{"id":8799,"npaid":"NPA008799","original_name":"Isosilybin A","mol_formula":"C25H22O10","mol_weight":"482.4410","exact_mass":"482.1213","inchikey":"FDQAOULAVFHKBX-HKTJVKLFSA-N","smiles":"COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=CC(=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O","cluster_id":860,"node_id":744,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1","m_plus_h":"483.1286","m_plus_na":"505.1105","origin_reference":{"doi":"10.1021/np400955q","pmid":24456525,"authors":"El-Elimat, Tamam; Raja, Huzefa A.; Graf, Tyler N.; Faeth, Stanley H.; Cech, Nadja B.; Oberlies, Nicholas H.","title":"Flavonolignans from Aspergillus iizukae, a fungal endophyte of milk thistle (Silybum marianum)","journal":"Journal of Natural Products","year":2014,"volume":"77","issue":"2","pages":"193-199"},"origin_organism":{"id":974,"type":"Fungus","genus":"Aspergillus","species":"iizukae","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":["10.1021/ol503303w"],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1021/np400955q","structure_smiles":"COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=CC(=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"gnps","external_db_code":"CCMSLIB00012110033%Suspect related to Isosilybin A (predicted molecular formula SIRIUS: unknown / BUDDY: C26H26O11) with delta m/z 32.026 (putative explanation: unspecified; atomic difference: 1C,4H,1O) [M-H-H2O]-%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009949827%Suspect related to Isosilybin A (predicted molecular formula: unknown) with delta m/z -30.01 (putative explanation: Decarboxylation|Demethoxylation|Proline oxidation to pyrrolidinone|Ser->Gly substitution|Thr->Ala substitution; 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":"CCMSLIB00009949828%Suspect related to Isosilybin A (predicted molecular formula: unknown) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009949829%Suspect related to Isosilybin A (predicted molecular formula: unknown) 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":"CCMSLIB00009949830%Suspect related to Isosilybin A (predicted molecular formula: unknown) with delta m/z 32.026 (putative explanation: unspecified; atomic difference: 1C,4H,1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777697%Massbank:FIO01027 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777784%Massbank:FIO01006 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777824%Massbank:FIO01005 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777890%Massbank:FIO01029 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777904%Massbank:FIO01030 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777965%Massbank:FIO01007 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777975%Massbank:FIO01024 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005777978%Massbank:FIO01031 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778033%Massbank:FIO01000 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778082%Massbank:FIO01026 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778140%Massbank:FIO01004 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778142%Massbank:FIO01008 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778149%Massbank:FIO01002 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778153%Massbank:FIO01028 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778166%Massbank:FIO01032 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778169%Massbank:FIO01025 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778188%Massbank:FIO01033 Isosilybin A%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778227%Massbank:FIO01003 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778296%Massbank:FIO01001 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005778313%Massbank:FIO00999 Isosilybin B%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012110030%Suspect related to Isosilybin A (predicted molecular formula SIRIUS: unknown / BUDDY: C24H20O9) with delta m/z -30.01 (putative explanation: Decarboxylation|Demethoxylation|Proline oxidation to pyrrolidinone|Ser->Gly substitution|Thr->Ala substitution; atomic difference: -1C,-2H,-1O|-1C,-2H,-1O|-1C,-2H,-1O|-1C,-2H,-1O|-1C,-2H,-1O) [M-H-H2O]-%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012110031%Suspect