Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
Pathway Tools
Intro Tutorial
discounted registration ends Sept 5, 2015 (Sat)
twitter

MetaCyc Compound: L-arabitol

Synonyms: arabitol, arabinitol, 1,2,3,4,5-pentanepentol, L-arabinol, L-arabinitol, L-lyxitol

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

L-arabitol compound structure

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

InChI: InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m0/s1

InChIKey: InChIKey=HEBKCHPVOIAQTA-IMJSIDKUSA-N

Unification Links: CAS:7643-75-6 , ChEBI:18403 , ChemSpider:388391 , HMDB:HMDB01851 , KEGG:C00532 , MetaboLights:MTBLC18403 , PubChem:439255

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

Reactions known to consume the compound:

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

Reactions known to both consume and produce the compound:

L-arabinose degradation II :
L-arabitol + NADP+ ↔ L-arabinopyranose + NADPH + H+
L-arabitol + NAD+ ↔ L-xylulose + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
L-arabitol + NAD+ = aldehydo-L-arabinose + NADH + H+
L-arabitol + NAD+ = L-ribulose + NADH + H+

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 L-arabitol, 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: diffusion of glycerol


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 Sat Sep 5, 2015, biocyc11.