{"id":3152,"npaid":"NPA003152","original_name":"Frenolicin C","mol_formula":"C23H27NO10S","mol_weight":"509.5330","exact_mass":"509.1356","inchikey":"LBTDZXFVMNOCLO-BLKQOEIDSA-N","smiles":"CCC[C@@H]1[C@@]2(C(=O)C3=C(C=CC=C3O)C(=O)[C@]2(C[C@H](O1)CC(=O)O)SC[C@@H](C(=O)O)NC(=O)C)O","cluster_id":814,"node_id":707,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C23H27NO10S/c1-3-5-16-23(33)20(30)18-13(6-4-7-15(18)26)19(29)22(23,9-12(34-16)8-17(27)28)35-10-14(21(31)32)24-11(2)25/h4,6-7,12,14,16,26,33H,3,5,8-10H2,1-2H3,(H,24,25)(H,27,28)(H,31,32)/t12-,14+,16-,22+,23+/m1/s1","m_plus_h":"510.1429","m_plus_na":"532.1248","origin_reference":{"doi":"10.1021/np400231r","pmid":23944931,"authors":"Wang, Xiachang; Shaaban, Khaled A.; Elshahawi, Sherif I.; Ponomareva, Larissa V.; Sunkara, Manjula; Zhang, Yinan; Copley, Gregory C.; Hower, James C.; Morris, Andrew J.; Kharel, Madan K.; Thorson, Jon S.","title":"Frenolicins C-G, Pyranonaphthoquinones from streptomyces sp. RM-4-15","journal":"Journal of Natural Products","year":2013,"volume":"76","issue":"8","pages":"1441-1447"},"origin_organism":{"id":609,"type":"Bacterium","genus":"Streptomyces","species":"sp. RM-4-15","taxon":{"id":283,"name":"Streptomyces","rank":"genus","taxon_db":"lpsn","external_id":"517119","ncbi_id":1883,"ancestors":[{"id":1,"name":"Bacteria","rank":"domain","taxon_db":"lpsn","external_id":"0","ncbi_id":2},{"id":203,"name":"Actinobacteria","rank":"phylum","taxon_db":"lpsn","external_id":"0","ncbi_id":201174},{"id":204,"name":"Actinobacteria","rank":"class","taxon_db":"lpsn","external_id":"0","ncbi_id":null},{"id":275,"name":"Streptomycetales","rank":"order","taxon_db":"lpsn","external_id":"0","ncbi_id":85011},{"id":276,"name":"Streptomycetaceae","rank":"family","taxon_db":"lpsn","external_id":"0","ncbi_id":2062}]}},"syntheses":[],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1021/np400231r","structure_smiles":"CCC[C@@H]1[C@@]2(C(=O)C3=C(C=CC=C3O)C(=O)[C@]2(C[C@H](O1)CC(=O)O)SC[C@@H](C(=O)O)NC(=O)C)O","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"npmrd","external_db_code":"NP0012008"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001640","name":"Naphthopyrans","chemont_id":"CHEMONTID:0001640","description":"Compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon  made up of two fused benzene rings."},"smiles":"CCC[C@H]1O[C@H](CC(O)=O)C[C@]2(SC[C@H](NC(C)=O)C(O)=O)C(=O)C3=C(C(O)=CC=C3)C(=O)[C@@]12O","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=LBTDZXFVMNOCLO-BLKQOEIDSA-N","subclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001641","name":"Naphthopyranones","chemont_id":"CHEMONTID:0001641","description":"Compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system."},"ancestors":["1-hydroxy-2-unsubstituted benzenoids","1-hydroxy-4-unsubstituted benzenoids","Acetamides","Alcohols and polyols","Alpha amino acids and derivatives","Amino acids and derivatives","Amino acids, peptides, and analogues","Aryl alkyl ketones","Aryl ketones","Benzenoids","C-glycosyl compounds","Carbohydrates and carbohydrate conjugates","Carbonyl compounds","Carboxylic acid amides","Carboxylic acid derivatives","Carboxylic acids","Carboxylic acids and derivatives","Chemical entities","Cyclic ketones","Cysteine and derivatives","Dialkyl ethers","Dialkylthioethers","Dicarboxylic acids and derivatives","Ethers","Glycosyl compounds","Hydrocarbon derivatives","Ketones","N-acyl-L-alpha-amino acids","N-acyl-alpha amino acids","N-acyl-alpha amino acids and derivatives","Naphthalenes","Naphthopyranone glycosides","Naphthopyranones","Naphthopyrans","Naphthoquinones","Organic acids and derivatives","Organic compounds","Organic nitrogen compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organonitrogen compounds","Organooxygen compounds","Organopnictogen compounds","Organosulfur compounds","Oxacyclic compounds","Oxanes","Phenols","Pyranones and derivatives","Pyrans","Quinones","Secondary carboxylic acid amides","Sulfenyl compounds","Tertiary alcohols","Tetralins","Thioethers","Vinylogous acids"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000002","name":"Organoheterocyclic compounds","chemont_id":"CHEMONTID:0000002","description":"Compounds containing a ring with least one carbon atom and one non-carbon atom."