{"id":5369,"npaid":"NPA005369","original_name":"Loline","mol_formula":"C8H14N2O","mol_weight":"154.2130","exact_mass":"154.1106","inchikey":"OPMNROCQHKJDAQ-JAFIHTMFSA-N","smiles":"CNC1[C@H]2CN3C1[C@@H](O2)CC3","cluster_id":2648,"node_id":1534,"has_exclusions":false,"synonyms":[],"inchi":"InChI=1S/C8H14N2O/c1-9-7-6-4-10-3-2-5(11-6)8(7)10/h5-9H,2-4H2,1H3/t5-,6+,7?,8?/m0/s1","m_plus_h":"155.1179","m_plus_na":"177.0998","origin_reference":{"doi":"10.1016/S0031-9422(01)00272-2","pmid":null,"authors":"Jimmy D. Blankenship, Martin J. Spiering, Heather H. Wilkinson, Franklin F. Fannin, Lowell P. Bush, Christopher L. Schardl","title":"Production of loline alkaloids by the grass endophyte, Neotyphodium uncinatum, in defined media","journal":"Phytochemistry","year":2001,"volume":"58","issue":"3","pages":"395-401"},"origin_organism":{"id":2097,"type":"Fungus","genus":"Neotyphodium","species":"uncinatum","taxon":{"id":948,"name":"Neotyphodium","rank":"genus","taxon_db":"mycobank","external_id":"27615","ncbi_id":45284,"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":938,"name":"Clavicipitaceae","rank":"family","taxon_db":"mycobank","external_id":"82061","ncbi_id":34397}]}},"syntheses":["10.1038/nchem.1072","10.1021/jo502493e"],"reassignments":[],"mol_structures":[{"current_structure":true,"reference_doi":"10.1016/S0031-9422(01)00272-2","structure_smiles":"CNC1[C@H]2CN3C1[C@@H](O2)CC3","is_reassignment":false,"version":1}],"exclusions":[],"external_ids":[{"external_db_name":"mibig","external_db_code":"BGC0000815"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000204783%3%Massbank:BML00097&Loline"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000204793%3%Massbank:BML00109&Loline"},{"external_db_name":"gnps","external_db_code":"CCMSLIB00000204803%3%Massbank:BML00121&Loline"},{"external_db_name":"cmmc","external_db_code":"https://cmmc-kb.gnps2.org/structurepage/?inchikey=OPMNROCQHKJDAQ-JAFIHTMFSA-N"}],"classyfire":{"class":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002656","name":"Loline alkaloids and derivatives","chemont_id":"CHEMONTID:0002656","description":"Alkaloids with a structure characterized by  a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species."},"smiles":"[H][C@@]12CCN3C[C@@]([H])(O1)C([H])(NC)C23[H]","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=OPMNROCQHKJDAQ-JAFIHTMFSA-N","subclass":null,"ancestors":["1,4-oxazepines","Alkaloids and derivatives","Amines","Azacyclic compounds","Chemical entities","Dialkyl ethers","Dialkylamines","Ethers","Hydrocarbon derivatives","Loline alkaloids and derivatives","Morpholines","N-alkylpyrrolidines","Organic compounds","Organic nitrogen compounds","Organic oxygen compounds","Organoheterocyclic compounds","Organonitrogen compounds","Organooxygen compounds","Organopnictogen compounds","Oxacyclic compounds","Oxazepines","Oxazinanes","Pyrrolidines","Pyrrolizidines","Secondary amines","Tertiary amines","Tetrahydrofurans","Trialkylamines"],"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 loline alkaloids and derivatives. These are alkaloids with a structure characterized by  a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species.","substituents":["Loline","Pyrrolizidine","Para-oxazepine","N-alkylpyrrolidine","Oxazinane","Morpholine","Tetrahydrofuran","Pyrrolidine","Tertiary aliphatic amine","Tertiary amine","Oxacycle","Azacycle","Organoheterocyclic compound","Secondary amine","Ether","Secondary aliphatic amine","Dialkyl ether","Organic nitrogen compound","Organic oxygen compound","Organopnictogen compound","Hydrocarbon derivative","Organooxygen compound","Organonitrogen compound","Amine","Aliphatic heteropolycyclic compound"],"direct_parent":{"url":"http://classyfire.wishartlab.com/tax_nodes/C0002656","name":"Loline alkaloids and derivatives","chemont_id":"CHEMONTID:0002656","description":"Alkaloids with a structure characterized by  a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species."},"intermediate_nodes":[],"alternative_parents":[{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000220","name":"Pyrrolizidines","chemont_id":"CHEMONTID:0000220","description":"Compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0001339","name":"1,4-oxazepines","chemont_id":"CHEMONTID:0001339","description":"Organic compounds containing an aromatic seven-membered wring containing a nitrogen and an oxygen atom, a positions 1 and 4, respectively."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0003449","name":"N-alkylpyrrolidines","chemont_id":"CHEMONTID:0003449","description":"Compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms."},{"url":"http://classyfire.wishartlab.com/tax_nodes/C0000392","name":"Morpholines","chemont_id":"CHEMONTID:0000392","description":"Organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively."},{"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/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/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/C0002228","name":"Dialkylamines","chemont_id":"CHEMONTID:0002228","description":"Organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen."},{"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/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/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."}],"molecular_framework":"Aliphatic heteropolycyclic compounds","external_descriptors":[],"predicted_chebi_terms":["pyrrolizines (CHEBI:38522)","oxacycle (CHEBI:38104)","organonitrogen heterocyclic compound (CHEBI:38101)","N-alkylpyrrolidine (CHEBI:46775)","morpholines (CHEBI:38785)","oxolanes (CHEBI:26912)","tertiary amino compound (CHEBI:50996)","secondary amino compound (CHEBI:50995)","ether (CHEBI:25698)","pnictogen molecular entity (CHEBI:33302)","organic molecular entity (CHEBI:50860)","organic molecule (CHEBI:72695)","alkaloid (CHEBI:22315)","chemical entity (CHEBI:24431)","organic heterocyclic compound (CHEBI:24532)","pyrrolidines (CHEBI:38260)","oxazinane (CHEBI:46952)","nitrogen molecular entity (CHEBI:51143)","organonitrogen compound (CHEBI:35352)","amine (CHEBI:32952)","tertiary amine (CHEBI:32876)","secondary amine (CHEBI:32863)","oxygen molecular entity (CHEBI:25806)","organooxygen compound (CHEBI:36963)"],"classification_version":"2.1","predicted_lipidmaps_terms":[]},"npclassifier":{"isglycoside":false,"class_results":["Pyrrolizidine alkaloids"],"pathway_results":["Alkaloids"],"superclass_results":["Ornithine alkaloids"]}}