{"id":26353,"npaid":"NPA026353","original_name":"Penazaphilone H","mol_formula":"C23H28ClNO5","mol_weight":"433.9320","exact_mass":"433.1656","inchikey":"ZQLIAKJHIRHCFA-JWNBNHKJSA-N","smiles":"CC[C@H](C)/C=C(C)/C=C/C1=CC2=C(Cl)C(=O)[C@@](C)(OC(C)=O)C(=O)C2=CN1CCO","cluster_id":106,"node_id":101,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C23H28ClNO5/c1-6-14(2)11-15(3)7-8-17-12-18-19(13-25(17)9-10-26)21(28)23(5,30-16(4)27)22(29)20(18)24/h7-8,11-14,26H,6,9-10H2,1-5H3/b8-7+,15-11+/t14-,23-/m0/s1","m_plus_h":"434.1729","m_plus_na":"456.1548","origin_reference":{"doi":"10.1021/acs.jafc.8b05628","pmid":30702881,"authors":"Tang, Jia-Lin; Zhou, Zong-Yuan; Yang, Tao; Yao, Can; Wu, Lin-Wei; Li, Guo-You","title":"Azaphilone Alkaloids with Anti-inflammatory Activity from Fungus Penicillium sclerotiorum cib-411","journal":"Journal of Agricultural and Food Chemistry","year":2019,"volume":"67","issue":"8","pages":"2175-2182"},"origin_organism":{"id":9498,"type":"Fungus","genus":"Penicillium","species":"sclerotiorum cib-411","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":[],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1021/acs.jafc.8b05628","structure_smiles":"CC[C@H](C)/C=C(C)/C=C/C1=CC2=C(Cl)C(=O)[C@@](C)(OC(C)=O)C(=O)C2=CN1CCO","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130943%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula SIRIUS: C17H21N13O7 / BUDDY: C29H29NO6S) with delta m/z 86.0 (putative explanation: Malonylation|Serine analog; atomic difference: 3C,2H,3O|3C,5H,1N,2O) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000846974%NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate%1"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722748%NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate [IIN-based on: CCMSLIB00000846974]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722749%NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate [IIN-based: Match]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722750%NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate [IIN-based on: CCMSLIB00000846974]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722751%NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate [IIN-based on: CCMSLIB00000846974]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00005722752%NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate [IIN-based on: CCMSLIB00000846974]%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000846162%NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate%1"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970736%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula: C21H25O5S) with delta m/z -44.026 (putative explanation: Dealkoxylation, dehydroxyethylation|Thr->Gly substitution; atomic difference: -1C,-2H,-1O|-2C,-4H,-1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970737%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula: C14H25N11O5S) with delta m/z 26.016 (putative explanation: Acetaldehyde +26|Ala->Pro substitution|unspecified; atomic difference: 2C,2H|2C,2H|2C,2H)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970738%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula: C27H25O7) with delta m/z 27.995 (putative explanation: Formylation|Ser->Asp substitution|Thr->Glu substitution; atomic difference: 1C,1O|1C,1O|1C,1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970739%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula: C28H27O7) with delta m/z 42.01 (putative explanation: Acetylation|Ser->Glu substitution|unspecified; atomic difference: 2C,2H,1O|2C,2H,1O|3N)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009970740%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula: C17H21N13O7) with delta m/z 86.0 (putative explanation: Malonylation|Serine analog; atomic difference: 3C,2H,3O|3C,5H,1N,2O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00004685090%isochromophilone VI%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00004685091%isochromophilone VI%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130939%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula SIRIUS: C21H25O5S / BUDDY: C24H23NO2S) with delta m/z -44.026 (putative explanation: Dealkoxylation, dehydroxyethylation|Thr->Gly substitution; atomic difference: -1C,-2H,-1O|-2C,-4H,-1O) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130940%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula SIRIUS: C14H25N11O5S / BUDDY: C26H25N3O5) with delta m/z 26.016 (putative explanation: Acetaldehyde +26|Ala->Pro substitution|unspecified; atomic difference: 2C,2H|2C,2H|2C,2H) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130941%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula SIRIUS: C27H25O7 / BUDDY: C30H23NO4) with delta m/z 27.995 (putative explanation: Formylation|Ser->Asp substitution|Thr->Glu substitution; atomic difference: 1C,1O|1C,1O|1C,1O) [M+H]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012130942%Suspect related to NCGC00347765-02![(7R)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-2-(2-hydroxyethyl)-7-methyl-6,8-dioxoisoquinolin-7-yl] acetate (predicted molecular formula SIRIUS: C28H27O7 / BUDDY: C31H25NO4) with delta m/z 42.01 (putative explanation: Acetylation|Ser->Glu substitution|unspecified; atomic difference: 2C,2H,1O|2C,2H,1O|3N) [M+H]+%4"},{"external_db_name":"npmrd","external_db_code":"NP0019166"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003477","name":"Azaphilones","chemont_id":"CHEMONTID:0003477","description":"A structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center."},"smiles":"CC[C@H](C)\\C=C(/C)\\C=C\\C1=CC2=C(Cl)C(=O)[C@@](C)(OC(C)=O)C(=O)C2=CN1CCO","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=ZQLIAKJHIRHCFA-JWNBNHKJSA-N","subclass":null,"ancestors":["1,2-aminoalcohols","Alcohols and polyols","Alkanolamines","Allylamines","Alpha-acyloxy carbonyl compounds","Alpha-acyloxy ketones","Alpha-chloroketones","Alpha-haloketones","Amines","Amino acids and derivatives","Amino acids, peptides, and analogues","Azacyclic compounds","Azaphilones","Carbonyl compounds","Carboxylic acid derivatives","Carboxylic acid esters","Carboxylic acids and derivatives","Chemical entities","Chloroalkenes","Cyclic ketones","Cyclohexenones","Dihydropyridines","Enamines","Haloalkenes","Hydrocarbon derivatives","Hydropyridines","Isoquinolines and derivatives","Isoquinolones and derivatives","Ketones","Monocarboxylic acids and derivatives","Organic acids and derivatives","Organic compounds","Organic nitrogen compounds","Organic oxides","Organic oxygen compounds","Organochlorides","Organohalogen compounds","Organoheterocyclic compounds","Organonitrogen compounds","Organooxygen compounds","Organopnictogen compounds","Primary alcohols","Pyridines and derivatives","Tertiary amines","Tetrahydroisoquinolines","Trialkylamines","Vinyl chlorides","Vinyl halides","Vinylogous amides"],"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 azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.","substituents":["Azaphilone","Isoquinolone","Tetrahydroisoquinoline","Cyclohexenone","Alpha-acyloxy ketone","Dihydropyridine","Alpha-haloketone","Alpha-chloroketone","Vinylogous amide","Cyclic ketone","Tertiary aliphatic amine","Tertiary amine","Ketone","Carboxylic acid ester","Amino acid or derivatives","1,2-aminoalcohol","Allylamine","Azacycle","Chloroalkene","Haloalkene","Vinyl halide","Vinyl chloride","Monocarboxylic acid or derivatives","Enamine","Carboxylic acid derivative","Alkanolamine","Organic nitrogen compound","Organic oxygen compound","Organopnictogen compound","Organic oxide","Hydrocarbon derivative","Primary alcohol","Organooxygen compound","Organonitrogen compound","Organochloride","Organohalogen compound","Carbonyl group","Amine","Alcohol","Aliphatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003477","name":"Azaphilones","chemont_id":"CHEMONTID:0003477","description":"A structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002054","name":"Isoquinolones and derivatives","chemont_id":"CHEMONTID:0002054","description":"Aromatic polycyclic compounds containing a ketone bearing isoquinoline moiety."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002955","name":"Tetrahydroisoquinolines","chemont_id":"CHEMONTID:0002955","description":"Tetrahydrogenated isoquinoline derivatives."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000367","name":"Dihydropyridines","chemont_id":"CHEMONTID:0000367","description":"Compounds containing a dihydropyridine moiety, which is a semi-saturated pyridine derivative with two double bonds."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004325","name":"Cyclohexenones","chemont_id":"CHEMONTID:0004325","description":"Compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003420","name":"Alpha-acyloxy ketones","chemont_id":"CHEMONTID:0003420","description":"Ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003890","name":"Vinylogous amides","chemont_id":"CHEMONTID:0003890","description":"Organic compounds containing an amine group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004809","name":"Alpha-chloroketones","chemont_id":"CHEMONTID:0004809","description":"Organic compounds contaning a chlorine atom attached to the alpha carbon atom relative to C=O group."