{"id":10085,"npaid":"NPA010085","original_name":"Roquefortine D","mol_formula":"C22H25N5O2","mol_weight":"391.4750","exact_mass":"391.2008","inchikey":"IQVNREJWRXOHEO-UHFFFAOYSA-N","smiles":"CC(C)(C=C)C12CC3C(=O)NC(C(=O)N3C1NC4=CC=CC=C24)CC5=CN=CN5","cluster_id":26,"node_id":25,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C22H25N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-8,11-12,16-17,20,26H,1,9-10H2,2-3H3,(H,23,24)(H,25,28)","m_plus_h":"392.2081","m_plus_na":"414.1900","origin_reference":{"doi":"10.1271/bbb1961.42.2387","pmid":null,"authors":"Ohmomo, Sadahiro; Oguma, Kiyoshi; Ohashi, Tsutomu; Abe, Matazo","title":"Isolation of a new indole alkaloid, roquefortine D, from the cultures of Penicillium roqueforti","journal":"Agricultural and Biological Chemistry","year":1978,"volume":"42","issue":"12","pages":"2387-2389"},"origin_organism":{"id":43,"type":"Fungus","genus":"Fusarium","species":"sp.","taxon":{"id":927,"name":"Fusarium","rank":"genus","taxon_db":"mycobank","external_id":"8284","ncbi_id":5506,"ancestors":[{"id":599,"name":"Eukarya","rank":"domain","taxon_db":"mycobank","external_id":"0","ncbi_id":2759},{"id":600,"name":"Fungi","rank":"kingdom","taxon_db":"mycobank","external_id":"90157","ncbi_id":4751},{"id":617,"name":"Ascomycota","rank":"phylum","taxon_db":"mycobank","external_id":"90031","ncbi_id":4890},{"id":879,"name":"Sordariomycetes","rank":"class","taxon_db":"mycobank","external_id":"90350","ncbi_id":147550},{"id":899,"name":"Hypocreales","rank":"order","taxon_db":"mycobank","external_id":"90477","ncbi_id":5125},{"id":921,"name":"Nectriaceae","rank":"family","taxon_db":"mycobank","external_id":"81059","ncbi_id":110618}]}},"syntheses":[],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1271/bbb1961.42.2387","structure_smiles":"CC(C)(C=C)C12CC3C(=O)NC(C(=O)N3C1NC4=CC=CC=C24)CC5=CN=CN5","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"mibig","external_db_code":"BGC0000420"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009952974%Suspect related to Massbank:AC000808 Roquefortine D|(3S,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula: C22H23N5O2) with delta m/z -2.016 (putative explanation: 2-amino-3-oxo-butanoic_acid|Intact disulfide bridge|Val->Pro substitution; atomic difference: -2H|-2H|-2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009969427%Suspect related to NCGC00180346-02_C22H25N5O2_3-(1H-Imidazol-4-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula: C17H19N5O6) with delta m/z -2.07 (putative explanation: unspecified; atomic difference: unspecified)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009969428%Suspect related to NCGC00180346-02_C22H25N5O2_3-(1H-Imidazol-4-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula: C22H23N5O2) with delta m/z -2.016 (putative explanation: 2-amino-3-oxo-butanoic_acid|Intact disulfide bridge|Val->Pro substitution; atomic difference: -2H|-2H|-2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009969429%Suspect related to NCGC00180346-02_C22H25N5O2_3-(1H-Imidazol-4-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula: C23H27N5O3) with delta m/z 30.011 (putative explanation: Ala->Thr substitution|Gly->Ser substitution|desmethylation + reduction of sulfoxide|formaldehyde induced modifications|hydroxymethyl; atomic difference: 1C,2H,1O|1C,2H,1O|1C,2H,1O|1C,2H,1O|1C,2H,1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727042%Massbank:AC000806 Roquefortine D|(3S,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727162%Massbank:AC000809 Roquefortine D|(3S,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727685%Massbank:AC000808 Roquefortine D|(3S,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727696%Massbank:AC000807 Roquefortine D|(3S,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727950%Massbank:AC000810 Roquefortine D|(3S,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000851783%NCGC00180346-02_C22H25N5O2_3-(1H-Imidazol-4-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetra%1"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012129631%Suspect related to NCGC00180346-02_C22H25N5O2_3-(1H-Imidazol-4-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula SIRIUS: C22H23N5O2 / BUDDY: C22H23N5O2) with delta m/z -2.016 (putative explanation: 2-amino-3-oxo-butanoic_acid|Intact disulfide bridge|Val->Pro substitution; atomic difference: -2H|-2H|-2H) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012129632%Suspect related to NCGC00180346-02_C22H25N5O2_3-(1H-Imidazol-4-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula SIRIUS: C23H27N5O3 / BUDDY: C28H27N3O) with delta m/z 30.011 (putative explanation: Ala->Thr substitution|Gly->Ser