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MetaCyc Compound: (-)-trans-isopiperitenol

Superclasses: a lipidan isoprenoida terpenoida terpenoid derivativea monoterpenoid derivativea monoterpenol
a secondary metabolitea terpenoida terpenoid derivativea monoterpenoid derivativea monoterpenol
an alcohola monoterpenol

Chemical Formula: C10H16O

Molecular Weight: 152.24 Daltons

Monoisotopic Molecular Weight: 152.1201151357 Daltons

(-)-trans-isopiperitenol compound structure

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 Formation (ΔfG in kcal/mol): 166.02794Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

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 :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
a 6-phospho-β-D-galactoside + H2O → D-galactopyranose 6-phosphate + an alcohol
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 → 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

In Reactions of unknown directionality:

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

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+
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
trans-cinnamoyl-β-D-glucoside + an alcohol = alkyl cinnamate + D-glucopyranose
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 Pathway Tools version 19.5 (software by SRI International) on Sat Apr 30, 2016, biocyc13.