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CHEBI:65610 - chaetominine

ChEBI IDCHEBI:65610
ChEBI Namechaetominine
Stars
DefinitionAn organic heterotetracyclic compound that consists of 4,5,5a,9c-tetrahydro-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione substituted by a hydroxy group at position 5, a methyl group at position 2 and a 4-oxoquinazolin-3(4H)-yl group at position 4 (the 2S,4R,5aS,9cS stereoisomer). It is a cytotoxic alkaloid isolated from the endophytic fungus Chaetomium.
Last Modified4 September 2012
DownloadsMolfile
FormulaC22H18N4O4
Net Charge0
Average Mass402.410
Monoisotopic Mass402.13281
SMILES[H][C@@]12N3C(=O)[C@H](C)N1C(=O)[C@H](n1cnc4ccccc4c1=O)C[C@]2(O)c1ccccc13
InChIInChI=1S/C22H18N4O4/c1-12-18(27)26-16-9-5-3-7-14(16)22(30)10-17(20(29)25(12)21(22)26)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1
InChIKeyGEURDGODABUDHB-TYTLQBBQSA-N
Species of MetaboliteComponentSourceComments
Chaetomium (ncbitaxon:5149) - PubMed (17134253) Endophytic fungus on the leaves of Adenophora axilliflora Strain: IFB-E015
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
chaetominine (CHEBI:65610) has role metabolite (CHEBI:25212)
chaetominine (CHEBI:65610) is a indole alkaloid (CHEBI:38958)
chaetominine (CHEBI:65610) is a lactam (CHEBI:24995)
chaetominine (CHEBI:65610) is a organic heterotetracyclic compound (CHEBI:38163)
chaetominine (CHEBI:65610) is a quinazolines (CHEBI:38530)
IUPAC Name 
(2S,4R,5aS,9cS)-5a-hydroxy-2-methyl-4-(4-oxoquinazolin-3(4H)-yl)-4,5,5a,9c-tetrahydro-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione
Manual XrefsDatabases
CN101463074Patent
Registry NumbersSources
Reaxys:10601737Reaxys
Citations