{
    "accession": "MITE0000396",
    "status": "active",
    "comment": "Fungal aromatic prenyltransferase from Aspergillus terreus active on phloroglucinol substrates",
    "changelog": [
        {
            "version": "1",
            "date": "2026-05-06",
            "contributors": [
                "0009-0005-5325-1764"
            ],
            "reviewers": [
                "0000-0003-4819-2251"
            ],
            "comment": "New entry. Reviewer 1 added minor additions to textual fields, correction of reaction SMARTS and substrate-product SMILES."
        }
    ],
    "enzyme": {
        "name": "AtaPT",
        "description": "Aromatic prenyltransferase",
        "references": [
            "doi:10.1021/acs.orglett.6b03594"
        ],
        "databaseIds": {
            "uniprot": "A0A1B0UHJ4",
            "genpept": "AMB20850.1"
        }
    },
    "reactions": [
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "C-prenylation of acylphloroglucinols",
            "reactionSMARTS": "[#6:1]1:[#6:10](-[#8:11]):[#6:7](-[#6:8](-[#6:12])=[#8:9]):[#6:5](-[#8:6]):[#6:4]:[#6:2]:1-[#8:3]>>[#6:4]1(:[#6:5](-[#8:6]):[#6:7](-[#6:8](-[#6:12])=[#8:9]):[#6:10](-[#8:11]):[#6:1]:[#6:2]:1-[#8:3])-[#6:4]-[#6:5]=[#6:7](-[#6:10])-[#6:8]",
            "reactions": [
                {
                    "substrate": "CC(C)C(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCc1c(O)cc(O)c(C(=O)C(C)C)c1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)CC(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCc1c(O)cc(O)c(C(=O)CC(C)C)c1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "O=C(c1ccccc1)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCc1c(O)cc(O)c(C(=O)c2ccccc2)c1O"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "O-prenylation of acylphloroglucinols",
            "reactionSMARTS": "[#6:1]1:[#6:11](-[#8:12]):[#6:7](-[#6:8](-[#6:10])=[#8:9]):[#6:5](-[#8:6]):[#6:4]:[#6:2]:1-[#8:3]>>[#6:4]1:[#6:5](-[#8:6]):[#6:7](-[#6:8](-[#6:10])=[#8:9]):[#6:11](-[#8:12]):[#6:1]:[#6:2]:1-[#8:3]-[#6:4]-[#6:5]=[#6:7](-[#6:11])-[#6:8]",
            "reactions": [
                {
                    "substrate": "CC(C)C(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCOc1cc(O)c(C(=O)C(C)C)c(O)c1"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)CC(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCOc1cc(O)c(C(=O)CC(C)C)c(O)c1"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "gem-diprenylation of acylphloroglucinols",
            "reactionSMARTS": "[#6:1]-[#6:2](=[#8:17])-[#6:3]1:[#6:15](-[#8:16]):[#6:14]:[#6:12](-[#8:13]):[#6:6](-[#6:7]-[#6:8]=[#6:9](-[#6:11])-[#6:10]):[#6:4]:1-[#8:5]>>[#6:1]-[#6:2](=[#8:17])-[#6:3]1-[#6:15](=[#8:16])-[#6:14]=[#6:12](-[#8:13])-[#6:6](-[#6:6]-[#6:4]=[#6:3](-[#6:15])-[#6:2])(-[#6:7]-[#6:8]=[#6:9](-[#6:11])-[#6:10])-[#6:4]=1-[#8:5]",
            "reactions": [
                {
                    "substrate": "CC(C)=CCc1c(O)cc(O)c(C(=O)C(C)C)c1O",
                    "products": [
                        "CC(C)=CCC1(CC=C(C)C)C(O)=CC(=O)C(C(=O)C(C)C)=C1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)=CCc1c(O)cc(O)c(C(=O)CC(C)C)c1O",
                    "products": [
                        "CC(C)=CCC1(CC=C(C)C)C(O)=CC(=O)C(C(=O)CC(C)C)=C1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)=CCc1c(O)cc(O)c(C(=O)c2ccccc2)c1O",
                    "products": [
                        "CC(C)=CCC1(CC=C(C)C)C(O)=CC(=O)C(C(=O)c2ccccc2)=C1O"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "O-prenylation of prenylated acylphloroglucinol 2D1",
            "reactionSMARTS": "[#6:1]-[#6:2](=[#6:4]-[#6:5]-[#6:6]1:[#6:19](-[#8:20]):[#6:12](-[#6:13](-[#6:15]-[#6:16](-[#6:18])-[#6:17])=[#8:14]):[#6:10](-[#8:11]):[#6:9]:[#6:7]:1-[#8:8])-[#6:3]>>[#6:1]-[#6:2](=[#6:4]-[#6:5]-[#6:6]1:[#6:19](-[#8:20]):[#6:12](-[#6:13](-[#6:15]-[#6:16](-[#6:17])-[#6:18])=[#8:14]):[#6:10](-[#8:11]):[#6:9]:[#6:7]:1-[#8:8]-[#6:6]-[#6:5]-[#6:4]=[#6:2](-[#6:3])-[#6:1])-[#6:3]",
