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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-03-01 03:12:36 UTC
Secondary Accession Numbers
  • HMDB00565
Metabolite Identification
Common NameGalactonic acid
DescriptionGalactonic acid is a sugar acid that is a metabolic breakdown product of galactose. Galactose dehydrogenase is responsible for converting galactose to galactonolactone, which then spontaneously or enzymatically converts to galactonic acid. Once formed, galactonic acid may enter the pentose phosphate pathway. Galactonic acid is increased in red blood cells of galactosemic patients, due to a galactose-1-phosphate uridyltransferase (GALT) deficiency (PMID: 14680973 , OMMBID: The Online Metabolic and Molecular Bases of Inherited Disease, Ch.72). When present in sufficiently high levels, galactonic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactonic acid are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactonic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, liver abnormalities (jaundice), kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated galactosemia. Many affected children with organic acidemias experience intellectual disability or delayed development. High levels of galactonic acid in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure.
D-Galactonic acidKegg
Galactonic acid, (D)-isomerMeSH
Galactonic acid, monopotassium saltMeSH
Galactonic acid, (L)-isomerMeSH
Chemical FormulaC6H12O7
Average Molecular Weight196.1553
Monoisotopic Molecular Weight196.058302738
IUPAC Name(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
Traditional Namegalactonic acid
CAS Registry Number13382-27-9
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
  • 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 Descriptors
Physiological effect

Health effect:

  Health condition:


Biological location:


  Biofluid and excreta:

  Cell and elements:



Physical Properties
Experimental Properties
Melting Point133 - 136 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility159 g/LALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.27 m³·mol⁻¹ChemAxon
Polarizability17.07 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0gb9-1973000000-8a50553fe225b27795e1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1973000000-8a50553fe225b27795e1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0931000000-64524701c5b50ec7e875View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tu-9500000000-abc0b019db16afd3352bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-03fr-6121297000-698854fa2453487a1d69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-056s-0900000000-9dfe4c3a61306fdf2051View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-03di-3900000000-a0e411580bfda8c3c12eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0300-9100000000-8235697c497449a4272dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-9081b4da0decbd05f2d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9400000000-79c4dcd310d5cacca35cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08i9-9000000000-62e401fc518adf3537bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0adu-9600000000-2d2f2523012a7bbe0e8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4u-9300000000-00e22f3157480a68e695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-87d75121bafb2a63a0f8View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Red Blood Cell
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified2.00 (0.69 - 3.84) uMChildren (1-13 years old)Both
BloodDetected and Quantified2.00 (0.69 - 3.84) uMChildren (1 - 13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
FecesDetected but not Quantified Infant (0-1 year old)Both
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected and Quantified43.25 +/- 28.14 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified3.00 (0.68 - 6.47) uMChildren (1-13 years old)Not Specified
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022122
KNApSAcK IDNot Available
Chemspider ID114198
KEGG Compound IDC00880
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound128869
PDB IDNot Available
ChEBI ID16534
Synthesis ReferenceLevene, P. A.; Simms, H. S. Lactone formation mono- and dicarboxylic sugar acids. Journal of Biological Chemistry (1925), 65 31-47.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  2. Shinka T, Inoue Y, Peng H, Zhen-Wei X, Ose M, Kuhara T: Urine screening of five-day-old newborns: metabolic profiling of neonatal galactosuria. J Chromatogr B Biomed Sci Appl. 1999 Sep 24;732(2):469-77. [PubMed:10517369 ]
  3. Yager CT, Chen J, Reynolds R, Segal S: Galactitol and galactonate in red blood cells of galactosemic patients. Mol Genet Metab. 2003 Nov;80(3):283-9. [PubMed:14680973 ]