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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:56 UTC
Update Date2018-05-20 06:59:16 UTC
HMDB IDHMDB0002545
Secondary Accession Numbers
  • HMDB0003348
  • HMDB02545
  • HMDB03348
Metabolite Identification
Common NameGalacturonic acid
DescriptionAldehydo-D-galacturonate, also known as D-galacturonic acid, 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. Aldehydo-D-galacturonate is soluble (in water) and a weakly acidic compound (based on its pKa). Aldehydo-D-galacturonate has been primarily detected in feces. Within the cell, aldehydo-D-galacturonate is primarily located in the cytoplasm. Aldehydo-D-galacturonate exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, aldehydo-D-galacturonate can be found in a number of food items such as cocoa bean, wild celery, sunflower, and okra. This makes aldehydo-D-galacturonate a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoic acidChEBI
D-Galacturonic acidChEBI
(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxy-6-oxohexanoateGenerator
GalacturonateGenerator
D-GalacturonateGenerator
DL-Galacturonic acidHMDB
D-Galactopyranuronic acidHMDB
Galacturonic acid, (D)-isomerMeSH
Galacturonic acid, (alpha-D)-isomerMeSH
Galacturonic acid, calcium, sodium salt, (D)-isomerMeSH
Galacturonic acid, monosodium salt, (D)-isomerMeSH
Chemical FormulaC6H10O7
Average Molecular Weight194.1394
Monoisotopic Molecular Weight194.042652674
IUPAC Name(2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid
Traditional Namealdehydo-D-galacturonic acid
CAS Registry Number14982-50-4
SMILES
O[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O
InChI Identifier
InChI=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
InChI KeyIAJILQKETJEXLJ-RSJOWCBRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as glucuronic acid derivatives. These 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-9800000000-1d25ab641e968717daf1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00n0-3139450000-1762a4c61557c689a607View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03e9-0900000000-04b6c8cb4b4b2c077202View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0lk9-9700000000-4260c2e124c927041b62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-650b5bb9db964b1c3e87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9410000000-180d0e747dbcb5b21b01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056s-2900000000-86606b8382ffe403bc8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9500000000-af67bc97552641417beeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-205a7cff1e298283a080View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05p9-9700000000-ee070fab487c9f3e49b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9400000000-284825e422ba9585f17bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-64d4f9d758e2a4eeba68View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001161
KNApSAcK IDC00001120
Chemspider ID76444
KEGG Compound IDC08348
BioCyc IDD-GALACTURONATE
BiGG IDNot Available
Wikipedia LinkD-Galacturonic acid
METLIN ID6713
PubChem Compound84740
PDB IDDGU
ChEBI ID47962
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wu AM, Song SC, Chen YY, Gilboa-Garber N: Defining the carbohydrate specificities of aplysia gonad lectin exhibiting a peculiar D-galacturonic acid affinity. J Biol Chem. 2000 May 12;275(19):14017-24. [PubMed:10799474 ]
  2. Hommes FA, Varghese M: High-performance liquid chromatography of urinary oligosaccharides in the diagnosis of glycoprotein degradation disorders. Clin Chim Acta. 1991 Dec 16;203(2-3):211-24. [PubMed:1777982 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215