| Common Name |
Galactonic acid
| Description |
Galactonate is increased in red blood cells of galactosemic patients, due to a galactose-1-phosphate uridyltransferase (GALT) deficiency ((PMID 14680973 , OMMBID: The Metabolic and Molecliar Bases of Inherited Disease, Ch.72).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
D-Galactonic acidKegg
D-GalactonateGenerator
GalactonateGenerator
Galactonic acid, (D)-isomerMeSH
Galactonic acid, monopotassium saltMeSH
Galactonic acid, (L)-isomerMeSH
| Chemical Formlia |
C6H12O7
| Average Molecliar Weight |
196.1553
| Monoisotopic Molecliar Weight |
196.058302738
| IUPAC Name |
(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
| Traditional Name |
galactonic acid
| CAS Registry Number |
13382-27-9
| SMILES |
OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O
| InChI Identifier |
InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3+,4+,5-/m1/s1
| InChI Key |
RGHNJXZEOKUKBD-MGCNEYSASA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Hydroxy acids and derivatives
| Direct Parent |
Medium-chain hydroxy acids and derivatives
| Alternative Parents |
Medium-chain fatty acids
Hydroxy fatty acids
Beta hydroxy acids and derivatives
Monosaccharides
Alpha hydroxy acids and derivatives
Secondary alcohols
Polyols
Monocarboxylic acids and derivatives
Carboxylic acids
Primary alcohols
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
galactonic acid (CHEBI:16534 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point133 – 136 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
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
Polarizability17.07 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (6 TMS)splash10-0gb9-1973000000-8a50553fe225b27795e1View in MoNA
| GC-MS |
GC-MS Spectrum – GC-EI-TOFsplash10-0002-0931000000-64524701c5b50ec7e875View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, N/A (Annotated)splash10-056s-0900000000-9dfe4c3a61306fdf2051View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, N/A (Annotated)splash10-03di-3900000000-a0e411580bfda8c3c12eView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, N/A (Annotated)splash10-0300-9100000000-8235697c497449a4272dView in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Feces
Urine
| Tissue Location |
Red Blood Cell
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified2.00 (0.69 – 3.84) uMChildren (1-13 years old)Both
Normal
14680973
details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
22411374
details
UrineDetected but not Quantified Adlit (>18 years old)BothNormal
21389975
details
UrineDetected and Quantified43.25 +/- 28.14 umol/mmol creatinineInfant (0-1 year old)BothNormal
2026685
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified3.00 (0.68 – 6.47) uMChildren (1-13 years old)Not Specified
Galactosemia
14680973
details
| Associated Disorders and Diseases |
| Disease References |
| Galactosemia type 1 |
- 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 ]
| Associated OMIM IDs |
230400 (Galactosemia type 1)
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022122
| KNApSAcK ID |
Not Available
| Chemspider ID |
114198
| KEGG Compound ID |
C00880
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00565
| Metagene Link |
HMDB00565
| METLIN ID |
3336
| PubChem Compound |
128869
| PDB ID |
Not Available
| ChEBI ID |
16534
Product: TN1
References |
| Synthesis Reference |
Levene, 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 |
- 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 ]
- 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 ]
- 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 ]
|
PMID: 16682967