Record Information
Version1.0
Created at2020-03-19 00:26:15 UTC
Updated at2020-11-18 16:34:57 UTC
CannabisDB IDCDB000238
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-d-Glucose
Descriptionα-D-Glucopyranose is one of the four cyclic isomers of D-glucose. Glucose (CAS: 50-99-7) is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is the most abundant monosaccharide, a subcategory of carbohydrates and it is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, as such it is also found in Cannabis sativa (PMID: 6991645 ). In plants and algae, it is used to make cellulose in cell walls, which is the most abundant carbohydrate polymer found in nature. 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. In animals, glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. D-Glucose is found to be associated with 3-methyl-crotonyl-glycinuria, growth hormone deficiency, and primary hypomagnesemia, which are inborn errors of metabolism. Glucose is used therapeutically in fluid and nutrient replacement.
Structure
Thumb
Synonyms
ValueSource
alpha-D-GLCChEBI
alpha-DextroseChEBI
a-D-GLCGenerator
Α-D-GLCGenerator
a-DextroseGenerator
Α-dextroseGenerator
a-D-GlucoseGenerator
Α-D-glucoseGenerator
a-D-GlucopyranoseHMDB
a-GlucoseHMDB
alpha-D-GlucopyranoseHMDB
alpha-delta-GlucopyranoseHMDB
alpha-delta-GlucoseHMDB
alpha-GlucoseHMDB
HexopyranoseHMDB
Anhydrous dextroseHMDB
D GlucoseHMDB
D-GlucoseHMDB
DextroseHMDB
Dextrose, anhydrousHMDB
GlucoseHMDB
Glucose monohydrateHMDB
Glucose, (DL)-isomerHMDB
Glucose, (L)-isomerHMDB
Glucose, (alpha-D)-isomerHMDB
Glucose, (beta-D)-isomerHMDB
L GlucoseHMDB
L-GlucoseHMDB
Monohydrate, glucoseHMDB
1,3-alpha-D-GlucanHMDB
alpha-1,3-GlucanHMDB
alpha-D-GlucopyranosideHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.16
Monoisotopic Molecular Weight180.0634
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
Disposition

Route of exposure:

Source:

Biological location:

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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSalpha-d-Glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bSpectrum
Predicted GC-MSalpha-d-Glucose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bSpectrum
Predicted GC-MSalpha-d-Glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9100000000-57ee067515dbaeec1e272021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-311a61760b7c0dc3a7e12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-f2beec08615d57ac1a022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-eb694004566014e0b2672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-906b2fd231873b000e082021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3cd19dc7a445df26b86d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9100000000-53278ff57ca00e1b5d1a2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0079-9000000000-c4182c64988208ac78b02012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a9522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac8672016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a363982016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-2448926b508622464fe72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-8900000000-4c073cb93b78120113e62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-ece70093ab5d3c331ac42021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c022016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a35182016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0900000000-04ceb34d441ff6a757632021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9400000000-a8f1ceab155611f949c12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9000000000-358f68fc2b7a72c275462021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldose reductaseAKR1B17q35P15121 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
GlucokinaseGCK7p15.3-p15.1P35557 details
Hexokinase-3HK35q35.2P52790 details
Hexokinase-2HK22p13P52789 details
Hexokinase-1HK110q22P19367 details
Sucrase-isomaltase, intestinalSIP14410 details
Lactase-phlorizin hydrolaseLCT2q21P09848 details
Glycogen debranching enzymeAGLP35573 details
ADP-dependent glucokinaseADPGK15q24.1Q9BRR6 details
TrehalaseTREH11q23.3O43280 details
Glucose-6-phosphataseG6PC17q21P35575 details
Beta-galactosidaseGLB1P16278 details
GlucosylceramidaseGBA1q21P04062 details
Lysosomal alpha-glucosidaseGAAP10253 details
Alpha-amylase 1AMY1AP04745 details
Glucokinase regulatory proteinGCKR2p23Q14397 details
Cytosolic beta-glucosidaseGBA3Q9H227 details
Maltase-glucoamylase, intestinalMGAMO43451 details
Glucose-6-phosphatase 2G6PC22q24.3Q9NQR9 details
Neutral alpha-glucosidase CGANCQ8TET4 details
Aldose 1-epimeraseGALM2p22.1Q96C23 details
Aldo-keto reductase family 1 member B10AKR1B10O60218 details
Putative hexokinase HKDC1HKDC110q22.1Q2TB90 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
ADP-dependent glucokinaseADPGK15q24.1Q9BRR6 details
Alpha-amylase 1AMY1AP04745 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1ENPP16q22-q23P22413 details
GlucosylceramidaseGBA1q21P04062 details
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.92 mg/g dry wt
    • David S. Wishart,...
details
Sensi StarDetected and Quantified3.71 mg/g dry wt
    • David S. Wishart,...
details
Tangerine DreamDetected and Quantified23.24 mg/g dry wt
    • David S. Wishart,...
details
HMDB IDHMDB0003345
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 IDNot Available
ChEBI ID17925
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Only showing the first 10 proteins. There are 31 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
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
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK3
Uniprot ID:
P52790
Molecular weight:
99024.56
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK2
Uniprot ID:
P52789
Molecular weight:
102379.06
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
HK1
Uniprot ID:
P19367
Molecular weight:
102485.1
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
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
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
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

Only showing the first 10 proteins. There are 31 proteins in total.