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Identification
YMDB IDYMDB00830
NameD-mannitol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionMannitol is a six-carbon sugar alcohol. It is one of the most abundant energy and carbon storage molecules in nature, produced by a plethora of organisms, including bacteria, yeasts, fungi, algae, lichens, and many plants. A fructose to mannitol metabolic pathway, known as the mannitol cycle in fungi, has been discovered in a type of red algae (Caloglossa leprieurii), and it is highly possible that other microorganisms employ similar such pathways.
Structure
Thumb
Synonyms
  • (2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexaol
  • (2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
  • 1,2,3,4,5,6-Hexanehexol
  • Cordycepate
  • Cordycepic acid
  • D-(-)-Mannitol
  • D-mannite
  • D-mannitol
  • D(-)-Mannitol
  • Diosmol
  • Hexahydroxyhexane
  • Hexanhexol
  • Hexitol
  • Invenex
  • Isotol
  • Manicol
  • manita
  • Maniton-s
  • Manna sugar
  • Mannazucker
  • Mannidex
  • Mannigen
  • Mannistol
  • Mannit
  • Mannit p
  • Mannite
  • Mannitol
  • Mannitol, D-
  • Mushroom sugar
  • Osmitrol
  • Osmofundin
  • Osmosal
  • Resectisol
  • SORBITOL-MANNITOL
  • Dulcite
  • e 421
  • e-421
  • e421
  • Tobrex
  • Bronchitol
  • Maniton S
  • Mannogem 2080
  • Marine crystal
  • SDM No. 35
  • (L)-Mannitol
CAS number69-65-8
WeightAverage: 182.1718
Monoisotopic: 182.07903818
InChI KeyFBPFZTCFMRRESA-KVTDHHQDSA-N
InChIInChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
IUPAC Name(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC Namemannitol
Chemical FormulaC6H14O6
SMILESOC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
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
Physical Properties
StateSolid
Charge0
Melting point166 °C
Experimental Properties
PropertyValueReference
Water Solubility216 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.10 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility229 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB001982
SMPDB PathwaysNot Available
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1020 ± 51 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Quain, D. E., Boulton, C. A. (1987). "Growth and metabolism of mannitol by strains of Saccharomyces cerevisiae." J Gen Microbiol 133:1675-1684.3117965
Synthesis Reference:Zhang, Chaohui; Wang, Jianping; He, Junlin. Preparation of mannitol from sucrose with high yield. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 11 pp.
External Links:
ResourceLink
CHEBI ID16899
HMDB IDHMDB00765
Pubchem Compound ID6251
Kegg IDC00392
ChemSpider ID6015
FOODB IDFDB001982
WikipediaMannitol
BioCyc IDNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DSF1
Uniprot ID:
P39941
Molecular weight:
56469.69922
Reactions
D-mannitol + NAD+ → D-fructose + NADH + H+