Record Information |
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Version | 2.0 |
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Creation Date | 2014-08-29 06:33:43 UTC |
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Update Date | 2015-06-05 21:10:43 UTC |
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Accession Number | T3D4356 |
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Identification |
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Common Name | D-Glucose |
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Class | Small Molecule |
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Description | Glucose 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 water solution both forms are in equilibrium and at pH 7 the cyclic one is the predominant. 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. |
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Compound Type | - Animal Toxin
- Food Toxin
- Household Toxin
- Metabolite
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | (+)-Glucose | Anhydrous dextrose | Cerelose | Cerelose 2001 | Clearsweet 95 | Clintose L | Corn sugar | CPC hydrate | D(+)-Glucose | Dextropur | Dextrose | Dextrosol | Glucodin | Glucolin | Glucose | Goldsugar | Grape sugar | Meritose | Roferose st | Staleydex 111 | Staleydex 95M | Tabfine 097(HS) | Vadex |
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Chemical Formula | C6H12O6 |
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Average Molecular Mass | 180.156 g/mol |
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Monoisotopic Mass | 180.063 g/mol |
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CAS Registry Number | 50-99-7 |
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IUPAC Name | (3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol |
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Traditional Name | glucose |
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SMILES | [H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O |
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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 |
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InChI Key | InChIKey=WQZGKKKJIJFFOK-GASJEMHNSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Hexoses |
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Alternative Parents | |
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Substituents | - Hexose monosaccharide
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | - Endoplasmic reticulum
- Extracellular
- Golgi apparatus
- Lysosome
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | - Adipose Tissue
- Adrenal Cortex
- Adrenal Gland
- Adrenal Medulla
- Beta Cell
- Bladder
- Brain
- Brain Plaques
- Epidermis
- Eye Lens
- Fetus
- Fibroblasts
- Gonads
- Gut
- Intestine
- Kidney
- Liver
- Lung
- Mouth
- Muscle
- Myelin
- Nerve Cells
- Neuron
- Pancreas
- Placenta
- Prostate
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Pathways | Name | SMPDB Link | KEGG Link |
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Galactose Metabolism | SMP00043 | map00052 | Gluconeogenesis | SMP00128 | Not Available | Glucose-Alanine Cycle | SMP00127 | Not Available | Glycolysis | SMP00040 | Not Available | Lactose Degradation | SMP00457 | Not Available | Lactose Synthesis | SMP00444 | Not Available | Transfer of Acetyl Groups into Mitochondria | SMP00466 | Not Available | Glucose Transporter Defect (SGLT2) | SMP00245 | Not Available | Isovaleric Aciduria | SMP00238 | Not Available | Pyruvate Carboxylase Deficiency | SMP00350 | Not Available | Renal Glucosuria | SMP00184 | Not Available |
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Applications | Not Available |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 146 - 150°C | Boiling Point | Not Available | Solubility | 1200.0 mg/mL | LogP | -3.24 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-00kb-1931000000-ec21c3af97621f7bf95a | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS) | splash10-0fr2-1920000000-f53c5f0d5ad84d32679f | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX) | splash10-00di-9821000000-dbc697213e3b7cc9d4fe | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS; 1 MEOX) | splash10-00di-9621000000-9d1d8057758d3da8caca | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-014i-2490000000-3ed4c4fd34c05bad95f7 | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS) | splash10-066r-1952000000-3378cb724e551e8b0267 | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0udl-0690000000-c8fda4276ff69235f30d | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 5 TMS) | splash10-0ldi-1942000000-5d531ed23a4e82023d1c | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0udi-0790000000-7ebe75cd633c58d761fa | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-1931000000-ec21c3af97621f7bf95a | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fr2-1920000000-f53c5f0d5ad84d32679f | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9821000000-dbc697213e3b7cc9d4fe | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9621000000-9d1d8057758d3da8caca | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-2490000000-3ed4c4fd34c05bad95f7 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-066r-1952000000-3378cb724e551e8b0267 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udl-0690000000-c8fda4276ff69235f30d | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0ldi-1942000000-5d531ed23a4e82023d1c | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0udi-0790000000-7ebe75cd633c58d761fa | 2017-09-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0np0-9700000000-e8d638dc817e46b97d7b | 2016-09-22 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-004i-6122690000-eaf6f7adf34ccd0c667b | 2017-10-06 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-0002-9300000000-839f41cf94a071fcdb37 | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0002-9000000000-807f75d14f3d0b66f5bd | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-000t-9000000000-b89668f86992a8363664 | 2012-07-24 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-7900000000-9a673c2e4b82ca397421 | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0a4r-9100000000-b70415588e768ddce5ef | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0a4i-9000000000-73dc84dd88d8ae69fe02 | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0a4i-9000000000-ba39d4ed9431a1d01eab | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0a4i-9000000000-a61efd1469735758b317 | 2012-08-31 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-7900000000-9a673c2e4b82ca397421 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4r-9100000000-9c25b149885d8a48aab5 