AFCDB: D-Galactose (FDB012703)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:19 UTC

Update date

2019-11-26 03:07:25 UTC

Primary ID

FDB012703

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Galactose

Description

The free sugar has been detected in some fruits. Polysaccharides agar, gum arabic, mesquite gum, western larch gum and many plant mucilages and gums contain galactose 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 in the body. 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. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-Galactose-1-phosphate. Classic galactosemia-a term that denotes the presence of D-Galactose in the blood is the rare inborn error of D-Galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-Galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene. (PMID: 15256214, 11020650, 10408771); In organic chemistry, a hexose is a monosaccharide with six carbon atoms, having the chemical formula C6H12O6. Hexoses are classified by functional group, with aldohexoses having an aldehyde at position 1, and ketohexoses having a ketone at position 2. Galactose in the urine is a biomarker for the consumption of milk.

CAS Number

59-23-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H12O6

IUPAC name

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

InChI Identifier

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

InChI Key

WQZGKKKJIJFFOK-SVZMEOIVSA-N

Isomeric SMILES

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

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

Classification

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

galactopyranose (CHEBI:4139 )
D-galactose (CHEBI:4139 )
Aldoses (C00124 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.00%; H 6.71%; O 53.28%	DFC
Melting Point	Mp 118-120° (monohydrate)	DFC
Boiling Point	Not Available
Experimental Water Solubility	683 mg/mL	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	pKa1 12.35 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0941000000-8f1b68655e0a5ed179e3	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0941000000-84c771fab416aa0a40d8	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-6f37a774d1ab64585c8d	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0931000000-9945093085ef7b0de618	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0931000000-1ed532d5d2897be775df	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9731000000-af5bd67ad0bbb2997839	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9621000000-9dad5bd1760a891ace2a	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-0920000000-d0bbaf502997c43971ba	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-1920000000-f47f0b66263744db15ba	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0941000000-8f1b68655e0a5ed179e3	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0941000000-84c771fab416aa0a40d8	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ktb-0931000000-6f37a774d1ab64585c8d	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-066s-0931000000-9945093085ef7b0de618	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0ldj-0931000000-1ed532d5d2897be775df	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9731000000-af5bd67ad0bbb2997839	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-00di-9621000000-9dad5bd1760a891ace2a	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-0920000000-d0bbaf502997c43971ba	Spectrum
GC-MS	L-Galactose, non-derivatized, GC-MS Spectrum	splash10-0fr2-1920000000-f47f0b66263744db15ba	Spectrum
Predicted GC-MS	L-Galactose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-08g0-9700000000-d7fbea2263840ca358b3	Spectrum
Predicted GC-MS	L-Galactose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-01ot-2900000000-358281e9439d096e0a76	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-ecd0aedc67c9a2eec60f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-2900000000-e4daf22c7320ccc41812	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9200000000-91fc3940732f782a88bb	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-e9f3e728d1b340759a09	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-5900000000-c0a478f2b9c5bbc6c4ba	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-06852e2088bf1c6b38c4	2015-09-15	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

4139

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00143

CRC / DFC (Dictionary of Food Compounds) ID

GZN85-U:HJX97-A

EAFUS ID

Not Available

Dr. Duke ID

D-GALACTOSE|GALACTOSE

BIGG ID

33945

KNApSAcK ID

C00019681

HET ID

GLA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Galactose

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Alpha-galactosidase A	GLA	P06280
Lactase-phlorizin hydrolase	LCT	P09848
Beta-galactosidase	GLB1	P16278
Maltase-glucoamylase, intestinal	MGAM	O43451
Neutral alpha-glucosidase C	GANC	Q8TET4
N-acetylgalactosamine kinase	GALK2	Q01415
Galactokinase	GALK1	P51570
Hexokinase-3	HK3	P52790
Hexokinase-2	HK2	P52789
Hexokinase-1	HK1	P19367
Galactocerebrosidase	GALC	P54803

Pathways

Name	SMPDB Link	KEGG Link
Galactose Metabolism	SMP00043	map00052
Lactose Degradation	SMP00457	Not Available
Nucleotide Sugars Metabolism	SMP00010	map00520

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).

D-Galactose (FDB012703)

Structure for FDB012703 (D-Galactose)