Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	1 proteins
Enzyme class ^help_outline	EC 1.14.14.63 beta-amyrin 16beta-monooxygenase
GO Molecular Function ^help_outline	GO:0102601 cytochrome P450 dependent beta-amyrin 16beta-hydroxylase activity

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Name ^help_outline β-amyrin Identifier CHEBI:10352 (CAS: 559-70-6) ^help_outline Charge 0 Formula C30H50O InChIKey^help_outline JFSHUTJDVKUMTJ-QHPUVITPSA-N SMILES^help_outline [H][C@@]12CC(C)(C)CC[C@]1(C)CC[C@]1(C)C2=CC[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C 2D coordinates Mol file for the small molecule Search links Involved in 9 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline O₂ Identifier CHEBI:15379 (CAS: 7782-44-7) ^help_outline Charge 0 Formula O2 InChIKey^help_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILES^help_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name^help_outline reduced [NADPH—hemoprotein reductase] Identifier RHEA-COMP:11964 Reactive part ^help_outline
- Name ^help_outline FMNH₂ Identifier CHEBI:57618 (Beilstein: 6258176) ^help_outline Charge -2 Formula C17H21N4O9P InChIKey^help_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILES^help_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])([O-])=O)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 771 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 711 reaction(s) Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H₂O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) ^help_outline Charge 0 Formula H2O InChIKey^help_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILES^help_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline maniladiol Identifier CHEBI:138945 (CAS: 595-17-5) ^help_outline Charge 0 Formula C30H50O2 InChIKey^help_outline VLRYIIPJIVGFIV-QQSFYHFXSA-N SMILES^help_outline [C@@]12(C([C@@]3(CC(CC[C@@]3([C@H](C1)O)C)(C)C)[H])=CC[C@]4([C@]2(CC[C@@]5([C@@]4(CC[C@@H](C5(C)C)O)C)[H])C)[H])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 oxidized [NADPH—hemoprotein reductase] Identifier RHEA-COMP:11965 Reactive part ^help_outline
- Name ^help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKey^help_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILES^help_outline C12=NC([N-]C(C1=NC=3C(N2C[C@@H]([C@@H]([C@@H](COP(=O)([O-])[O-])O)O)O)=CC(=C(C3)C)C)=O)=O 2D coordinates Mol file for the small molecule Search links Involved in 781 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Search links Involved in 711 reaction(s) Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:55440	RHEA:55441	RHEA:55442	RHEA:55443
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	1 proteins	1 proteins
EC numbers ^help_outline	1.14.14.63
Gene Ontology ^help_outline	GO:0102601
KEGG ^help_outline				R11975
MetaCyc ^help_outline		RXN-15385

Publications

Cytochrome P450 monooxygenase CYP716A141 is a unique beta-amyrin C-16beta oxidase involved in triterpenoid saponin biosynthesis in Platycodon grandiflorus.

Tamura K., Teranishi Y., Ueda S., Suzuki H., Kawano N., Yoshimatsu K., Saito K., Kawahara N., Muranaka T., Seki H.

The roots of Platycodon grandiflorus are widely used as a crude drug. The active components include a variety of triterpenoid saponins. Recent studies have revealed that Cyt P450 monooxygenases (P450s) function as triterpene oxidases in triterpenoid saponin biosynthesis in many plant species. Howe ... >> More

The roots of Platycodon grandiflorus are widely used as a crude drug. The active components include a variety of triterpenoid saponins. Recent studies have revealed that Cyt P450 monooxygenases (P450s) function as triterpene oxidases in triterpenoid saponin biosynthesis in many plant species. However, there have been no reports regarding triterpene oxidases in P. grandiflorus. In this study, we performed transcriptome analysis of three different P. grandiflorus tissues (roots, leaves and petals) using RNA sequencing (RNA-Seq) technology. We cloned six P450 genes that were highly expressed in roots, and classified them as belonging to the CYP716A, CYP716D and CYP72A subfamilies. We heterologously expressed these P450s in an engineered yeast strain that produces β-amyrin, one of the most common triterpenes in plants. Two of the CYP716A subfamily P450s catalyzed oxidation reactions of the β-amyrin skeleton. One of these P450s, CYP716A140v2, catalyzed a three-step oxidation reaction at C-28 on β-amyrin to produce oleanolic acid, a reaction performed by CYP716A subfamily P450s in a variety of plant species. The other P450, CYP716A141, catalyzed the hydroxylation of β-amyrin at C-16β. This reaction is unique among triterpene oxidases isolated to date. These results enhance our knowledge of functional variation among CYP716A subfamily enzymes involved in triterpenoid biosynthesis, and provide novel molecular tools for use in synthetic biology to produce triterpenoid saponins with pre-defined structures. << Less

Plant Cell Physiol. 58:874-884(2017) [PubMed] [EuropePMC]

This publication is cited by 1 other entry.

RHEA:55440 beta-amyrin + O2 + reduced [NADPH--hemoprotein reductase] = H(+) + H2O + maniladiol + oxidized [NADPH--hemoprotein reductase]

Enzymes

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Cross-references

Publications

Cytochrome P450 monooxygenase CYP716A141 is a unique beta-amyrin C-16beta oxidase involved in triterpenoid saponin biosynthesis in Platycodon grandiflorus.