substitution|desmethylation + reduction of sulfoxide|formaldehyde induced modifications|hydroxymethyl; atomic difference: 1C,2H,1O|1C,2H,1O|1C,2H,1O|1C,2H,1O|1C,2H,1O) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012113177%Suspect related to Massbank:AC000808 Roquefortine D|(3S,5aS,10bR,11aS)-3-(1H-Imidazol-5-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula SIRIUS: C22H23N5O2 / BUDDY: C21H27NO6) with delta m/z -2.016 (putative explanation: 2-amino-3-oxo-butanoic_acid|Intact disulfide bridge|Val->Pro substitution; atomic difference: -2H|-2H|-2H) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012129630%Suspect related to NCGC00180346-02_C22H25N5O2_3-(1H-Imidazol-4-ylmethyl)-10b-(2-methyl-3-buten-2-yl)-6,10b,11,11a-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione (predicted molecular formula SIRIUS: C17H19N5O6 / BUDDY: C21H19N5OS) with delta m/z -2.07 (putative explanation: unspecified; atomic difference: unspecified) [M+H]+%4"},{"external_db_name":"npmrd","external_db_code":"NP0233010"},{"external_db_name":"cmmc","external_db_code":"https://cmmc-kb.gnps2.org/structurepage/?inchikey=IQVNREJWRXOHEO-UHFFFAOYSA-N"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000211","name":"Indoles and derivatives","chemont_id":"CHEMONTID:0000211","description":"Organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring."},"smiles":"CC(C)(C=C)C12CC3N(C1NC1=CC=CC=C21)C(=O)C(CC1=CN=CN1)NC3=O","kingdom":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000000","name":"Organic compounds","chemont_id":"CHEMONTID:0000000","description":"Compounds that contain at least one carbon atom, excluding isocyanide/cyanide and their non-hydrocarbyl derivatives, thiophosgene, carbon diselenide, carbon monosulfide, carbon disulfide, carbon subsulfide, carbon monoxide, carbon dioxide, Carbon suboxide, and dicarbon monoxide."},"inchikey":"InChIKey=IQVNREJWRXOHEO-UHFFFAOYSA-N","subclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001733","name":"Pyrroloindoles","chemont_id":"CHEMONTID:0001733","description":"Compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic  compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring."},"ancestors":["2,5-dioxopiperazines","Alpha amino acids and derivatives","Amines","Amino acids and derivatives","Amino acids, peptides, and analogues","Azacyclic compounds","Azoles","Benzenoids","Carbonyl compounds","Carboxylic acid amides","Carboxylic acid derivatives","Carboxylic acids and derivatives","Chemical entities","Diazinanes","Dioxopiperazines","Heteroaromatic compounds","Hydrocarbon derivatives","Imidazoles","Indoles","Indoles and derivatives","Indolines","Lactams","N-alkylpiperazines","Organic acids and derivatives","Organic compounds","Organic nitrogen compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organonitrogen compounds","Organooxygen compounds","Organopnictogen compounds","Piperazines","Pyrroles","Pyrrolidines","Pyrroloindoles","Secondary carboxylic acid amides","Tertiary carboxylic acid amides"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000002","name":"Organoheterocyclic compounds","chemont_id":"CHEMONTID:0000002","description":"Compounds containing a ring with least one carbon atom and one non-carbon atom."},"description":"This compound belongs to the class of organic compounds known as pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic  compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.","substituents":["Pyrroloindole","Alpha-amino acid or derivatives","Indole","Dihydroindole","Dioxopiperazine","2,5-dioxopiperazine","N-alkylpiperazine","1,4-diazinane","Piperazine","Benzenoid","Heteroaromatic compound","Pyrrolidine","Pyrrole","Tertiary carboxylic acid amide","Azole","Imidazole","Secondary carboxylic acid amide","Lactam","Carboxamide group","Azacycle","Carboxylic acid derivative","Amine","Organic oxygen compound","Organic nitrogen compound","Organic oxide","Hydrocarbon derivative","Carbonyl group","Organonitrogen compound","Organooxygen compound","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001733","name":"Pyrroloindoles","chemont_id":"CHEMONTID:0001733","description":"Compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic  compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000060","name":"Alpha amino acids and derivatives","chemont_id":"CHEMONTID:0000060","description":"Amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002497","name":"Indoles","chemont_id":"CHEMONTID:0002497","description":"Compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001146","name":"Indolines","chemont_id":"CHEMONTID:0001146","description":"Compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene  to form 2,3-dihydroindole."