ECMDB: beta-D-Galactose (ECMDB04025) (M2MDB000565)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)Transporters (9)XML

Proteins (11)

Record Information

Version

2.0

Creation Date

2012-05-31 14:02:34 -0600

Update Date

2015-09-13 12:56:13 -0600

Secondary Accession Numbers

ECMDB04025

Identification

Name:

beta-D-Galactose

Description

Galactose is an optical isomer of glucose. An aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. Galactose is less sweet than glucose and not very water-soluble. Galactose is a monosaccharide constituent, together with glucose, of the disaccharide lactose. Galactose is produced by hydrolysis of lactose by galactosidase. This enzyme is produced by the lac operon in Escherichia coli (E. coli). Galactan is a polymer of the sugar galactose. It is found in hemicellulose and can be converted to galactose by hydrolysis.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol
b D-Galactose
b-D-Galactopyranose
B-D-Galactose
B-D-Galactoside
b-D-Galactosides
b-delta-Galactoside
b-delta-Galactosides
B-Galactose
b-δ-Galactoside
b-δ-Galactosides
Beta D-Galactose
Beta-D-Galactopyranose
Beta-D-Galactose
Beta-D-Galactoside
Beta-D-Galactosides
Beta-delta-Galactoside
Beta-delta-galactosides
Beta-Galactose
Cerebrose
D-galactose
Delta-Galactose
Galactopyranose
Galactopyranoside
Galactose
β D-Galactose
β-D-Galactopyranose
β-D-Galactose
β-D-Galactoside
β-D-Galactosides
β-Galactose
β-δ-Galactoside
β-δ-Galactosides
δ-Galactose

Chemical Formula:

C₆H₁₂O₆

Weight:

Average: 180.1559
Monoisotopic: 180.063388116

InChI Key:

WQZGKKKJIJFFOK-FPRJBGLDSA-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:

7296-64-2

IUPAC Name:

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

Traditional IUPAC Name:

β D-galactose

SMILES:

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

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:27667 )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

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	16.33 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

Reactions:

beta-D-Galactose > D-Galactose
Alpha-D-Galactose > beta-D-Galactose
beta-D-Galactose > Alpha-D-Galactose
alpha-Lactose + Water > beta-D-Galactose + Beta-D-Glucose + b-D-Glucose

SMPDB Pathways:

Galactose metabolism	PW000821
galactose degradation/Leloir Pathway	PW000884
inner membrane transport	PW000786

KEGG Pathways:

Galactose metabolism ec00052

EcoCyc Pathways:

galactose degradation I (Leloir pathway) GALACTMETAB-PWY
lactose degradation III BGALACT-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0019-3900000000-3b00dcca100b6e3bb228	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9000000000-867bfd833e01f3033747	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-066r-9000000000-65a7d765a9429db38b1f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0ab9-9000000000-524ca56240af3dffbacb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-b0bc47623e7b2ca31c02	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-648e1637af29cf2a3518	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9200000000-9e6f46a1cbf52d6e347a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-a4ec4f0b1e29e360a952	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-ec2bf4918640a0a36398	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-2448926b508622464fe7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-8900000000-4c073cb93b78120113e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-ece70093ab5d3c331ac4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-0900000000-04ceb34d441ff6a75763	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9400000000-a8f1ceab155611f949c1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ow-9000000000-358f68fc2b7a72c27546	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Bhavanandan VP, Puch S, Guo X, Jiang W: Galectins and other endogenous carbohydrate-binding proteins of animal bladder. Adv Exp Med Biol. 2001;491:95-108. Pubmed: 14533792
Chen YT, Mattison DR, Bercu BB, Schulman JD: Resistance of the male gonad to a high galactose diet. Pediatr Res. 1984 Apr;18(4):345-8. Pubmed: 6718090
Furuhashi M, Suzuki S, Tomoda Y, Suganuma N: Role of the Pro-Leu-Arg motif in glycosylation of human gonadotropin alpha-subunit. Endocrinology. 1995 May;136(5):2270-5. Pubmed: 7536667
Goluboff ET, Mertz JR, Tres LL, Kierszenbaum AL: Galactosyl receptor in human testis and sperm is antigenically related to the minor C-type (Ca(2+)-dependent) lectin variant of human and rat liver. Mol Reprod Dev. 1995 Apr;40(4):460-6. Pubmed: 7598912
Hanisch FG, Heimbuchel G, Baldus SE, Uhlenbruck G, Schmits R, Pfreundschuh M, Schwonzen M, Vierbuchen M, Bara J, Peter-Katalinic J: Monoclonal antibody FW6 defines an epitope on alpha 3/4-monofucosylated polylactosaminoglycans expressed by fetal and colon carcinoma-associated mucins. Cancer Res. 1993 Sep 15;53(18):4367-75. Pubmed: 8364932
Kalichman MW, Powell HC, Mizisin AP: Reactive, degenerative, and proliferative Schwann cell responses in experimental galactose and human diabetic neuropathy. Acta Neuropathol (Berl). 1998 Jan;95(1):47-56. Pubmed: 9452821
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
Mizoguchi N, Ono H, Eguchi T, Sakura N: Galactose metabolites in blood from neonates with and without hypergalactosaemia detected by mass screening. Eur J Pediatr. 2000 Nov;159(11):851-3. Pubmed: 11079200
Muthusamy A, Erickson DR, Sheykhnazari M, Bhavanandan VP: Enhanced binding of modified pentosan polysulfate and heparin to bladder--a strategy for improved treatment of interstitial cystitis. Urology. 2006 Jan;67(1):209-13. Pubmed: 16413377
Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. Pubmed: 3757018
Niebroj-Dobosz I, Janik P, Jamrozik Z, Kwiecinski H: Immunochemical quantification of glycoconjugates in serum and cerebrospinal fluid of amyotrophic lateral sclerosis patients. Eur J Neurol. 1999 May;6(3):335-40. Pubmed: 10210915
Ning C, Reynolds R, Chen J, Yager C, Berry GT, McNamara PD, Leslie N, Segal S: Galactose metabolism by the mouse with galactose-1-phosphate uridyltransferase deficiency. Pediatr Res. 2000 Aug;48(2):211-7. Pubmed: 10926297
Ono H, Mawatari H, Mizoguchi N, Eguchi T, Sakura N, Hamakawa M: Transient galactosemia detected by neonatal mass screening. Pediatr Int. 1999 Jun;41(3):281-4. Pubmed: 10365579
Puch S, Bhavanandan VP: Endogenous carbohydrate-binding proteins of rabbit and human bladder. Urology. 1999 Apr;53(4):848-52. Pubmed: 10197873
Rapoport EM, Nekrasov MV, Khaidukov SV, Svirshchevskaya EV, Zhigis LS, Kozlov LV, Batalova TN, Zubov VP, Bovin NV: Cellular localization of the galactose-binding lectin from human serum. Biochemistry (Mosc). 2000 Nov;65(11):1316-20. Pubmed: 11112850
Schmidt LE, Ott P, Tygstrup N: Galactose elimination capacity as a prognostic marker in patients with severe acetaminophen-induced hepatotoxicity: 10 years' experience. Clin Gastroenterol Hepatol. 2004 May;2(5):418-24. Pubmed: 15118981
Seiler CA, Renner EL, Czerniak A, Didonna D, Buchler MW, Reichen J: Early acute cellular rejection: no effect on late hepatic allograft function in man. Transpl Int. 1999;12(3):195-201. Pubmed: 10429957
Stanley A, Osler T: Senescence and the healing rates of venous ulcers. J Vasc Surg. 2001 Jun;33(6):1206-11. Pubmed: 11389419
Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
van den Nieuwenhof IM, Renardel de Lavalette C, Diaz N, van Die I, van den Berg TK: Differential galactosylation of neuronal and haematopoietic signal regulatory protein-alpha determines its cellular binding-specificity. J Cell Sci. 2001 Apr;114(Pt 7):1321-9. Pubmed: 11256998
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Wan H, Perez DR: Quail carry sialic acid receptors compatible with binding of avian and human influenza viruses. Virology. 2006 Mar 15;346(2):278-86. Epub 2005 Dec 2. Pubmed: 16325879
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

Synthesis Reference:

Wolfrom, M. L.; Thompson, A.; Inatome, M. Acyl migration in the D-galactose structure. Journal of the American Chemical Society (1957), 79 3868-71.

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
CHEBI ID	27667
HMDB ID	HMDB03449
Pubchem Compound ID	439353
Kegg ID	C00962
ChemSpider ID	388476
Wikipedia	GAL
BioCyc ID	GALACTOSE
EcoCyc ID	GALACTOSE
Ligand Expo	GLB

Enzymes

Protein Details

1. Beta-galactosidase

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.

Protein Details

2. Aldose 1-epimerase

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.

Protein Details

3. ABC transporter periplasmic-binding protein ytfQ

General function:: Carbohydrate transport and metabolism
Specific function:: Specific function unknown
Gene Name:: ytfQ
Uniprot ID:: P39325
Molecular weight:: 34344

Protein Details

4. Galactoside transport system permease protein mglC

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

Transporters

Protein Details

1. Melibiose carrier protein

General function:: Involved in transporter activity
Specific function:: Responsible for melibiose transport. It is capable of using hydrogen, sodium, and lithium cations as coupling cations for cotransport, depending on the particular sugar transported (symport system)
Gene Name:: melB
Uniprot ID:: P02921
Molecular weight:: 52217

Protein Details

2. Sugar efflux transporter A

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. Can transport IPTG, lactose and glucose. Has broad substrate specificity, with preferences for glucosides or galactosides with alkyl or aryl substituents
Gene Name:: setA
Uniprot ID:: P31675
Molecular weight:: 42713

Protein Details

3. Sugar efflux transporter C

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

Protein Details

4. ABC transporter periplasmic-binding protein ytfQ

General function:: Carbohydrate transport and metabolism
Specific function:: Specific function unknown
Gene Name:: ytfQ
Uniprot ID:: P39325
Molecular weight:: 34344

Protein Details

5. Galactoside transport system permease protein mglC

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

Protein Details

6. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

7. Outer membrane pore protein E

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

Protein Details

8. Outer membrane protein F

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

Protein Details

9. Outer membrane protein C

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

beta-D-Galactose (ECMDB04025) (M2MDB000565)

Structure for #<Compound:0xab15a120>

Enzymes

Reactions

Reactions

Transporters