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Record Information
Version3.6
Creation Date2006-08-12 19:09:59 UTC
Update Date2014-10-29 17:55:38 UTC
HMDB IDHMDB03345
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlpha-D-Glucose
DescriptionAlpha-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.
Structure
Thumb
Synonyms
  1. a-D-Glucopyranose
  2. a-D-Glucose
  3. a-Dextrose
  4. a-Glucose
  5. alpha-D-Glucopyranose
  6. alpha-D-Glucose
  7. alpha-delta-Glucopyranose
  8. alpha-delta-Glucose
  9. alpha-Dextrose
  10. alpha-Glucose
  11. Hexopyranose
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameα-D-glucose
CAS Registry Number492-62-6
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 KeyWQZGKKKJIJFFOK-DVKNGEFBSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • D-galactopyranose(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusDetected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Galactose metabolism
  • Component of Nucleotide sugars metabolism
  • Component of Starch and sucrose metabolism
  • Component of Streptomycin biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point146 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility500 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
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 Area110.38ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92ChemAxon
Polarizability16.09ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Saliva
Tissue Location
  • Epidermis
  • Intestine
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
Galactose MetabolismSMP00043map00052
GluconeogenesisSMP00128map00010
GlycolysisSMP00040map00010
Nucleotide Sugars MetabolismSMP00010map00520
Retinol MetabolismSMP00074map00830
Starch and Sucrose MetabolismSMP00058map00500
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011829
KNApSAcK IDC00001122
Chemspider ID71358
KEGG Compound IDC00267
BioCyc IDALPHA-GLUCOSE-16-BISPHOSPHATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03345
Metagene LinkHMDB03345
METLIN ID6897
PubChem Compound79025
PDB IDGLC
ChEBI ID17925
References
Synthesis ReferenceSimmons, Blake A.; Volponi, Joanne V.; Ingersoll, David; Walker, Andrew. Conversion of sucrose to b-D-glucose using three-stage immobilized enzyme process. U.S. (2007), 12pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Onyshchenko AM, Korobkova KS, Kovalenko NK, Kasumova SO, Skrypal' IH: [The role of the carbohydrate composition of the glycocalyx in some species of lactobacilli in the manifestation of their adhesive properties] Mikrobiol Z. 1999 Nov-Dec;61(6):22-8. Pubmed: 10733280
  2. Georgiou S, Pasmatzi E, Monastirli A, Sakkis T, Alachioti S, Tsambaos D: Age-related alterations in the carbohydrate residue composition of the cell surface in the unexposed normal human epidermis. Gerontology. 2005 May-Jun;51(3):155-60. Pubmed: 15832040
  3. Skrypal' IH, Tokovenko IP, Malynovs'ka LP: [Carbohydrate receptors for Mycoplasma fermentans adhesion on human epithelial tissues] Mikrobiol Z. 1995 Jul-Aug;57(4):17-22. Pubmed: 8548067
  4. Dalmau SR, Freitas CS: Sugar inhibition of the lectin jacalin: comparison of three assays. Braz J Med Biol Res. 1989;22(5):601-10. Pubmed: 2620170

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
Sorbitol + NADP → Alpha-D-Glucose + NADPH + Hydrogen Iondetails
General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
ENPP1
Uniprot ID:
P22413
Molecular weight:
104923.58
General function:
Involved in ATP binding
Specific function:
Catalyzes the initial step in utilization of glucose by the beta-cell and liver at physiological glucose concentration. Glucokinase has a high Km for glucose, and so it is effective only when glucose is abundant. The role of GCK is to provide G6P for the synthesis of glycogen. Pancreatic glucokinase plays an important role in modulating insulin secretion. Hepatic glucokinase helps to facilitate the uptake and conversion of glucose by acting as an insulin-sensitive determinant of hepatic glucose usage.
Gene Name:
GCK
Uniprot ID:
P35557
Molecular weight:
52191.07
Reactions
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
Reactions
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK2
Uniprot ID:
P52789
Molecular weight:
102379.06
Reactions
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK1
Uniprot ID:
P19367
Molecular weight:
102485.1
Reactions
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:
SI
Uniprot ID:
P14410
Molecular weight:
Not Available
Reactions
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails
Isomaltose + Water → Alpha-D-Glucose + D-Glucosedetails
Dextrin + Water → Alpha-D-Glucose + Dextrindetails
Neohancoside D + Water → D-Fructose + Alpha-D-Glucosedetails
+ Water → Alpha-D-Glucose + details
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
LPH splits lactose in the small intestine.
Gene Name:
LCT
Uniprot ID:
P09848
Molecular weight:
218584.77
Reactions
beta-Lactose + Water → Alpha-D-Glucose + Beta-D-Galactosedetails
General function:
Involved in catalytic activity
Specific function:
Multifunctional enzyme acting as 1,4-alpha-D-glucan:1,4-alpha-D-glucan 4-alpha-D-glycosyltransferase and amylo-1,6-glucosidase in glycogen degradation.
