D-Galactose (YMDB00072)

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Identification

YMDB ID

YMDB00072

Name

D-Galactose

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-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 is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Galactose exists in all living species, ranging from bacteria to humans. D-Galactose is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(+)-Galactose
5abp
8abp
Alpha d-galactose
Alpha-d-galactopyranose
Alpha-d-galactose
D-(+)-Galactose
D-Galactose
d-hexose
GAL
Galactose
Galactose (NF)
GLA
GLC
Hexose
alpha-D-Gal
Gal-alpha
a D-GALACTOSE
Α D-galactose
a-D-Gal
Α-D-gal
Gal-a
Gal-α
a-D-Galactose
Α-D-galactose
SHU 508 a
SH-TA-508
SHU 508
Levovist
SHU-508

CAS number

59-23-4

Weight

Average: 180.1559
Monoisotopic: 180.063388116

InChI Key

WQZGKKKJIJFFOK-PHYPRBDBSA-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

IUPAC Name

(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Traditional IUPAC Name

galactose

Chemical Formula

C₆H₁₂O₆

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@]([H])(O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@@]1([H])O[H]

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-galactopyranose (CHEBI:28061 )

Physical Properties

State

Solid

Charge

Melting point

170 °C

Experimental Properties

Property	Value	Reference
Water Solubility	683 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	782 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.92 m³·mol⁻¹	ChemAxon
Polarizability	16.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm, Extracellular

Organoleptic Properties

Not Available

SMPDB Pathways

Amino sugar and nucleotide sugar metabolism	PW002413
Leloir Pathway	PW002397

KEGG Pathways

Amino sugar and nucleotide sugar metabolism	ec00520
Galactose metabolism	ec00052

SMPDB Reactions

Beta-D-Galactose → D-Galactose

Adenosine triphosphate + D-Galactose → ADP + hydron + Galactose 1-phosphate

Galactosylceramide (d18:1/16:0) + D-Galactose ← Galabiosylceramide (d18:1/22:0)

KEGG Reactions

Adenosine triphosphate + D-Galactose → Galactose 1-phosphate + hydron + ADP

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-066s-0941000000-8f1b68655e0a5ed179e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ldj-0941000000-84c771fab416aa0a40d8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ktb-0931000000-6f37a774d1ab64585c8d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-066s-0931000000-9945093085ef7b0de618	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ldj-0931000000-1ed532d5d2897be775df	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9731000000-af5bd67ad0bbb2997839	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-9dad5bd1760a891ace2a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-0920000000-d0bbaf502997c43971ba	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-1920000000-f47f0b66263744db15ba	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-066s-0941000000-8f1b68655e0a5ed179e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ldj-0941000000-84c771fab416aa0a40d8	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ktb-0931000000-6f37a774d1ab64585c8d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-066s-0931000000-9945093085ef7b0de618	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ldj-0931000000-1ed532d5d2897be775df	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9731000000-af5bd67ad0bbb2997839	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-9dad5bd1760a891ace2a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-0920000000-d0bbaf502997c43971ba	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fr2-1920000000-f47f0b66263744db15ba	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0f6t-0900000000-70d3989fddd34b894c77	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ri-9700000000-d454170b4e3ed18ed2d9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9300000000-81f5f12f84924a34e2c0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-059i-9100000000-33aacf4c62b17cfa394e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-0a4i-9000000000-79ea696263aaad168701	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-0a4i-9000000000-480461c1cdd9d138dce2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-059i-9100000000-33aacf4c62b17cfa394e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-79ea696263aaad168701	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-480461c1cdd9d138dce2	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-b0bc47623e7b2ca31c02	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-648e1637af29cf2a3518	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9200000000-9e6f46a1cbf52d6e347a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-a4ec4f0b1e29e360a952	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-ec2bf4918640a0a36398	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-2448926b508622464fe7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-8900000000-4c073cb93b78120113e6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-ece70093ab5d3c331ac4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-0900000000-04ceb34d441ff6a75763	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9400000000-a8f1ceab155611f949c1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ow-9000000000-358f68fc2b7a72c27546	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
DOUGLAS, H. C., HAWTHORNE, D. C. (1964). "ENZYMATIC EXPRESSION AND GENETIC LINKAGE OF GENES CONTROLLING GALACTOSE UTILIZATION IN SACCHAROMYCES." Genetics 49:837-844.14158615
Luttik, M. A., Overkamp, K. M., Kotter, P., de Vries, S., van Dijken, J. P., Pronk, J. T. (1998). "The Saccharomyces cerevisiae NDE1 and NDE2 genes encode separate mitochondrial NADH dehydrogenases catalyzing the oxidation of cytosolic NADH." J Biol Chem 273:24529-24534.9733747

