{"id":16889,"npaid":"NPA016889","original_name":"Cylindrol B","mol_formula":"C23H30O4","mol_weight":"370.4890","exact_mass":"370.2144","inchikey":"AQCKKGIVKOHRLM-HBFAXEOFSA-N","smiles":"C[C@@H]1CCC(=O)[C@@H]([C@@]1(C)/C=C/C(=C/CC2=C(C=C(C(=C2O)C=O)C)O)/C)C","cluster_id":1134,"node_id":969,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C23H30O4/c1-14(10-11-23(5)16(3)7-9-20(25)17(23)4)6-8-18-21(26)12-15(2)19(13-24)22(18)27/h6,10-13,16-17,26-27H,7-9H2,1-5H3/b11-10+,14-6+/t16-,17+,23+/m1/s1","m_plus_h":"371.2217","m_plus_na":"393.2036","origin_reference":{"doi":"10.1021/jo961074p","pmid":11667727,"authors":"Singh, Sheo B.; Ball, Richard G.; Bills, Gerald F.; Cascales, Carmen; Gibbs, Jackson B.; Goetz, Michael A.; Hoogsteen, Karst; Jenkins, Rosalind G.; Liesch, Jerrold M.; Lingham, Russell B.; Silverman, Keith C.; Zink, Deborah L.","title":"Chemistry and biology of cylindrols: Novel inhibitors of Ras farnesyl-protein transferase from Cylindrocarpon lucidum","journal":"Journal of Organic Chemistry","year":1996,"volume":"61","issue":"22","pages":"7727-7737"},"origin_organism":{"id":1279,"type":"Fungus","genus":"Cylindrocarpon","species":"lucidum","taxon":{"id":925,"name":"Cylindrocarpon","rank":"genus","taxon_db":"mycobank","external_id":"7866","ncbi_id":13474,"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":879,"name":"Sordariomycetes","rank":"class","taxon_db":"mycobank","external_id":"90350","ncbi_id":147550},{"id":899,"name":"Hypocreales","rank":"order","taxon_db":"mycobank","external_id":"90477","ncbi_id":5125},{"id":921,"name":"Nectriaceae","rank":"family","taxon_db":"mycobank","external_id":"81059","ncbi_id":110618}]}},"syntheses":[],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1021/jo961074p","structure_smiles":"C[C@@H]1CCC(=O)[C@@H]([C@@]1(C)/C=C/C(=C/CC2=C(C=C(C(=C2O)C=O)C)O)/C)C","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"gnps","external_db_code":"CCMSLIB00004685109%3%2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00004685110%3%2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00004685111%3%2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00004685112%3%2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000846934%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocycloh%1!CCMSLIB00000846936%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocycloh%1!CCMSLIB00000846939%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocycloh%1!CCMSLIB00000845519%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocycloh%1"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130776%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based: Match] (predicted molecular formula SIRIUS: C23H32O3 / BUDDY: C23H32O3) with delta m/z -13.981 (putative explanation: Asp->Thr substitution; atomic difference: 2H,-1O) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130777%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based: Match] (predicted molecular formula SIRIUS: C23H32O4 / BUDDY: C23H32O4) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722577%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722578%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722579%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based: Match]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722580%NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970570%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934] (predicted molecular formula: C23H32O4) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970571%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934] (predicted molecular formula: C22H30O5) with delta m/z 3.995 (putative explanation: Pro->Thr substitution|tryptophan oxidation to kynurenin|Oxidative cleavage; atomic difference: -1C,1O|-1C,1O|1O,-1C)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970572%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934] (predicted molecular formula: C23H32O5) with delta m/z 18.01 (putative explanation: Proline oxidation to 5-hydroxy-2-aminovaleric acid|water; atomic difference: 2H,1O|2H,1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970573%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based: Match] (predicted molecular formula: C23H32O3) with delta m/z -13.981 (putative explanation: Asp->Thr substitution; atomic difference: 2H,-1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970574%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based: Match] (predicted molecular formula: C23H32O4) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130773%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934] (predicted molecular formula SIRIUS: C23H32O4 / BUDDY: C20H36O4S) with delta m/z 2.016 (putative explanation: Pro->Val substitution|reduction; atomic difference: 2H|2H) [M-H2O+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130774%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934] (predicted molecular formula SIRIUS: C22H30O5 / BUDDY: C22H30O5) with delta m/z 3.995 (putative explanation: Pro->Thr substitution|tryptophan oxidation to kynurenin|Oxidative