related to Isosilybin A (predicted molecular formula SIRIUS: unknown / BUDDY: C24H24N2O7S) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H) [M-H-H2O]-%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012110032%Suspect related to Isosilybin A (predicted molecular formula SIRIUS: unknown / BUDDY: C25H22O11) with delta m/z 15.995 (putative explanation: Ala->Ser substitution|Oxidation or Hydroxylation|Phe->Tyr substitution; atomic difference: 1O|1O|1O) [M-H-H2O]-%4"},{"external_db_name":"npmrd","external_db_code":"NP0012442"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001844","name":"Flavonolignans","chemont_id":"CHEMONTID:0001844","description":"Non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety."},"smiles":"COC1=C(O)C=CC(=C1)[C@H]1OC2=C(O[C@@H]1CO)C=C(C=C2)[C@H]1OC2=CC(O)=CC(O)=C2C(=O)[C@@H]1O","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=FDQAOULAVFHKBX-HKTJVKLFSA-N","subclass":null,"ancestors":["1-benzopyrans","1-hydroxy-2-unsubstituted benzenoids","1-hydroxy-4-unsubstituted benzenoids","3-hydroxyflavonoids","5-hydroxyflavonoids","7-hydroxyflavonoids","Alcohols and polyols","Alkyl aryl ethers","Anisoles","Aryl alkyl ketones","Aryl ketones","Benzene and substituted derivatives","Benzenoids","Benzo-1,4-dioxanes","Benzodioxanes","Benzopyrans","Carbonyl compounds","Chemical entities","Chromones","Dioxins","Ethers","Flavanones","Flavanonols","Flavans","Flavonoids","Flavonolignans","Hydrocarbon derivatives","Hydroxyflavonoids","Ketones","Lignans, neolignans and related compounds","Methoxybenzenes","Methoxyphenols","Organic acids and derivatives","Organic compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organooxygen compounds","Oxacyclic compounds","Para dioxins","Phenol ethers","Phenols","Phenoxy compounds","Phenylbenzo-1,4-dioxanes","Phenylbenzodioxanes","Phenylpropanoids and polyketides","Polyols","Primary alcohols","Secondary alcohols","Vinylogous acids"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001392","name":"Lignans, neolignans and related compounds","chemont_id":"CHEMONTID:0001392","description":"Plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed."},"description":"This compound belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.","substituents":["Flavonolignan","Hydroxyflavonoid","3-hydroxyflavonoid","Flavanonol","Flavanone","7-hydroxyflavonoid","5-hydroxyflavonoid","Flavan","Phenylbenzodioxane","2-phenylbenzo-1,4-dioxane","Chromone","1-benzopyran","Methoxyphenol","Benzopyran","Chromane","Benzodioxane","Benzo-1,4-dioxane","Phenoxy compound","Anisole","Methoxybenzene","Aryl alkyl ketone","Aryl ketone","Phenol ether","Alkyl aryl ether","1-hydroxy-2-unsubstituted benzenoid","Phenol","1-hydroxy-4-unsubstituted benzenoid","Benzenoid","Para-dioxin","Monocyclic benzene moiety","Vinylogous acid","Secondary alcohol","Ketone","Polyol","Organoheterocyclic compound","Ether","Oxacycle","Alcohol","Organooxygen compound","Organic oxygen compound","Organic oxide","Hydrocarbon derivative","Primary alcohol","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001844","name":"Flavonolignans","chemont_id":"CHEMONTID:0001844","description":"Non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002914","name":"3-hydroxyflavonoids","chemont_id":"CHEMONTID:0002914","description":"Flavonoids that bear one hydroxyl group at the C-3 position of the flavonoid skeleton."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002992","name":"5-hydroxyflavonoids","chemont_id":"CHEMONTID:0002992","description":"Flavonoids that bear one hydroxyl group at the C-5 position of the flavonoid skeleton."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002993","name":"7-hydroxyflavonoids","chemont_id":"CHEMONTID:0002993","description":"Flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001362","name":"Flavanonols","chemont_id":"CHEMONTID:0001362","description":"Compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002707","name":"Phenylbenzo-1,4-dioxanes","chemont_id":"CHEMONTID:0002707","description":"Benzo-1,3-dioxanes having a phenyl group attached to the 1,4-dioxane moiety."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000144","name":"Chromones","chemont_id":"CHEMONTID:0000144","description":"Compounds containing a benzopyran-4-one moiety."