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002239","name":"Trialkylamines","chemont_id":"CHEMONTID:0002239","description":"Organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001238","name":"Carboxylic acid esters","chemont_id":"CHEMONTID:0001238","description":"Carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000347","name":"Amino acids and derivatives","chemont_id":"CHEMONTID:0000347","description":"Organic compounds containing an amine group, a carboxylic acid group (or a derivative thereof), and a side-chain that is specific to each amino acid."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001897","name":"1,2-aminoalcohols","chemont_id":"CHEMONTID:0001897","description":"Organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002863","name":"Vinyl chlorides","chemont_id":"CHEMONTID:0002863","description":"Vinyl halides in which a chlorine atom is bonded to an sp2-hybridised carbon atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001137","name":"Monocarboxylic acids and derivatives","chemont_id":"CHEMONTID:0001137","description":"Carboxylic acids containing exactly one carboxyl groups."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000470","name":"Enamines","chemont_id":"CHEMONTID:0000470","description":"Compounds containing the enamine functional group with the general structure R1N(R2)CR=C(R3)R4."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003905","name":"Chloroalkenes","chemont_id":"CHEMONTID:0003905","description":"Compounds derived from an alkene by replacing a hydrogen atom with a chlorine atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004139","name":"Azacyclic compounds","chemont_id":"CHEMONTID:0004139","description":"Organic compounds containing an heterocycle with at least one nitrogen atom and one carbon atom linked to each other."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004218","name":"Allylamines","chemont_id":"CHEMONTID:0004218","description":"Organic compound containing an allyl group and an amine group, with the general structure R2C=C(H)N(R'2), where R-R'=H or organyl."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000286","name":"Primary alcohols","chemont_id":"CHEMONTID:0000286","description":"Compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl)."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0004557","name":"Organopnictogen compounds","chemont_id":"CHEMONTID:0004557","description":"Compounds containing a bond between carbon a pnictogen atom. Pnictogens are p-block element atoms that are in the group 15 of the periodic table."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001516","name":"Organochlorides","chemont_id":"CHEMONTID:0001516","description":"Compounds containing a chemical bond between a carbon atom and a chlorine 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":"Aliphatic heteropolycyclic compounds","external_descriptors":[],"predicted_chebi_terms":["isoquinolines (CHEBI:24922)","dihydropyridine (CHEBI:50075)","cyclohexenones (CHEBI:48953)","ketone (CHEBI:17087)","carboxylic ester (CHEBI:33308)","lignan (CHEBI:25036)","enone (CHEBI:51689)","enamine (CHEBI:47989)","organochlorine compound (CHEBI:36683)","tertiary amino compound (CHEBI:50996)","organonitrogen compound (CHEBI:35352)","organooxygen compound (CHEBI:36963)","amino alcohol (CHEBI:22478)","carbonyl compound (CHEBI:36586)","chloroalkene (CHEBI:36387)","organonitrogen heterocyclic compound (CHEBI:38101)","amine (CHEBI:32952)","primary alcohol (CHEBI:15734)","pnictogen molecular entity (CHEBI:33302)","organic molecular entity (CHEBI:50860)","organic oxide (CHEBI:25701)","organic molecule (CHEBI:72695)","azaphilone (CHEBI:50941)","chemical entity (CHEBI:24431)","organic heterocyclic compound (CHEBI:24532)","pyridines (CHEBI:26421)","oxygen molecular entity (CHEBI:25806)","cyclic ketone (CHEBI:3992)","organohalogen compound (CHEBI:36684)","nitrogen molecular entity (CHEBI:51143)","tertiary amine (CHEBI:32876)","amino acid (CHEBI:33709)","peptide (CHEBI:16670)","polyol (CHEBI:26191)","organic hydroxy compound (CHEBI:33822)","alcohol (CHEBI:30879)"],"classification_version":"2.1","predicted_lipidmaps_terms":[]},"npclassifier":{"isglycoside":false,"class_results":["Azaphilones"],"pathway_results":["Polyketides"],"superclass_results":["Chromanes"]}}