{"id":13937,"npaid":"NPA013937","original_name":"Penifulvin A","mol_formula":"C18H26O4","mol_weight":"306.4020","exact_mass":"306.1831","inchikey":"DROISJUYARPXHO-ATIWLJMLSA-N","smiles":"CC1(C)C[C@]2(C)CC(=O)O[C@@]3(C)OC(=O)[C@]4(C)CC[C@]1(C)[C@@]234","cluster_id":5043,"node_id":3614,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C18H26O4/c1-13(2)10-14(3)9-11(19)21-17(6)18(14)15(4,12(20)22-17)7-8-16(13,18)5/h7-10H2,1-6H3/t14-,15-,16-,17-,18-/m0/s1","m_plus_h":"307.1904","m_plus_na":"329.1723","origin_reference":{"doi":"10.1021/ol060107c","pmid":16524309,"authors":"Shim, Sang Hee; Swenson, Dale C; Gloer, James B; Dowd, Patrick F; Wicklow, Donald T","title":"Penifulvin A: a sesquiterpenoid-derived metabolite containing a novel dioxa[5,5,5,6]fenestrane ring system from a fungicolous isolate of Penicillium griseofulvum","journal":"Organic Letters","year":2006,"volume":"8","issue":"6","pages":"1225-1228"},"origin_organism":{"id":4014,"type":"Fungus","genus":"Penicillium","species":"griseofulvum","taxon":{"id":1239,"name":"Penicillium","rank":"genus","taxon_db":"mycobank","external_id":"9257","ncbi_id":5073,"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/ja8083048","10.1021/ol500768w"],"reassignments":[{"reference_doi":"10.1021/ja8083048","structure_smiles":"CC1(C)C[C@]2(C)CC(=O)O[C@@]3(C)OC(=O)[C@]4(C)CC[C@]1(C)[C@@]234"}],"mol_structures":[{"current_structure":false,"reference_doi":"10.1021/ol060107c","structure_smiles":"C[C@@]12CC(=O)O[C@@H]3[C@@]14[C@@H](CC[C@H]4C(C2)(C)C)C(=O)O3","is_reassignment":false,"version":1},{"current_structure":true,"reference_doi":"10.1021/ja8083048","structure_smiles":"CC1(C)C[C@]2(C)CC(=O)O[C@@]3(C)OC(=O)[C@]4(C)CC[C@]1(C)[C@@]234","is_reassignment":true,"version":2}],"exclusions":[],"external_ids":[{"external_db_name":"mibig","external_db_code":"BGC0002557"},{"external_db_name":"npmrd","external_db_code":"NP0006245"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000259","name":"Prenol lipids","chemont_id":"CHEMONTID:0000259","description":"Lipids synthesized from the five-carbon-unit precursors isopentenyl diphosphate and dimethylallyl diphosphate."},"smiles":"CC1(C)C[C@]2(C)CC(=O)O[C@H]3OC(=O)[C@@H]4CC[C@@H]1[C@]234","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=NGAMYGLHRNCUQC-AWPZLMCQSA-N","subclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001283","name":"Terpene lactones","chemont_id":"CHEMONTID:0001283","description":"Prenol lipids containing a lactone ring."},"ancestors":["Acetals","Acylals","Carbonyl compounds","Carboxylic acid derivatives","Carboxylic acid esters","Carboxylic acids and derivatives","Chemical entities","Delta valerolactones","Dicarboxylic acids and derivatives","Ethers","Furans","Furopyrans","Gamma butyrolactones","Hydrocarbon derivatives","Iridoids and derivatives","Lactones","Lipids and lipid-like molecules","Monoterpenoids","Organic acids and derivatives","Organic compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organooxygen compounds","Oxacyclic compounds","Oxanes","Oxolanes","Prenol lipids","Pyrans","Terpene lactones"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000012","name":"Lipids and lipid-like molecules","chemont_id":"CHEMONTID:0000012","description":"Fatty acids and their derivatives, and substances related biosynthetically or functionally to these compounds."},"description":"This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.","substituents":["Terpene lactone","Iridoid-skeleton","Monoterpenoid","Furopyran","Delta valerolactone","Delta_valerolactone","Acylal","Dicarboxylic acid or derivatives","Gamma butyrolactone","Oxane","Pyran","Furan","Oxolane","Lactone","Carboxylic acid ester","Organoheterocyclic compound","Oxacycle","Acetal","Carboxylic acid derivative","Hydrocarbon derivative","Organic oxide","Organic oxygen compound","Organooxygen compound","Carbonyl group","Aliphatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001283","name":"Terpene lactones","chemont_id":"CHEMONTID:0001283","description":"Prenol lipids containing a lactone ring."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001565","name":"Iridoids and derivatives","chemont_id":"CHEMONTID:0001565","description":"Monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001818","name":"Furopyrans","chemont_id":"CHEMONTID:0001818","description":"Organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001244","name":"Delta valerolactones","chemont_id":"CHEMONTID:0001244","description":"Cyclic organic compounds containing an oxan-2- one moiety."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003989","name":"Acylals","chemont_id":"CHEMONTID:0003989","description":"Diesters of geminal diols."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000086","name":"Pyrans","chemont_id":"CHEMONTID:0000086","description":"Compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and  two ring double bonds."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002012","name":"Oxanes","chemont_id":"CHEMONTID:0002012","description":"Compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001245","name":"Gamma butyrolactones","chemont_id":"CHEMONTID:0001245","description":"Compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000346","name":"Dicarboxylic acids and derivatives","chemont_id":"CHEMONTID:0000346","description":"Organic compounds containing exactly two carboxylic acid groups."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001967","name":"Oxolanes","chemont_id":"CHEMONTID:0001967","description":"Organic compounds containing an oxolane (tetrahydrofuran) ring, which is a saturated aliphatic five-member ring containing one oxygen and five carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000076","name":"Furans","chemont_id":"CHEMONTID:0000076","description":"Compounds containing a furan ring, which is a five-member aromatic ring with one oxygen atom, four carbon atoms."},{"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/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/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."},{"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."}],"molecular_framework":"Aliphatic heteropolycyclic compounds","external_descriptors":[],"predicted_chebi_terms":["iridoid monoterpenoid (CHEBI:50563)","furopyran (CHEBI:74927)","delta-lactone (CHEBI:18946)","carboxylic ester (CHEBI:33308)","pyrans (CHEBI:26407)","oxanes (CHEBI:46942)","gamma-lactone (CHEBI:37581)","dicarboxylic acid (CHEBI:35692)","oxolanes (CHEBI:26912)","furans (CHEBI:24129)","oxacycle (CHEBI:38104)","acetal (CHEBI:59769)","organic oxide (CHEBI:25701)","organic molecule (CHEBI:72695)","carbonyl compound (CHEBI:36586)","terpene lactone (CHEBI:37668)","chemical entity (CHEBI:24431)","lipid (CHEBI:18059)","ether lipid (CHEBI:64611)","monoterpenoid (CHEBI:25409)","organic heterocyclic compound (CHEBI:24532)","lactone (CHEBI:25000)","organic acid (CHEBI:64709)","carboxylic acid (CHEBI:33575)","organooxygen compound (CHEBI:36963)","oxygen molecular entity (CHEBI:25806)","organic molecular entity (CHEBI:50860)","ether (CHEBI:25698)"],"classification_version":"2.1","predicted_lipidmaps_terms":["Iridoid, 10-alkyliridoid and secoiridoid monoterpenoids (PR010207)","Dicarboxylic acids (FA0117)","Prenol Lipids (PR)","C10 isoprenoids (monoterpenes) (PR0102)"]},"npclassifier":{"isglycoside":false,"class_results":["Silphinane sesquiterpenoids"],"pathway_results":["Terpenoids"],"superclass_results":["Sesquiterpenoids"]}}