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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: (-)-trans-isopiperitenol

Superclasses: a lipid an isoprenoid a terpenoid a terpenoid derivative a monoterpenoid derivative a monoterpenol
a secondary metabolite a terpenoid a terpenoid derivative a monoterpenoid derivative a monoterpenol
an alcohol a monoterpenol

Chemical Formula: C10H16O

Molecular Weight: 152.24 Daltons

Monoisotopic Molecular Weight: 152.1201151357 Daltons

SMILES: C=C(C)C1(CCC(C)=CC(O)1)

InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6,9-11H,1,4-5H2,2-3H3/t9-,10+/m1/s1

InChIKey: InChIKey=OLAKPNFIICOONC-ZJUUUORDSA-N

Unification Links: ChEBI:15406 , ChemSpider:388526 , KEGG:C01123 , LIPID MAPS:LMPR0102090006 , MetaboLights:MTBLC15406 , PubChem:439410

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 166.02794 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

menthol biosynthesis :
(-)-trans-isopiperitenol + NAD+ → (-)-isopiperitenone + NADH + H+

linoleate biosynthesis I (plants) :
oleoyl-CoA + a lipid + H+ → a lipid oleoyl-group + coenzyme A

Reactions known to produce the compound:

menthol biosynthesis :
(4S)-limonene + NADPH + H+ + oxygen → (-)-trans-isopiperitenol + NADP+ + H2O

Not in pathways:
a monoterpenyl diphosphate + H2O → a monoterpenol + diphosphate + H+

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

glutathione redox reactions I :
a lipid hydroperoxide + 2 glutathione + H+a lipid + glutathione disulfide + 2 H2O

In Reactions of unknown directionality:

Not in pathways:
a monoterpenol + acetyl-CoA + H+ = a monoterpenol acetate ester + coenzyme A


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

Enzymes activated by (-)-trans-isopiperitenol, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoenolpyruvate carboxylase [Izui83]


References

Izui83: Izui K, Matsuda Y, Kameshita I, Katsuki H, Woods AE (1983). "Phosphoenolpyruvate carboxylase of Escherichia coli. Inhibition by various analogs and homologs of phosphoenolpyruvate." J Biochem (Tokyo) 1983;94(6);1789-95. PMID: 6368527

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


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 Mon Nov 24, 2014, BIOCYC13B.