Bovine Metabolome Database: Showing metabocard for Alpha-D-Glucose (BMDB0003345)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (8) Show 8 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:03:52 UTC

Update Date

2020-06-04 20:32:38 UTC

BMDB ID

BMDB0003345

Secondary Accession Numbers

BMDB03345

Metabolite Identification

Common Name

Alpha-D-Glucose

Description

Alpha-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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
alpha-D-GLC	ChEBI
alpha-Dextrose	ChEBI
a-D-GLC	Generator
Α-D-GLC	Generator
a-Dextrose	Generator
Α-dextrose	Generator
a-D-Glucose	Generator
Α-D-glucose	Generator
a-D-Glucopyranose	HMDB
a-Glucose	HMDB
alpha-D-Glucopyranose	HMDB
alpha-delta-Glucopyranose	HMDB
alpha-delta-Glucose	HMDB
alpha-Glucose	HMDB
Hexopyranose	HMDB
Anhydrous dextrose	HMDB
D Glucose	HMDB
D-Glucose	HMDB
Dextrose	HMDB
Dextrose, anhydrous	HMDB
Glucose	HMDB
Glucose monohydrate	HMDB
Glucose, (DL)-isomer	HMDB
Glucose, (L)-isomer	HMDB
Glucose, (alpha-D)-isomer	HMDB
Glucose, (beta-D)-isomer	HMDB
L Glucose	HMDB
L-Glucose	HMDB
Monohydrate, glucose	HMDB
1,3-alpha-D-Glucan	HMDB
alpha-1,3-Glucan	HMDB
alpha-D-Glucopyranoside	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

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

Traditional Name

α-glucose

CAS Registry Number

492-62-6

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 Key

WQZGKKKJIJFFOK-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.

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-glucopyranose (CHEBI:17925 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	146 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	500 mg/mL at 20 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	16.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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 - 10V, Negative	splash10-0a4i-9100000000-57ee067515dbaeec1e27	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9100000000-311a61760b7c0dc3a7e1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9100000000-f2beec08615d57ac1a02	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9100000000-eb694004566014e0b267	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-906b2fd231873b000e08	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-3cd19dc7a445df26b86d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9100000000-53278ff57ca00e1b5d1a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0079-9000000000-c4182c64988208ac78b0	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	splash10-01q9-0900000000-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, 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 (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Colostrum
Epidermis
Intestine
Muscle
Ruminal Fluid

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fructose and Mannose Degradation		Not Available
Nucleotide Sugars Metabolism		Not Available
Glycolysis		Not Available
Gluconeogenesis		Not Available
Galactose Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22370585	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24440255	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Ruminal Fluid	Detected and Quantified	763.813 +/- 751.731 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Ruminal Fluid	Detected and Quantified	2415.813 +/- 1248.434 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0003345

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6897

PubChem Compound

79025

PDB ID

Not Available

ChEBI ID

17925

References

Synthesis Reference

Simmons, 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 References

Not 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-Glucose	details

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 + Water	details

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-Glucose	details

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 + Water	details
4 Alpha-D-Glucose → Glycogen	details
Dextrin →3 Alpha-D-Glucose	details
D-Maltose →2 Alpha-D-Glucose	details

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-phosphate	details
Alpha-D-Glucose + Adenosine triphosphate → Glucose 6-phosphate + ADP	details

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 + Water	details

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-Glucose	details

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-Glucose	details

Showing metabocard for Alpha-D-Glucose (BMDB0003345)

Structure for BMDB0003345 (Alpha-D-Glucose)

Enzymes

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