{
    "accession": "MITE0000120",
    "status": "active",
    "comment": "\u03b1KG dependent enzyme that catalyzes oxidative ring contraction in the zopfiellin biosynthetic pathway. Previously referenced retired MIBiG ID BGC0002224.",
    "changelog": [
        {
            "version": "1",
            "date": "2024-07-30",
            "contributors": [
                "AAAAAAAAAAAAAAAAAAAAAAAA"
            ],
            "reviewers": [
                "0000-0003-0443-9902",
                "0000-0001-6534-6609"
            ],
            "comment": "Initial entry. Reviewer fixed reactionSMARTS:reactionSMARTS. Reviewer fixed reactions:substrate. Reviewer fixed reactions:products. Reviewer 2 fixed incorrect protein databaseIDs (pointed to ZopA instead); fixed reaction SMARTS numbering"
        },
        {
            "version": "2",
            "date": "2025-08-13",
            "contributors": [
                "AAAAAAAAAAAAAAAAAAAAAAAA"
            ],
            "reviewers": [
                "0000-0001-6534-6609"
            ],
            "comment": "Fixed enzyme name to be more computer readable."
        },
        {
            "version": "3",
            "date": "2026-04-13",
            "contributors": [
                "0000-0002-3677-2972"
            ],
            "reviewers": [
                "0000-0003-4819-2251",
                "0000-0001-6534-6609"
            ],
            "comment": "Added additional reference and evidence qualifier (heterologous expression). Reviewer 2 fixed retired uniprot entry and removed retired MIBIG ID."
        }
    ],
    "enzyme": {
        "name": "ZopL9/ZopK",
        "description": "Alpha-ketoglutarate dependent dioxygenase",
        "references": [
            "doi:10.1039/d0sc04309e",
            "doi:10.1039/d5ra02147b",
            "doi:10.1021/acs.orglett.0c00340"
        ],
        "auxiliaryEnzymes": [
            {
                "name": "ZopL2/ZopQ",
                "description": "Isochorismatase-like enzyme",
                "databaseIds": {
                    "uniprot": "UPI001AF1AE05",
                    "genpept": "QTE75990.1"
                }
            }
        ],
        "databaseIds": {
            "uniprot": "UPI001AFA59BC",
            "genpept": "QTE75983.1"
        },
        "cofactors": {
            "organic": [
                "a-Ketoglutaric acid"
            ],
            "inorganic": [
                "Fe"
            ]
        }
    },
    "reactions": [
        {
            "tailoring": [
                "Ring contraction"
            ],
            "description": "Catalyzes ring contraction of a nine-membered ring to an eight-membered ring.",
            "reactionSMARTS": "[#6:1]-[#6:2]-[#6:3]-[#6:4]-[#6:5]\\[#6@:6]1-[#6:24]2-[#6:25](-[#8:27]-[#6:28](=[#8:29])-[#6:23]=2-[#6:22]-[#6@@:17](\\[#6:18]-[#6:19]-[#6:20]-[#6:21])-[#6@@](\\[#8])-[#6:9]2-[#6:10](-[#8:12]-[#6:13](=[#8:14])-[#6:8]=2-[#6:7]-1)=[#8:11])=[#8:26]>>[#6:1]-[#6:2]-[#6:3]-[#6:4]-[#6:5]\\[#6@:6]1-[#6:24]2-[#6:25](-[#8:27]-[#6:28](=[#8:29])-[#6:23]=2-[#6:22]-[#6@@:17](\\[#6:18]-[#6:19]-[#6:20]-[#6:21])-[#6:9]2-[#6:10](-[#8:12]-[#6:13](=[#8:14])-[#6:8]=2-[#6:7]-1)=[#8:11])=[#8:26]",
            "reactions": [
                {
                    "substrate": "CCCCC[C@@H]1CC2=C(C(=O)OC2=O)[C@H](O)[C@H](CCCC)CC2=C1C(=O)OC2=O",
                    "products": [
                        "CCCCC[C@@H]1CC2=C(C(=O)OC2=O)[C@H](CCCC)CC2=C1C(=O)OC2=O"
                    ],
                    "isIntermediate": true,
                    "description": "Ring contraction of 5-hydroxy-deoxyscytalidin to deoxyzopfiellin"
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "In vitro assay",
                    "Knock-out studies"
                ],
                "references": [
                    "doi:10.1039/d0sc04309e",
                    "doi:10.1039/d5ra02147b",
                    "doi:10.1021/acs.orglett.0c00340"
                ]
            }
        },
        {
            "tailoring": [
                "Hydroxylation"
            ],
            "description": "Hydroxylation of nine-membered central ring in preparation of ring contraction",
            "reactionSMARTS": "[#6:1]-[#6:2]-[#6:3]-[#6:4]-[#6:5]\\[#6@:6]1-[#6:18]2-[#6:19](-[#8:21]-[#6:22](=[#8:23])-[#6:17]=2-[#6:16]-[#6@@:11](\\[#6:12]-[#6:13]-[#6:14]-[#6:15])-[#6:10]-[#6:9]2-[#6:24](-[#8:26]-[#6:27](=[#8:28])-[#6:8]=2-[#6:7]-1)=[#8:25])=[#8:20]>>[#6:1]-[#6:2]-[#6:3]-[#6:4]-[#6:5]\\[#6@:6]1-[#6:18]2-[#6:19](-[#8:21]-[#6:22](=[#8:23])-[#6:17]=2-[#6:16]-[#6@@:11](\\[#6:12]-[#6:13]-[#6:14]-[#6:15])-[#6@@:10](\\[#8])-[#6:9]2-[#6:24](-[#8:26]-[#6:27](=[#8:28])-[#6:8]=2-[#6:7]-1)=[#8:25])=[#8:20]",
            "reactions": [
                {
                    "substrate": "CCCCC[C@@H]1CC2=C(C[C@H](CCCC)CC3=C1C(=O)OC3=O)C(=O)OC2=O",
                    "products": [
                        "CCCCC[C@@H]1CC2=C(C(=O)OC2=O)[C@H](O)[C@H](CCCC)CC2=C1C(=O)OC2=O"
                    ],
                    "isIntermediate": true,
                    "description": "Hydroxylation of deoxyscytalidin (C5) to 5-hydroxy-deoxyscytalidin"
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "Heterologous expression",
                    "In vitro assay",
                    "Knock-out studies"
                ],
                "references": [
                    "doi:10.1039/d0sc04309e",
                    "doi:10.1039/d5ra02147b",
                    "doi:10.1021/acs.orglett.0c00340"
                ]
            }
        }
    ]
}