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Record Information
Version1.0
Creation Date2016-09-30 22:20:07 UTC
Update Date2020-06-04 21:05:04 UTC
BMDB IDBMDB0000143
Secondary Accession Numbers
  • BMDB00143
Metabolite Identification
Common NameD-Galactose
DescriptionD-Galactose, also known as alpha-D-gal or alpha D-galactose, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-Galactose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Galactose exists in all living species, ranging from bacteria to humans. D-Galactose participates in a number of enzymatic reactions, within cattle. In particular, D-Galactose and sorbitol can be converted into melibiitol through its interaction with the enzyme Alpha-galactosidase a. In addition, D-Galactose and D-mannose can be converted into epimelibiose through its interaction with the enzyme Alpha-galactosidase a. In cattle, D-galactose is involved in the metabolic pathway called the galactose metabolism pathway. D-Galactose is a potentially toxic compound. D-Galactose has been found to be associated with several diseases known as eosinophilic esophagitis, patent ductus venosus, and colorectal cancer; also d-galactose has been linked to several inborn metabolic disorders including galactose-1-phosphate uridyltransferase deficiency and galactosemia type 1.
Structure
Thumb
Synonyms
ValueSource
ALPHA D-GALACTOSEChEBI
alpha-D-GalChEBI
Gal-alphaChEBI
alpha-D-GalactoseKegg
a D-GALACTOSEGenerator
Α D-galactoseGenerator
a-D-GalGenerator
Α-D-galGenerator
Gal-aGenerator
Gal-αGenerator
a-D-GalactoseGenerator
Α-D-galactoseGenerator
(+)-GalactoseHMDB
5AbpHMDB
8AbpHMDB
alpha-D-GalactopyranoseHMDB
D-(+)-GalactoseHMDB
D-HexoseHMDB
GALHMDB
GalactoseHMDB
Galactose (NF)HMDB
GLAHMDB
GLCHMDB
HexoseHMDB
SHU 508 aMeSH, HMDB
SH-TA-508MeSH, HMDB
SHU 508MeSH, HMDB
LevovistMeSH, HMDB
SHU-508MeSH, HMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number59-23-4
SMILESNot Available
InChI Identifier
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4+,5-,6+/m1/s1
InChI KeyWQZGKKKJIJFFOK-PHYPRBDBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point170 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility683.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
  • Mitochondria
Biospecimen Locations
  • Blood
  • Brain
  • Liver
  • Milk
  • Prostate Tissue
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified730.39 +/- 277.50 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified500 - 1700 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified1200 - 1760 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified67719.0879 +/- 8881.192 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified443 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified300 +/- 18 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified334 +/- 15 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified318 +/- 19 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified310 +/- 39 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified416.306 (216.479-494.0166) uMNot SpecifiedNot Specified
Normal
    • Esperanza Troyano...
details
MilkDetected and Quantified901.88 +/- 624.82 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified190-260 uMNot SpecifiedNot Specified
Normal
    • Faulkner, A., Cha...
details
MilkDetected and Quantified932.526 +/- 68.274 uMNot SpecifiedNot Specified
Normal
    • RAJAN SHARMA YUDH...
details
MilkDetected and Quantified224.250 +/- 4.996 uMNot SpecifiedNot Specified
Normal
    • Tommaso R.I. Cata...
details
MilkDetected and Quantified310 +/- 39 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified300 +/- 18 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified334 +/- 15 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified318 +/- 19 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1023.29 +/- 936.59 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified763.813 +/- 751.731 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis
details
Ruminal FluidDetected and Quantified2415.813 +/- 1248.434 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000143
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021787
KNApSAcK IDC00001119
Chemspider IDNot Available
KEGG Compound IDC00984
BioCyc IDALPHA-D-GALACTOSE
BiGG IDNot Available
Wikipedia LinkGalactose
METLIN IDNot Available
PubChem Compound439357
PDB IDNot Available
ChEBI ID28061
References
Synthesis ReferenceAvigad, Gad. Synthesis of D-galactose-6-t and D-galactosides-6-t. Carbohydrate Research (1967), 3(4), 430-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Faulkner A, Pollock HT: Changes in the concentration of metabolites in milk from cows fed on diets supplemented with soyabean oil or fatty acids. J Dairy Res. 1989 May;56(2):179-83. [PubMed:2760296 ]
  2. Nakamura T, Kawase H, Kimura K, Watanabe Y, Ohtani M, Arai I, Urashima T: Concentrations of sialyloligosaccharides in bovine colostrum and milk during the prepartum and early lactation. J Dairy Sci. 2003 Apr;86(4):1315-20. doi: 10.3168/jds.S0022-0302(03)73715-1. [PubMed:12741556 ]
  3. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  4. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  5. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  6. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  7. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  8. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Major enzyme for galactose metabolism.
