CHEBI:65610 - chaetominine

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ChEBI Name chaetominine
ChEBI ID CHEBI:65610
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H18N4O4
Net Charge 0
Average Mass 402.40270
Monoisotopic Mass 402.13281
InChI InChI=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
InChIKey GEURDGODABUDHB-TYTLQBBQSA-N
SMILES [H][C@]12N3[C@@H](C)C(=O)N1c1ccccc1[C@@]2(O)C[C@H](C3=O)n1cnc2ccccc2c1=O
Metabolite of Species Details
Chaetomium (NCBI:txid5149) Endophytic fungus on the leaves of Adenophora axilliflora of strain IFB-E015 See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Xref Database
CN101463074 Patent
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Registry Number Type Source
10601737 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17134253 PubMed citation Europe PMC
Last Modified
04 September 2012