{"id":16066,"npaid":"NPA016066","original_name":"Ochratoxin A","mol_formula":"C20H18ClNO6","mol_weight":"403.8180","exact_mass":"403.0823","inchikey":"RWQKHEORZBHNRI-BMIGLBTASA-N","smiles":"C[C@@H]1CC2=C(C=C(C(=C2C(=O)O1)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)Cl","cluster_id":3329,"node_id":2522,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1","m_plus_h":"404.0896","m_plus_na":"426.0715","origin_reference":{"doi":"10.1039/jr9650007083","pmid":null,"authors":"Van der Merwe, KJ; Steyn, PS; Fourie, L","title":"1304. Mycotoxins. Part II. The constitution of ochratoxins A, B, and C, metabolites of Aspergillus ochraceus wilh","journal":"Journal of the Chemical Society","year":1965,"volume":null,"issue":null,"pages":"7083-7088"},"origin_organism":{"id":869,"type":"Fungus","genus":"Aspergillus","species":"ochraceus","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":["10.1016/j.bmc.2009.10.050"],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1039/jr9650007083","structure_smiles":"C[C@@H]1CC2=C(C=C(C(=C2C(=O)O1)O)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)Cl","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"mibig","external_db_code":"BGC0001030"},{"external_db_name":"mibig","external_db_code":"BGC0002609"},{"external_db_name":"mibig","external_db_code":"BGC0002598"},{"external_db_name":"mibig","external_db_code":"BGC0002605"},{"external_db_name":"mibig","external_db_code":"BGC0002606"},{"external_db_name":"mibig","external_db_code":"BGC0002607"},{"external_db_name":"mibig","external_db_code":"BGC0002608"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010122982%CCRIS 2382 CollisionEnergy:205060%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010122983%CCRIS 2382 CollisionEnergy:205060%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010122984%CCRIS 2382 CollisionEnergy:205060%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009967397%Suspect related to NCGC00162403-05_C20H18ClNO6_L-Phenylalanine, N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]- (predicted molecular formula: C17H26N2O10) with delta m/z 15.069 (putative explanation: unspecified; atomic difference: unspecified)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009977324%Suspect related to Ochratoxin A (predicted molecular formula: C22H15N3O6) with delta m/z 14.016 (putative explanation: Asn->Gln substitution|Asp->Glu substitution|Gly->Ala substitution|Methylation|Ser->Thr substitution|Val->Leu/Ile substitution|chain elongation; atomic difference: 1C,2H|1C,2H|1C,2H|1C,2H|1C,2H|1C,2H|1C,2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727046%Massbank:AC000213 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727118%Massbank:AC000208 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727084%Massbank:AC000212 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727086%Massbank:AC000204 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727127%Massbank:AC000210 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727629%Massbank:AC000209 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727645%Massbank:AC000207 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727757%Massbank:AC000205 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727767%Massbank:AC000206 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005727785%Massbank:AC000211 Ochratoxin A|OTA|(-)-N-((5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl)-3-phenylalanine%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005772393%Massbank:AU596602 Ochratoxin A|Alanine, (-)-|2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoic acid%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005773251%Massbank:AU596603 Ochratoxin A|Alanine, (-)-|2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoic acid%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005773589%Massbank:AU596601 Ochratoxin A|Alanine, (-)-|2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoic acid%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005775447%Massbank:AU596600 Ochratoxin A|Alanine, (-)-|2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoic acid%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005776608%Massbank:AU596604 Ochratoxin A|Alanine, (-)-|2-[(5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl)amino]-3-phenylpropanoic