Gene Name:
GALK1
Uniprot ID:
A6H768
Molecular weight:
42227.0
Reactions
D-Galactose + Adenosine triphosphate → Galactose 1-phosphate + ADPdetails
General function:
Involved in 20-alpha-hydroxysteroid dehydrogenase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols. Displays enzymatic activity towards endogenous metabolites such as aromatic and aliphatic aldehydes, ketones, monosacharides, bile acids and xenobiotics substrates. Key enzyme in the polyol pathway, catalyzes reduction of glucose to sorbitol during hyperglycemia. Reduces steroids and their derivatives and prostaglandins. Displays low enzymatic activity toward all-trans-retinal, 9-cis-retinal, and 13-cis-retinal. Catalyzes the reduction of diverse phospholipid aldehydes such as 1-palmitoyl-2-(5-oxovaleroyl)-sn -glycero-3-phosphoethanolamin (POVPC) and related phospholipid aldehydes that are generated from the oxydation of phosphotidylcholine and phosphatdyleethanolamides. Plays a role in detoxifying dietary and lipid-derived unsaturated carbonyls, such as crotonaldehyde, 4-hydroxynonenal, trans-2-hexenal, trans-2,4-hexadienal and their glutathione-conjugates carbonyls (GS-carbonyls).
Gene Name:
AKR1B1
Uniprot ID:
P16116
Molecular weight:
35919.0
Reactions
D-Galactose + NAD → Galactitol + NADHdetails
General function:
Carbohydrate transport and metabolism
Specific function:
Essential for the degradation of glycogen in lysosomes (PubMed:10723725). Has highest activity on alpha-1,4-linked glycosidic linkages, but can also hydrolyze alpha-1,6-linked glucans.
Gene Name:
GAA
Uniprot ID:
Q9MYM4
Molecular weight:
104757.0
Reactions
Sucrose + Water → D-Galactose + D-Fructosedetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Scavenger receptor that displays several functions associated with host defense. Promotes binding and phagocytosis of Gram-positive, Gram-negative bacteria and yeast. Mediates the recognition, internalization and degradation of oxidatively modified low density lipoprotein (oxLDL) by vascular endothelial cells. Binds to several carbohydrates including Gal-type ligands, D-galactose, L- and D-fucose, GalNAc, T and Tn antigens in a calcium-dependent manner and internalizes specifically GalNAc in nurse-like cells. Binds also to sialyl Lewis X or a trisaccharide and asialo-orosomucoid (ASOR) (By similarity).
Gene Name:
COLEC12
Uniprot ID:
A6QP79
Molecular weight:
81751.0
General function:
Carbohydrate transport and metabolism
Specific function:
Lectin that binds to various sugars: mannose = ManNAc > fucose > GlcNAc > glucose = maltose > galactose > lactose > GalNAc. Could play a role in immune defense.
Gene Name:
CL43
Uniprot ID:
P42916
Molecular weight:
33616.0
General function:
Involved in lipid binding
Specific function:
Component of triglyceride-rich very low density lipoproteins (VLDL) and high density lipoproteins (HDL) in plasma. Plays a multifaceted role in triglyceride homeostasis. Intracellularly, promotes hepatic very low density lipoprotein 1 (VLDL1) assembly and secretion; extracellularly, attenuates hydrolysis and clearance of triglyceride-rich lipoproteins (TRLs). Impairs the lipolysis of TRLs by inhibiting lipoprotein lipase and the hepatic uptake of TRLs by remnant receptors. Formed of several curved helices connected via semiflexible hinges, so that it can wrap tightly around the curved micelle surface and easily adapt to the different diameters of its natural binding partners.
Gene Name:
APOC3
Uniprot ID:
P19035
Molecular weight:
10692.0
General function:
Not Available
Specific function:
Removes terminal alpha-N-acetylgalactosamine residues from glycolipids and glycopeptides. Required for the breakdown of glycolipids (By similarity).
Gene Name:
NAGA
Uniprot ID:
Q58DH9
Molecular weight:
46533.0
Reactions
D-Galactose + Sorbitol → Melibiitoldetails
D-Galactose + D-Mannose → Epimelibiosedetails
D-Galactose + Glycerol → Galactosylglyceroldetails
Stachyose → Raffinose + D-Galactosedetails
Raffinose → Sucrose + D-Galactosedetails
Alpha-Lactose → Melibiose + D-Galactosedetails
Melibiose →2 D-Galactosedetails
Galactosylceramide (d18:1/16:0) + D-Galactose → Galabiosylceramide (d18:1/22:0)details
General function:
Not Available
Specific function:
Not Available
Gene Name:
LCT
Uniprot ID:
E1BK89
Molecular weight:
219131.0
Reactions
Alpha-D-Glucose + D-Galactose → Alpha-Lactose + Waterdetails
Alpha-Lactose + Water → D-Glucose + D-Galactosedetails