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D-glucitol (YMDB00656)

Identification
YMDB IDYMDB00656
NameD-glucitol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSorbitol, also known as neosorb or D-glucitol, 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. Sorbitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Sorbitol exists in all living species, ranging from bacteria to humans. sorbitol can be converted into keto-D-fructose; which is catalyzed by the enzyme sorbitol dehydrogenase. In yeast, sorbitol is involved in the metabolic pathway called the fructose metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (-)-Sorbitol
  • (2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
  • 1,2,3,4,5,6-Hexanehexol
  • Cholaxine
  • clucitol
  • Cystosol
  • D-(-)-Sorbitol
  • D-1,2,3,4,5,6-hexanehexol
  • d-Galactitol
  • D-Glucitol
  • d-sorbit
  • d-Sorbite
  • D-Sorbitol
  • D-Sorbol
  • Diakarmon
  • Esasorb
  • Glucarine
  • glucitol
  • Glucitol, D-
  • gulitol
  • Hexahydric alcohol
  • Hexitol
  • Karion
  • l-gulitol
  • Multitol
  • Nivitin
  • Orbit
  • Probilagol
  • Resulax
  • Sionit
  • Sionit K
  • Sionite
  • Sionon
  • Siosan
  • Sorban
  • Sorbelite C
  • Sorbicolan
  • Sorbilande
  • Sorbilax
  • sorbite
  • Sorbitol
  • Sorbitur
  • Sorbo
  • Sorbol
  • Sorbostryl
  • Sorbostyl
  • Sorvilande
  • e 420
  • e-420
  • e420
  • g-Ol
  • GLC-Ol
  • Sorbitol 3% in plastic container
  • Foodol D 70
  • Karion instant
  • Kyowa powder 50m
  • Neosorb
  • Neosorb 20/60dC
  • Neosorb 70/02
  • Neosorb 70/70
  • Neosorb p 20/60
  • Neosorb p 60
  • Neosorb p 60W
  • Sorbex m
  • Sorbex R
  • Sorbex RP
  • Sorbex S
  • Sorbex X
  • Sorbit
  • Sorbit D 70
  • Sorbit D-powder
  • Sorbit DP
  • Sorbit DP 50
  • Sorbit kyowa powder 50m
  • Sorbit L 70
  • Sorbit S
  • Sorbit T 70
  • Sorbit W 70
  • Sorbit W-powder
  • Sorbit W-powder 50
  • Sorbit WP
  • Sorbitol F
  • Sorbitol FK
  • Sorbitol FP
  • Sorbitol S
  • Sorbitol syrup C
  • Sorbogem 712
  • Medefield brand OF sorbitol
  • Sorbitol pfizer brand
  • Yal
  • Klysma sorbit
  • Medevac
  • Trommsdorff brand OF sorbitol
  • Baxter brand OF sorbitol
  • Pfizer brand OF sorbitol
CAS number50-70-4
WeightAverage: 182.1718
Monoisotopic: 182.07903818
InChI KeyFBPFZTCFMRRESA-JGWLITMVSA-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,5S)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC NameD-sorbitol
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
StateLiquid
Charge0
Melting point11 °C
Experimental Properties
PropertyValueReference
Water Solubility2750 mg/mL at 30 oC [MULLIN,JW (1972)]PhysProp
LogP-2.20 [SANGSTER (1994)]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
Polarizability17.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
CaramelFDB011676
OdorlessFDB011676
SweetFDB011676
SMPDB Pathways
Fructose MetabolismPW002390 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fructose and mannose metabolismec00051 Map00051
Galactose metabolismec00052 Map00052
SMPDB Reactions
D-glucitol + NAD → NADH + hydron + keto-D-fructose
KEGG Reactions
NAD + D-glucitol → NADH + D-Fructose + hydron
D-Glucose + NADPH + hydron → NADP + D-glucitol
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0ldj-0941000000-19d96a9ba7ba0c482c83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-014i-1973000000-d907b75f68a7927501a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldj-0941000000-19d96a9ba7ba0c482c83JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1973000000-d907b75f68a7927501a7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0931000000-4ffadb4b25e8e2510d93JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03k9-9500000000-97c5853d3e9b96f9d054JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-0a6s-7141193000-dcd9245e12314ee0ced4JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-017j-8900000000-700285f86eac0a3501d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-066r-9000000000-84676b839b145250d67dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052f-9000000000-dce72cab270c488d65daJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-2900000000-26a16e983791be7818f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0ik9-2900000000-6513771e890cbff9c402JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0900000000-58e6917626e28d1830a2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-83169b2192f847cc0636JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0900000000-4cd721d87e359527adf3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0900000000-b44f68c64bc74e79e9fcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0900000000-bbb5e957a9e67ddc411eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-772c3052966c05f29842JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-d1fbea514e7f1c1628f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0790000000-b5b098cd5b4b4ec10821JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0690000000-41d4e48d49836c63485cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0002-9200000000-9b9f891e480758a7d333JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-6ed9009701977f0a1c00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kb-1900000000-7cc0793661b053aaf61eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-2900000000-ef92b9091ecf5d15cdeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-47f19bd4e51bff726536JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9100000000-60d5147d8e349337fe97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07ju-8900000000-36f0fe0f346a6424162aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0c0c-9200000000-36e85b5ec098a45204c3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-77703ee971336704163fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3900000000-6801fbed6b67e0df2d20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9000000000-4454dcd4b817c183328bJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Sarthy, A. V., Schopp, C., Idler, K. B. (1994). "Cloning and sequence determination of the gene encoding sorbitol dehydrogenase from Saccharomyces cerevisiae." Gene 140:121-126.8125328
Synthesis Reference:Liu, Haichao; Luo, Chen. Method for manufacturing sorbitol and mannitol with cellulose. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 8pp.
External Links:
ResourceLink
CHEBI ID17924
HMDB IDHMDB00247
Pubchem Compound ID5780
Kegg IDC00794
ChemSpider ID24533858
FOODB IDFDB011676
WikipediaSorbitol
BioCyc IDSORBITOL

Enzymes

Protein Details
1. Sorbitol dehydrogenase 1
General function:
Involved in zinc ion binding
Specific function:
L-iditol + NAD(+) = L-sorbose + NADH
Gene Name:
SOR1
Uniprot ID:
P35497
Molecular weight:
38165.39844
Reactions
L-iditol + NAD(+) → L-sorbose + NADH.
Protein Details
2. NADPH-dependent aldose reductase GRE3
General function:
Involved in oxidoreductase activity
Specific function:
Reduces the cytotoxic compound methylglyoxal (MG) to (R)-lactaldehyde similar to GRE2. MG is synthesized via a bypath of glycolysis from dihydroxyacetone phosphate and is believed to play a role in cell cycle regulation and stress adaptation. In pentose-fermenting yeasts, aldose reductase catalyzes the reduction of xylose into xylitol. The purified enzyme catalyzes this reaction, but the inability of S.cerevisiae to grow on xylose as sole carbon source indicates that the physiological function is more likely methylglyoxal reduction
Gene Name:
GRE3
Uniprot ID:
P38715
Molecular weight:
37118.5
Reactions
Alditol + NAD(P)(+) → aldose + NAD(P)H.
(R)-lactaldehyde + NADP(+) → methylglyoxal + NADPH.