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Human Metabolome Database Version 3.5

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Showing metabocard for Alpha-D-Glucose (HMDB03345)

Record Information
Version 3.5
Creation Date 2006-08-12 13:09:59 -0600
Update Date 2013-02-08 17:12:27 -0700
HMDB ID HMDB03345
Secondary Accession Numbers None
Metabolite Identification
Common Name Alpha-D-Glucose
Description Alpha-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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 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 IUPAC Name α-D-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
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
  • Component of Galactose metabolism
  • Component of Nucleotide sugars metabolism
  • Component of Starch and sucrose metabolism
  • Component of Streptomycin biosynthesis
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
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
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 16.09 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Intestine
  • Epidermis
Pathways
Name SMPDB Link KEGG Link
Gluconeogenesis SMP00128 map00010 Link_out
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Retinol Metabolism SMP00074 map00830 Link_out
Starch and Sucrose Metabolism SMP00058 map00500 Link_out
Glycolysis SMP00040 map00010 Link_out
Galactose Metabolism SMP00043 map00052 Link_out
Nucleotide Sugars Metabolism SMP00010 map00520 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB011829
KNApSAcK ID C00001122 Link_out
Chemspider ID 71358 Link_out
KEGG Compound ID C00267 Link_out
BioCyc ID ALPHA-GLUCOSE-16-BISPHOSPHATE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03345 Link_out
Metagene Link HMDB03345 Link_out
METLIN ID 6897 Link_out
PubChem Compound 79025 Link_out
PDB ID GLC Link_out
ChEBI ID 17925 Link_out
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) 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Aldose reductase
Reactions:
  • alditol + NAD(P)+ = aldose + NAD(P)H + H+ [RN:R02819 R02820]
Gene Name: AKR1B1
Uniprot ID: P15121 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
Reactions:
  • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
Gene Name: ENPP1
Uniprot ID: P22413 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucokinase
Reactions:
  • ATP + D-glucose = ADP + D-glucose 6-phosphate [RN:R00299]
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-1
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK1
Uniprot ID: P19367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sucrase-isomaltase, intestinal
Reactions:
  • Hydrolysis of sucrose and maltose by an alpha-D-glucosidase-type action [RN:R00801 R06087] ALL_REAC R00801 R06087(G) > R00802 R06088(G)
Gene Name: SI
Uniprot ID: P14410 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactase-phlorizin hydrolase
Reactions:
  • lactose + H2O = D-galactose + D-glucose [RN:R01100 R06114]
Gene Name: LCT
Uniprot ID: P09848 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycogen debranching enzyme
Reactions:
  • Hydrolysis of (1->6)-alpha-D-glucosidic branch linkages in glycogen phosphorylase limit dextrin ALL_REAC (other) R02109 R06158(G)
Gene Name: AGL
Uniprot ID: P35573 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucose-6-phosphatase
Reactions:
  • D-glucose 6-phosphate + H2O = D-glucose + phosphate [RN:R00303]
Gene Name: G6PC
Uniprot ID: P35575 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-galactosidase
Reactions:
  • Hydrolysis of terminal non-reducing beta-D-galactose residues in beta-D-galactosides ALL_REAC (other) R01100 R01105 R01678 R03355 R04633 R04783 R05112 R05994(G) R06010(G) R06098(G) R06099(G) R06114(G) R06144(G) R06202(G) R07807(G)
Gene Name: GLB1
Uniprot ID: P16278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucosylceramidase
Reactions:
  • D-glucosyl-N-acylsphingosine + H2O = D-glucose + N-acylsphingosine [RN:R01498]
Gene Name: GBA
Uniprot ID: P04062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysosomal alpha-glucosidase
Reactions:
  • Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of D-glucose ALL_REAC (other) R00028 R00801 R00802 R06084(G) R06087(G) R06088(G) INHIBITOR Castanospermine [CPD:C02256]
Gene Name: GAA
Uniprot ID: P10253 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-amylase 1
Reactions:
  • Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units ALL_REAC (other) R02108 R06209(G)
Gene Name: AMY1A
Uniprot ID: P04745 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucokinase regulatory protein
Reactions:
    Gene Name: GCKR
    Uniprot ID: Q14397 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Cytosolic beta-glucosidase
    Reactions:
    • Hydrolysis of terminal, non-reducing beta-D-glucosyl residues with release of beta-D-glucose ALL_REAC (other) R00026 R02887 R03527 R04949 R04998 R06077(G) R06092(G)
    Gene Name: GBA3
    Uniprot ID: Q9H227 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Maltase-glucoamylase, intestinal
    Reactions:
    • Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of D-glucose ALL_REAC (other) R00028 R00801 R00802 R06084(G) R06087(G) R06088(G) INHIBITOR Castanospermine [CPD:C02256]
    Gene Name: MGAM
    Uniprot ID: O43451 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glucose-6-phosphatase 2
    Reactions:
    • D-glucose 6-phosphate + H2O = D-glucose + phosphate [RN:R00303]
    Gene Name: G6PC2
    Uniprot ID: Q9NQR9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Neutral alpha-glucosidase C
    Reactions:
    • Hydrolysis of terminal, non-reducing (1->4)-linked alpha-D-glucose residues with release of D-glucose ALL_REAC (other) R00028 R00801 R00802 R06084(G) R06087(G) R06088(G) INHIBITOR Castanospermine [CPD:C02256]
    Gene Name: GANC
    Uniprot ID: Q8TET4 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aldose 1-epimerase
    Reactions:
    • alpha-D-glucose = beta-D-glucose [RN:R01602]
    Gene Name: GALM
    Uniprot ID: Q96C23 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA