2.0 2012-05-31 13:01:09 -0600 2015-09-13 12:56:09 -0600 ECMDB00765 M2MDB000185 Mannitol Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. Chemically, mannitol is an alcohol and a sugar, or a polyol; it is similar to xylitol or sorbitol. However, mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this, it is not uncommon to add a substance to adjust its pH, such as sodium bicarbonate.; Mannitol is a non-permeating molecule i.e. it cannot cross biological membranes.; Mannitol is a sorbitol isomer. 1,2,3,4,5,6-Hexanehexol Cordycepate Cordycepic acid D-Mannitol Diosmol Hexahydroxyhexane Hexanhexol Invenex Isotol Manicol Maniton S Maniton-S Manna sugar Mannazucker Mannidex Mannigen Mannistol Mannit Mannit p Mannite Mannitol Mannogem 2080 Marine crystal Mitobronitol Mushroom sugar Osmitrol Osmofundin Osmosal Resectisol SDM No. 35 C6H14O6 182.1718 182.07903818 (2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol mannitol 69-65-8 OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1 FBPFZTCFMRRESA-KVTDHHQDSA-N Solid Extra-organism Periplasm logp -2.68 ALOGPS logs 0.10 ALOGPS solubility 2.29e+02 g/l ALOGPS melting_point 166 oC logp -3.7 ChemAxon pka_strongest_acidic 12.59 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol ChemAxon average_mass 182.1718 ChemAxon mono_mass 182.07903818 ChemAxon smiles OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO ChemAxon formula C6H14O6 ChemAxon inchi InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1 ChemAxon inchikey FBPFZTCFMRRESA-KVTDHHQDSA-N ChemAxon polar_surface_area 121.38 ChemAxon refractivity 38.4 ChemAxon polarizability 17.04 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Phosphotransferase system (PTS) ec02060 ABC transporters ec02010 glycolysis and pyruvate dehydrogenase Fructose metabolism begins with the transport of Beta-D-glucose 6-phosphate through a glucose PTS permease, resulting in a Beta-D-glucose 6-phosphate. This compound is isomerized by a glucose-6-phosphate isomerase resulting in a fructose 6-phosphate. This compound can be phosphorylated by two different enzymes, a pyridoxal phosphatase/fructose 1,6-bisphosphatase or a ATP driven-6-phosphofructokinase-1 resulting in a fructose 1,6-biphosphate. This compound can either react with a fructose bisphosphate aldolase class 1 resulting in D-glyceraldehyde 3-phosphate and a dihydroxyacetone phosphate or through a fructose biphosphate aldolase class 2 resulting in a D-glyceraldehyde 3-phosphate. This compound can then either react in a reversible triosephosphate isomerase resulting in a dihydroxyacetone phosphate or react with a phosphate through a NAD dependent Glyceraldehyde 3-phosphate dehydrogenase resulting in a glyceric acid 1,3-biphosphate. This compound is desphosphorylated by a phosphoglycerate kinase resulting in a 3-phosphoglyceric acid.This compound in turn can either react with a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase or a 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 2-phospho-D-glyceric acid. This compound interacts with an enolase resulting in a phosphoenolpyruvic acid and water. Phosphoenolpyruvic acid can react either through a AMP driven phosphoenoylpyruvate synthase or a ADP driven pyruvate kinase protein complex resulting in a pyruvic acid. Pyruvic acid reacts with CoA through a NAD driven pyruvate dehydrogenase complex resulting in a carbon dioxide and a Acetyl-CoA which gets incorporated into the TCA cycle pathway. PW000785 Metabolic Specdb::CMs 645 Specdb::CMs 646 Specdb::CMs 1652 Specdb::CMs 2554 Specdb::CMs 29715 Specdb::CMs 29716 Specdb::CMs 30337 Specdb::CMs 30620 Specdb::CMs 31225 Specdb::CMs 