{"id":3891,"npaid":"NPA003891","original_name":"Berkelic acid","mol_formula":"C29H40O9","mol_weight":"532.6300","exact_mass":"532.2672","inchikey":"KUPCHRRTAPZASB-FZIMWOAESA-N","smiles":"CCCCC[C@@H]1CC2=CC(O)=C(C(=O)O)C3=C2[C@H](C[C@]2(OC[C@@H](CC(=O)[C@](C)(CC)C(=O)OC)[C@@H]2C)O3)O1","cluster_id":2095,"node_id":1677,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C29H40O9/c1-6-8-9-10-19-11-17-12-20(30)24(26(32)33)25-23(17)21(37-19)14-29(38-25)16(3)18(15-36-29)13-22(31)28(4,7-2)27(34)35-5/h12,16,18-19,21,30H,6-11,13-15H2,1-5H3,(H,32,33)/t16-,18+,19+,21-,28-,29-/m0/s1","m_plus_h":"533.2745","m_plus_na":"555.2564","origin_reference":{"doi":"10.1021/jo060018d","pmid":16808526,"authors":"Stierle, Andrea A.; Stierle, Donald B.; Kelly, Kal","title":"Berkelic Acid, A Novel Spiroketal with Selective Anticancer Activity from an Acid Mine Waste Fungal Extremophile","journal":"Journal of Organic Chemistry","year":2006,"volume":"71","issue":"14","pages":"5357-5360"},"origin_organism":{"id":113,"type":"Fungus","genus":"Penicillium","species":"sp.","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/ja905387r","10.1002/chem.201001133","10.1002/anie.201109076","10.1016/j.tet.2018.01.021"],"reassignments":[{"reference_doi":"10.1021/jo901221a","structure_smiles":"CCCCC[C@@H]1CC2=CC(O)=C(C(=O)O)C3=C2[C@H](C[C@]2(OC[C@@H](CC(=O)[C@](C)(CC)C(=O)OC)[C@@H]2C)O3)O1"}],"mol_structures":[{"current_structure":false,"reference_doi":"10.1021/jo060018d","structure_smiles":"CCCCC[C@@H]1CC2=CC(=C(C3=C2C(O1)C[C@]4(O3)[C@@H]([C@H](CO4)CC(=O)C(C)(CC)C(=O)OC)C)C(=O)O)O","is_reassignment":false,"version":1},{"current_structure":true,"reference_doi":"10.1021/jo901221a","structure_smiles":"CCCCC[C@@H]1CC2=CC(O)=C(C(=O)O)C3=C2[C@H](C[C@]2(OC[C@@H](CC(=O)[C@](C)(CC)C(=O)OC)[C@@H]2C)O3)O1","is_reassignment":true,"version":2}],"exclusions":[],"external_ids":[{"external_db_name":"npmrd","external_db_code":"NP0006449"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002279","name":"Benzene and substituted derivatives","chemont_id":"CHEMONTID:0002279","description":"Aromatic compounds containing one monocyclic ring system consisting of benzene."},"smiles":"[H][C@]1(CC(=O)C(C)(CC)C(=O)OC)CO[C@]2(CC3([H])O[C@]([H])(CCCCC)CC4=CC(O)=C(C(O)=O)C(O2)=C34)[C@]1([H])C","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=KUPCHRRTAPZASB-YKVDFVGGSA-N","subclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000176","name":"Benzoic acids and derivatives","chemont_id":"CHEMONTID:0000176","description":"Organic compounds containing a carboxylic acid substituent attached to a benzene ring."},"ancestors":["1-benzopyrans","1-hydroxy-2-unsubstituted benzenoids","2-benzopyrans","Acetals","Benzene and substituted derivatives","Benzenoids","Benzoic acids and derivatives","Benzopyrans","Beta-keto acids and derivatives","Carbonyl compounds","Carboxylic acid derivatives","Carboxylic acid esters","Carboxylic acids","Carboxylic acids and derivatives","Chemical entities","Dialkyl ethers","Dicarboxylic acids and derivatives","Ethers","Fatty Acyls","Fatty acid esters","Hydrocarbon derivatives","Hydroxybenzoic acid derivatives","Ketals","Keto acids and derivatives","Ketones","Lipids and lipid-like molecules","Methyl esters","Organic acids and derivatives","Organic compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organooxygen compounds","Oxacyclic compounds","Phenols","Salicylic acid and derivatives","Tetrahydrofurans","Vinylogous acids"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002448","name":"Benzenoids","chemont_id":"CHEMONTID:0002448","description":"Aromatic compounds containing one or more benzene rings."