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-76d92ea96364c24ecfb0 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-ba39d4ed9431a1d01eab | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-9000000000-a61efd1469735758b317 | 2017-09-14 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-0900000000-b0bc47623e7b2ca31c02 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03ea-3900000000-648e1637af29cf2a3518 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0007-9200000000-9e6f46a1cbf52d6e347a | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-a4ec4f0b1e29e360a952 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9100000000-ec2bf4918640a0a36398 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-1900000000-6e953691e4c61d5123d9 | 2021-10-21 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000j-9200000000-42768e14d42bd5ebe785 | 2021-10-21 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08ov-9000000000-ee9eba654c17ccffa05f | 2021-10-21 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a6r-9700000000-b92609de9f7db41f6d8f | 2021-10-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4l-9100000000-31314220c313e7443171 | 2021-10-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-2a9c77b5036ec23fe0d4 | 2021-10-22 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | 2012-12-04 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Very high serum levels of glucose are found in untreated diabetic (type I or type II) patients. Glucose in chronic excess causes toxic effects on the structure and function of many cells and organs, including the pancreas and pancreatic islet cells. Multiple biochemical pathways and mechanisms of action for glucose toxicity have been suggested. These include glyceraldehyde auto-oxidation, protein kinase C activation, methylglyoxal formation and glycation, hexosamine metabolism, sorbitol formation, and oxidative phosphorylation. All these pathways have in common the formation of reactive oxygen species that, in excess and over time, cause chronic oxidative stress, which in turn causes defective insulin gene expression and insulin secretion as well as increased apoptosis. Exposure of endothelial cells to high glucose causes GAPDH inhibition through reactive oxygen species-activated poly(ADP-ribosyl)ation of GAPDH by poly(ADP-ribose) polymerase. Three products from glucose metabolism (glyoxal, methylglyoxal, and 3-deoxyglucosone) form advanced glycation end products (AGEs) by reacting with amino groups on intracellular and extracellular proteins. AGEs play important roles in the pathogenesis of secondary complications of diabetes, especially with regard to microvascular disease in the retina, nerves, and kidney and likely islets. Glycated hemoglobin is a particularly important AGE. A 1% increase in absolute concentrations of glycated hemoglobin is associated with about 10-20% increase in cardiovascular disease risk. |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | High blood glucose (>7 mM) produces the symptoms of frequent urination, increased thirst, and increased hunger. Chronic exposure to high blood glucose (i.e. untreated diabetes) can cause many complications. Acute complications include diabetic ketoacidosis (characterized by nausea, vomiting and abdominal pain, the smell of acetone on the breath) and nonketotic hyperosmolar coma. Serious long-term complications include heart disease, stroke, kidney failure, foot ulcers and damage to the eyes. The major long-term complications relate to damage to blood vessels. Diabetes doubles the risk of cardiovascular disease and about 75% of deaths in diabetics are due to coronary artery disease. Other "macrovascular" diseases are stroke, and peripheral vascular disease. The primary microvascular complications of diabetes include damage to the eyes, kidneys, and nerves. Damage to the eyes, known as diabetic retinopathy, is caused by damage to the blood vessels in the retina of the eye, and can result in gradual vision loss and potentially blindness. Damage to the kidneys, known as diabetic nephropathy, can lead to tissue scarring, urine protein loss, and eventually chronic kidney disease, sometimes requiring dialysis or kidney transplant. Damage to the nerves of the body, known as diabetic neuropathy, is the most common complication of diabetes. The symptoms can include numbness, tingling, pain, and altered pain sensation, which can lead to damage to the skin. Diabetes-related foot problems (such as diabetic foot ulcers) may occur, and can be difficult to treat, occasionally requiring amputation. Gestational diabetes can damage the health of the fetus or mother. Risks to the baby include macrosomia (high birth weight), congenital cardiac and central nervous system anomalies, and skeletal muscle malformations. Increased fetal insulin may inhibit fetal surfactant production and cause respiratory distress syndrome. Hyperbilirubinemia may result from red blood cell destruction. |
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Symptoms | Not Available |
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Treatment | Treatment involves a healthy diet, physical exercise, not using tobacco, and being a normal body weight. Blood pressure control and proper foot care are also important for people with the disease. Type 1 diabetes must be managed with insulin injections. Type 2 diabetes may be treated with medications with or without insulin. |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB02379 |
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HMDB ID | HMDB00122 |
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PubChem Compound ID | 5793 |
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ChEMBL ID | CHEMBL1222250 |
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ChemSpider ID | 5589 |
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KEGG ID | C00031 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 4167 |
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BioCyc ID | GLC |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | BGC |
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ACToR ID | Not Available |
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Wikipedia Link | Dextrose |
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References |
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Synthesis Reference | Chen Gong, “Method for preparation of 2’-deoxy-2’, 2’-difluoro-beta-cytidine or pharmaceutically acceptable salts thereof by using 1,6-anhydro-beta-D-glucose as raw material.” U.S. Patent US20060003963, issued January 05, 2006. |
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MSDS | T3D4356.pdf |
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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