{"id":17108,"npaid":"NPA017108","original_name":"Cytochalasin E","mol_formula":"C28H33NO7","mol_weight":"495.5720","exact_mass":"495.2257","inchikey":"LAJXCUNOQSHRJO-ZYGJITOWSA-N","smiles":"C[C@H]1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4[C@]2(C(=O)N[C@H]4CC5=CC=CC=C5)OC(=O)O/C=C/[C@@](C1=O)(C)O)C)C","cluster_id":57,"node_id":53,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+/t16-,17-,19-,20-,21-,23-,26+,27+,28+/m0/s1","m_plus_h":"496.2330","m_plus_na":"518.2149","origin_reference":{"doi":"10.7164/antibiotics.55.585","pmid":12195965,"authors":"Takamatsu, Satoshi; Zhang, Qinglin; Schrader, Kevin K.; ElSohly, Hala N.; Walker, Larry A.","title":"Characterization of Mycotypha metabolites found to be inhibitors of cell adhesion molecules","journal":"Journal of Antibiotics","year":2002,"volume":"55","issue":"6","pages":"585-592"},"origin_organism":{"id":1828,"type":"Fungus","genus":"Mycotypha","species":"sp. UMF-006","taxon":{"id":614,"name":"Mycotypha","rank":"genus","taxon_db":"mycobank","external_id":"20355","ncbi_id":64629,"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":601,"name":"Mucoromycota","rank":"phylum","taxon_db":"mycobank","external_id":"90756","ncbi_id":1913637},{"id":602,"name":"Mucoromycetes","rank":"class","taxon_db":"mycobank","external_id":"90755","ncbi_id":2212703},{"id":603,"name":"Mucorales","rank":"order","taxon_db":"mycobank","external_id":"90437","ncbi_id":4827},{"id":613,"name":"Mycotyphaceae","rank":"family","taxon_db":"mycobank","external_id":"81045","ncbi_id":70408}]}},"syntheses":[],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.7164/antibiotics.55.585","structure_smiles":"C[C@H]1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4[C@]2(C(=O)N[C@H]4CC5=CC=CC=C5)OC(=O)O/C=C/[C@@](C1=O)(C)O)C)C","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"mibig","external_db_code":"BGC0000983"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00012105443%Suspect related to Cytochalasin E (predicted molecular formula SIRIUS: C25H35O11 / BUDDY: C28H33NO8) with delta m/z 15.995 (putative explanation: Ala->Ser substitution|Oxidation or Hydroxylation|Phe->Tyr substitution; atomic difference: 1O|1O|1O) [M+Na]+%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00009945240%Suspect related to Cytochalasin E (predicted molecular formula: C25H35O11) with delta m/z 15.995 (putative explanation: Ala->Ser substitution|Oxidation or Hydroxylation|Phe->Tyr substitution; atomic difference: 1O|1O|1O)%4"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000855305%NCGC00380287-01_C28H33NO7_(1E,4S,6R,7E,11aS,14S,14aS,15S,15aR,16aS,16bS)-14-Benzyl-6-hydroxy-4,6,15,%1!CCMSLIB00000855307%NCGC00380287-01_C28H33NO7_(1E,4S,6R,7E,11aS,14S,14aS,15S,15aR,16aS,16bS)-14-Benzyl-6-hydroxy-4,6,15,%1!CCMSLIB00000855309%NCGC00380287-01_C28H33NO7_(1E,4S,6R,7E,11aS,14S,14aS,15S,15aR,16aS,16bS)-14-Benzyl-6-hydroxy-4,6,15,%1!CCMSLIB00000850187%NCGC00380287-01_C28H33NO7_(1E,4S,6R,7E,11aS,14S,14aS,15S,15aR,16aS,16bS)-14-Benzyl-6-hydroxy-4,6,15,%1!CCMSLIB00000850190%NCGC00380287-01_C28H33NO7_(1E,4S,6R,7E,11aS,14S,14aS,15S,15aR,16aS,16bS)-14-Benzyl-6-hydroxy-4,6,15,%1"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010112051%CCG-208187 CollisionEnergy:102040%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010112052%CCG-208187 CollisionEnergy:102040%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010112053%CCG-208187 CollisionEnergy:102040%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010112054%CCG-208187 CollisionEnergy:102040%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010123385%CCG-208187 CollisionEnergy:205060%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010123386%CCG-208187 CollisionEnergy:205060%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010123387%CCG-208187 CollisionEnergy:205060%3"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00010123388%CCG-208187 CollisionEnergy:205060%3"},{"external_db_name":"npmrd","external_db_code":"NP0004301"},{"external_db_name":"npmrd","external_db_code":"NP0288551"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001821","name":"Cytochalasans","chemont_id":"CHEMONTID:0001821","description":"Fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D,  H, and K."},"smiles":"C[C@H]1[C@H]2[C@H](CC3=CC=CC=C3)NC(=O)[C@]22OC(=O)O\\C=C\\[C@@](C)(O)C(=O)[C@@H](C)C\\C=C\\[C@H]2[C@@H]2O[C@]12C","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=LAJXCUNOQSHRJO-ZYGJITOWSA-N","subclass":null,"ancestors":["Acyloins","Alcohols and polyols","Alkaloids and derivatives","Azacyclic compounds","Benzene and substituted derivatives","Benzenoids","Carbonic acid diesters","Carbonyl compounds","Carboxylic acid amides","Carboxylic acid derivatives","Carboxylic acid esters","Carboxylic acids and derivatives","Chemical entities","Cyclic ketones","Cytochalasans","Dialkyl ethers","Enol esters","Epoxides","Ethers","Hydrocarbon derivatives","Isoindoles and derivatives","Isoindolines","Isoindolones","Ketones","Lactams","Macrolactams","Organic acids and derivatives","Organic carbonic acids and derivatives","Organic compounds","Organic nitrogen compounds","Organic oxides","Organic oxygen compounds","Organoheterocyclic compounds","Organonitrogen compounds","Organooxygen compounds","Organopnictogen compounds","Oxacyclic compounds","Oxepanes","Phenylpropanoids and polyketides","Pyrrolidine-2-ones","Pyrrolidines","Pyrrolidones","Secondary carboxylic acid amides","Tertiary alcohols"],"superclass":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000279","name":"Alkaloids and derivatives","chemont_id":"CHEMONTID:0000279","description":"Naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus."},"description":"This compound belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D,  H, and K.","substituents":["Cytoglobosin skeleton","Cytochalasan","Macrolactam","Isoindolone","Isoindoline","Isoindole or derivatives","Oxepane","Monocyclic benzene moiety","Carbonic acid diester","Benzenoid","Acyloin","2-pyrrolidone","Pyrrolidone","Enol ester","Tertiary alcohol","Pyrrolidine","Carboxamide group","Cyclic ketone","Ketone","Lactam","Secondary carboxylic acid amide","Carbonic acid derivative","Carboxylic acid derivative","Organoheterocyclic compound","Azacycle","Ether","Oxirane","Oxacycle","Dialkyl ether","Organooxygen compound","Organic oxygen compound","Organic nitrogen compound","Alcohol","Organopnictogen compound","Organic oxide","Hydrocarbon derivative","Carbonyl group","Organonitrogen compound","Aromatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001821","name":"Cytochalasans","chemont_id":"CHEMONTID:0001821","description":"Fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D,  H, and K."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000064","name":"Macrolactams","chemont_id":"CHEMONTID:0000064","description":"Cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.  They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001820","name":"Isoindolones","chemont_id":"CHEMONTID:0001820","description":"Aromatic polycyclic compounds that an isoindole bearing a ketone."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001729","name":"Oxepanes","chemont_id":"CHEMONTID:0001729","description":"Compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003031","name":"Pyrrolidine-2-ones","chemont_id":"CHEMONTID:0003031","description":"Pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002088","name":"Acyloins","chemont_id":"CHEMONTID:0002088","description":"Organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups."},{"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."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001611","name":"Carbonic acid diesters","chemont_id":"CHEMONTID:0001611","description":"Compounds comprising the carbonic acid diester functional group."},{"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/C0002354","name":"Enol esters","chemont_id":"CHEMONTID:0002354","description":"Ester derivatives of enols. They have the general formula RC=COC(=O)R' where R, R' = H or organyl group."},{"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/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/C0000160","name":"Lactams","chemont_id":"CHEMONTID:0000160","description":"Compounds containing a lactam ring, which is a cyclic amide of amino carboxylic acids, having a 1-azacycloalkan-2-one structure (or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring)."},{"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/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/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/C0000159","name":"Epoxides","chemont_id":"CHEMONTID:0000159","description":"Compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms)."},{"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/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/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/C0000278","name":"Organonitrogen compounds","chemont_id":"CHEMONTID:0000278","description":"Organic compounds containing a nitrogen atom."}],"molecular_framework":"Aromatic heteropolycyclic compounds","external_descriptors":[{"source":"CHEBI","source_id":"CHEBI:68201","annotations":["cytochalasan alkaloid"]}],"predicted_chebi_terms":["azamacrocycle (CHEBI:52898)","isoindoles (CHEBI:24897)","oxacycle (CHEBI:38104)","pyrrolidin-2-ones (CHEBI:74223)","ketone (CHEBI:17087)","organic hydroxy compound (CHEBI:33822)","benzenes (CHEBI:22712)","carbonate ester (CHEBI:46722)","tertiary alcohol (CHEBI:26878)","ester (CHEBI:35701)","carboxamide (CHEBI:37622)","cyclic ketone (CHEBI:3992)","lactam (CHEBI:24995)","organonitrogen heterocyclic compound (CHEBI:38101)","ether (CHEBI:25698)","epoxide (CHEBI:32955)","organic oxide (CHEBI:25701)","pnictogen molecular entity (CHEBI:33302)","organic molecular entity (CHEBI:50860)","organic molecule (CHEBI:72695)","organonitrogen compound (CHEBI:35352)","cytochalasan alkaloid (CHEBI:75946)","chemical entity (CHEBI:24431)","organooxygen compound (CHEBI:36963)","organic heterocyclic compound (CHEBI:24532)","pyrrolidines (CHEBI:38260)","pyrrolidinone (CHEBI:38275)","oxygen molecular entity (CHEBI:25806)","carbonyl compound (CHEBI:36586)","benzenoid aromatic compound (CHEBI:33836)","polyol (CHEBI:26191)","alcohol (CHEBI:30879)","carboxylic ester (CHEBI:33308)","amide (CHEBI:32988)","nitrogen molecular entity (CHEBI:51143)","alkaloid (CHEBI:22315)"],"classification_version":"2.1","predicted_lipidmaps_terms":["Cytochalasins (PK11)"]},"npclassifier":{"isglycoside":false,"class_results":["Cytochalasan alkaloids"],"pathway_results":["Alkaloids"],"superclass_results":["Pseudoalkaloids (transamidation)"]}}