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Literature summary extracted from
- Metabolism of monoterpenes: oxidation of isopiperitenol to isopiperitenone, and subsequent isomerization to piperitenone by soluble enzyme preparations from peppermint (Mentha piperita) leaves (1985), Arch. Biochem. Biophys., 238, 49-60.
General Stability
| EC Number | General Stability | Organism |
|---|---|---|
| 1.1.1.223 | stabilized with bovine serum albumin | Mentha x piperita |
| 5.3.3.11 | stable to dialysis at pH 5.5-9.5 | Mentha x piperita |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.1.1.223 | iodacetamide | slight inhibition | Mentha x piperita |  |
| 1.1.1.223 | N-ethylmaleimide | slight inhibition | Mentha x piperita | |
| 1.1.1.223 | p-hydroxymercuribenzoate | complete inhibition at 0.025 nM | Mentha x piperita | |
| 5.3.3.11 | NEM | - |
Mentha x piperita | |
| 5.3.3.11 | p-hydroxymercuribenzoate | - |
Mentha x piperita | |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.1.1.223 | 0.017 | - |
NAD+ | - |
Mentha x piperita | |
| 1.1.1.223 | 0.02 | - |
(+)-trans-isoperitenol | - |
Mentha x piperita | |
| 1.1.1.223 | 0.02 | - |
(-)-trans-isoperitenol | - |
Mentha x piperita | |
| 1.1.1.223 | 0.08 | - |
(-)-cis-isoperitenol | - |
Mentha x piperita | |
| 1.1.1.223 | 0.08 | - |
(+)-cis-isopiperitenol | - |
Mentha x piperita | |
| 1.1.1.223 | 2.5 | - |
NADP+ | - |
Mentha x piperita | |
| 5.3.3.11 | 0.27 | - |
isopiperitenone | - |
Mentha x piperita | |
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 1.1.1.223 | soluble | - |
Mentha x piperita | - |
- |
Metals/Ions
| EC Number | Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.1.1.223 | Hg2+ | complete inhibition at 0.1 mM | Mentha x piperita | |
Molecular Weight [Da]
| EC Number | Molecular Weight [Da] | Molecular Weight Maximum [Da] | Comment | Organism |
|---|---|---|---|---|
| 1.1.1.223 | 66000 | - |
gel filtration | Mentha x piperita |
| 5.3.3.11 | 54000 | - |
gel filtration | Mentha x piperita |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.1.1.223 | (-)-trans-isopiperitenol + NAD+ | Mentha x piperita | central enzyme in menthol biosynthesis pathway | (-)-isopiperitenone + NADH | - |
r | |
| 5.3.3.11 | Isopiperitenone | Mentha x piperita | key step in the metabolic pathway for the conversion of the initially formed cyclic olefin (+/-)-limonene, to (-)-menthol and related monoterpenes characteristic of peppermint | ? | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.1.1.223 | Mentha x piperita | - |
peppermint | - |
| 5.3.3.11 | Mentha x piperita | - |
- |
- |
Purification (Commentary)
| EC Number | Purification (Comment) | Organism |
|---|---|---|
| 5.3.3.11 | partial | Mentha x piperita |
Reaction
| EC Number | Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|---|
| 5.3.3.11 | Isopiperitenone = piperitenone | double bond migration catalyzed by this enzyme involves an intramolecular 1,3-hydrogen transfer | Mentha x piperita |
Source Tissue
| EC Number | Source Tissue | Comment | Organism | Textmining |
|---|---|---|---|---|
| 1.1.1.223 | leaf | - |
Mentha x piperita | - |
| 5.3.3.11 | leaf | - |
Mentha x piperita | - |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.1.1.223 | (+)-cis-isopiperitenol + NAD+ | - |
Mentha x piperita | (+)-isopiperitenone + NADH + H+ | - |
r | |
| 1.1.1.223 | (+)-isomenthol + NAD+ | activity less than 2% of that of (-)-trans-isopiperitenol | Mentha x piperita | (+)-isomenthone + NADH | - |
? | |
| 1.1.1.223 | (+)-trans-isopiperitenol + NAD+ | 95% activity of that of (-)-trans-isopiperitenol | Mentha x piperita | (+)-isopiperitenone + NADH | - |
? | |
| 1.1.1.223 | (+)-trans-pulegol + NAD+ | 19% activity of that of (-)-trans-isopiperitenol | Mentha x piperita | (R)-pulegone + NADH | - |
? | |
| 1.1.1.223 | (+,-)-cis-isopiperitenol + NAD+ | - |
Mentha x piperita | (+,-)-isopiperitenone | - |
? | |
| 1.1.1.223 | (-)-trans-isopiperitenol + NAD+ | preferred substrate, not readily reversible in pH range 6.5-10.5 | Mentha x piperita | (-)-isopiperitenone + NADH | - |
r | |
| 1.1.1.223 | (-)-trans-isopiperitenol + NAD+ | central enzyme in menthol biosynthesis pathway | Mentha x piperita | (-)-isopiperitenone + NADH | - |
r | |
| 1.1.1.223 | (-)-trans-isopiperitenol + NADP+ | - |
Mentha x piperita | (-)-isopiperitenone + NADPH + H+ | - |
? | |
| 5.3.3.11 | Isopiperitenone | - |
Mentha x piperita | Piperitenone | - |
? | |
| 5.3.3.11 | Isopiperitenone | key step in the metabolic pathway for the conversion of the initially formed cyclic olefin (+/-)-limonene, to (-)-menthol and related monoterpenes characteristic of peppermint | Mentha x piperita | ? | - |
? | |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.1.1.223 | 8.5 | 10.5 | - |
Mentha x piperita |
| 5.3.3.11 | 7.5 | 8.5 | - |
Mentha x piperita |
pH Range
| EC Number | pH Minimum | pH Maximum | Comment | Organism |
|---|---|---|---|---|
| 1.1.1.223 | 7.5 | 11 | half maximum activity at both pH | Mentha x piperita |
| 5.3.3.11 | 7 | 9 | half-maximal activities at pH 7 and 9 | Mentha x piperita |
Cofactor
| EC Number | Cofactor | Comment | Organism | Structure |
|---|---|---|---|---|
| 1.1.1.223 | additional information | FAD completely ineffective | Mentha x piperita | |
| 1.1.1.223 | NAD+ | - |
Mentha x piperita | |
| 1.1.1.223 | NADP+ | less than 10% of the activity with NAD | Mentha x piperita | |
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Release 2023.1 (January 2023)
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