| IED ID | IndEnz0002002853 |
| Enzyme Type ID | protease002853 |
| Protein Name |
Cytochrome P450 71D178 + -trans-isopiperitenol synthase EC 1.14.14.- Carvacrol synthase EC 1.14.14.- Carveol synthase EC 1.14.14.51 Gamma-terpinene hydroxylase Limonene hydroxylase Thymol synthase EC 1.14.14.- |
| Gene Name | CYP71D178 |
| Organism | Origanum vulgare (Wild marjoram) |
| Taxonomic Lineage | cellular organisms Eukaryota Viridiplantae Streptophyta Streptophytina Embryophyta Tracheophyta Euphyllophyta Spermatophyta Magnoliopsida Mesangiospermae eudicotyledons Gunneridae Pentapetalae asterids lamiids Lamiales Lamiaceae Nepetoideae Mentheae Origanum (marjorams) Origanum vulgare (Wild marjoram) |
| Enzyme Sequence | MDISISWVVIILLVLSYLILMEKWRAAKLPKNLPPGPPKLPVIGHLHLLGGGLPQHVLRGITQKYGPVAHVQLGEVSSVVLSSTEAARQAMKVLDPAFADRFVNIGSRIMWYDSEDIIFSRYNDHWRQIRKICVSELLSPKNVKSFGYIRQDEMARLIRLFESSEGAAINVSEEISKTVCTIVSRVAFGSVVKDQSLLLNLVKESLRMASGFELADLFPSSWLLNLLCFNKYRLWGMRRRLDNFLDGFLEEHRVKKSGEYGGEDIIDVLYRMQKDSQMKVPITNNGIKGFIYDVFSAGTDTSAATILWALSELMRNPEKMAKAQAEVREILKGKTNVDMAEVHELKYLRSVVKEALRLHPPFPIIPRLCIQESEVTGYTIPANTRILINVWSIGRDPLYWNEPDTFNPDRYDEVPRDIIGNDFELIPFGSGRRICPGLHFGLANIEVPLAQLLYHFDWKLPQGMTAADIDMTEKPGLSGPRKNPLILVPTIHNPTS |
| Enzyme Length | 496 |
| Uniprot Accession Number | P0DO35 |
| Absorption | |
| Active Site | |
| Activity Regulation | |
| Binding Site | |
| Calcium Binding | |
| catalytic Activity | CATALYTIC ACTIVITY: Reaction=(4S)-limonene + O2 + reduced [NADPH--hemoprotein reductase] = (1S,5R)-carveol + H(+) + H2O + oxidized [NADPH--hemoprotein reductase]; Xref=Rhea:RHEA:17945, Rhea:RHEA-COMP:11964, Rhea:RHEA-COMP:11965, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379, ChEBI:CHEBI:15383, ChEBI:CHEBI:15389, ChEBI:CHEBI:57618, ChEBI:CHEBI:58210; EC=1.14.14.51; Evidence={ECO:0000269|Ref.1};PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:17946; Evidence={ECO:0000269|Ref.1}; CATALYTIC ACTIVITY: Reaction=gamma-terpinene + 2 O2 + 2 reduced [NADPH--hemoprotein reductase] = carvacrol + 2 H(+) + 3 H2O + 2 oxidized [NADPH--hemoprotein reductase]; Xref=Rhea:RHEA:67404, Rhea:RHEA-COMP:11964, Rhea:RHEA-COMP:11965, ChEBI:CHEBI:3440, ChEBI:CHEBI:10577, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379, ChEBI:CHEBI:57618, ChEBI:CHEBI:58210; Evidence={ECO:0000269|Ref.1};PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:67405; Evidence={ECO:0000269|Ref.1}; CATALYTIC ACTIVITY: Reaction=gamma-terpinene + 2 O2 + 2 reduced [NADPH--hemoprotein reductase] = 2 H(+) + 3 H2O + 2 oxidized [NADPH--hemoprotein reductase] + thymol; Xref=Rhea:RHEA:67408, Rhea:RHEA-COMP:11964, Rhea:RHEA-COMP:11965, ChEBI:CHEBI:10577, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379, ChEBI:CHEBI:27607, ChEBI:CHEBI:57618, ChEBI:CHEBI:58210; Evidence={ECO:0000269|Ref.1};PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:67409; Evidence={ECO:0000269|Ref.1}; CATALYTIC ACTIVITY: Reaction=(4R)-limonene + O2 + reduced [NADPH--hemoprotein reductase] = (1R,6S)-isopiperitenol + H(+) + H2O + oxidized [NADPH--hemoprotein reductase]; Xref=Rhea:RHEA:67416, Rhea:RHEA-COMP:11964, Rhea:RHEA-COMP:11965, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379, ChEBI:CHEBI:15382, ChEBI:CHEBI:57618, ChEBI:CHEBI:58210, ChEBI:CHEBI:169979; Evidence={ECO:0000269|Ref.1};PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:67417; Evidence={ECO:0000269|Ref.1}; |
