{"id":15449,"npaid":"NPA015449","original_name":"Iso-α-cyclopiazonic acid","mol_formula":"C20H20N2O3","mol_weight":"336.3910","exact_mass":"336.1474","inchikey":"SZINUGQCTHLQAZ-OAUYIBNBSA-N","smiles":"CC(=O)C1=C([C@H]2[C@@H]3[C@@H](CC4=C5C3=CNC5=CC=C4)C(N2C1=O)(C)C)O","cluster_id":979,"node_id":844,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,24H,7H2,1-3H3/t12-,16+,17-/m1/s1","m_plus_h":"337.1547","m_plus_na":"359.1366","origin_reference":{"doi":"10.1007/s10600-009-9433-8","pmid":null,"authors":"Lin, Ai-Qun; Du, Lin; Fang, Yu-Chun; Wang, Fa-Zuo; Zhu, Tian-Jiao; Gu, Qian-Qun; Zhu, Wei-Ming","title":"iso-α-Cyclopiazonic acid, a new natural product isolated from the marine-derived fungus Aspergillus flavus C-F-3","journal":"Chemistry of Natural Compounds","year":2009,"volume":"45","issue":"5","pages":"569-571"},"origin_organism":{"id":4970,"type":"Fungus","genus":"Aspergillus","species":"flavus (strain C-F-3)","taxon":{"id":1237,"name":"Aspergillus","rank":"genus","taxon_db":"mycobank","external_id":"7248","ncbi_id":5052,"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":1212,"name":"Eurotiomycetes","rank":"class","taxon_db":"mycobank","external_id":"501483","ncbi_id":147545},{"id":1235,"name":"Eurotiales","rank":"order","taxon_db":"mycobank","external_id":"90472","ncbi_id":5042},{"id":1236,"name":"Aspergillaceae","rank":"family","taxon_db":"mycobank","external_id":"80489","ncbi_id":1131492}]}},"syntheses":[],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1007/s10600-009-9433-8","structure_smiles":"CC(=O)C1=C([C@H]2[C@@H]3[C@@H](CC4=C5C3=CNC5=CC=C4)C(N2C1=O)(C)C)O","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"mibig","external_db_code":"BGC0000977"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00006718077%Cyclopiazonic acid%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009945231%Suspect related to Cyclopiazonic acid (predicted molecular formula: C17H22NO7) with delta m/z 15.995 (putative explanation: Ala->Ser substitution|Oxidation or Hydroxylation|Phe->Tyr substitution; atomic difference: 1O|1O|1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009945232%Suspect related to Cyclopiazonic acid (predicted molecular formula: C21H22N2O4) 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":"CCMSLIB00009945233%Suspect related to Cyclopiazonic acid (predicted molecular formula: C23H20N2O5) with delta m/z 67.99 (putative explanation: unspecified; atomic difference: 3C,2O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009952805%Suspect related to Massbank:AC000054 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one (predicted molecular formula: C10H20N4O6) with delta m/z -44.016 (putative explanation: nan (reverse)|heavy acetylation (reverse); atomic difference: -1C,-2H,-1N,-1O|-2C[13],-2H,-1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009952806%Suspect related to Massbank:AC000054 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one (predicted molecular formula: C20H22N2O3) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727198%Massbank:AC000050 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727201%Massbank:AC000054 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727228%Massbank:AC000052 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727305%Massbank:AC000053 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727334%Massbank:AC000051 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012105434%Suspect related to Cyclopiazonic acid (predicted molecular formula SIRIUS: C17H22NO7 / BUDDY: C20H20N2O4) with delta m/z 15.995 (putative explanation: Ala->Ser substitution|Oxidation or Hydroxylation|Phe->Tyr substitution; atomic difference: 1O|1O|1O) [M-H]-%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012105435%Suspect related to Cyclopiazonic acid (predicted molecular formula SIRIUS: C21H22N2O4 / BUDDY: C21H22N2O4) 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":"CCMSLIB00012105436%Suspect related to Cyclopiazonic acid (predicted molecular formula SIRIUS: C23H20N2O5 / BUDDY: C17H24O11) with delta m/z 67.99 (putative explanation: unspecified; atomic difference: 3C,2O) [M-H]-%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012113008%Suspect related to Massbank:AC000054 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one (predicted molecular formula SIRIUS: C10H20N4O6 / BUDDY: C11H16N8O2) with delta m/z -44.016 (putative explanation: nan (reverse)|heavy acetylation (reverse); atomic difference: -1C,-2H,-1N,-1O|-2C[13],-2H,-1O) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012113009%Suspect related to Massbank:AC000054 alpha-Cyclopiazonic acid|(6aR,11aS,11bR)-10-Acetyl-11-hydroxy-7,7-dimethyl-2,6,6a,7,11a,11b-hexahydro-9H-pyrrolo[1',2':2,3]isoindolo[4,5,6-cd]indol-9-one (predicted molecular formula SIRIUS: C20H22N2O3 / BUDDY: C20H22N2O3) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H) [M+H]+%4"},{"external_db_name":"npmrd","external_db_code":"NP0154273"}],"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(=O)C1=C(O)[C@H]2[C@@H]3[C@@H](CC4=C5C(NC=C35)=CC=C4)C(C)(C)N2C1=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=SZINUGQCTHLQAZ-OAUYIBNBSA-N","subclass":{"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."