB00565
Pubchem Compound ID604
Kegg IDC15930
ChemSpider ID584
Wikipedia IDNot Available
BioCyc IDD-GALACTONATE
EcoCyc IDD-GALACTONATE

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the NADPH-dependent reduction of glyoxylate and hydroxypyruvate into glycolate and glycerate, respectively. Can also reduce 2,5-diketo-D-gluconate (25DKG) to 5-keto-D- gluconate (5KDG), 2-keto-D-gluconate (2KDG) to D-gluconate, and 2- keto-L-gulonate (2KLG) to L-idonate (IA), but it is not its physiological function. Inactive towards 2-oxoglutarate, oxaloacetate, pyruvate, 5-keto-D-gluconate, D-fructose and L- sorbose. Activity with NAD is very low
Gene Name:
ghrB
Uniprot ID:
P37666
Molecular weight:
35395
Reactions
Glycolate + NADP(+) = glyoxylate + NADPH.
D-glycerate + NAD(P)(+) = hydroxypyruvate + NAD(P)H.
D-gluconate + NADP(+) = 2-dehydro-D-gluconate + NADPH.
General function:
Involved in zinc ion binding
Specific function:
Catalyzes the NADH/NADPH-dependent oxidation of L- idonate to 5-ketogluconate (5KG)
Gene Name:
idnD
Uniprot ID:
P39346
Molecular weight:
37146
Reactions
L-idonate + NAD(P)(+) = 5-dehydrogluconate + NAD(P)H.
General function:
Involved in galactonate dehydratase activity
Specific function:
Catalyzes the dehydration of D-galactonate to 2-keto-3- deoxy-D-galactonate
Gene Name:
dgoD
Uniprot ID:
Q6BF17
Molecular weight:
42523
Reactions
D-galactonate = 2-dehydro-3-deoxy-D-galactonate + H(2)O.
General function:
Involved in zinc ion binding
Specific function:
Putative L-galactonate oxidoreductase that is required for growth on L-galactonate as the sole carbon source
Gene Name:
yjjN
Uniprot ID:
P39400
Molecular weight:
36448

Transporters

General function:
Involved in transporter activity
Specific function:
Intake of galactonate into the cell
Gene Name:
dgoT
Uniprot ID:
P0AA76
Molecular weight:
47076
General function:
Involved in gluconate transmembrane transporter activity
Specific function:
Transports L-idonate, D-gluconate and 5-keto-D- gluconate, from the periplasm across the inner membrane
Gene Name:
idnT
Uniprot ID:
P39344
Molecular weight:
46041
General function:
Involved in transmembrane transport
Specific function:
Responsible for the transport of L-galactonate from the periplasm across the inner membrane (Probable). Is essential for growth on L-galactonate as the sole carbon source
Gene Name:
yjjL
Uniprot ID:
P39398
Molecular weight:
49440
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