D-Galactose (PAMDB000054)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000054
Identification
Name: D-Galactose
Description:D-Galactose is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules. Metabolic pathways for D-Galactose are important not only for the provision of these pathways but also for the prevention of D-Galactose and D-Galactose metabolite accumulation. The main source of D-Galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-Galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-Galactose-1-phosphate. In the presence of D-Galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-Galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. (PMID: 15256214, 11020650, 10408771)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-galactose
  • (+)-Galactose
  • 5abp
  • 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol
  • 8abp
  • a D-Galactose
  • a-D-Galactopyranose
  • a-D-Galactose
  • a-Galactose
  • Alpha D-Galactose
  • Alpha-D-Galactopyranose
  • Alpha-D-Galactose
  • Alpha-Galactose
  • Cerebrose
  • D-(+)-Galactose
  • D-Galactose
  • D-hexose
  • GAL
  • Galactopyranose
  • Galactopyranoside
  • Galactose
  • Galactose (NF)
  • GLA
  • GLC
  • Hexose
  • α D-Galactose
  • α-D-Galactopyranose
  • α-D-Galactose
  • α-Galactose
Chemical Formula: C6H12O6
Average Molecular Weight: 180.1559
Monoisotopic Molecular Weight: 180.063388116
InChI Key: WQZGKKKJIJFFOK-SVZMEOIVSA-N
InChI: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
CAS number: 59-23-4
IUPAC Name:(3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name: (+)-galactose
SMILES:OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Monosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 170 °C
Experimental Properties:
PropertyValueSource
Water Solubility:683.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility782.0 mg/mLALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m3·mol-1ChemAxon
Polarizability16.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Water + D-Galactose > ADP + D-Galactose + Hydrogen ion + Phosphate
Adenosine triphosphate + Water + D-Galactose > ADP + D-Galactose + Hydrogen ion + Phosphate
Adenosine triphosphate + D-Galactose + Alpha-D-Galactose <> ADP + Galactose 1-phosphate + Hydrogen ion
Water + alpha-Lactose > D-Galactose + D-Glucose
beta-D-Galactose > D-Galactose
Galactose 1-phosphate + Water > D-Galactose + Phosphate
Water + Melibiose > D-Galactose + D-Glucose
Adenosine triphosphate + D-Galactose <> ADP + Galactose 1-phosphate
Galactan + Water <> D-Galactose + Galactan
alpha-Lactose + Water <> alpha-D-Glucose + D-Galactose
beta-D-Galactosyl-1,4-beta-D-glucosylceramide + Water <> Glucosylceramide + D-Galactose
Digalactosylceramide + Water <> Galactosylceramide + D-Galactose
Digalactosyl-diacylglycerol + Water <> 1,2-Diacyl-3-beta-D-galactosyl-sn-glycerol + D-Galactose
D-Gal alpha 1->6D-Gal alpha 1->6D-Glucose + Water <> D-Galactose + Melibiose
Water + Globotriaosylceramide <> D-Galactose + Lactosylceramide
Melibiose + Water <> D-Galactose + D-Glucose
Lactose + Water <> D-Glucose + D-Galactose
D-Galactose + NAD 3-keto-&beta;-D-galactose + NADH + Hydrogen ion
-->-->D-Galactose <> D-Galactose
D-Galactose <> D-Galactose
Water + Melibiose > D-Galactose + b-D-Glucose
Water + alpha-Lactose > D-Galactose + b-D-Glucose
D-Galactose + Adenosine triphosphate > Hydrogen ion + Galactose 1-phosphate + ADP
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lai, K., Klapa, M. I. (2004). "Alternative pathways of galactose assimilation: could inverse metabolic engineering provide an alternative to galactosemic patients?" Metab Eng 6:239-244. Pubmed: 15256214
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Synthesis Reference: Avigad, 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
External Links:
ResourceLink
CHEBI ID28061
HMDB IDHMDB00143
Pubchem Compound ID439357
Kegg IDC00124
ChemSpider ID388480
WikipediaGalactose
BioCyc IDALPHA-D-GALACTOSE
EcoCyc IDALPHA-D-GALACTOSE

Enzymes

Protein Details
• Periplasmic beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing beta-D- glucosyl residues with release of beta-D-glucose
Gene Name:
bglX
Locus Tag:
PA1726
Molecular weight:
83 kDa
Reactions
Hydrolysis of terminal, non-reducing beta-D-glucosyl residues with release of beta-D-glucose.

Transporters