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
DescriptionD-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:(2S,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
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
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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.13 ųChemAxon
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 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-066s-0941000000-8f1b68655e0a5ed179e3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0941000000-84c771fab416aa0a40d8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-6f37a774d1ab64585c8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-066s-0931000000-9945093085ef7b0de618View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0931000000-1ed532d5d2897be775dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9731000000-af5bd67ad0bbb2997839View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-9dad5bd1760a891ace2aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0920000000-d0bbaf502997c43971baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-1920000000-f47f0b66263744db15baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-066s-0941000000-8f1b68655e0a5ed179e3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0941000000-84c771fab416aa0a40d8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-6f37a774d1ab64585c8dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-066s-0931000000-9945093085ef7b0de618View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0931000000-1ed532d5d2897be775dfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9731000000-af5bd67ad0bbb2997839View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-9dad5bd1760a891ace2aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0920000000-d0bbaf502997c43971baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-1920000000-f47f0b66263744db15baView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f6t-0900000000-70d3989fddd34b894c77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ri-9700000000-d454170b4e3ed18ed2d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-007a-9300000000-81f5f12f84924a34e2c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-059i-9100000000-33aacf4c62b17cfa394eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, negativesplash10-0a4i-9000000000-79ea696263aaad168701View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, negativesplash10-0a4i-9000000000-480461c1cdd9d138dce2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-059i-9100000000-33aacf4c62b17cfa394eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-79ea696263aaad168701View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-480461c1cdd9d138dce2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a3518View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a36398View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-2448926b508622464fe7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-8900000000-4c073cb93b78120113e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-ece70093ab5d3c331ac4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0900000000-04ceb34d441ff6a75763View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9400000000-a8f1ceab155611f949c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9000000000-358f68fc2b7a72c27546View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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