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MetaCyc Compound: ribitol

Synonyms: meso-ribitol, adonitol, (2R,3s,4S)-pentane-1,2,3,4,5-pentol, D-ribitol

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

Chemical Formula: C5H12O5

Molecular Weight: 152.15 Daltons

Monoisotopic Molecular Weight: 152.0684734957 Daltons

ribitol compound structure

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

InChI: InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-

InChIKey: InChIKey=HEBKCHPVOIAQTA-ZXFHETKHSA-N

Unification Links: CAS:488-81-3 , ChEBI:15963 , HMDB:HMDB00508 , KEGG:C00474 , MetaboLights:MTBLC15963

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -65.766556 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

ribitol degradation :
ribitol + NAD+ → D-ribulose + NADH + H+

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

Reactions known to produce the compound:

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

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

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
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

In Reactions of unknown directionality:

Not in pathways:
riboflavin + H+ + H2O = lumichrome + ribitol

Not in pathways:
a sugar alcohol + NAD(P)+ = an aldose + NAD(P)H + H+

Not in pathways:
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-glucopyranose + 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 + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Enzymes inhibited by ribitol, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: L-arabinose isomerase [Patrick68]

Inhibitor (Mechanism unknown) of: D-arabinose isomerase [Boulter73] , L-fucose isomerase [Boulter73] , D-arabinose isomerase [Boulter73]

This compound has been characterized as an alternative substrate of the following enzymes: L-arabinitol 4-dehydrogenase , diffusion of glycerol , D-galactitol dehydrogenase , D-sorbitol dehydrogenase , xylitol dehydrogenase , mannitol dehydrogenase , D-ribulokinase , D-ribulokinase


References

Boulter73: Boulter JR, Gielow WO (1973). "Properties of D-arabinose isomerase purified from two strains of Escherichia coli." J Bacteriol 113(2);687-96. PMID: 4632320

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

Patrick68: Patrick JW, Lee N (1968). "Purification and properties of an L-arabinose isomerase from Escherichia coli." J Biol Chem 1968;243(16);4312-8. PMID: 4878429


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 19.0 on Fri Sep 4, 2015, biocyc13.