32306 Specdb::CMs 37752 Specdb::CMs 167128 Specdb::CMs 1074858 Specdb::CMs 1074860 Specdb::CMs 1074862 Specdb::CMs 1074864 Specdb::CMs 1074866 Specdb::CMs 1074867 Specdb::CMs 1074869 Specdb::CMs 1074871 Specdb::CMs 1074873 Specdb::CMs 1074874 Specdb::CMs 1074876 Specdb::CMs 1074878 Specdb::CMs 1074879 Specdb::EiMs 1985 Specdb::NmrOneD 1531 Specdb::NmrOneD 4978 Specdb::NmrOneD 4979 Specdb::NmrOneD 7622 Specdb::NmrOneD 7623 Specdb::NmrOneD 7624 Specdb::NmrOneD 7625 Specdb::NmrOneD 7626 Specdb::NmrOneD 7627 Specdb::NmrOneD 7628 Specdb::NmrOneD 7629 Specdb::NmrOneD 7630 Specdb::NmrOneD 7631 Specdb::NmrOneD 7632 Specdb::NmrOneD 7633 Specdb::NmrOneD 7634 Specdb::NmrOneD 7635 Specdb::NmrOneD 7636 Specdb::NmrOneD 7637 Specdb::NmrOneD 7638 Specdb::NmrOneD 7639 Specdb::NmrOneD 7640 Specdb::NmrOneD 7641 Specdb::MsMs 1101 Specdb::MsMs 1102 Specdb::MsMs 1103 Specdb::MsMs 4658 Specdb::MsMs 178434 Specdb::MsMs 178435 Specdb::MsMs 178436 Specdb::MsMs 180753 Specdb::MsMs 180754 Specdb::MsMs 180755 Specdb::MsMs 439272 Specdb::MsMs 439752 Specdb::MsMs 439753 Specdb::MsMs 447484 Specdb::MsMs 449869 Specdb::MsMs 449870 Specdb::MsMs 449871 Specdb::MsMs 449872 Specdb::MsMs 2238417 Specdb::MsMs 2239141 Specdb::MsMs 2244732 Specdb::MsMs 2245367 Specdb::MsMs 2246871 Specdb::MsMs 2247436 Specdb::MsMs 2248848 Specdb::NmrTwoD 1477 HMDB00765 6251 6015 C00392 16899 MANNITOL MTL Mannitol Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. 7710082 Polderman KH, van de Kraats G, Dixon JM, Vandertop WP, Girbes AR: Increases in spinal fluid osmolarity induced by mannitol. Crit Care Med. 2003 Feb;31(2):584-90. 12576970 Zunkeler B, Carson RE, Olson J, Blasberg RG, DeVroom H, Lutz RJ, Saris SC, Wright DC, Kammerer W, Patronas NJ, Dedrick RL, Herscovitch P, Oldfield EH: Quantification and pharmacokinetics of blood-brain barrier disruption in humans. J Neurosurg. 1996 Dec;85(6):1056-65. 8929495 Dreher F, Patouillet C, Fouchard F, Zanini M, Messager A, Roguet R, Cottin M, Leclaire J, Benech-Kieffer F: Improvement of the experimental setup to assess cutaneous bioavailability on human skin models: dynamic protocol. Skin Pharmacol Appl Skin Physiol. 2002;15 Suppl 1:31-9. 12476007 Schramm-Baxter J, Mitragotri S: Needle-free jet injections: dependence of jet penetration and dispersion in the skin on jet power. J Control Release. 2004 Jul 7;97(3):527-35. 15212884 Megson GM, Stevens DA, Hamilton JR, Denning DW: D-mannitol in cerebrospinal fluid of patients with AIDS and cryptococcal meningitis. J Clin Microbiol. 1996 Jan;34(1):218-21. 8748311 Koskela HO, Hyvarinen L, Brannan JD, Chan HK, Anderson SD: Responsiveness to three bronchial provocation tests in patients with asthma. Chest. 2003 Dec;124(6):2171-7. 14665497 Zhao G, Wang CY, Wang F, Xiong JX: Clinical study on nutrition support in patients with severe acute pancreatitis. World J Gastroenterol. 2003 Sep;9(9):2105-8. 12970916 Kiyoshima A, Kudo K, Hino Y, Ikeda N: Sensitive and simple determination of mannitol in human brain tissues by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):103-8. 11482728 Ware ML, Nemani VM, Meeker M, Lee C, Morabito DJ, Manley GT: Effects of 23.4% sodium chloride solution in reducing intracranial pressure in patients with traumatic brain injury: a preliminary study. Neurosurgery. 2005 Oct;57(4):727-36; discussion 727-36. 16239885 Tang H, Blankschtein D, Langer R: Effects of low-frequency ultrasound on the transdermal permeation of mannitol: comparative studies with in vivo and in vitro skin. J Pharm Sci. 2002 Aug;91(8):1776-94. 12115805 Graefe H, Gutschow B, Gehring H, Dibbelt L: Sensitive and specific photometric determination of mannitol in human serum. Clin Chem Lab Med. 2003 Aug;41(8):1049-55. 