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chaetominine
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.


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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619] > chaetominine [CHEBI:65610]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 chaetominine [CHEBI:65610] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Fungi, Yeasts, Molds and Mildews (348) 
 Dikarya (97) 
 Ascomycota (82) 
 Pezizomycotina (82) 
 Sordariomycetes (72) 
 Sordariomycetidae (30) 
 Sordariales (30) 
 Chaetomiaceae (28) 
 Chaetomium (28)
07. Part of Biological Source of Chemical 
07. Part of Biological Source of Chemical
 unspecified structure [PO:0000004] (703)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 amide [CHEBI:32988] (1863) 
 cyclic amide [CHEBI:3990] (252) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 indole alkaloid [CHEBI:38958] (144) 
 chaetominine [CHEBI:65610] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 chaetominine [CHEBI:65610] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 indole alkaloid [CHEBI:38958] (144) 
 chaetominine [CHEBI:65610] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 chaetominine [CHEBI:65610] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 polycyclic compound [CHEBI:33635] (4078) 
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 chaetominine [CHEBI:65610] (1)
 bicyclic compound [CHEBI:33636] (1511) 
 heterobicyclic compound [CHEBI:33672] (1315) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 chaetominine [CHEBI:65610] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 chaetominine [CHEBI:65610] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 chaetominine [CHEBI:65610] (1)
 heterobicyclic compound [CHEBI:33672] (1315) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 chaetominine [CHEBI:65610] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 quinazolines [CHEBI:38530] (18) 
 chaetominine [CHEBI:65610] (1)
 organic heterotetracyclic compound [CHEBI:38163] (128) 
 chaetominine [CHEBI:65610] (1)
ChEBI Compound Accession Identifier  [CHEBI:65610]
ChEBI Compound Description  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.
ChEBI Compound Identification Number  65610
ChEBI InChI Value  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
ChEBI InChIKey Value  GEURDGODABUDHB-TYTLQBBQSA-N
ChEBI Compound Name  chaetominine
ChEBI SMILES Value  [H][C@]12N3[C@@H](C)C(=O)N1c1ccccc1[C@@]2(O)C[C@H](C3=O)n1cnc2ccccc2c1=O
ChEBI Substance ID  160645207
ChEBI URL  ChEBI:65610
ChemSpider ID  17253564
Ontomatica Chemical Accession Key (OnChAKey)  GEURDGODABUDHB_TYTLQBBQSA_N_000_000000
PubChem Compound ID  16095273