Showing metabocard for Alpha-D-Glucose (BMDB0003345)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (8) Show 8 proteinsXML
Show more...Show more...
Record Information
Version1.0
Creation Date2016-09-30 23:03:52 UTC
Update Date2020-06-04 20:32:38 UTC
BMDB IDBMDB0003345
Secondary Accession Numbers
  • BMDB03345
Metabolite Identification
Common NameAlpha-D-Glucose
DescriptionAlpha-D-Glucose, also known as alpha-D-GLC or alphalpha-d-glucose, 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. Alpha-D-Glucose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Alpha-D-Glucose exists in all living species, ranging from bacteria to humans. Alpha-D-Glucose participates in a number of enzymatic reactions, within cattle. In particular, Alpha-D-Glucose can be converted into glucose 6-phosphate; which is catalyzed by the enzyme glucokinase. In addition, Alpha-D-Glucose and D-fructose can be converted into sucrose through its interaction with the enzyme sucrase-isomaltase, intestinal. In cattle, Alpha-D-glucose is involved in the metabolic pathway called the starch and sucrose metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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-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
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
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 Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9100000000-57ee067515dbaeec1e27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-311a61760b7c0dc3a7e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-f2beec08615d57ac1a02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-eb694004566014e0b267View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-906b2fd231873b000e08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3cd19dc7a445df26b86dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9100000000-53278ff57ca00e1b5d1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0079-9000000000-c4182c64988208ac78b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a952View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a36398View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-2448926b508622464fe7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-8900000000-4c073cb93b78120113e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-ece70093ab5d3c331ac4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a3518View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0900000000-04ceb34d441ff6a75763View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9400000000-a8f1ceab155611f949c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9000000000-358f68fc2b7a72c27546View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Colostrum
  • Epidermis
  • Intestine
  • Muscle
  • Ruminal Fluid
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Ruminal FluidDetected and Quantified2415.813 +/- 1248.434 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
 details
HMDB IDHMDB0003345
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011829
KNApSAcK IDC00001122
Chemspider ID71358
KEGG Compound IDC00267
BioCyc IDALPHA-GLUCOSE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6897
PubChem Compound79025
PDB IDNot Available
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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Aldose 1-epimerase
General function:
Carbohydrate transport and metabolism
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:
Q5EA79
Molecular weight:
37614.0
Reactions
Alpha-D-Glucose → Beta-D-Glucosedetails
Enzyme Details
2. Glucose-6-phosphatase
General function:
Involved in glucose-6-phosphatase 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 (By similarity).
Gene Name:
G6PC
Uniprot ID:
Q29RU6
Molecular weight:
40827.0
Reactions
Alpha-D-Glucose + Hydrogen phosphate → Glucose 6-phosphate + Waterdetails
Enzyme Details
3. Aldo-keto reductase family 1 member B1
General function:
Involved in 20-alpha-hydroxysteroid dehydrogenase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols. Displays enzymatic activity towards endogenous metabolites such as aromatic and aliphatic aldehydes, ketones, monosacharides, bile acids and xenobiotics substrates. Key enzyme in the polyol pathway, catalyzes reduction of glucose to sorbitol during hyperglycemia. Reduces steroids and their derivatives and prostaglandins. Displays low enzymatic activity toward all-trans-retinal, 9-cis-retinal, and 13-cis-retinal. Catalyzes the reduction of diverse phospholipid aldehydes such as 1-palmitoyl-2-(5-oxovaleroyl)-sn -glycero-3-phosphoethanolamin (POVPC) and related phospholipid aldehydes that are generated from the oxydation of phosphotidylcholine and phosphatdyleethanolamides. Plays a role in detoxifying dietary and lipid-derived unsaturated carbonyls, such as crotonaldehyde, 4-hydroxynonenal, trans-2-hexenal, trans-2,4-hexadienal and their glutathione-conjugates carbonyls (GS-carbonyls).
Gene Name:
AKR1B1
Uniprot ID:
P16116
Molecular weight:
35919.0
Reactions
NADP + Sorbitol → NADPH + Alpha-D-Glucosedetails
Enzyme Details
4. Lysosomal alpha-glucosidase
General function:
Carbohydrate transport and metabolism
Specific function:
Essential for the degradation of glycogen in lysosomes (PubMed:10723725). Has highest activity on alpha-1,4-linked glycosidic linkages, but can also hydrolyze alpha-1,6-linked glucans.
Gene Name:
GAA
Uniprot ID:
Q9MYM4
Molecular weight:
104757.0
Reactions
Alpha-D-Glucose + D-Fructose → Sucrose + Waterdetails
4 Alpha-D-Glucose → Glycogendetails
Dextrin →3 Alpha-D-Glucosedetails
D-Maltose →2 Alpha-D-Glucosedetails
Enzyme Details
5. Hexokinase-1
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:
HK1
Uniprot ID:
P27595
Molecular weight:
103064.0
Reactions
Adenosine triphosphate + Alpha-D-Glucose → ADP + Glucose 6-phosphatedetails
Alpha-D-Glucose + Adenosine triphosphate → Glucose 6-phosphate + ADPdetails
Enzyme Details
6. Lactase
General function:
Not Available
Specific function:
Not Available
Gene Name:
LCT
Uniprot ID:
E1BK89
Molecular weight:
219131.0
Reactions
Alpha-D-Glucose + D-Galactose → Alpha-Lactose + Waterdetails
Enzyme Details
7. Amylo-alpha-1, 6-glucosidase, 4-alpha-glucanotransferase
General function:
Not Available
Specific function:
Not Available
Gene Name:
AGL
Uniprot ID:
F1MHT1
Molecular weight:
174087.0
Reactions
4 Amylose → Glycogen +2 Alpha-D-Glucosedetails
Enzyme Details
8. Trehalase
General function:
Not Available
Specific function:
Not Available
Gene Name:
TREH
Uniprot ID:
E1B8N4
Molecular weight:
65887.0
Reactions
Trehalose + Water → Beta-D-Glucose + Alpha-D-Glucosedetails