12964813 Koskela HO, Hyvarinen L, Brannan JD, Chan HK, Anderson SD: Sensitivity and validity of three bronchial provocation tests to demonstrate the effect of inhaled corticosteroids in asthma. Chest. 2003 Oct;124(4):1341-9. 14555564 Barben J, Roberts M, Chew N, Carlin JB, Robertson CF: Repeatability of bronchial responsiveness to mannitol dry powder in children with asthma. Pediatr Pulmonol. 2003 Dec;36(6):490-4. 14618640 Keating FK, Sobel BE, Schneider DJ: Effects of increased concentrations of glucose on platelet reactivity in healthy subjects and in patients with and without diabetes mellitus. Am J Cardiol. 2003 Dec 1;92(11):1362-5. 14636925 Kiyoshima A, Kudo K, Goto Y, Tobimatsu S, Ikeda N: Changes of the cerebral mannitol concentrations in the course of brain death of a rodent model. Leg Med (Tokyo). 2004 Apr;6(2):117-24. 15039055 Koskela HO, Hyvarinen L, Brannan JD, Chan HK, Anderson SD: Coughing during mannitol challenge is associated with asthma. Chest. 2004 Jun;125(6):1985-92. 15189912 Rikitake Y, Liao JK: Rho-kinase mediates hyperglycemia-induced plasminogen activator inhibitor-1 expression in vascular endothelial cells. Circulation. 2005 Jun 21;111(24):3261-8. Epub 2005 Jun 13. 15956119 Lee J, Chung BC: Simultaneous measurement of urinary polyols using gas chromatography/mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 2;831(1-2):126-31. Epub 2005 Dec 13. 16356788 Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. 6821187 Cruz J, Minoja G, Okuchi K: Improving clinical outcomes from acute subdural hematomas with the emergency preoperative administration of high doses of mannitol: a randomized trial. Neurosurgery. 2001 Oct;49(4):864-71. 11564247 Cruz J, Minoja G, Okuchi K: Major clinical and physiological benefits of early high doses of mannitol for intraparenchymal temporal lobe hemorrhages with abnormal pupillary widening: a randomized trial. Neurosurgery. 2002 Sep;51(3):628-37; discussion 637-8. 12188940 Cruz J, Minoja G, Okuchi K, Facco E: Successful use of the new high-dose mannitol treatment in patients with Glasgow Coma Scale scores of 3 and bilateral abnormal pupillary widening: a randomized trial. J Neurosurg. 2004 Mar;100(3):376-83. 15035271 Wakai A, Roberts I, Schierhout G: Mannitol for acute traumatic brain injury. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD001049. 16235278 Roberts I, Smith R, Evans S: Doubts over head injury studies. BMJ. 2007 Feb 24;334(7590):392-4. 17322250 Zhang, Chaohui; Wang, Jianping; He, Junlin. Preparation of mannitol from sucrose with high yield. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 11 pp. http://hmdb.ca/system/metabolites/msds/000/000/684/original/HMDB00765.pdf?1358894839 PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Mannitol-specific cryptic phosphotransferase enzyme IIA component P69824 PTMA_ECOLI cmtB http://ecmdb.ca/proteins/P69824.xml PTS system mannitol-specific cryptic EIICB component P69826 PTMCB_ECOLI cmtA http://ecmdb.ca/proteins/P69826.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system mannitol-specific EIICBA component P00550 PTM3C_ECOLI mtlA http://ecmdb.ca/proteins/P00550.xml PTS system mannitol-specific cryptic EIICB component P69826 PTMCB_ECOLI cmtA http://ecmdb.ca/proteins/P69826.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-156 Protein N(pi)-phospho-L-histidine + Mannitol <> Protein histidine + Sorbitol-6-phosphate R02704 Phosphoenolpyruvic acid + Mannitol > Sorbitol-6-phosphate + Pyruvic acid TRANS-RXN-156 Mannitol + HPr - phosphorylated > Mannitol 1-phosphate + HPr PW_RCT000171