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Human Metabolome Database Version 3.5

Showing metabocard for Beta-D-Glucose (HMDB00516)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

enzymes (15)

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2005-11-16 08:48:42 -0700
Update Date	2013-04-19 16:40:22 -0600
HMDB ID	HMDB00516
Secondary Accession Numbers	HMDB03340
Metabolite Identification
Common Name	Beta-D-Glucose
Description	Beta-D-Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. This group contains a benzene and also an ethylene group, being derived from styrolene. Coniferin, C16H22O8, occurs in the cambium of conifer wood. Emulsin converts it into glucose and coniferyl alcohol, while oxidation gives glycovanillin, which yields with emulsin glucose and vanillin. Syringin, which occurs in the bark of Syringe vulgaris, is a methoxyconiferin. Phloridzus occurs in the root-bark of various fruit trees; it hydrolyses to glucose and phloretin, which is the phloroglucin ester of paraoxyhydratropic acid. It is related to the pentosides naringin, C21HEOi1, which hydrolyses to rhamnose and naringenin, the phioroglucin ester of para-oxycinnamic acid, and hesperidin, which hydrolyses to rhamnose and hesperetin, the phloroglucin ester of meta-oxy-para-methoxycinnamic acid or isoferulic acid, C10H10O4. Classification of the glucosides is a matter of some difficulty. One based on the chemical constitution of the non-glucose part of the molecules has been proposed that frames four groups: (I) ethylene derivatives, (2) benzene derivatives, (3) styrolene derivatives, (4) anthracene derivatives. A group may also be made to include the cyanogenetic glucosides, i.e. those containing prussic acid. Other classifications follow a botanical classification, which has several advantages; in particular, plants of allied genera contain similar compounds. In this article the chemical classification will be followed, and only the more important compounds will be discussed here.
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	b-D-Glucopyranose b-Dextrose b-Glucose beta-D-Glucopyranose beta-D-Glucose beta-delta-Glucopyranose beta-Dextrose beta-Glucose
Chemical Formula	C6H12O6
Average Molecular Weight	180.1559
Monoisotopic Molecular Weight	180.063388116
IUPAC Name	(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name	glucoside
CAS Registry Number	492-61-5
SMILES	OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
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-VFUOTHLCSA-N
Chemical Taxonomy
Kingdom	Organic Compounds
Super Class	Carbohydrates and Carbohydrate Conjugates
Class	Monosaccharides
Sub Class	Hexoses
Other Descriptors	Aliphatic Heteromonocyclic Compounds Carbohydrates and Carbohydrate Conjugates D-galactopyranose(ChEBI)
Substituents	1,2 Diol Hemiacetal Oxane Primary Alcohol Secondary Alcohol
Direct Parent	Hexoses
Ontology
Status	Expected and Not Quantified
Origin	Endogenous
Biofunction	Not Available
Application	Not Available
Cellular locations	Cytoplasm
Physical Properties
State	Solid
Experimental Properties	Property Value Reference Melting Point Not Available Not Available Boiling Point Not Available Not Available Water Solubility Not Available Not Available LogP -3.24 SANGSTER (1994)
Predicted Properties	Property Value Source Water Solubility 782 g/L ALOGPS LogP -2.57 ALOGPS LogP -2.9 ChemAxon LogS 0.64 ALOGPS pKa (strongest acidic) 11.3 ChemAxon pKa (strongest basic) -3 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 110.38 A2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 35.92 ChemAxon Polarizability 16.43 ChemAxon Formal Charge 0 ChemAxon Physiological Charge 0 ChemAxon
Spectra
	Not Available
Biological Properties
Cellular Locations	Cytoplasm
Biofluid Locations	Not Available
Tissue Location	Not Available
Pathways	Name SMPDB Link KEGG Link Glycolysis SMP00040 map00010 Gluconeogenesis SMP00128 map00010 Trehalose Degradation SMP00467 Not Available
Normal Concentrations
	Not Available
Abnormal Concentrations
	Not Available
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
DrugBank Metabolite ID	Not Available
Phenol Explorer Compound ID	Not Available
Phenol Explorer Metabolite ID	Not Available
FoodDB ID	FDB011824
KNApSAcK ID	Not Available
Chemspider ID	58238
KEGG Compound ID	C00221
BioCyc ID	Not Available
BiGG ID	Not Available
Wikipedia Link	Not Available
NuGOwiki Link	HMDB00516
Metagene Link	HMDB00516
METLIN ID	3755
PubChem Compound	64689
PDB ID	BGC
ChEBI ID	15903
References
Synthesis Reference	Wenck, Helmut; Kinedt, Claudia; Bader, Hans Joachim. Production of b-D-glucose. Praxis der Naturwissenschaften, Chemie (1986), 35(4), 23.
Material Safety Data Sheet (MSDS)	Not Available
General References	Not Available

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Enzymes
Name: Glucokinase Reactions: Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details Gene Name: GCK Uniprot ID: P35557 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Hexokinase-3 Reactions: Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details Gene Name: HK3 Uniprot ID: P52790 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Hexokinase-2 Reactions: Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details Gene Name: HK2 Uniprot ID: P52789 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Hexokinase-1 Reactions: Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details Gene Name: HK1 Uniprot ID: P19367 Protein Sequence: FASTA Gene Sequence: FASTA
Name: GDH/6PGL endoplasmic bifunctional protein Reactions: Beta-D-Glucose + NAD(P)(+) unknown Gluconolactone + NAD(P)H details Gene Name: H6PD Uniprot ID: O95479 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Lactase-phlorizin hydrolase Reactions: Not Available Gene Name: LCT Uniprot ID: P09848 Protein Sequence: FASTA Gene Sequence: FASTA
Name: ADP-dependent glucokinase Reactions: Beta-D-Glucose + ADP unknown Beta-D-Glucose 6-phosphate + Adenosine monophosphate details Gene Name: ADPGK Uniprot ID: Q9BRR6 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Trehalase Reactions: Trehalose + Water unknown Beta-D-Glucose + Alpha-D-Glucose details Gene Name: TREH Uniprot ID: O43280 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Beta-galactosidase Reactions: Not Available Gene Name: GLB1 Uniprot ID: P16278 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glucosylceramidase Reactions: Not Available Gene Name: GBA Uniprot ID: P04062 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Glucokinase regulatory protein Reactions: Not Available Gene Name: GCKR Uniprot ID: Q14397 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Cytosolic beta-glucosidase Reactions: Cellobiose + Water unknown Beta-D-Glucose details Cellulose + Water unknown Cellulose + Beta-D-Glucose details Dhurrin + Water unknown (S)-4-Hydroxymandelonitrile + Beta-D-Glucose details Lotaustralin + Water unknown (2R)-2-Hydroxy-2-methylbutanenitrile + Beta-D-Glucose details Linamarin + Water unknown Acetone cyanohydrin + Beta-D-Glucose details Gene Name: GBA3 Uniprot ID: Q9H227 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Maltase-glucoamylase, intestinal Reactions: Not Available Gene Name: MGAM Uniprot ID: O43451 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Aldose 1-epimerase Reactions: Alpha-D-Glucose unknown Beta-D-Glucose details Gene Name: GALM Uniprot ID: Q96C23 Protein Sequence: FASTA Gene Sequence: FASTA
Name: Putative hexokinase HKDC1 Reactions: Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details Gene Name: HKDC1 Uniprot ID: Q2TB90 Protein Sequence: FASTA

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