Synthesis Reference:

Avigad, Gad. Synthesis of D-galactose-6-t and D-galactosides-6-t. Carbohydrate Research (1967), 3(4), 430-4.

External Links:

Resource	Link
CHEBI ID	28061
HMDB ID	HMDB00143
Pubchem Compound ID	439357
Kegg ID	C00124
ChemSpider ID	23184483
FOODB ID	FDB021787
Wikipedia	Galactose
BioCyc ID	GALACTOSE

Enzymes

Protein Details

1. Galactokinase

General function:: Involved in galactokinase activity
Specific function:: ATP + D-galactose = ADP + alpha-D-galactose 1- phosphate
Gene Name:: GAL1
Uniprot ID:: P04385
Molecular weight:: 57943.80078

Reactions

ATP + D-galactose → ADP + alpha-D-galactose 1-phosphate.

Protein Details

2. Hexokinase-2

General function:: Involved in ATP binding
Specific function:: Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:: HXK2
Uniprot ID:: P04807
Molecular weight:: 53942.0

Reactions

ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate

Protein Details

3. Putative hexokinase YLR446W

General function:: Involved in ATP binding
Specific function:: ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:: Not Available
Uniprot ID:: Q06204
Molecular weight:: 48968.80078

Reactions

ATP + D-hexose → ADP + D-hexose 6-phosphate.

Protein Details

4. Hexokinase-1

General function:: Involved in ATP binding
Specific function:: ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:: HXK1
Uniprot ID:: P04806
Molecular weight:: 53737.89844

Reactions

ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate

Protein Details

5. Bifunctional protein GAL10

General function:: Involved in isomerase 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:: GAL10
Uniprot ID:: P04397
Molecular weight:: 78194.70313

Reactions

UDP-glucose → UDP-galactose.
Alpha-D-glucose → beta-D-glucose.

Transporters

Protein Details

1. Hexose transporter HXT9

General function:: Involved in transmembrane transporter activity
Specific function:: Probable glucose transporter
Gene Name:: HXT9
Uniprot ID:: P40885
Molecular weight:: 62857.19922

Protein Details

2. Hexose transporter HXT14

General function:: Involved in transmembrane transporter activity
Specific function:: Probable glucose transporter
Gene Name:: HXT14
Uniprot ID:: P42833
Molecular weight:: 60978.10156

Protein Details

3. Galactose transporter

General function:: Involved in transmembrane transporter activity
Specific function:: GAL2 is a facilitated diffusion transporter required for both the high-affinity galactokinase-dependent and low-affinity galactokinase-independent galactose transport processes
Gene Name:: GAL2
Uniprot ID:: P13181
Molecular weight:: 63625.39844

Protein Details

4. Sugar transporter STL1

General function:: Involved in transmembrane transporter activity
Specific function:: Not Available
Gene Name:: STL1
Uniprot ID:: P39932
Molecular weight:: 63531.19922

Protein Details

5. Hexose transporter HXT11

General function:: Involved in transmembrane transporter activity
Specific function:: Probable glucose transporter
Gene Name:: HXT11
Uniprot ID:: P54862
Molecular weight:: 62732.19922

Protein Details

6. Hexose transporter HXT10

General function:: Involved in transmembrane transporter activity
Specific function:: Probable glucose transporter
Gene Name:: HXT10
Uniprot ID:: P43581
Molecular weight:: 60661.5

Structure for #<Compound:0xafa9effc>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters