Record Information
Version2.0
Creation Date2012-05-31 10:21:49 -0600
Update Date2015-06-03 15:53:14 -0600
Secondary Accession Numbers
  • ECMDB00143
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
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
Weight:Average: 180.1559
Monoisotopic: 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
DescriptionThis compound belongs to the class of chemical entities known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
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:
SMPDB Pathways:
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-08g0-9700000000-d7fbea2263840ca358b3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-066s-0941000000-8f1b68655e0a5ed179e3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ldj-0941000000-84c771fab416aa0a40d8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ktb-0931000000-6f37a774d1ab64585c8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-066s-0931000000-9945093085ef7b0de618View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ldj-0931000000-1ed532d5d2897be775dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9731000000-af5bd67ad0bbb2997839View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-9621000000-9dad5bd1760a891ace2aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fr2-0920000000-d0bbaf502997c43971baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fr2-1920000000-f47f0b66263744db15baView in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-2900000000-358281e9439d096e0a76View in MoNA
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

General function:
Involved in beta-galactosidase activity
Specific function:
Hydrolysis of terminal non-reducing beta-D- galactose residues in beta-D-galactosides
Gene Name:
lacZ
Uniprot ID:
P00722
Molecular weight:
116482
Reactions
Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing alpha-D- galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids
Gene Name:
melA
Uniprot ID:
P06720
Molecular weight:
50657
Reactions
Hydrolysis of terminal, non-reducing alpha-D-galactose residues in alpha-D-galactosides, including galactose oligosaccharides, galactomannans and galactolipids.
General function:
Involved in beta-galactosidase activity
Specific function:
The wild-type enzyme is an ineffective lactase. Two classes of point mutations dramatically improve activity of the enzyme
Gene Name:
ebgA
Uniprot ID:
P06864
Molecular weight:
117878
Reactions
Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides.
General function:
Involved in galactokinase activity
Specific function:
ATP + D-galactose = ADP + alpha-D-galactose 1- phosphate
Gene Name:
galK
Uniprot ID:
P0A6T3
Molecular weight:
41442
Reactions
ATP + D-galactose = ADP + alpha-D-galactose 1-phosphate.
General function:
Involved in aldose 1-epimerase activity
Specific function:
Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose
Gene Name:
galM
Uniprot ID:
P0A9C3
Molecular weight:
38190
Reactions
Alpha-D-glucose = beta-D-glucose.
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex MglABC involved in galactose/methyl galactoside import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
mglA
Uniprot ID:
P0AAG8
Molecular weight:
56415
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in acid phosphatase activity
Specific function:
Absolutely required for the growth of E.coli in a high- phosphate medium containing G-1-P as the sole carbon source
Gene Name:
agp
Uniprot ID:
P19926
Molecular weight:
45683
Reactions
Alpha-D-glucose 1-phosphate + H(2)O = D-glucose + phosphate.
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
Uniprot ID:
P33363
Molecular weight:
83459
Reactions
Hydrolysis of terminal, non-reducing beta-D-glucosyl residues with release of beta-D-glucose.
General function:
Involved in nucleotide binding
Specific function:
Specific function unknown
Gene Name:
ytfR
Uniprot ID:
Q6BEX0
Molecular weight:
55259
General function:
Involved in transporter activity
Specific function:
Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yjfF
Uniprot ID:
P37772
Molecular weight:
34977
General function:
Carbohydrate transport and metabolism
Specific function:
Specific function unknown
Gene Name:
ytfQ
Uniprot ID:
P39325
Molecular weight:
34344
General function:
Involved in transporter activity
Specific function:
Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ytfT
Uniprot ID:
P39328
Molecular weight:
35659
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for galactoside. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
mglC
Uniprot ID:
P23200
Molecular weight:
35550
General function:
Involved in transferase activity
Specific function:
Specific function unknown
Gene Name:
wcaK
Uniprot ID:
P71242
Molecular weight:
47343
General function:
Carbohydrate transport and metabolism
Specific function:
This protein is involved in the active transport of galactose and glucose. It plays a role in the chemotaxis towards the two sugars by interacting with the trg chemoreceptor
Gene Name:
mglB
Uniprot ID:
P0AEE5
Molecular weight:
35712
General function:
Not Available
Specific function:
Not Available
Gene Name:
ebgC
Uniprot ID:
P0AC73
Molecular weight:
Not Available
General function:
carbohydrate metabolic process
Specific function:
Not Available
Gene Name:
lacZ
Uniprot ID:
G0ZKW2
Molecular weight:
116482
Reactions
=

Transporters

General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex MglABC involved in galactose/methyl galactoside import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
mglA
Uniprot ID:
P0AAG8
Molecular weight:
56415
Reactions
ATP + H(2)O + monosaccharide(Out) = ADP + phosphate + monosaccharide(In).
General function:
Involved in nucleotide binding
Specific function:
Specific function unknown
Gene Name:
ytfR
Uniprot ID:
Q6BEX0
Molecular weight:
55259
General function:
Involved in transmembrane transporter activity
Specific function:
Uptake of galactose across the boundary membrane with the concomitant transport of protons into the cell (symport system)
Gene Name:
galP
Uniprot ID:
P0AEP1
Molecular weight:
50982
General function:
Involved in transmembrane transport
Specific function:
Involved in the efflux of sugars. The physiological role may be the detoxification of non-metabolizable sugar analogs
Gene Name:
setC
Uniprot ID:
P31436
Molecular weight:
43493
General function:
Involved in transporter activity
Specific function:
Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
yjfF
Uniprot ID:
P37772
Molecular weight:
34977
General function:
Carbohydrate transport and metabolism
Specific function:
Specific function unknown
Gene Name:
ytfQ
Uniprot ID:
P39325
Molecular weight:
34344
General function:
Involved in transporter activity
Specific function:
Probably part of a binding-protein-dependent transport system. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ytfT
Uniprot ID:
P39328
Molecular weight:
35659
General function:
Involved in transporter activity
Specific function:
Part of the binding-protein-dependent transport system for galactoside. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
mglC
Uniprot ID:
P23200
Molecular weight:
35550
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Carbohydrate transport and metabolism
Specific function:
This protein is involved in the active transport of galactose and glucose. It plays a role in the chemotaxis towards the two sugars by interacting with the trg chemoreceptor
Gene Name:
mglB
Uniprot ID:
P0AEE5
Molecular weight:
35712
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368