},"ancestors":["3-alkylindoles","Azacyclic compounds","Benzenoids","Carbonyl compounds","Carboxylic acid amides","Carboxylic acid derivatives","Carboxylic acids and derivatives","Chemical entities","Enols","Heteroaromatic compounds","Hydrocarbon derivatives","Indoles","Indoles and derivatives","Isoindoles and derivatives","Isoindolines","Ketones","Lactams","Organic acids and derivatives","Organic compounds","Organic nitrogen compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organonitrogen compounds","Organooxygen compounds","Organopnictogen compounds","Pyrroles","Pyrrolidines","Pyrrolines","Pyrrolizines","Tertiary carboxylic acid amides","Vinylogous acids"],"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 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.","substituents":["3-alkylindole","Isoindole or derivatives","Isoindoline","Pyrrolizine","Benzenoid","Heteroaromatic compound","Vinylogous acid","Tertiary carboxylic acid amide","Pyrroline","Pyrrolidine","Pyrrole","Lactam","Ketone","Carboxamide group","Azacycle","Enol","Carboxylic acid derivative","Organic nitrogen compound","Organic oxygen compound","Organopnictogen compound","Organic oxide","Hydrocarbon derivative","Organooxygen compound","Organonitrogen compound","Carbonyl group","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004196","name":"3-alkylindoles","chemont_id":"CHEMONTID:0004196","description":"Compounds containing an indole moiety that carries an alkyl chain at the 3-position."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002496","name":"Isoindolines","chemont_id":"CHEMONTID:0002496","description":"Heterocyclic compounds containing a 2,3-dihydro-1H-iso-indole moiety."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000219","name":"Pyrrolizines","chemont_id":"CHEMONTID:0000219","description":"Compounds containing a pyrrolizine moiety, which consists of a pyrrole ring fused to a pyrrolidine ring."},{"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/C0003889","name":"Vinylogous acids","chemont_id":"CHEMONTID:0003889","description":"Organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety."},{"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/C0000091","name":"Pyrrolines","chemont_id":"CHEMONTID:0000091","description":"Compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring 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/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/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/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/C0000118","name":"Ketones","chemont_id":"CHEMONTID:0000118","description":"Organic compounds  in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000132","name":"Enols","chemont_id":"CHEMONTID:0000132","description":"Compounds containing the enol functional group, with the structure HO(R)C=CR'. Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol."},{"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/C0004557","name":"Organopnictogen compounds","chemont_id":"CHEMONTID:0004557","description":"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000278","name":"Organonitrogen compounds","chemont_id":"CHEMONTID:0000278","description":"Organic compounds containing a nitrogen atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003940","name":"Organic oxides","chemont_id":"CHEMONTID:0003940","description":"Organic compounds containing an oxide group."},{"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."}],"molecular_framework":"Aromatic heteropolycyclic compounds","external_descriptors":[],"predicted_chebi_terms":["isoindoles (CHEBI:24897)","pyrrolizines (CHEBI:38522)","benzenoid aromatic compound (CHEBI:33836)","enone (CHEBI:51689)","enol (CHEBI:33823)","carboxamide (CHEBI:37622)","pyrroline (CHEBI:23763)","pyrrolidines (CHEBI:38260)","pyrroles (CHEBI:26455)","organic aromatic compound (CHEBI:33659)","lactam (CHEBI:24995)","ketone (CHEBI:17087)","organonitrogen heterocyclic compound (CHEBI:38101)","pnictogen molecular entity (CHEBI:33302)","organic molecular entity (CHEBI:50860)","organonitrogen compound (CHEBI:35352)","organic oxide (CHEBI:25701)","organic molecule (CHEBI:72695)","indoles (CHEBI:24828)","chemical entity (CHEBI:24431)","organic heterocyclic compound (CHEBI:24532)","organooxygen compound (CHEBI:36963)","amide (CHEBI:32988)","oxygen molecular entity (CHEBI:25806)","carbonyl compound (CHEBI:36586)","nitrogen molecular entity (CHEBI:51143)"],"classification_version":"2.1","predicted_lipidmaps_terms":[]},"npclassifier":{"isglycoside":false,"class_results":["Cyclopiazonic acid-tpye tetramate alkaloids"],"pathway_results":["Alkaloids","Amino acids and Peptides"],"superclass_results":["Tetramate alkaloids"]}}