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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-12 19:09:59 UTC
Update Date2017-12-20 20:33:03 UTC
HMDB IDHMDB0003345
Secondary Accession Numbers
  • HMDB03345
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
ValueSource
alpha-D-GLCChEBI
alpha-DextroseChEBI
a-D-GLCGenerator
α-D-GLCGenerator
a-D-GlucoseGenerator
α-D-glucoseGenerator
a-DextroseGenerator
α-dextroseGenerator
a-D-GlucopyranoseHMDB
a-GlucoseHMDB
alpha-D-GlucopyranoseHMDB
alpha-delta-GlucopyranoseHMDB
alpha-delta-GlucoseHMDB
alpha-GlucoseHMDB
HexopyranoseHMDB
Anhydrous dextroseMeSH
D GlucoseMeSH
D-GlucoseMeSH
DextroseMeSH
Dextrose, anhydrousMeSH
GlucoseMeSH
Glucose monohydrateMeSH
Glucose, (DL)-isomerMeSH
Glucose, (L)-isomerMeSH
Glucose, (alpha-D)-isomerMeSH
Glucose, (beta-D)-isomerMeSH
L GlucoseMeSH
L-GlucoseMeSH
Monohydrate, glucoseMeSH
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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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 Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.09 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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
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, 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, 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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
Tissue Location
  • Epidermis
  • Intestine
Pathways
NameSMPDB/PathwhizKEGG
Fanconi-bickel syndromeThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Fructose and Mannose DegradationThumbThumb?image type=greyscaleThumb?image type=simpleMap00051
Fructose intolerance, hereditaryThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Fructose-1,6-diphosphatase deficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
FructosuriaThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)MaleNormal details
FecesDetected but not Quantified Adult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)MaleGout details
FecesDetected but not Quantified Adult (>18 years old)Femaleankylosing spondylitis details
FecesDetected but not Quantified Adult (>18 years old)Femalerheumatoid arthritis details
FecesDetected but not Quantified Adult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not Quantified Adult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Irritable Bowel Syndrome
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011829
KNApSAcK IDC00001122
Chemspider ID71358
KEGG Compound IDC00267
BioCyc IDALPHA-GLUCOSE
BiGG IDNot Available
Wikipedia LinkNot Available
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 ]

Only showing the first 10 proteins. There are 24 proteins in total.

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

Only showing the first 10 proteins. There are 24 proteins in total.