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Identification
YMDB IDYMDB00724
NameL-glucitol
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSorbitol, also known as D-sorbit or L-gulitol, 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.
Structure
Thumb
Synonyms
  • (2R,3S,4S,5S)-hexane-1,2,3,4,5,6-hexol
  • D-Gulitol
  • L-glucitol
  • L-Sorbitol
  • (-)-Sorbitol
  • (2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexol
  • D-(-)-Sorbitol
  • D-Sorbit
  • D-SORBITOL
  • e 420
  • e-420
  • e420
  • g-Ol
  • GLC-Ol
  • L-Gulitol
  • D-Glucitol
  • Sorbitol 3% in plastic container
  • D-Sorbol
  • Diakarmon
  • Esasorb
  • Foodol D 70
  • Glucarine
  • Glucitol
  • Karion
  • Karion instant
  • Kyowa powder 50m
  • Multitol
  • Neosorb
  • Neosorb 20/60dC
  • Neosorb 70/02
  • Neosorb 70/70
  • Neosorb P 20/60
  • Neosorb P 60
  • Neosorb P 60W
  • Nivitin
  • Resulax
  • Sionit
  • Sionit K
  • Sionite
  • Sionon
  • Siosan
  • Sorbex m
  • Sorbex R
  • Sorbex RP
  • Sorbex S
  • Sorbex X
  • Sorbilande
  • Sorbilax
  • 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
  • Sorbite
  • Sorbitol F
  • Sorbitol FK
  • Sorbitol FP
  • Sorbitol S
  • Sorbitol syrup C
  • Sorbitur
  • Sorbo
  • Sorbogem 712
  • Sorbol
  • Sorbostyl
  • Medefield brand OF sorbitol
  • Sorbitol pfizer brand
  • Yal
  • Klysma sorbit
  • Medevac
  • Trommsdorff brand OF sorbitol
  • Baxter brand OF sorbitol
  • Pfizer brand OF sorbitol
CAS number6706-59-8
WeightAverage: 182.1718
Monoisotopic: 182.07903818
InChI KeyFBPFZTCFMRRESA-FSIIMWSLSA-N
InChIInChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m0/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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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 PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
NAD + L-glucitolNADH + hydron + L-Sorbose
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
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
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H 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
  • Gasch, A. P., Spellman, P. T., Kao, C. M., Carmel-Harel, O., Eisen, M. B., Storz, G., Botstein, D., Brown, P. O. (2000). "Genomic expression programs in the response of yeast cells to environmental changes." Mol Biol Cell 11:4241-4257.11102521
  • Hirasawa, T., Ashitani, K., Yoshikawa, K., Nagahisa, K., Furusawa, C., Katakura, Y., Shimizu, H., Shioya, S. (2006). "Comparison of transcriptional responses to osmotic stresses induced by NaCl and sorbitol additions in Saccharomyces cerevisiae using DNA microarray." J Biosci Bioeng 102:568-571.17270724
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID28789
HMDB IDHMDB0000247
Pubchem Compound ID82170
Kegg IDC01722
ChemSpider ID24533858
FOODB IDFDB011676
WikipediaSorbitol
BioCyc IDNot Available

Enzymes

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.