cleavage; atomic difference: -1C,1O|-1C,1O|1O,-1C) [M-H2O+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130775%Suspect related to NCGC00347666-02!2,4-dihydroxy-6-methyl-3-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]benzaldehyde [IIN-based on: CCMSLIB00000846934] (predicted molecular formula SIRIUS: C23H32O5 / BUDDY: C23H32O5) with delta m/z 18.01 (putative explanation: Proline oxidation to 5-hydroxy-2-aminovaleric acid|water; atomic difference: 2H,1O|2H,1O) [M-H2O+H]+%4"},{"external_db_name":"npmrd","external_db_code":"NP0003899"},{"external_db_name":"cmmc","external_db_code":"https://cmmc-kb.gnps2.org/structurepage/?inchikey=AQCKKGIVKOHRLM-HBFAXEOFSA-N"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000323","name":"Organooxygen compounds","chemont_id":"CHEMONTID:0000323","description":"Organic compounds containing a bond between a carbon atom and an oxygen atom."},"smiles":"C[C@@H]1CCC(=O)[C@H](C)[C@@]1(C)\\C=C\\C(\\C)=C\\CC1=C(O)C=C(C)C(C=O)=C1O","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=AQCKKGIVKOHRLM-HBFAXEOFSA-N","subclass":{"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."},"ancestors":["1-hydroxy-2-unsubstituted benzenoids","1-hydroxy-4-unsubstituted benzenoids","Aldehydes","Aryl-aldehydes","Benzaldehydes","Benzene and substituted derivatives","Benzenediols","Benzenoids","Benzoyl derivatives","Carbonyl compounds","Chemical entities","Cresols","Cyclic ketones","Hydrocarbon derivatives","Hydroxybenzaldehydes","Ketones","Meta cresols","Organic acids and derivatives","Organic compounds","Organic oxides","Organic oxygen compounds","Organooxygen compounds","Phenols","Resorcinols","Toluenes","Vinylogous acids"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004603","name":"Organic oxygen compounds","chemont_id":"CHEMONTID:0004603","description":"Organic compounds that contain one or more oxygen atoms."},"description":"This compound belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.","substituents":["Hydroxybenzaldehyde","Benzoyl","M-cresol","Resorcinol","1-hydroxy-4-unsubstituted benzenoid","1-hydroxy-2-unsubstituted benzenoid","Toluene","Phenol","Monocyclic benzene moiety","Benzenoid","Vinylogous acid","Ketone","Cyclic ketone","Hydrocarbon derivative","Organic oxide","Aromatic homomonocyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003978","name":"Hydroxybenzaldehydes","chemont_id":"CHEMONTID:0003978","description":"Organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group."},"intermediate_nodes":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000124","name":"Aldehydes","chemont_id":"CHEMONTID:0000124","description":"Organic compounds containing the aldehyde functional group."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003213","name":"Aryl-aldehydes","chemont_id":"CHEMONTID:0003213","description":"Compounds containing an aldehyde group directly attached to an aromatic ring."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001345","name":"Benzaldehydes","chemont_id":"CHEMONTID:0001345","description":"Organic compounds containing a benzene ring with a formyl substituent."}],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000137","name":"Resorcinols","chemont_id":"CHEMONTID:0000137","description":"Compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001273","name":"Meta cresols","chemont_id":"CHEMONTID:0001273","description":"Aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000321","name":"Benzoyl derivatives","chemont_id":"CHEMONTID:0000321","description":"Organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001091","name":"Toluenes","chemont_id":"CHEMONTID:0001091","description":"Compounds containing a benzene ring which bears a methane group."},{"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/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/C0003487","name":"Cyclic ketones","chemont_id":"CHEMONTID:0003487","description":"Organic compounds containing a ketone that is conjugated to a cyclic moiety."},{"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 homomonocyclic compounds","external_descriptors":[],"predicted_chebi_terms":["resorcinols (CHEBI:33572)","hydroxytoluene (CHEBI:24751)","carbonyl compound (CHEBI:36586)","toluenes (CHEBI:27024)","phenols (CHEBI:33853)","enone (CHEBI:51689)","enol (CHEBI:33823)","cyclic ketone (CHEBI:3992)","organic oxide (CHEBI:25701)","organic molecule (CHEBI:72695)","hydroxybenzaldehyde (CHEBI:24673)","chemical entity (CHEBI:24431)","benzenoid aromatic compound (CHEBI:33836)","benzenediols (CHEBI:33570)","methoxybenzene (CHEBI:51683)","benzenes (CHEBI:22712)","organic acid (CHEBI:64709)","oxygen molecular entity (CHEBI:25806)","organic molecular entity (CHEBI:50860)","organooxygen compound (CHEBI:36963)","ketone (CHEBI:17087)","aldehyde (CHEBI:17478)","arenecarbaldehyde (CHEBI:33855)","benzaldehydes (CHEBI:22698)"],"classification_version":"2.1","predicted_lipidmaps_terms":[]},"npclassifier":{"isglycoside":false,"class_results":["Tetraketide meroterpenoids"],"pathway_results":["Polyketides","Terpenoids"],"superclass_results":["Meroterpenoids"]}}