{
    "accession": "MITE0000223",
    "status": "active",
    "comment": "Catalyzes two rounds of prenylation on the guanidine moiety of Argicyclamide C to yield Argicyclamide A",
    "changelog": [
        {
            "version": "1",
            "date": "2025-11-11",
            "contributors": [
                "0000-0002-8834-593X"
            ],
            "reviewers": [
                "0000-0001-6534-6609",
                "0000-0003-4819-2251"
            ],
            "comment": "new entry. Reviewers added second prenylation."
        }
    ],
    "enzyme": {
        "name": "AgcF",
        "description": "Guanidine prenyltransferase",
        "references": [
            "doi:10.1021/jacs.1c05732"
        ],
        "databaseIds": {
            "uniprot": "UPI001AF07BD7",
            "genpept": "BCR82584.1"
        },
        "cofactors": {
            "inorganic": [
                "Mg"
            ]
        }
    },
    "reactions": [
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "N-prenylation on guanidine moiety of arginine residue of Argicyclamide C",
            "reactionSMARTS": "[#6:1]-[#6:2]-[#6@@:3](-[#6@:5]1\\[#6:36](-[#7:38]/[#6@@:39](-[#6:64](-[#6:66])-[#6:65])-[#6:40](-[#7:42]\\[#6@:43](-[#6:48](-[#7:50]2-[#6@:54](/[#6:55](-[#7:57]3-[#6@:61](/[#6:62](-[#7:25]\\[#6@@:24](-[#6:26]-[#6:27]-[#6:28]-[#7:29]-[#6:30](-[#7:32])=[#7:31])-[#6:22](=[#8:23])-[#7:21]-[#6@@:20](-[#6:33](-[#6:35])-[#6:34])\\[#6:18](=[#8:19])-[#7:17]-[#6@@:9](-[#6:10]-[#6:11]4:[#6:16]:[#6:15]:[#6:14]:[#6:13]:[#6:12]:4)\\[#6:7](=[#8:8])-[#7:6]-1)=[#8:63])-[#6:60]-[#6:59]-[#6:58]-3)=[#8:56])-[#6:53]-[#6:52]-[#6:51]-2)=[#8:49])-[#6:44]-[#6:45](-[#6:47])-[#6:46])=[#8:41])=[#8:37])\\[#6:4]>>[#6:1]-[#6:2]-[#6@@:3](-[#6@:5]1\\[#6:36](-[#7:38]/[#6@@:39](-[#6:64](-[#6:65])-[#6:66])-[#6:40](-[#7:42]\\[#6@:43](-[#6:48](-[#7:50]2-[#6@:54](/[#6:55](-[#7:57]3-[#6@:61](/[#6:62](-[#7:25]\\[#6@@:24](-[#6:26]-[#6:27]-[#6:28]-[#7:29]-[#6:30](-[#7:32]-[#6]-[#6]=[#6](-[#6])-[#6])=[#7:31])-[#6:22](=[#8:23])-[#7:21]-[#6@@:20](-[#6:33](-[#6:34])-[#6:35])\\[#6:18](=[#8:19])-[#7:17]-[#6@@:9](-[#6:10]-[#6:11]4:[#6:12]:[#6:13]:[#6:14]:[#6:15]:[#6:16]:4)\\[#6:7](=[#8:8])-[#7:6]-1)=[#8:63])-[#6:60]-[#6:59]-[#6:58]-3)=[#8:56])-[#6:53]-[#6:52]-[#6:51]-2)=[#8:49])-[#6:44]-[#6:45](-[#6:46])-[#6:47])=[#8:41])=[#8:37])\\[#6:4]",
            "reactions": [
                {
                    "substrate": "CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC1=O",
                    "products": [
                        "CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)NCC=C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC1=O"
                    ],
                    "isIntermediate": false
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "Heterologous expression",
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/jacs.1c05732"
                ]
            }
        },
        {
            "tailoring": [
                "Prenylation"
            ],
            "description": "N-prenylation on guanidine moiety of arginine residue of Argicyclamide C",
            "reactionSMARTS": "[#6:1]-[#6:2]-[#6@@:3](-[#6@:5]1\\[#6:36](-[#7:38]/[#6@@:39](-[#6:64](-[#6:65])-[#6:66])-[#6:40](-[#7:42]\\[#6@:43](-[#6:48](-[#7:50]2-[#6@:54](/[#6:55](-[#7:57]3-[#6@:61](/[#6:62](-[#7:25]\\[#6@@:24](-[#6:26]-[#6:27]-[#6:28]-[#7:29]-[#6:30](-[#7:32]-[#6:99]-[#6:98]=[#6:97](-[#6:96])-[#6:95])=[#7:31])-[#6:22](=[#8:23])-[#7:21]-[#6@@:20](-[#6:33](-[#6:34])-[#6:35])\\[#6:18](=[#8:19])-[#7:17]-[#6@@:9](-[#6:10]-[#6:11]4:[#6:12]:[#6:13]:[#6:14]:[#6:15]:[#6:16]:4)\\[#6:7](=[#8:8])-[#7:6]-1)=[#8:63])-[#6:60]-[#6:59]-[#6:58]-3)=[#8:56])-[#6:53]-[#6:52]-[#6:51]-2)=[#8:49])-[#6:44]-[#6:45](-[#6:46])-[#6:47])=[#8:41])=[#8:37])\\[#6:4]>>[#6:1]-[#6:2]-[#6@@:3](-[#6@:5]1\\[#6:36](-[#7:38]/[#6@@:39](-[#6:64](-[#6:65])-[#6:66])-[#6:40](-[#7:42]\\[#6@:43](-[#6:48](-[#7:50]2-[#6@:54](/[#6:55](-[#7:57]3-[#6@:61](/[#6:62](-[#7:25]\\[#6@@:24](-[#6:26]-[#6:27]-[#6:28]-[#7:29]-[#6:30](-[#7:32]-[#6:99]-[#6:98]=[#6:97](-[#6:96])-[#6:95])=[#7:31]-[#6]-[#6]=[#6](-[#6])-[#6])-[#6:22](=[#8:23])-[#7:21]-[#6@@:20](-[#6:33](-[#6:34])-[#6:35])\\[#6:18](=[#8:19])-[#7:17]-[#6@@:9](-[#6:10]-[#6:11]4:[#6:12]:[#6:13]:[#6:14]:[#6:15]:[#6:16]:4)\\[#6:7](=[#8:8])-[#7:6]-1)=[#8:63])-[#6:60]-[#6:59]-[#6:58]-3)=[#8:56])-[#6:53]-[#6:52]-[#6:51]-2)=[#8:49])-[#6:44]-[#6:45](-[#6:46])-[#6:47])=[#8:41])=[#8:37])\\[#6:4]",
            "reactions": [
                {
                    "substrate": "CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=N)NCC=C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC1=O",
                    "products": [
                        "CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCNC(=NCC=C(C)C)NCC=C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC1=O"
                    ],
                    "isIntermediate": false
                }
            ],
            "evidence": {
                "evidenceCode": [
                    "Heterologous expression",
                    "In vitro assay"
                ],
                "references": [
                    "doi:10.1021/jacs.1c05732"
                ]
            }
        }
    ]
}