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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:20 UTC
HMDB IDHMDB00765
Secondary Accession Numbers
  • HMDB01363
Metabolite Identification
Common NameMannitol
DescriptionMannitol is a diuretic and renal diagnostic aid related to sorbitol. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. 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 or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6) is an osmotic diuretic agent and a weak renal vasodilator. It is a sorbitol isomer.
Structure
Thumb
Synonyms
ValueSource
(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexaolChEBI
(2R,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexolChEBI
D-(-)-MannitolChEBI
e 421ChEBI
e-421ChEBI
e421ChEBI
Manna sugarChEBI
ManniteChEBI
MannitolChEBI
OsmitrolChEBI
1,2,3,4,5,6-HexanehexolHMDB
CordycepateHMDB
Cordycepic acidHMDB
DiosmolHMDB
HexahydroxyhexaneHMDB
HexanhexolHMDB
InvenexHMDB
IsotolHMDB
ManicolHMDB
Maniton SHMDB
Maniton-SHMDB
MannazuckerHMDB
MannidexHMDB
MannigenHMDB
MannistolHMDB
MannitHMDB
Mannit PHMDB
Mannogem 2080HMDB
Marine crystalHMDB
Mushroom sugarHMDB
OsmofundinHMDB
OsmosalHMDB
ResectisolHMDB
SDM no. 35HMDB
Chemical FormulaC6H14O6
Average Molecular Weight182.1718
Monoisotopic Molecular Weight182.07903818
IUPAC Name(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
Traditional Namemannitol
CAS Registry Number69-65-8
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI Identifier
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
InChI KeyInChIKey=FBPFZTCFMRRESA-KVTDHHQDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar alcohols
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
  • Microbial
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point166 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility216 mg/mL at 25 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP-3.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility229.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m3·mol-1ChemAxon
Polarizability16.82 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-0ktb-0931000000-b481d576c5f24dd1b1d5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-066s-0942000000-20043a375d72ca08dce9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-066r-1974000000-38a4beaca17ab8c750b6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014j-9600000000-26f4335f7ef7c81ca261View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-9000000000-73db1fbd51fb8c061becView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9000000000-45a4dea1d21286c4b8daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0089-6900000000-961d76d6550bc342ffa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Brain
  • Skin
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified34.0 +/- 18.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified4.49 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4.8 +/- 2.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified5.6 +/-1.7 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4.61 (3.30-5.92) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified62.692 +/- 69.964 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.26 +/- 9.14 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified120.0 (0.0-245.0) umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified32.4 (5.2-85.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.63 (1.14-2.12) uMAdult (>18 years old)Both
Cytochrome C oxidase deficiency
details
BloodDetected and Quantified2.0 (0.0-5.0) uMAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified5.6 +/-1.1 uMAdult (>18 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified5.54 +/- 0.82 uMNot SpecifiedNot SpecifiedAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified48.9 (8.24-144) uMAdult (>18 years old)Both
AIDS
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Cryptosporidium infection
details
UrineDetected and Quantified116.989 +/- 152.291 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified41.0 (0.0-486.0) umol/mmol creatinineNot SpecifiedBothLung cancer details
Associated Disorders and Diseases
Disease References
AIDS
  1. 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 ]
Alzheimer's disease
  1. Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [8595727 ]
Cytochrome C oxidase deficiency
  1. 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 ]
Lung Cancer
  1. Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [18953024 ]
Ribose-5-phosphate isomerase deficiency
  1. Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [14988808 ]
Associated OMIM IDs
DrugBank IDDB00742
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001982
KNApSAcK IDC00001165
Chemspider ID6015
KEGG Compound IDC00392
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMannitol
NuGOwiki LinkHMDB00765
Metagene LinkHMDB00765
METLIN ID142
PubChem Compound6251
PDB IDMTL
ChEBI ID16899
References
Synthesis ReferenceZhang, Chaohui; Wang, Jianping; He, Junlin. Preparation of mannitol from sucrose with high yield. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 11 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. [6821187 ]
  21. 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 ]
  22. 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 ]
  23. 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 ]
  24. Wakai A, Roberts I, Schierhout G: Mannitol for acute traumatic brain injury. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD001049. [16235278 ]
  25. Roberts I, Smith R, Evans S: Doubts over head injury studies. BMJ. 2007 Feb 24;334(7590):392-4. [17322250 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Faassen F, Vogel G, Spanings H, Vromans H: Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22. [12954186 ]