L-glucitol (YMDB00724)

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Identification

YMDB ID

YMDB00724

Name

L-glucitol

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Sorbitol, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 number

6706-59-8

Weight

Average: 182.1718
Monoisotopic: 182.07903818

InChI Key

FBPFZTCFMRRESA-FSIIMWSLSA-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-/m0/s1

IUPAC Name

(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol

Traditional IUPAC Name

D-sorbitol

Chemical Formula

C₆H₁₄O₆

SMILES

OC[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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates 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

glucitol (CHEBI:17924 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	229 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.7	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.4 m³·mol⁻¹	ChemAxon
Polarizability	17.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

NAD + L-glucitol → NADH + hydron + L-Sorbose

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0ldj-0941000000-19d96a9ba7ba0c482c83	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-014i-1973000000-d907b75f68a7927501a7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ldj-0941000000-19d96a9ba7ba0c482c83	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-1973000000-d907b75f68a7927501a7	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ktb-0931000000-4ffadb4b25e8e2510d93	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03k9-9500000000-97c5853d3e9b96f9d054	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positive	splash10-0a6s-7141193000-dcd9245e12314ee0ced4	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-017j-8900000000-700285f86eac0a3501d1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-066r-9000000000-84676b839b145250d67d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-052f-9000000000-dce72cab270c488d65da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0ik9-2900000000-26a16e983791be7818f2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0ik9-2900000000-6513771e890cbff9c402	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014j-0900000000-58e6917626e28d1830a2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-83169b2192f847cc0636	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0900000000-4cd721d87e359527adf3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0900000000-b44f68c64bc74e79e9fc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-001i-0900000000-bbb5e957a9e67ddc411e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-772c3052966c05f29842	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-d1fbea514e7f1c1628f2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0790000000-b5b098cd5b4b4ec10821	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0690000000-41d4e48d49836c63485c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0002-9200000000-9b9f891e480758a7d333	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0900000000-6ed9009701977f0a1c00	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-1900000000-7cc0793661b053aaf61e	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-ef92b9091ecf5d15cdee	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-47f19bd4e51bff726536	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9100000000-60d5147d8e349337fe97	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07ju-8900000000-36f0fe0f346a6424162a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0c0c-9200000000-36e85b5ec098a45204c3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9000000000-77703ee971336704163f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3900000000-6801fbed6b67e0df2d20	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-9000000000-4454dcd4b817c183328b	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	28789
HMDB ID	HMDB0000247
Pubchem Compound ID	82170
Kegg ID	C01722
ChemSpider ID	24533858
FOODB ID	FDB011676
Wikipedia	Sorbitol
BioCyc ID	Not Available

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.

Structure for #<Compound:0xaa835914>

Enzymes

Reactions