acid%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000855764%NCGC00162403-05_C20H18ClNO6_L-Phenylalanine, N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-%1!CCMSLIB00000855766%NCGC00162403-05_C20H18ClNO6_L-Phenylalanine, N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-%1!CCMSLIB00000850370%NCGC00162403-05_C20H18ClNO6_L-Phenylalanine, N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-%1"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005725544%Ochratoxin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00006718074%Ochratoxin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00003138899%Spectral Match to Ochratoxin A from NIST14%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010111648%CCRIS 2382 CollisionEnergy:102040%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010111649%CCRIS 2382 CollisionEnergy:102040%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010111650%CCRIS 2382 CollisionEnergy:102040%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012127600%Suspect related to NCGC00162403-05_C20H18ClNO6_L-Phenylalanine, N-[[(3R)-5-chloro-3,4-dihydro-8-hydroxy-3-methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]- (predicted molecular formula SIRIUS: C17H26N2O10 / BUDDY: C22H26O8) with delta m/z 15.069 (putative explanation: unspecified; atomic difference: unspecified) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012137527%Suspect related to Ochratoxin A (predicted molecular formula SIRIUS: C22H15N3O6 / BUDDY: C19H19N3O6S) with delta m/z 14.016 (putative explanation: Asn->Gln substitution|Asp->Glu substitution|Gly->Ala substitution|Methylation|Ser->Thr substitution|Val->Leu/Ile substitution|chain elongation; atomic difference: 1C,2H|1C,2H|1C,2H|1C,2H|1C,2H|1C,2H|1C,2H) [M+H]+%4"},{"external_db_name":"npmrd","external_db_code":"NP0045356"},{"external_db_name":"cmmc","external_db_code":"https://cmmc-kb.gnps2.org/structurepage/?inchikey=RWQKHEORZBHNRI-BMIGLBTASA-N"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001787","name":"Ochratoxins and related substances","chemont_id":"CHEMONTID:0001787","description":"A group of chemically related metabolites containing a 3,4-dihydro-3-methylisocoumarin moiety linked through a carboxyl group to L-beta-phenylalanine by a secondary amine bond."},"smiles":"C[C@@H]1CC2=C(Cl)C=C(C(=O)N[C@@H](CC3=CC=CC=C3)C(O)=O)C(O)=C2C(=O)O1","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=RWQKHEORZBHNRI-BMIGLBTASA-N","subclass":null,"ancestors":["2-benzopyrans","Alpha amino acids and derivatives","Amino acids and derivatives","Amino acids, peptides, and analogues","Amphetamines and derivatives","Aryl chlorides","Aryl halides","Benzene and substituted derivatives","Benzenoids","Benzoic acids and derivatives","Benzopyrans","Carbonyl compounds","Carboxylic acid amides","Carboxylic acid derivatives","Carboxylic acid esters","Carboxylic acids","Carboxylic acids and derivatives","Chemical entities","Dicarboxylic acids and derivatives","Hydrocarbon derivatives","Hydroxybenzoic acid derivatives","Lactones","N-acyl-alpha amino acids","N-acyl-alpha amino acids and derivatives","Ochratoxins and related substances","Organic acids and derivatives","Organic compounds","Organic nitrogen compounds","Organic oxides","Organic oxygen compounds","Organochlorides","Organohalogen compounds","Organoheterocyclic compounds","Organonitrogen compounds","Organooxygen compounds","Organopnictogen compounds","Oxacyclic compounds","Phenethylamines","Phenylalanine and derivatives","Phenylpropanoic acids","Phenylpropanoids and polyketides","Salicylic acid and derivatives","Secondary carboxylic acid amides","Vinylogous acids"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000261","name":"Phenylpropanoids and polyketides","chemont_id":"CHEMONTID:0000261","description":"Organic compounds that are synthesized either from the amino acid phenylalanine (phenylpropanoids) or the decarboxylative condensation of malonyl-CoA (polyketides). Phenylpropanoids are aromatic compounds based on the phenylpropane skeleton. Polyketides usually consist of alternating carbonyl and methylene groups (beta-polyketones), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations."},"description":"This compound belongs to the class of organic compounds known as ochratoxins and related substances. These are a group of chemically related metabolites containing a 3,4-dihydro-3-methylisocoumarin moiety linked through a carboxyl group to L-beta-phenylalanine by a secondary amine bond.","substituents":["Ochratoxin-skeleton","Phenylalanine or derivatives","N-acyl-alpha amino acid or derivatives","N-acyl-alpha-amino acid","3-phenylpropanoic-acid","Alpha-amino acid or derivatives","Amphetamine or derivatives","Salicylic acid or derivatives","2-benzopyran","Isochromane","Benzopyran","Aryl halide","Benzenoid","Aryl chloride","Dicarboxylic acid or derivatives","Monocyclic benzene moiety","Vinylogous acid","Carboxamide group","Carboxylic acid ester","Secondary carboxylic acid amide","Lactone","Carboxylic acid","Carboxylic acid derivative","Organoheterocyclic compound","Oxacycle","Organopnictogen compound","Organic oxygen compound","Organic nitrogen compound","Carbonyl group","Hydrocarbon derivative","Organic oxide","Organooxygen compound","Organonitrogen compound","Organochloride","Organohalogen compound","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001787","name":"Ochratoxins and related substances","chemont_id":"CHEMONTID:0001787","description":"A group of chemically related metabolites containing a 3,4-dihydro-3-methylisocoumarin moiety linked through a carboxyl group to L-beta-phenylalanine by a secondary amine bond."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004321","name":"Phenylalanine and derivatives","chemont_id":"CHEMONTID:0004321","description":"Compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002402","name":"N-acyl-alpha amino acids","chemont_id":"CHEMONTID:0002402","description":"Compounds 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RC(=O)N(R')H (R,R'=alkyl, aryl)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001238","name":"Carboxylic acid esters","chemont_id":"CHEMONTID:0001238","description":"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000050","name":"Lactones","chemont_id":"CHEMONTID:0000050","description":"Cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004140","name":"Oxacyclic compounds","chemont_id":"CHEMONTID:0004140","description":"Organic compounds containing an heterocycle with at least one oxygen atom linked to a ring carbon."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001205","name":"Carboxylic acids","chemont_id":"CHEMONTID:0001205","description":"Compounds containing a carboxylic acid group with the formula -C(=O)OH."},{"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/C0001516","name":"Organochlorides","chemont_id":"CHEMONTID:0001516","description":"Compounds containing a chemical bond between a carbon atom and a chlorine atom."},{"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/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":[{"source":"CHEBI","source_id":"CHEBI:7719","annotations":["monocarboxylic acid amide","organochlorine compound","phenylalanine derivative","N-acyl-L-phenylalanine","isochromanes"]},{"source":"KEGG","source_id":"C09955","annotations":["Mycotoxins"]}],"predicted_chebi_terms":["phenylalanine derivative (CHEBI:25985)","N-acyl-amino acid (CHEBI:51569)","benzenes (CHEBI:22712)","carboxylic acid (CHEBI:33575)","carbonyl compound (CHEBI:36586)","2-benzopyran (CHEBI:38444)","amphetamines (CHEBI:35338)","organochlorine compound (CHEBI:36683)","dicarboxylic acid (CHEBI:35692)","enone (CHEBI:51689)","enol (CHEBI:33823)","carboxamide (CHEBI:37622)","carboxylic ester (CHEBI:33308)","lactone (CHEBI:25000)","oxacycle (CHEBI:38104)","carboxylic acid anion (CHEBI:29067)","pnictogen molecular entity (CHEBI:33302)","organic molecular entity (CHEBI:50860)","organonitrogen compound (CHEBI:35352)","organic oxide (CHEBI:25701)","organic molecule (CHEBI:72695)","monocarboxylic acid amide (CHEBI:29347)","isochromanes (CHEBI:38762)","chemical entity (CHEBI:24431)","organooxygen compound (CHEBI:36963)","amino acid (CHEBI:33709)","peptide (CHEBI:16670)","benzenoid aromatic compound (CHEBI:33836)","hydroxybenzoic acid (CHEBI:24676)","organic heterocyclic compound (CHEBI:24532)","benzopyran (CHEBI:22727)","primary amine (CHEBI:32877)","organohalogen compound (CHEBI:36684)","haloarene (CHEBI:50887)","amide (CHEBI:32988)","oxygen molecular entity (CHEBI:25806)","nitrogen molecular entity (CHEBI:51143)"],"classification_version":"2.1","predicted_lipidmaps_terms":["Dicarboxylic acids (FA0117)","Benzopyranoids (PK1311)"]},"npclassifier":{"isglycoside":false,"class_results":["Isocoumarins"],"pathway_results":["Shikimates and Phenylpropanoids"],"superclass_results":["Coumarins"]}}