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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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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

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


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:

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+


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 + 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]


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 18.5 on Sat Nov 22, 2014, BIOCYC14A.