Gene Name:
AGL
Uniprot ID:
P35573
Molecular weight:
Not Available
Reactions
Starch + Water → Amylose + Alpha-D-Glucosedetails
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Catalyzes the phosphorylation of D-glucose to D-glucose 6-phosphate using ADP as the phosphate donor. GDP and CDP can replace ADP, but with reduced efficiency (By similarity).
Gene Name:
ADPGK
Uniprot ID:
Q9BRR6
Molecular weight:
53960.185
Reactions
Alpha-D-Glucose + ADP → Glucose 6-phosphate + Adenosine monophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Intestinal trehalase is probably involved in the hydrolysis of ingested trehalose.
Gene Name:
TREH
Uniprot ID:
O43280
Molecular weight:
66567.26
Reactions
Trehalose + Water → Beta-D-Glucose + Alpha-D-Glucosedetails
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes glucose-6-phosphate to glucose in the endoplasmic reticulum. Forms with the glucose-6-phosphate transporter (SLC37A4/G6PT) the complex responsible for glucose production through glycogenolysis and gluconeogenesis. Hence, it is the key enzyme in homeostatic regulation of blood glucose levels.
Gene Name:
G6PC
Uniprot ID:
P35575
Molecular weight:
40483.21
Reactions
Glucose 6-phosphate + Water → Alpha-D-Glucose + Phosphoric aciddetails
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Cleaves beta-linked terminal galactosyl residues from gangliosides, glycoproteins, and glycosaminoglycans. Isoform 2 has no beta-galactosidase catalytic activity, but plays functional roles in the formation of extracellular elastic fibers (elastogenesis) and in the development of connective tissue. Seems to be identical to the elastin-binding protein (EBP), a major component of the non-integrin cell surface receptor expressed on fibroblasts, smooth muscle cells, chondroblasts, leukocytes, and certain cancer cell types. In elastin producing cells, associates with tropoelastin intracellularly and functions as a recycling molecular chaperone which facilitates the secretions of tropoelastin and its assembly into elastic fibers.
Gene Name:
GLB1
Uniprot ID:
P16278
Molecular weight:
Not Available
Reactions
beta-Lactose + Water → Alpha-D-Glucose + Beta-D-Galactosedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GBA
Uniprot ID:
P04062
Molecular weight:
59715.745
General function:
Involved in catalytic activity
Specific function:
Essential for the degradation of glygogen to glucose in lysosomes.
Gene Name:
GAA
Uniprot ID:
P10253
Molecular weight:
Not Available
Reactions
D-Maltose + Water → Alpha-D-Glucosedetails
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY1A
Uniprot ID:
P04745
Molecular weight:
Not Available
General function:
Involved in enzyme inhibitor activity
Specific function:
Inhibits glucokinase by forming an inactive complex with this enzyme
Gene Name:
GCKR
Uniprot ID:
Q14397
Molecular weight:
68700.7
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
D-Glucoside + Water → ROH + Alpha-D-Glucosedetails
General function:
Involved in catalytic activity
Specific function:
May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
Gene Name:
MGAM
Uniprot ID:
O43451
Molecular weight:
Not Available
Reactions
D-Maltose + Water → Alpha-D-Glucosedetails
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails
Starch + Water → Alpha-D-Glucose + Starchdetails
Dextrin + Water → Alpha-D-Glucose + Dextrindetails
Neohancoside D + Water → D-Fructose + Alpha-D-Glucosedetails
+ Water → Alpha-D-Glucose + details
General function:
Involved in catalytic activity
Specific function:
May hydrolyze glucose-6-phosphate to glucose in the endoplasmic reticulum. May be responsible for glucose production through glycogenolysis and gluconeogenesis (By similarity).
Gene Name:
G6PC2
Uniprot ID:
Q9NQR9
Molecular weight:
17756.465
Reactions
Glucose 6-phosphate + Water → Alpha-D-Glucose + Phosphoric aciddetails
General function:
Involved in catalytic activity
Specific function:
Has alpha-glucosidase activity.
Gene Name:
GANC
Uniprot ID:
Q8TET4
Molecular weight:
Not Available
Reactions
D-Maltose + Water → Alpha-D-Glucosedetails
Sucrose + Water → D-Fructose + Alpha-D-Glucosedetails
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 (By similarity).
Gene Name:
GALM
Uniprot ID:
Q96C23
Molecular weight:
37765.365
Reactions
Alpha-D-Glucose → Beta-D-Glucosedetails
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available
Reactions
Sorbitol + NADP → Alpha-D-Glucose + NADPH + Hydrogen Iondetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
HKDC1
Uniprot ID:
Q2TB90
Molecular weight:
102513.88
Reactions
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails