Record Information
Version2.0
Creation Date2012-05-31 10:28:05 -0600
Update Date2015-09-13 12:56:08 -0600
Secondary Accession Numbers
  • ECMDB00639
Identification
Name:Galactaric acid
DescriptionGalactaric acid is the dicarboxylic sugar acid resulting from oxidation glactose with dilute nitric acid. It is a substrate of galactarate O-hydroxycinnamoyltransferase [EC 2.3.1.130]. (KEGG)
Structure
Thumb
Synonyms:
  • (2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioate
  • (2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
  • meso-galactarate
  • D-Galactarate
  • D-Galactaric acid
  • Galactarate
  • Galactaric acid
  • Galactosaccharate
  • Galactosaccharic acid
  • Hexarate
  • Hexaric acid
  • Meso-galactarate
  • Meso-galactaric acid
  • Mucate
  • Mucic acid
  • Saccharolactate
  • Saccharolactic acid
  • Schleimsaure
Chemical Formula:C6H10O8
Weight:Average: 210.1388
Monoisotopic: 210.037567296
InChI Key:DSLZVSRJTYRBFB-DUHBMQHGSA-N
InChI:InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-
CAS number:526-99-8
IUPAC Name:(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
Traditional IUPAC Name:mucin
SMILES:O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:220-225 °C
Experimental Properties:
PropertyValueSource
Water Solubility:3.3 mg/mL at 14 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility63.1 g/LALOGPS
logP-1.8ALOGPS
logP-3.1ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.14 m³·mol⁻¹ChemAxon
Polarizability16.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
superpathway of D-glucarate and D-galactarate degradationPW000795 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Ascorbate and aldarate metabolism ec00053
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-001l-0987000000-76d3c6748cb8a79adc39View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001l-0987000000-76d3c6748cb8a79adc39View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9400000000-b80ffbca6c943091f16eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-00b9-6011394000-83b916b3001ad13cf34dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-052r-9260000000-16fac7d5f0f85285824dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0abi-9000000000-80a4d5a9910d243f2e48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0abc-9000000000-144a5e96a20e3c66ca9dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0190000000-53cb6532b098f7615896View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-052r-9430000000-7bc8b56c9c00f7aed59fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-34bca663662f41b51683View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-05fr-9000000000-c1a4fdc6f3d7d8e237aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-05fr-9000000000-f2f36dc0c7eca0f78710View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-052r-9240000000-c24ca4338feeca20c7f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0190000000-53cb6532b098f7615896View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-9430000000-7bc8b56c9c00f7aed59fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-34bca663662f41b51683View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fr-9000000000-c1a4fdc6f3d7d8e237aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fr-9000000000-f2f36dc0c7eca0f78710View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-052r-9240000000-c24ca4338feeca20c7f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-1940000000-66a37b8eabfbc367df77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9700000000-ae255ce964e55a9644c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-fa70d3c1751580028d65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0adr-9820000000-19f2dbe53ca43b0a1195View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9500000000-e0ce27927a6119cf1489View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ap0-9100000000-0c338926a15f642737e1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
  • 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:Fauvarque, Jean-Francois; Guerin, Christophe; Petit, Serge; De Regis, Baynast. Process and electrolytic cell for preparing galactaric acid. Fr. Demande (1994), 14 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID30852
HMDB IDHMDB00639
Pubchem Compound ID3037582
Kegg IDC00879
ChemSpider ID2301286
WikipediaMucic acid
BioCyc IDD-GALACTARATE
EcoCyc IDD-GALACTARATE
Ligand ExpoGAE

Enzymes

General function:
Involved in hydro-lyase activity
Specific function:
D-galactarate = 5-dehydro-4-deoxy-D-glucarate + H(2)O
Gene Name:
garD
Uniprot ID:
P39829
Molecular weight:
56401
Reactions
D-galactarate = 5-dehydro-4-deoxy-D-glucarate + H(2)O.

Transporters

General function:
Involved in transporter activity
Specific function:
Uptake of D-glucarate
Gene Name:
gudP
Uniprot ID:
Q46916
Molecular weight:
49142
General function:
Involved in transporter activity
Specific function:
Uptake of D-galactarate
Gene Name:
garP
Uniprot ID:
P0AA80
Molecular weight:
49009
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