Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110553
Identification
Name: D-mannitol
Description:The D-enantiomer of mannitol.
Structure
Thumb
Synonyms:
  • D-mitobronitol
Chemical Formula: C6H14O6
Average Molecular Weight: 182.17
Monoisotopic Molecular Weight: 182.079038182
InChI Key: FBPFZTCFMRRESA-KVTDHHQDSA-N
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
CAS number: 69-65-8
IUPAC Name:D-mannitol
Traditional IUPAC Name: mannitol
SMILES:C(C(C(C(C(CO)O)O)O)O)O
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassOrganic oxygen compounds
Class Organooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent Sugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 166 °C
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
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
References
References:
  • Yu H, Liu X, Xing R, Liu S, Li C, Li P (2005)Radical scavenging activity of protein from tentacles of jellyfish Rhopilema esculentum. Bioorganic & medicinal chemistry letters 15, Pubmed: 15863337
  • Blanchfield JT, Dutton JL, Hogg RC, Gallagher OP, Craik DJ, Jones A, Adams DJ, Lewis RJ, Alewood PF, Toth I (2003)Synthesis, structure elucidation, in vitro biological activity, toxicity, and Caco-2 cell permeability of lipophilic analogues of alpha-conotoxin MII. Journal of medicinal chemistry 46, Pubmed: 12646037
  • Tian X, Field TB, Switzer AG, Mazur AW, Ebetino FH, Wos JA, Berberich SM, Jayasinghe LR, Obringer CM, Dowty ME, Pinney BB, Farmer JA, Crossdoersen D, Sheldon RJ (2006)Design, synthesis, and evaluation of proline and pyrrolidine based melanocortin receptor agonists. A conformationally restricted dipeptide mimic approach. Journal of medicinal chemistry 49, Pubmed: 16854081
  • Mandagere AK, Thompson TN, Hwang KK (2002)Graphical model for estimating oral bioavailability of drugs in humans and other species from their Caco-2 permeability and in vitro liver enzyme metabolic stability rates. Journal of medicinal chemistry 45, Pubmed: 11784135
  • Matsson P, Bergström CA, Nagahara N, Tavelin S, Norinder U, Artursson P (2005)Exploring the role of different drug transport routes in permeability screening. Journal of medicinal chemistry 48, Pubmed: 15658873
  • Hegde VL, Venkatesh YP (2007)Generation of antibodies specific to D-mannitol, a unique haptenic allergen, using reductively aminated D-mannose-bovine serum albumin conjugate as the immunogen. Immunobiology 212, Pubmed: 17336832
  • Sreenath K, Prabhasankar P, Venkatesh YP (2006)Generation of an antibody specific to erythritol, a non-immunogenic food additive. Food additives and contaminants 23, Pubmed: 16901854
  • Chan E, Amon M, Marano RJ, Wimmer N, Kearns PS, Manolios N, Rakoczy PE, Toth I (2007)Novel cationic lipophilic peptides for oligodeoxynucleotide delivery. Bioorganic & medicinal chemistry 15, Pubmed: 17420133
  • Chatterjee J, Ovadia O, Zahn G, Marinelli L, Hoffman A, Gilon C, Kessler H (2007)Multiple N-methylation by a designed approach enhances receptor selectivity. Journal of medicinal chemistry 50, Pubmed: 17973471
  • Baert B, Deconinck E, Van Gele M, Slodicka M, Stoppie P, Bodé S, Slegers G, Vander Heyden Y, Lambert J, Beetens J, De Spiegeleer B (2007)Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds. Bioorganic & medicinal chemistry 15, Pubmed: 17827020
  • Sreenath K, Venkatesh YP (2007)Reductively aminated D-xylose-albumin conjugate as the immunogen for generation of IgG and IgE antibodies specific to D-xylitol, a haptenic allergen. Bioconjugate chemistry 18, Pubmed: 17979222
  • Hess S, Ovadia O, Shalev DE, Senderovich H, Qadri B, Yehezkel T, Salitra Y, Sheynis T, Jelinek R, Gilon C, Hoffman A (2007)Effect of structural and conformation modifications, including backbone cyclization, of hydrophilic hexapeptides on their intestinal permeability and enzymatic stability. Journal of medicinal chemistry 50, Pubmed: 17983214
  • Mula S, Banerjee D, Patro BS, Bhattacharya S, Barik A, Bandyopadhyay SK, Chattopadhyay S (2008)Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages. Bioorganic & medicinal chemistry 16, Pubmed: 18207412
  • Ravi G, Venkatesh YP (2014)Recognition of flavin mononucleotide, Haemophilus influenzae type b and its capsular polysaccharide vaccines by antibodies specific to D-ribitol-5-phosphate. Glycoconjugate journal 31, Pubmed: 25108762
  • Hess S, Linde Y, Ovadia O, Safrai E, Shalev DE, Swed A, Halbfinger E, Lapidot T, Winkler I, Gabinet Y, Faier A, Yarden D, Xiang Z, Portillo FP, Haskell-Luevano C, Gilon C, Hoffman A (2008)Backbone cyclic peptidomimetic melanocortin-4 receptor agonist as a novel orally administrated drug lead for treating obesity. Journal of medicinal chemistry 51, Pubmed: 18220330
  • Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Analytical chemistry 84, Pubmed: 22770225
  • Ravi G, Venkatesh YP (2014)Recognition of riboflavin and the capsular polysaccharide of Haemophilus influenzae type b by antibodies generated to the haptenic epitope D-ribitol. Glycoconjugate journal 31, Pubmed: 24643482
Synthesis Reference: Zhang, 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)
External Links:
ResourceLink
CAS69-65-8
ChEBI16899
ChemSpider6015
DrugBankDB00742
HMDBHMDB00765
IAF126034845
KEGGC00392
MetaboLightsMTBLC16899
PubChem6251