            "reactions": [
                {
                    "substrate": "CC(C)=CCc1c(O)cc(O)c(C(=O)CC(C)C)c1O",
                    "products": [
                        "CC(C)=CCCOc1cc(O)c(C(=O)CC(C)C)c(O)c1CC=C(C)C"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "C-geranylation of acylphloroglucinols",
            "reactionSMARTS": "[#6:1]-[#6:2](-[#6:12]1:[#6:10](-[#8:11]):[#6:9]:[#6:7](-[#8:8]):[#6:6]:[#6:4]:1-[#8:5])=[#8:3]>>[#6:1]-[#6:2](-[#6:12]1:[#6:4](-[#8:5]):[#6:6](-[#6]-[#6]=[#6](-[#6])-[#6]-[#6]-[#6]=[#6](-[#6])-[#6]):[#6:7](-[#8:8]):[#6:9]:[#6:10]:1-[#8:11])=[#8:3]",
            "reactions": [
                {
                    "substrate": "CC(C)C(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCc1c(O)cc(O)c(C(=O)C(C)C)c1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)CC(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCc1c(O)cc(O)c(C(=O)CC(C)C)c1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "O=C(c1ccccc1)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCc1c(O)cc(O)c(C(=O)c2ccccc2)c1O"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "O-geranylation of acylphloroglucinols",
            "reactionSMARTS": "[#6:1]-[#6:2](-[#6:4]1:[#6:11](-[#8:12]):[#6:10]:[#6:8](-[#8:9]):[#6:7]:[#6:5]:1-[#8:6])=[#8:3]>>[#6:1]-[#6:2](-[#6:4]1:[#6:5](-[#8:6]):[#6:7]:[#6:8](-[#8:9]-[#6]-[#6]=[#6](-[#6])-[#6]-[#6]-[#6]=[#6](-[#6])-[#6]):[#6:10]:[#6:11]:1-[#8:12])=[#8:3]",
            "reactions": [
                {
                    "substrate": "CC(C)C(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCOc1cc(O)c(C(=O)C(C)C)c(O)c1"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)CC(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCOc1cc(O)c(C(=O)CC(C)C)c(O)c1"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "O=C(c1ccccc1)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCOc1cc(O)c(C(=O)c2ccccc2)c(O)c1"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "C-farnesylation of acylphloroglucinols",
            "reactionSMARTS": "[#6:1]-[#6:2](=[#8:3])-[#6:4]1:[#6:5](-[#8:6]):[#6:7]:[#6:8](-[#8:9]):[#6:10]:[#6:11]:1-[#8:12]>>[#6:1]-[#6:2](=[#8:3])-[#6:4]1:[#6:11](-[#8:12]):[#6:10]:[#6:8](-[#8:9]):[#6:7](-[#6]-[#6]=[#6](-[#6]-[#6]-[#6]=[#6](-[#6]-[#6]-[#6]=[#6](-[#6])-[#6])-[#6])-[#6]):[#6:5]:1-[#8:6]",
            "reactions": [
                {
                    "substrate": "CC(C)C(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCCC(C)=CCc1c(O)cc(O)c(C(=O)C(C)C)c1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)CC(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCCC(C)=CCc1c(O)cc(O)c(C(=O)CC(C)C)c1O"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "O=C(c1ccccc1)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCCC(C)=CCc1c(O)cc(O)c(C(=O)c2ccccc2)c1O"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "O-farnesylation of acylphloroglucinols",
            "reactionSMARTS": "[#6:1]-[#6:2](-[#6:4]1:[#6:11](-[#8:12]):[#6:10]:[#6:8](-[#8:9]):[#6:7]:[#6:5]:1-[#8:6])=[#8:3]>>[#6:1]-[#6:2](-[#6:4]1:[#6:5](-[#8:6]):[#6:7]:[#6:8](-[#8:9]-[#6]-[#6]=[#6](-[#6])-[#6]-[#6]-[#6]=[#6](-[#6])-[#6]-[#6]-[#6]=[#6](-[#6])-[#6]):[#6:10]:[#6:11]:1-[#8:12])=[#8:3]",
            "reactions": [
                {
                    "substrate": "CC(C)C(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCCC(C)=CCOc1cc(O)c(C(=O)C(C)C)c(O)c1"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "CC(C)CC(=O)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCCC(C)=CCOc1cc(O)c(C(=O)CC(C)C)c(O)c1"
                    ],
                    "isIntermediate": true
                },
                {
                    "substrate": "O=C(c1ccccc1)c1c(O)cc(O)cc1O",
                    "products": [
                        "CC(C)=CCCC(C)=CCCC(C)=CCOc1cc(O)c(C(=O)c2ccccc2)c(O)c1"
                    ],
                    "isIntermediate": true
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/acs.orglett.6b03594"
                ]
            }
        }
    ]
}