Cannabis Compound Database: Showing Compound Card for alpha-d-Glucose (CDB000238)

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Record Information

Version

1.0

Created at

2020-03-19 00:26:15 UTC

Updated at

2020-11-18 16:34:57 UTC

CannabisDB ID

CDB000238

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

alpha-d-Glucose

Description

Œ±-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

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

180.16

Monoisotopic Molecular Weight

180.0634

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

Epidermis

Organ and components:

Intestine

Biofluid and excreta:

Subcellular:

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	alpha-d-Glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	Spectrum
Predicted GC-MS	alpha-d-Glucose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	Spectrum
Predicted GC-MS	alpha-d-Glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9100000000-57ee067515dbaeec1e27	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9100000000-311a61760b7c0dc3a7e1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9100000000-f2beec08615d57ac1a02	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0ab9-9100000000-eb694004566014e0b267	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-906b2fd231873b000e08	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-3cd19dc7a445df26b86d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9100000000-53278ff57ca00e1b5d1a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0079-9000000000-c4182c64988208ac78b0	2012-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-a4ec4f0b1e29e360a952	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-ec2bf4918640a0a36398	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-2448926b508622464fe7	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-8900000000-4c073cb93b78120113e6	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-ece70093ab5d3c331ac4	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-b0bc47623e7b2ca31c02	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-648e1637af29cf2a3518	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9200000000-9e6f46a1cbf52d6e347a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01qa-0900000000-04ceb34d441ff6a75763	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9400000000-a8f1ceab155611f949c1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ow-9000000000-358f68fc2b7a72c27546	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Gluconeogenesis
Fructose and Mannose Degradation
Retinol Metabolism
Starch and Sucrose Metabolism
Glycolysis

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aldose reductase	AKR1B1	7q35	P15121	details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	ENPP1	6q22-q23	P22413	details
Glucokinase	GCK	7p15.3-p15.1	P35557	details
Hexokinase-3	HK3	5q35.2	P52790	details
Hexokinase-2	HK2	2p13	P52789	details
Hexokinase-1	HK1	10q22	P19367	details
Sucrase-isomaltase, intestinal	SI		P14410	details
Lactase-phlorizin hydrolase	LCT	2q21	P09848	details
Glycogen debranching enzyme	AGL		P35573	details
ADP-dependent glucokinase	ADPGK	15q24.1	Q9BRR6	details
Trehalase	TREH	11q23.3	O43280	details
Glucose-6-phosphatase	G6PC	17q21	P35575	details
Beta-galactosidase	GLB1		P16278	details
Glucosylceramidase	GBA	1q21	P04062	details
Lysosomal alpha-glucosidase	GAA		P10253	details
Alpha-amylase 1	AMY1A		P04745	details
Glucokinase regulatory protein	GCKR	2p23	Q14397	details
Cytosolic beta-glucosidase	GBA3		Q9H227	details
Maltase-glucoamylase, intestinal	MGAM		O43451	details
Glucose-6-phosphatase 2	G6PC2	2q24.3	Q9NQR9	details
Neutral alpha-glucosidase C	GANC		Q8TET4	details
Aldose 1-epimerase	GALM	2p22.1	Q96C23	details
Aldo-keto reductase family 1 member B10	AKR1B10		O60218	details
Putative hexokinase HKDC1	HKDC1	10q22.1	Q2TB90	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	ENPP1	6q22-q23	P22413	details
ADP-dependent glucokinase	ADPGK	15q24.1	Q9BRR6	details
Alpha-amylase 1	AMY1A		P04745	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	ENPP1	6q22-q23	P22413	details
Glucosylceramidase	GBA	1q21	P04062	details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.92 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	3.71 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	23.24 mg/g dry wt	David S. Wishart,...	details

External Links

HMDB ID

HMDB0003345

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

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.

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Enzymes

Enzyme Details

1. Aldose reductase

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

Enzyme Details

2. Ectonucleotide pyrophosphatase/phosphodiesterase family member 1

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

Enzyme Details

3. Glucokinase

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

Enzyme Details

4. Hexokinase-3

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK3
Uniprot ID:: P52790
Molecular weight:: 99024.56

Enzyme Details

5. Hexokinase-2

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK2
Uniprot ID:: P52789
Molecular weight:: 102379.06

Enzyme Details

6. Hexokinase-1

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK1
Uniprot ID:: P19367
Molecular weight:: 102485.1

Enzyme Details

7. Sucrase-isomaltase, intestinal

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

Enzyme Details

8. Lactase-phlorizin hydrolase

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

Enzyme Details

9. Glycogen debranching enzyme

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

Enzyme Details

10. ADP-dependent glucokinase

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.

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Showing Compound Card for alpha-d-Glucose (CDB000238)

Structure for CDB000238 (alpha-d-Glucose)

Enzymes