Reaction participants Show >> << Hide
- Name help_outline 2-hydroxymethyl-3-pentylphenol Identifier CHEBI:195220 Charge 0 Formula C12H18O2 InChIKeyhelp_outline BVZSJLRAINTEAD-UHFFFAOYSA-N SMILEShelp_outline CCCCCC1=C(CO)C(O)=CC=C1 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 O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,709 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_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 InChIKeyhelp_outline YTNIXZGTHTVJBW-SCRDCRAPSA-L SMILEShelp_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 794 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (8S)-annullatin E Identifier CHEBI:195221 Charge 0 Formula C12H18O3 InChIKeyhelp_outline PTXJXZCRKMFHHW-NSHDSACASA-N SMILEShelp_outline C=1C=C(C(=C(C1)[C@H](CCCC)O)CO)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,431 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 InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,204 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
oxidized [NADPH—hemoprotein reductase]
Identifier
RHEA-COMP:11965
Reactive part
help_outline
- Name help_outline FMN Identifier CHEBI:58210 Charge -3 Formula C17H18N4O9P InChIKeyhelp_outline ANKZYBDXHMZBDK-SCRDCRAPSA-K SMILEShelp_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 804 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:76419 | RHEA:76420 | RHEA:76421 | RHEA:76422 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Secondary Metabolites Produced by the Blue-Cheese Ripening Mold <i>Penicillium roqueforti</i>; Biosynthesis and Regulation Mechanisms.
Chavez R., Vaca I., Garcia-Estrada C.
Filamentous fungi are an important source of natural products. The mold <i>Penicillium roqueforti</i>, which is well-known for being responsible for the characteristic texture, blue-green spots, and aroma of the so-called blue-veined cheeses (French Bleu, Roquefort, Gorgonzola, Stilton, Cabrales, ... >> More
Filamentous fungi are an important source of natural products. The mold <i>Penicillium roqueforti</i>, which is well-known for being responsible for the characteristic texture, blue-green spots, and aroma of the so-called blue-veined cheeses (French Bleu, Roquefort, Gorgonzola, Stilton, Cabrales, and Valdeón, among others), is able to synthesize different secondary metabolites, including andrastins and mycophenolic acid, as well as several mycotoxins, such as Roquefortines C and D, PR-toxin and eremofortins, Isofumigaclavines A and B, festuclavine, and Annullatins D and F. This review provides a detailed description of the biosynthetic gene clusters and pathways of the main secondary metabolites produced by <i>P. roqueforti</i>, as well as an overview of the regulatory mechanisms controlling secondary metabolism in this filamentous fungus. << Less
J Fungi (Basel) 9:459-459(2023) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.
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Biosynthesis of Annullatin D in Penicillium roqueforti Implies Oxidative Lactonization between Two Hydroxyl Groups Catalyzed by a BBE-like Enzyme.
Xiang P., Kemmerich B., Yang L., Li S.M.
Annullatins from <i>Cordyceps annullata</i> are alkylated aromatic polyketides including annullatin D with a fused dihydrobenzofuran lactone ring system. Here, we report the identification of a silent biosynthetic gene cluster for annullatins from <i>Penicillium roqueforti</i> by heterologous expr ... >> More
Annullatins from <i>Cordyceps annullata</i> are alkylated aromatic polyketides including annullatin D with a fused dihydrobenzofuran lactone ring system. Here, we report the identification of a silent biosynthetic gene cluster for annullatins from <i>Penicillium roqueforti</i> by heterologous expression in <i>Aspergillus nidulans</i>, gene deletion, and feeding experiments as well as by biochemical characterization. The polyketide core structure is consecutively modified by hydroxylation and prenylation. A berberine bridge enzyme-like protein catalyzes the final step, an oxidative lactonization between two hydroxyl groups, to form (2<i>S</i>, 9<i>S</i>)-annullatin D. << Less
Org. Lett. 24:6072-6077(2022) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.