{"id":5925,"npaid":"NPA005925","original_name":"Sterigmatocystin","mol_formula":"C18H12O6","mol_weight":"324.2880","exact_mass":"324.0634","inchikey":"UTSVPXMQSFGQTM-DCXZOGHSSA-N","smiles":"COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=C(C2=O)C(=CC=C5)O","cluster_id":672,"node_id":7,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1","m_plus_h":"325.0707","m_plus_na":"347.0526","origin_reference":{"doi":"10.1039/jr9600002169","pmid":null,"authors":"Davies, JE; Kirkaldy, D; Roberts, John C","title":"437. Studies in mycological chemistry. Part VII. Sterigmatocystin, a metabolite of Aspergillus versicolor (Vuillemin) tiraboschi","journal":"Journal of the Chemical Society","year":1960,"volume":null,"issue":null,"pages":"2169-2178"},"origin_organism":{"id":3006,"type":"Fungus","genus":"Aspergillus","species":"versicolor (Vuillemin) 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Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005767525%Massbank:NA003661 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005767529%Massbank:NA002915 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005767726%Massbank:NA002916 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005768481%Massbank:NA003292 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005768557%Massbank:NA003291 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005768719%Massbank:NA002521 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005768885%Massbank:NA003293 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005769192%Massbank:NA003290 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005769277%Massbank:NA003660 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005769468%Massbank:NA002522 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005769500%Massbank:NA002525 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005769803%Massbank:NA003289 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005769828%Massbank:NA002918 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005770395%Massbank:NA003662 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005770488%Massbank:NA002914 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005770527%Massbank:NA002524 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005770683%Massbank:NA003659 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005770729%Massbank:NA003663 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005770853%Massbank:NA002523 Sterigmatocystin|(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one%3"},{"external_db_name":"npmrd","external_db_code":"NP0034325"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001817","name":"Sterigmatocystins","chemont_id":"CHEMONTID:0001817","description":"A group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. and Bipolaris spp."},"smiles":"COC1=C2C(=O)C3=C(OC2=C2[C@@H]4C=CO[C@@H]4OC2=C1)C=CC=C3O","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=UTSVPXMQSFGQTM-DCXZOGHSSA-N","subclass":null,"ancestors":["1-benzopyrans","1-hydroxy-2-unsubstituted benzenoids","1-hydroxy-4-unsubstituted benzenoids","Acetals","Alkyl aryl ethers","Anisoles","Benzenoids","Benzopyrans","Chemical entities","Chromones","Coumarans","Dibenzopyrans","Dihydrofurans","Ethers","Heteroaromatic compounds","Hydrocarbon derivatives","Organic acids and derivatives","Organic compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organooxygen compounds","Oxacyclic compounds","Phenol ethers","Phenols","Phenylpropanoids and polyketides","Pyranones and derivatives","Pyrans","Sterigmatocystins","Vinylogous acids","Vinylogous esters","Xanthenes","Xanthones"],"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 sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. and Bipolaris spp.","substituents":["Sterigmatocystin backbone","Xanthone","Dibenzopyran","Xanthene","Chromone","Benzopyran","1-benzopyran","Coumaran","Anisole","1-hydroxy-4-unsubstituted benzenoid","1-hydroxy-2-unsubstituted benzenoid","Alkyl aryl ether","Pyranone","Pyran","Benzenoid","Heteroaromatic compound","Dihydrofuran","Vinylogous ester","Vinylogous acid","Ether","Oxacycle","Acetal","Organoheterocyclic compound","Organic oxygen compound","Hydrocarbon derivative","Organooxygen compound","Organic oxide","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001817","name":"Sterigmatocystins","chemont_id":"CHEMONTID:0001817","description":"A group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. and Bipolaris spp."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000204","name":"Xanthones","chemont_id":"CHEMONTID:0000204","description":"Polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring."},{"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/C0004189","name":"Coumarans","chemont_id":"CHEMONTID:0004189","description":"Compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring."},{"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/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/C0000481","name":"Pyranones and derivatives","chemont_id":"CHEMONTID:0000481","description":"Compounds containing a pyran ring which bears a ketone."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001983","name":"Dihydrofurans","chemont_id":"CHEMONTID:0001983","description":"Compounds containing a dihydrofuran moiety, which is a furan derivative with only one double bond."},{"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/C0003891","name":"Vinylogous esters","chemont_id":"CHEMONTID:0003891","description":"Organic compounds containing an ester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety."},{"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/C0001656","name":"Acetals","chemont_id":"CHEMONTID:0001656","description":"Compounds having the structure R2C(OR')2 ( R' not Hydrogen) and thus diethers of geminal diols. Originally, the term was confined to derivatives of aldehydes (one R = H), but it now applies equally to derivatives of ketones (neither R = H ). Mixed acetals have different R' groups."},{"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/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/C0003940","name":"Organic oxides","chemont_id":"CHEMONTID:0003940","description":"Organic compounds containing an oxide group."}],"molecular_framework":"Aromatic heteropolycyclic compounds","external_descriptors":[{"source":"CHEBI","source_id":"CHEBI:18227","annotations":["sterigmatocystins"]},{"source":"KEGG","source_id":"C00961","annotations":["Aflatoxins and related substances","Mycotoxins"]},{"source":"LIPID MAPS","source_id":"LMPK10000001","annotations":["Aflatoxins and related substances"]}],"predicted_chebi_terms":["xanthones (CHEBI:51149)","chromones (CHEBI:23238)","1-benzofurans (CHEBI:38830)","methoxybenzene (CHEBI:51683)","phenols (CHEBI:33853)","aromatic ether (CHEBI:35618)","pyranone (CHEBI:37963)","dihydrofuran (CHEBI:51659)","enone (CHEBI:51689)","enol (CHEBI:33823)","enol ether (CHEBI:47985)","organic aromatic compound (CHEBI:33659)","acetal (CHEBI:59769)","oxacycle (CHEBI:38104)","organic molecule (CHEBI:72695)","organic oxide (CHEBI:25701)","sterigmatocystins (CHEBI:26759)","chemical entity (CHEBI:24431)","organic heterocyclic compound (CHEBI:24532)","benzopyran (CHEBI:22727)","1-benzopyran (CHEBI:38443)","dibenzopyran (CHEBI:39203)","xanthenes (CHEBI:38835)","benzenoid aromatic compound (CHEBI:33836)","oxygen molecular entity (CHEBI:25806)","organic molecular entity (CHEBI:50860)","organooxygen compound (CHEBI:36963)","ether (CHEBI:25698)","pyrans (CHEBI:26407)"],"classification_version":"2.1","predicted_lipidmaps_terms":["Dibenzofurans, griseofulvins, dibenzopyrans and xanthones (PK1306)","Benzopyranoids (PK1311)"]},"npclassifier":{"isglycoside":false,"class_results":["Aflatoxins","Methyl xanthones"],"pathway_results":["Polyketides"],"superclass_results":["Chromanes","Xanthones"]}}