Showing Compound Card for Mannitol (CDB006140)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:21:29 UTC
Updated at2020-12-07 19:06:54 UTC
CannabisDB IDCDB006140
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMannitol
DescriptionMannitol, also known ashexan-1,2,3,4,5,6-hexol (C6H8(OH)6), osmitrol or tobrex, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, and is produced by a plethora of organisms, including bacteria, fungi, algae, lichens, and many plants such as Cannabis (PMID:19578847 ). Mannitol is commonly used as a sweetener in diabetic foods as it is poorly absorbed by the intestines. Mannitol is also used as medication to decrease pressure in the eyes, (i.e. glaucoma) and to lower increased intracranial pressure. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. Mannitol can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function. Mannitol is commonly used as a research tool in cell biological studies, usually to control osmolarity. Chemically, mannitol as a sugar alcohol, is similar to xylitol or sorbitol and is considered an isomer of sorbitol. However, mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this reason, it is not uncommon to add a base to adjust its pH, such as sodium bicarbonate. Mannitol is a non-permeating molecule, meaning that it cannot cross biological membranes. Because of this inability to cross biological membranes, mannitol has been used for the determination of glomerular filtration rate (GFR). Altered levels of mannitol have been found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312 ; PMID: 29480337 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
DulciteChEBI
e 421ChEBI
e-421ChEBI
e421ChEBI
Manna sugarChEBI
ManniteChEBI
OsmitrolChEBI
D-MannitolKegg
TobrexKegg
BronchitolKegg
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
(L)-MannitolHMDB
MannitolChEBI
Chemical FormulaC6H14O6
Average Molecular Weight182.17
Monoisotopic Molecular Weight182.079
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 KeyFBPFZTCFMRRESA-KVTDHHQDSA-N
Chemical Taxonomy
Description 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 ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

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
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m³·mol⁻¹ChemAxon
Polarizability17.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00di-9000000000-d5db4fbf6c1eb9dd35642018-05-25View Spectrum
GC-MSMannitol, 6 TMS, GC-MS Spectrumsplash10-0ktb-0931000000-b481d576c5f24dd1b1d5Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066s-0942000000-20043a375d72ca08dce9Spectrum
GC-MSMannitol, 6 TMS, GC-MS Spectrumsplash10-066r-1974000000-38a4beaca17ab8c750b6Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-0229-9100000000-5655e9df8e0fdcaa72a0Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-001i-9200000000-0dad802ab0000303cb33Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-0ktb-0931000000-b481d576c5f24dd1b1d5Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066s-0942000000-20043a375d72ca08dce9Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066r-1974000000-38a4beaca17ab8c750b6Spectrum
GC-MSMannitol, non-derivatized, GC-MS Spectrumsplash10-066s-0942000000-f4df881aeebac32de5c7Spectrum
Predicted GC-MSMannitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-9500000000-97c5853d3e9b96f9d054Spectrum
Predicted GC-MSMannitol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a6s-7141193000-dcd9245e12314ee0ced4Spectrum
Predicted GC-MSMannitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMannitol, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014j-9600000000-26f4335f7ef7c81ca2612012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-9000000000-73db1fbd51fb8c061bec2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9000000000-45a4dea1d21286c4b8da2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0089-6900000000-961d76d6550bc342ffa12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0089-6900000000-061f88989a6ac71321e32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-1900000000-eb8ea056f3b1dfe2fb1f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-1900000000-6768b4744e1a4e56b18b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00kb-1900000000-0765563624accf132d032017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dr-0900000000-e159f4e76b7847313f352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0900-0910000000-8d56394cbc78dd3b5ca02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0079-0900000000-63517bff4abfbf09e1ca2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0w2l-0940000000-dc20c851073dcbc4dba92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-05ar-9500000000-c82bc4e2d1e173359c3e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-9000000000-47357f9a38864cba96682021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-066r-9000000000-9cd6979ccf800d067e032021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-02tj-9400000000-b72fa250b3caa4a876822021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-fc27b5c54b0dd6fc8a392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-9100000000-0436dafd7f39b7c910e92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066u-9000000000-fb4a8654ee07a1dcc56c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-ef92b9091ecf5d15cdee2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-47f19bd4e51bff7265362016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9100000000-60d5147d8e349337fe972016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07ju-8900000000-36f0fe0f346a6424162a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c0c-9200000000-36e85b5ec098a45204c32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-77703ee971336704163f2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
Transporters
Protein NameGene NameLocusUniprot IDDetails
Multidrug resistance protein 1ABCB17q21.12P08183 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000765
DrugBank IDDB00742
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112364
KNApSAcK IDC00001165
Chemspider ID6015
KEGG Compound IDC00392
BioCyc IDMANNITOL
BiGG IDNot Available
Wikipedia LinkMannitol
METLIN ID142
PubChem Compound6251
PDB IDNot Available
ChEBI ID16899
References
General References
  1. Song SH, Vieille C: Recent advances in the biological production of mannitol. Appl Microbiol Biotechnol. 2009 Aug;84(1):55-62. doi: 10.1007/s00253-009-2086-5. Epub 2009 Jul 4. [PubMed:19578847 ]
  2. Wisselink HW, Mars AE, van der Meer P, Eggink G, Hugenholtz J: Metabolic engineering of mannitol production in Lactococcus lactis: influence of overexpression of mannitol 1-phosphate dehydrogenase in different genetic backgrounds. Appl Environ Microbiol. 2004 Jul;70(7):4286-92. doi: 10.1128/AEM.70.7.4286-4292.2004. [PubMed:15240312 ]
  3. Zhang M, Gu L, Cheng C, Ma J, Xin F, Liu J, Wu H, Jiang M: Recent advances in microbial production of mannitol: utilization of low-cost substrates, strain development and regulation strategies. World J Microbiol Biotechnol. 2018 Feb 26;34(3):41. doi: 10.1007/s11274-018-2425-8. [PubMed:29480337 ]

Transporters

Enzyme Details
1. Multidrug resistance protein 1
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