},"description":"This compound belongs to the class of organic compounds known as salicylic acid and derivatives. These are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.","substituents":["2-benzopyran","1-benzopyran","Salicylic acid or derivatives","Isochromane","Benzopyran","Chromane","1-hydroxy-2-unsubstituted benzenoid","Ketal","Fatty acid ester","Beta-keto acid","Fatty acyl","Keto acid","Dicarboxylic acid or derivatives","Vinylogous acid","Methyl ester","Tetrahydrofuran","Ketone","Carboxylic acid ester","Oxacycle","Organoheterocyclic compound","Ether","Dialkyl ether","Carboxylic acid","Carboxylic acid derivative","Acetal","Organic oxygen compound","Organic oxide","Hydrocarbon derivative","Organooxygen compound","Carbonyl group","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000487","name":"Salicylic acid and derivatives","chemont_id":"CHEMONTID:0000487","description":"Compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof."},"intermediate_nodes":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001248","name":"Hydroxybenzoic acid derivatives","chemont_id":"CHEMONTID:0001248","description":"Compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups."}],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003411","name":"2-benzopyrans","chemont_id":"CHEMONTID:0003411","description":"Organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003410","name":"1-benzopyrans","chemont_id":"CHEMONTID:0003410","description":"Organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004472","name":"Ketals","chemont_id":"CHEMONTID:0004472","description":"Acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000324","name":"Fatty acid esters","chemont_id":"CHEMONTID:0000324","description":"Carboxylic ester derivatives of a fatty acid."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001114","name":"Beta-keto acids and derivatives","chemont_id":"CHEMONTID:0001114","description":"Organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom."},{"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/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/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/C0002648","name":"Tetrahydrofurans","chemont_id":"CHEMONTID:0002648","description":"Heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003416","name":"Methyl esters","chemont_id":"CHEMONTID:0003416","description":"Organic compounds containing a carboxyl group that is esterified with a methyl group. They have the general structure RC(=O)OR', where R=H or organyl group and R'=methyl group."},{"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/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/C0001167","name":"Dialkyl ethers","chemont_id":"CHEMONTID:0001167","description":"Organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups."},{"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/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":["2-benzopyran (CHEBI:38444)","1-benzopyran (CHEBI:38443)","ketal (CHEBI:59777)","fatty acid ester (CHEBI:35748)","oxo carboxylic acid (CHEBI:25754)","phenols (CHEBI:33853)","dicarboxylic acid (CHEBI:35692)","enone (CHEBI:51689)","enol (CHEBI:33823)","oxolanes (CHEBI:26912)","carboxylic ester (CHEBI:33308)","ketone (CHEBI:17087)","oxacycle (CHEBI:38104)","ether (CHEBI:25698)","carboxylic acid (CHEBI:33575)","carboxylic acid anion (CHEBI:29067)","organic oxide (CHEBI:25701)","organic molecule (CHEBI:72695)","carbonyl compound (CHEBI:36586)","benzenes (CHEBI:22712)","chemical entity (CHEBI:24431)","organic heterocyclic compound (CHEBI:24532)","benzopyran (CHEBI:22727)","oxygen molecular entity (CHEBI:25806)","organic molecular entity (CHEBI:50860)","organooxygen compound (CHEBI:36963)","acetal (CHEBI:59769)","lipid (CHEBI:18059)","benzenoid aromatic compound (CHEBI:33836)","hydroxybenzoic acid (CHEBI:24676)"],"classification_version":"2.1","predicted_lipidmaps_terms":["Fatty esters (FA07)","Dicarboxylic acids (FA0117)","Benzopyranoids (PK1311)","Fatty Acyls (FA)"]},"npclassifier":{"isglycoside":false,"class_results":[],"pathway_results":["Polyketides"],"superclass_results":[]}}