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000190","name":"Methoxyphenols","chemont_id":"CHEMONTID:0000190","description":"Compounds containing a methoxy group attached to the benzene ring of a phenol moiety."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002702","name":"Benzo-1,4-dioxanes","chemont_id":"CHEMONTID:0002702","description":"Heterocyclic compounds containing a benzene ring fused to a 1,4-dioxane ring."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004742","name":"Phenoxy compounds","chemont_id":"CHEMONTID:0004742","description":"Aromatic compounds contaning a phenoxy group."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000138","name":"Anisoles","chemont_id":"CHEMONTID:0000138","description":"Organic compounds containing a methoxybenzene or a derivative thereof."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004113","name":"Methoxybenzenes","chemont_id":"CHEMONTID:0004113","description":"Organic aromatic compounds containing a monocyclic benzene moiety carrying exactly or one more methoxy groups."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003671","name":"Aryl alkyl ketones","chemont_id":"CHEMONTID:0003671","description":"Ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004646","name":"1-hydroxy-2-unsubstituted benzenoids","chemont_id":"CHEMONTID:0004646","description":"Phenols that a unsubstituted at the 2-position."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004647","name":"1-hydroxy-4-unsubstituted benzenoids","chemont_id":"CHEMONTID:0004647","description":"Phenols that are unsubstituted at the 4-position."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000128","name":"Alkyl aryl ethers","chemont_id":"CHEMONTID:0000128","description":"Organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001386","name":"Para dioxins","chemont_id":"CHEMONTID:0001386","description":"Compounds containing a para dioxin moiety, which consists of an unsaturated six-member ring with two oxygen atoms at positions 1 and 4, as well as two CC double bonds."},{"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/C0001661","name":"Secondary alcohols","chemont_id":"CHEMONTID:0001661","description":"Compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl)."},{"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/C0002286","name":"Polyols","chemont_id":"CHEMONTID:0002286","description":"Organic compounds containing more than one hydroxyl groups."},{"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/C0000286","name":"Primary alcohols","chemont_id":"CHEMONTID:0000286","description":"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl)."},{"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":["hydroxyflavonoid (CHEBI:71968)","dihydroflavonols (CHEBI:48039)","benzodioxine (CHEBI:64096)","chromones (CHEBI:23238)","methoxybenzene (CHEBI:51683)","phenols (CHEBI:33853)","benzenes (CHEBI:22712)","aromatic ketone (CHEBI:76224)","aromatic ether (CHEBI:35618)","oxacycle (CHEBI:38104)","enone (CHEBI:51689)","enol (CHEBI:33823)","secondary alcohol (CHEBI:35681)","polyol (CHEBI:26191)","organic oxide (CHEBI:25701)","primary alcohol (CHEBI:15734)","organic molecule (CHEBI:72695)","flavonolignan (CHEBI:72709)","chemical entity (CHEBI:24431)","organooxygen compound (CHEBI:36963)","flavonoids (CHEBI:72544)","flavans (CHEBI:38672)","flavanones (CHEBI:28863)","organic heterocyclic compound (CHEBI:24532)","benzopyran (CHEBI:22727)","1-benzopyran (CHEBI:38443)","benzenoid aromatic compound (CHEBI:33836)","oxygen molecular entity (CHEBI:25806)","organic molecular entity (CHEBI:50860)","carbonyl compound (CHEBI:36586)","ketone (CHEBI:17087)","ether (CHEBI:25698)","organic acid (CHEBI:64709)","organic hydroxy compound (CHEBI:33822)","alcohol (CHEBI:30879)","phenylpropanoid (CHEBI:26004)"],"classification_version":"2.1","predicted_lipidmaps_terms":["Dihydroflavonols (PK1215)","Flavans, Flavanols and Leucoanthocyanidins (PK1202)","Flavanones (PK1214)","Benzopyranoids (PK1311)"]},"npclassifier":{"isglycoside":false,"class_results":["Flavonolignans"],"pathway_results":["Shikimates and Phenylpropanoids"],"superclass_results":["Lignans","Flavonoids"]}}