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Identification
YMDB IDYMDB00674
Namealdehydo-D-galacturonate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGalacturonic acid, also known as D-galacturonate or calcium pectate, 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. Galacturonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Galacturonic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • D-Galactopyranuronic acid
  • D-Galacturonate
  • D-Galacturonic acid
  • Galactopyranuronic acid, D-
  • Galacturonic acid, D-
  • hexuronic acid
  • (2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoic acid
  • (2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoate
  • Galacturonate
  • Aldehydo-D-galacturonic acid
  • DL-Galacturonic acid
  • Galacturonic acid, (D)-isomer
  • Galacturonic acid, (alpha-D)-isomer
  • Galacturonic acid, calcium, sodium salt, (D)-isomer
  • Galacturonic acid, monosodium salt, (D)-isomer
  • Anhydrogalacturonic acid
  • Calcium pectate
  • Calcium polygalacturonate
  • Galacturonan
  • Homogalacturonan
  • Pectate
  • Pectic acid
  • Polygalacturonic acid
  • Polygalacturonic acid homopolymer
  • Polygalacturonic acid, aluminum salt
  • Polygalacturonic acid, calcium salt
  • Polygalacturonic acid, homopolymer (D)-isomer
  • Polygalacturonic acid, homopolymer sodium salt
  • Polygalacturonic acid, sulfated
  • Sodium pectate
  • Sodium polygalacturonate
  • Aldehydo-D-galacturonate
CAS number685-73-4
WeightAverage: 194.1394
Monoisotopic: 194.042652674
InChI KeyIAJILQKETJEXLJ-RSJOWCBRSA-N
InChIInChI=1S/C6H10O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h1-5,8-11H,(H,12,13)/t2-,3+,4+,5-/m0/s1
IUPAC Name(2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
Traditional IUPAC Namealdehydo-D-galacturonic acid
Chemical FormulaC6H10O7
SMILES[H]C(=O)[C@H](O)[C@@H](O)[C@@H](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
  • Hexose monosaccharide
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Fatty acyl
  • Hydroxy acid
  • Fatty acid
  • Alpha-hydroxy acid
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Aldehyde
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point166 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility100 g/LALOGPS
logP-2.3ALOGPS
logP-3.2ChemAxon
logS-0.29ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.21 m³·mol⁻¹ChemAxon
Polarizability16.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Pentose and glucuronate interconversionsec00040 Map00040
Starch and sucrose metabolismec00500 Map00500
SMPDB ReactionsNot Available
KEGG Reactions
water + Pectin aldehydo-D-galacturonate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9800000000-1d25ab641e968717daf1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00n0-3139450000-1762a4c61557c689a607JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03e9-0900000000-04b6c8cb4b4b2c077202JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0lk9-9700000000-4260c2e124c927041b62JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-650b5bb9db964b1c3e87JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9410000000-180d0e747dbcb5b21b01JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056s-2900000000-86606b8382ffe403bc8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9500000000-af67bc97552641417beeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-205a7cff1e298283a080JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05p9-9700000000-ee070fab487c9f3e49b7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9400000000-284825e422ba9585f17bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-64d4f9d758e2a4eeba68JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID47962
HMDB IDHMDB0002545
Pubchem Compound ID439215
Kegg IDC00333
ChemSpider ID24770201
FOODB IDFDB001161
Wikipedia IDD-Galacturonic acid
BioCyc IDNot Available

Enzymes

General function:
Involved in polygalacturonase activity
Specific function:
Random hydrolysis of (1->4)-alpha-D- galactosiduronic linkages in pectate and other galacturonans
Gene Name:
PGU1
Uniprot ID:
P47180
Molecular weight:
37286.60156
Reactions