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2D Structure
Also known as: D-glc, D-glucopyranose, D-glucopyranoside, Glc, Glucopyranose, Glucopyranoside
Molecular Formula
C6H12O6
Molecular Weight
180.16  g/mol
InChI Key
WQZGKKKJIJFFOK-GASJEMHNSA-N

D-Glucose is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
2.1.2 InChI
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
2.1.3 InChI Key
WQZGKKKJIJFFOK-GASJEMHNSA-N
2.1.4 Canonical SMILES
C(C1C(C(C(C(O1)O)O)O)O)O
2.1.5 Isomeric SMILES
C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. D-glc

2. D-glucopyranose

3. D-glucopyranoside

4. Glc

5. Glucopyranose

6. Glucopyranoside

7. Glucose

8. 2280-44-6

9. Grape Sugar

10. D-glcp

11. (3r,4s,5s,6r)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

12. Traubenzucker

13. Glucose Solution

14. Dextrose Solution

15. Chebi:4167

16. Corn Sugar

17. Glucopyranose, D-

18. 54-17-1

19. (3r,4s,5s,6r)-6-(hydroxymethyl)tetrahydro-2h-pyran-2,3,4,5-tetraol

20. Dsstox_cid_2910

21. Rel-(3r,4s,5s,6r)-6-(hydroxymethyl)tetrahydro-2h-pyran-2,3,4,5-tetraol

22. Glucodin

23. Goldsugar

24. Meritose

25. Vadex

26. Clintose L

27. Cpc Hydrate

28. Roferose St

29. A-d-glucose

30. Clearsweet 95

31. A-d-glucopyranose

32. Staleydex 95m

33. Staleydex 111

34. (+)-glucose

35. Cerelose 2001

36. Tabfine 097(hs)

37. 2h-pyran-2,3,4,5-tetraol

38. D-glucopyranose, Anhydrous

39. Glc-ring

40. Cartose Cerelose

41. D-glucose-ring

42. Glucose Injection

43. Glucose 40

44. Staleydex 130

45. Einecs 218-914-5

46. Glc-oh

47. Meritose 200

48. Nchembio867-comp4

49. Dextrose, Unspecified

50. Glucose (jp17)

51. Starbld0000491

52. 6-(hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol

53. Anhydrous Glucose ,(s)

54. Glucose, Unspecified Form

55. Dextrose, Unspecified Form

56. Purified Glucose (jp17)

57. Epitope Id:142342

58. D-(+)-dextrose

59. Dsstox_rid_76784

60. Dsstox_rid_82925

61. Dsstox_gsid_22910

62. Dsstox_gsid_48729

63. Gtpl4536

64. Chembl1222250

65. Bdbm34103

66. Dtxsid501015215

67. Dtxsid901015217

68. Tox21_113165

69. Tox21_200145

70. Akos025147374

71. Nsc 287045

72. Cas-50-99-7

73. Ncgc00166293-01

74. Ncgc00257699-01

75. Bs-48662

76. Cas-58367-01-4

77. G0048

78. (3r,4s,5s,6r)-6-(hydroxymethyl)tetrahydro-

79. C00031

80. D00009

81. F71542

82. Q37525

83. Q23905964

84. N_full/o_full_10000000000000_gs_656

85. D-glucose (closed Ring Structure, Complete Stereochemistry)

86. Wurcs=2.0/1,1,0/[a2122h-1x_1-5]/1/

2.3 Create Date
2005-06-08
3 Chemical and Physical Properties
Molecular Weight 180.16 g/mol
Molecular Formula C6H12O6
XLogP3-2.6
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count1
Exact Mass180.06338810 g/mol
Monoisotopic Mass180.06338810 g/mol
Topological Polar Surface Area110 Ų
Heavy Atom Count12
Formal Charge0
Complexity151
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Glucose pharmaceutical formulations (oral tablets, injections) are indicated for caloric supply and carbohydrate supplementation in case of nutrient deprivation. It is also used in metabolic disorders such as hypoglycemia.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Blood glucose is an obligatory energy source in humans involved in various cellular activities, and it also acts as a signalling molecule for diverse glucose-sensing molecules and proteins. Glucose undergoes oxidation into carbon dioxide, water and yields energy molecules in the process of glycolysis and subsequent citric cycle and oxidative phosphorylation. Glucose is readily converted into fat in the body which can be used as a source of energy as required. Under a similar conversion into storage of energy, glucose is stored in the liver and muscles as glycogen. Glucose stores are mobilized in a regulated manner, depending on the tissues' metabolic demands. Oral glucose tablets or injections serve to increase the supply of glucose and oral glucose administration is more effective in stimulating insulin secretion because it stimulates the incretin hormones from the gut, which promotes insulin secretion.


5.2 ATC Code

B - Blood and blood forming organs

B05 - Blood substitutes and perfusion solutions

B05C - Irrigating solutions

B05CX - Other irrigating solutions

B05CX01 - Glucose


V - Various

V04 - Diagnostic agents

V04C - Other diagnostic agents

V04CA - Tests for diabetes

V04CA02 - Glucose


V - Various

V06 - General nutrients

V06D - Other nutrients

V06DC - Carbohydrates

V06DC01 - Glucose


5.3 Absorption, Distribution and Excretion

Absorption

Polysaccharides can be broken down into smaller units by pancreatic and intestinal glycosidases or intestinal flora. Sodium-dependent glucose transporter SGLT1 and GLUT2 (SLC2A2) play predominant roles in intestinal transport of glucose into the circulation. SGLT1 is located in the apical membrane of the intestinal wall while GLUT2 is located in the basolateral membrane, but it was proposed that GLUT2 can be recruited into the apical membrane after a high luminal glucose bolus allowing bulk absorption of glucose by facilitated diffusion. Oral preparation of glucose reaches the peak concentration within 40 minutes and the intravenous infusions display 100% bioavailability.


Route of Elimination

Glucose can be renally excreted.


Volume of Distribution

The mean volume of distribution after intravenous infusion is 10.6L.


Clearance

The mean metabolic clearance rate of glucose (MCR) for the 10 subjects studied at the higher insulin level was 2.27 0.37 ml/kg/min at euglycemia and fell to 1.510.21 ml/kg/ at hyperglycemia. The mean MCR for the six subjects studied at the lower insulin level was 1.91 0.31 ml/kg/min at euglyglycemia.


5.4 Metabolism/Metabolites

Glucose can undergo aerobic oxidation in conjunction to the synthesis of energy molecules. Glycolysis is the initial stage of glucose metabolism where one glucose molecule is degraded into 2 molecules of pyruvate via substrate-level phosphorylation. These products are transported to the mitochondria where they are further oxidized into oxygen and carbon dioxide.


5.5 Biological Half-Life

The approximate half-life is 14.3 minutes following intravenous infusion. Gut glucose half-life was markedly higher in females (79 2 min) than in males (65 3 min, P < 0.0001) and negatively related to body height (r = -0.481; P < 0.0001).


5.6 Mechanism of Action

Glucose supplies most of the energy to all tissues by generating energy molecules ATP and NADH during a series of metabolism reactions called glycolysis. Glycolysis can be divided into 2 main phases where the preparatory phase is initiated by the phosphorylation of glucose by a hexokinase to form glucose 6-phosphate. The addition of the high-energy phosphate group activates glucose for subsequent breakdown in later steps of glycolysis and is the rate-limiting step. Products end up as substrates for following reactions, to ultimately convert C6 glucose molecule into two C3 sugar molecules. These products enter the energy-releasing phase where total of 4ATP and 2NADH molecules are generated per one glucose molecule. The total aerobic metabolism of glucose can produce up to 36 ATP molecules. This energy-producing reactions of glucose is limited to D-glucose as L-glucose cannot be phosphorlyated by hexokinase. Glucose can act as precursors to generate other biomolecules such as vitamin C. It plays a role as a signaling molecule to control glucose and energy homeostasis. Glucose can regulate gene transcription, enzyme activity, hormone secretion, and the activity of glucoregulatory neurons. The types, number and kinetics of glucose transporters expressed depends on the tissues and fine-tunes glucose uptake, metabolism, and signal generation in order to preserve cellular and whole body metabolic integrity.