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- Name help_outline ent-copalyl diphosphate Identifier CHEBI:58553 Charge -3 Formula C20H33O7P2 InChIKeyhelp_outline JCAIWDXKLCEQEO-PGHZQYBFSA-K SMILEShelp_outline [C@@H]1(CC/C(/C)=C/COP(OP(=O)([O-])[O-])(=O)[O-])C(=C)CC[C@]2([C@@]1(C)CCCC2(C)C)[H] 2D coordinates Mol file for the small molecule Search links Involved in 16 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ent-atiserene Identifier CHEBI:138219 (CAS: 20230-48-2) help_outline Charge 0 Formula C20H32 InChIKeyhelp_outline LFRRHLVVLXYROS-YQXATGRUSA-N SMILEShelp_outline C1CCC([C@@]2([C@@]1([C@]3([C@]4(CC2)CC([C@H](C3)CC4)=C)[H])C)[H])(C)C 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,188 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:54496 | RHEA:54497 | RHEA:54498 | RHEA:54499 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Functional diversification of kaurene synthase-like genes in Isodon rubescens.
Jin B., Cui G., Guo J., Tang J., Duan L., Lin H., Shen Y., Chen T., Zhang H., Huang L.
<i>Ent</i>-kaurene diterpenoids are the largest group of known <i>Isodon</i> diterpenoids. Among them, oridonin is accumulated in the leaves, and is the most frequently studied compound because of its antitumor and antibacterial activities. We have identified five copalyl diphosphate synthase (CPS ... >> More
<i>Ent</i>-kaurene diterpenoids are the largest group of known <i>Isodon</i> diterpenoids. Among them, oridonin is accumulated in the leaves, and is the most frequently studied compound because of its antitumor and antibacterial activities. We have identified five copalyl diphosphate synthase (CPS) and six kaurene synthase-like (KSL) genes by transcriptome profiling of <i>Isodon rubescens</i> leaves. An in vitro assay assigns ten of them to five different diterpene biosynthesis pathways, except IrCPS3 that has a mutation in the catalytic motif. The Lamiaceae-specific clade genes (IrCPS1 and IrCPS2) synthesize the intermediate copalyl diphosphate (normal-CPP), while IrCPS4 and IrCPS5 synthesize the intermediate <i>ent</i>-copalyl diphosphate (<i>ent</i>-CPP). IrKSL2, IrKSL4, and IrKSL5 react with <i>ent</i>-CPP to produce an <i>ent</i>-isopimaradiene-like compound, <i>ent</i>-atiserene and <i>ent</i>-kaurene, respectively. Correspondingly, the Lamiaceae-specific clade genes IrKSL1 or IrKSL3 combined with normal-CPP led to the formation of miltiradiene. The compound then underwent aromatization and oxidization with a cytochrome P450 forming two related compounds, abietatriene and ferruginol, which were detected in the root bark. IrKSL6 reacts with normal-CPP to produce isopimaradiene. IrKSL3 and IrKSL6 have the γβα tridomain structure, as these proteins tend to possess the bidomain structure of IrKSL1, highlighting the evolutionary history of KSL gene domain loss and further elucidating chemical diversity evolution from a macroevolutionary stance in Lamiaceae. << Less