| DNA Binding | |
| EC Number | 1.14.14.-; 1.14.14.51 |
| Enzyme Function | FUNCTION: Involved in the biosynthesis of phenolic monoterpenes natural products thymol and carvacrol which have a broad range of biological activities acting as antimicrobial compounds, insecticides, antioxidants and pharmaceutical agents (Ref.1, PubMed:26156773). Catalyzes the C2- and C3-hydroxylation of gamma-terpinene to produce carvacrol and thymol, respectively (Ref.1). Mediates also the C6-hydroxylation of (4S)-limonene to form carveol and the C3-hydroxylation of (4R)-limonene to generate (+)-trans-isopiperitenol (Ref.1). {ECO:0000269|PubMed:26156773, ECO:0000269|Ref.1}. |
| Temperature Dependency | |
| PH Dependency | BIOPHYSICOCHEMICAL PROPERTIES: pH dependence: Optimum pH is 6.8-7. {ECO:0000269|Ref.1}; |
| Pathway | PATHWAY: Secondary metabolite biosynthesis; terpenoid biosynthesis. {ECO:0000250|UniProtKB:A0A165U5Z9}. |
| nucleotide Binding | |
| Features | Chain (1); Metal binding (1); Transmembrane (1) |
| Keywords | Heme;Iron;Membrane;Metal-binding;Monooxygenase;Oxidoreductase;Signal-anchor;Transmembrane;Transmembrane helix |
| Interact With | |
| Induction | INDUCTION: Induced by jasmonic acid (MeJA), salicylic acid (SA) and UV-C irradiation (PubMed:28365519). Accumulates upon root colonization by Myrmica ants (Myrmica sabuleti and Myrmica scabrinodis) concomitantly with jasmonates induction; this leads to the production of carvacrol, an attractant for the phytophagous-predaceous butterfly Maculinea arion, whose larvae initially feed on Origanum vulgare flowerheads before switching to parasitize Myrmica ant colonies for their main period of growth (PubMed:26156773). Slightly repressed by Spodoptera littoralis, an herbivory insect (PubMed:30231481). {ECO:0000269|PubMed:26156773, ECO:0000269|PubMed:28365519, ECO:0000269|PubMed:30231481}. |
| Subcellular Location | SUBCELLULAR LOCATION: Membrane {ECO:0000255}; Single-pass type II membrane protein {ECO:0000305}. |
| Modified Residue | |
| Post Translational Modification | |
| Signal Peptide | |
| Structure 3D | |
| Cross Reference PDB | - |
| Mapped Pubmed ID | - |
| Motif | |
| Gene Encoded By | |
| Mass | 56,091 |
| Kinetics | BIOPHYSICOCHEMICAL PROPERTIES: Kinetic parameters: KM=37.2 uM for gamma-terpinene {ECO:0000269|Ref.1}; |
| Metal Binding | METAL 435; /note=Iron (heme axial ligand); /evidence=ECO:0000250|UniProtKB:Q96242 |
| Rhea ID | RHEA:17945; RHEA:17946; RHEA:67404; RHEA:67405; RHEA:67408; RHEA:67409; RHEA:67416; RHEA:67417 |
| Cross Reference Brenda |