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MetaCyc Compound: D-sorbitol

Synonyms: L-gulitol, D-glucitol, meglumine, iso-sorbide

Superclasses: all carbohydrates a carbohydrate a glycan a sugar a sugar alcohol a hexitol
an alcohol a sugar alcohol a hexitol

Chemical Formula: C6H14O6

Molecular Weight: 182.17 Daltons

Monoisotopic Molecular Weight: 182.079038182 Daltons

SMILES: C(C(C(C(C(CO)O)O)O)O)O

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

InChIKey: InChIKey=FBPFZTCFMRRESA-JGWLITMVSA-N

Unification Links: CAS:50-70-4 , ChEBI:17924 , ChemSpider:5576 , DrugBank:DB01638 , HMDB:HMDB00247 , IAF1260:36018 , KEGG:C00794 , MetaboLights:MTBLC17924 , PubChem:5780

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -81.51431 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2-keto-L-gulonate biosynthesis , L-ascorbate biosynthesis III :
D-sorbitol + an oxidized electron acceptor → keto-L-sorbose + a reduced electron acceptor

Not in pathways:
a sugar alcohol + oxygen → an aldose + hydrogen peroxide

Reactions known to produce the compound:

sorbitol biosynthesis I :
D-sorbitol 6-phosphate + H2O → D-sorbitol + phosphate

sorbitol biosynthesis II :
keto-D-fructose + D-glucopyranose → D-glucono-1,5-lactone + D-sorbitol

Not in pathways:
a thioglucoside + H2O → a sugar + a thiol
a sugar phosphate + H2O → a sugar + phosphate
glycosyl-N-acylsphingosine + H2O → a ceramide + a sugar


an N-acetyl-β-D-galactosalaminyl-[glycan] + H2O → a glycan + N-acetyl-β-D-galactosamine

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition , phosphate utilization in cell wall regeneration :
a phosphate monoester + H2O ↔ an alcohol + phosphate


an alcohol + NAD+ + H2O ← an organic hydroperoxide + NADH + H+
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → β-primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol
a 6-phospho-β-D-galactoside + H2O → α-D-galactose 6-phosphate + an alcohol

Reactions known to both consume and produce the compound:

D-sorbitol degradation I :
D-sorbitol + NAD+ ↔ keto-D-fructose + NADH + H+

galactose degradation IV :
L-xylo-3-hexulose + NADPH + H+D-sorbitol + NADP+
D-sorbitol + NAD+ ↔ keto-D-fructose + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
D-sorbitol + NADP+ = keto-L-sorbose + NADPH + H+


a sugar alcohol + NAD(P)+ = an aldose + NAD(P)H + H+


an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
trans-cinnamoyl-β-D-glucoside + an alcohol = β-D-glucose + alkyl cinnamate
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + D-sorbitol[periplasmic space] → D-sorbitol 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine ,
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Enzymes inhibited by D-sorbitol, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: D-mannonate dehydratase [RobertBaudouy73] , sorbitol-6-phosphate phosphatase [Zhou03]

Inhibitor (Mechanism unknown) of: transport and phosphorylation of D-mannitol [Jacobson83a]


References

Jacobson83a: Jacobson GR, Tanney LE, Kelly DM, Palman KB, Corn SB (1983). "Substrate and phospholipid specificity of the purified mannitol permease of Escherichia coli." J Cell Biochem 23(1-4);231-40. PMID: 6427236

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

RobertBaudouy73: Robert-Baudouy JM, Stoeber FR (1973). "[Purification and properties of D-mannonate hydrolyase from Escherichia coli K12]." Biochim Biophys Acta 1973;309(2);473-85. PMID: 4581499

Zhou03: Zhou R., Cheng L., Wayne R. (2003). "Purification and characterization of sorbitol-6-phosphate phosphatase from apple leaves." Plant Science 165:227-232.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Feb 1, 2015, biocyc13.