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003684","name":"2,5-dioxopiperazines","chemont_id":"CHEMONTID:0003684","description":"Organic heterocyclic compounds that contain a piperazine with the oxo groups at the 2- and 5-positions. Piperazine is a six-membered heterocyclic compound consisting of two nitrogen atoms and four carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003357","name":"N-alkylpiperazines","chemont_id":"CHEMONTID:0003357","description":"Organic compounds containing a piperazine ring where the nitrogen ring atom carries an alkyl group."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002448","name":"Benzenoids","chemont_id":"CHEMONTID:0002448","description":"Aromatic compounds containing one or more benzene rings."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000090","name":"Pyrroles","chemont_id":"CHEMONTID:0000090","description":"Compounds containing a pyrrole ring, which is a five-member aromatic heterocycle with one nitrogen atom and four carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000218","name":"Pyrrolidines","chemont_id":"CHEMONTID:0000218","description":"Compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000078","name":"Imidazoles","chemont_id":"CHEMONTID:0000078","description":"Compounds containing an imidazole ring, which is an aromatic five-member ring with two nitrogen atoms at positions 1 and 3, and three carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004144","name":"Heteroaromatic compounds","chemont_id":"CHEMONTID:0004144","description":"Compounds containing an aromatic ring where a carbon atom is linked to an hetero atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001664","name":"Tertiary carboxylic acid amides","chemont_id":"CHEMONTID:0001664","description":"Compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000160","name":"Lactams","chemont_id":"CHEMONTID:0000160","description":"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001663","name":"Secondary carboxylic acid amides","chemont_id":"CHEMONTID:0001663","description":"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004139","name":"Azacyclic compounds","chemont_id":"CHEMONTID:0004139","description":"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004150","name":"Hydrocarbon derivatives","chemont_id":"CHEMONTID:0004150","description":"Derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. They contain at least one carbon atom and heteroatom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001831","name":"Carbonyl compounds","chemont_id":"CHEMONTID:0001831","description":"Organic compounds containing a carbonyl group, with the general structure RC(=O)R', where R=organyl, R'=H, N, O, organyl group or halide group."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002449","name":"Amines","chemont_id":"CHEMONTID:0002449","description":"Compounds formally derived from ammonia by replacing one, two or three hydrogen atoms by hydrocarbyl groups, and having the general structures RNH2 (primary amines), R2NH (secondary amines), R3N (tertiary amines)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003940","name":"Organic oxides","chemont_id":"CHEMONTID:0003940","description":"Organic compounds containing an oxide group."}],"molecular_framework":"Aromatic heteropolycyclic compounds","external_descriptors":[],"predicted_chebi_terms":["organonitrogen compound (CHEBI:35352)","organooxygen compound (CHEBI:36963)","indoles (CHEBI:24828)","piperazinone (CHEBI:46846)","N-alkylpiperazine (CHEBI:46845)","benzenoid aromatic compound (CHEBI:33836)","pyrroles (CHEBI:26455)","pyrrolidines (CHEBI:38260)","imidazoles (CHEBI:24780)","organic aromatic compound (CHEBI:33659)","carboxamide (CHEBI:37622)","lactam (CHEBI:24995)","organonitrogen heterocyclic compound (CHEBI:38101)","organic molecule (CHEBI:72695)","carbonyl compound (CHEBI:36586)","amine (CHEBI:32952)","organic oxide (CHEBI:25701)","pyrroloindole (CHEBI:48133)","chemical entity (CHEBI:24431)","organic acid (CHEBI:64709)","carboxylic acid (CHEBI:33575)","organic heterocyclic compound (CHEBI:24532)","organic heteromonocyclic compound (CHEBI:25693)","piperazines (CHEBI:26144)","azole (CHEBI:68452)","amide (CHEBI:32988)","oxygen molecular entity (CHEBI:25806)","organic molecular entity (CHEBI:50860)","nitrogen molecular entity (CHEBI:51143)","amino acid (CHEBI:33709)","peptide (CHEBI:16670)"],"classification_version":"2.1","predicted_lipidmaps_terms":[]},"npclassifier":{"isglycoside":false,"class_results":["Other indole diketopiperazine alkaloids"],"pathway_results":["Alkaloids","Amino acids and Peptides"],"superclass_results":["Peptide alkaloids"]}}