},"description":"This compound belongs to the class of organic compounds known as naphthopyranone glycosides. These are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety.","substituents":["Naphthopyranone glycoside","N-acyl-alpha-amino acid","N-acyl-alpha amino acid or derivatives","N-acyl-l-alpha-amino acid","Cysteine or derivatives","Naphthoquinone","C-glycosyl compound","Glycosyl compound","Alpha-amino acid or derivatives","Naphthalene","Tetralin","Quinone","Aryl alkyl ketone","Aryl ketone","1-hydroxy-4-unsubstituted benzenoid","1-hydroxy-2-unsubstituted benzenoid","Phenol","Pyranone","Pyran","Benzenoid","Oxane","Dicarboxylic acid or derivatives","Tertiary alcohol","Vinylogous acid","Acetamide","Secondary carboxylic acid amide","Carboxamide group","Ketone","Sulfenyl compound","Thioether","Dialkylthioether","Carboxylic acid derivative","Carboxylic acid","Dialkyl ether","Ether","Oxacycle","Organosulfur compound","Alcohol","Organic nitrogen compound","Organooxygen compound","Organic oxygen compound","Organic oxide","Hydrocarbon derivative","Carbonyl group","Organonitrogen compound","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001646","name":"Naphthopyranone glycosides","chemont_id":"CHEMONTID:0001646","description":"Compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004148","name":"N-acyl-L-alpha-amino acids","chemont_id":"CHEMONTID:0004148","description":"N-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004313","name":"Cysteine and derivatives","chemont_id":"CHEMONTID:0004313","description":"Compounds containing cysteine or a derivative thereof resulting from reaction of cysteine 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/C0000153","name":"Naphthoquinones","chemont_id":"CHEMONTID:0000153","description":"Compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002204","name":"C-glycosyl compounds","chemont_id":"CHEMONTID:0002204","description":"Glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000048","name":"Tetralins","chemont_id":"CHEMONTID:0000048","description":"Polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002495","name":"Quinones","chemont_id":"CHEMONTID:0002495","description":"Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included)."},{"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/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/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/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/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/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/C0001670","name":"Tertiary alcohols","chemont_id":"CHEMONTID:0001670","description":"Compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H )."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003922","name":"Acetamides","chemont_id":"CHEMONTID:0003922","description":"Organic compounds with the general formula RNHC(=O)CH3, where R= organyl group."},{"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/C0001663","name":"Secondary carboxylic acid amides","chemont_id":"CHEMONTID:0001663","description":"Compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003260","name":"Sulfenyl compounds","chemont_id":"CHEMONTID:0003260","description":"Organosulfur compounds a sulfenyl group with the general formula RS (R = organyl)."},{"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/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/C0003862","name":"Dialkylthioethers","chemont_id":"CHEMONTID:0003862","description":"Organosulfur compounds containing a thioether group that is substituted by two alkyl groups."},{"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":[],"predicted_chebi_terms":["N-acyl-L-alpha-amino acid (CHEBI:48927)","cysteine derivative (CHEBI:23509)","naphthoquinone (CHEBI:25481)","C-glycosyl compound (CHEBI:20857)","tetralins (CHEBI:36786)","quinone (CHEBI:36141)","aromatic ketone (CHEBI:76224)","pyranone (CHEBI:37963)","phenols (CHEBI:33853)","oxanes (CHEBI:46942)","dicarboxylic acid (CHEBI:35692)","tertiary alcohol (CHEBI:26878)","acetamides (CHEBI:22160)","enone (CHEBI:51689)","enol (CHEBI:33823)","carboxamide (CHEBI:37622)","organosulfur compound (CHEBI:33261)","oxacycle (CHEBI:38104)","carboxylic acid (CHEBI:33575)","ether (CHEBI:25698)","aliphatic sulfide (CHEBI:22327)","organonitrogen compound (CHEBI:35352)","organic oxide (CHEBI:25701)","organic molecule (CHEBI:72695)","glycoside (CHEBI:24400)","benzochromenone (CHEBI:64986)","chemical entity (CHEBI:24431)","organic acid (CHEBI:64709)","carbonyl compound (CHEBI:36586)","organooxygen compound (CHEBI:36963)","N-acyl-amino acid (CHEBI:51569)","benzenoid aromatic compound (CHEBI:33836)","naphthalenes (CHEBI:25477)","oxygen molecular entity (CHEBI:25806)","organic molecular entity (CHEBI:50860)","carbohydrates and carbohydrate derivatives (CHEBI:78616)","ketone (CHEBI:17087)","cyclic ketone (CHEBI:3992)","organic heterocyclic compound (CHEBI:24532)","pyrans (CHEBI:26407)","polyol (CHEBI:26191)","organic hydroxy compound (CHEBI:33822)","alcohol (CHEBI:30879)","amide (CHEBI:32988)","organic sulfide (CHEBI:16385)","nitrogen molecular entity (CHEBI:51143)","organic heterotricyclic compound (CHEBI:26979)","carboxylic acid anion (CHEBI:29067)","amino acid (CHEBI:33709)","peptide (CHEBI:16670)"],"classification_version":"2.1","predicted_lipidmaps_terms":["Naphthalenes and naphthoquinones (PK1302)","Dicarboxylic acids (FA0117)"]},"npclassifier":{"isglycoside":false,"class_results":["Naphthoquinones"],"pathway_results":["Polyketides"],"superclass_results":["Naphthalenes"]}}