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circumdatin H
An organic heteropentacyclic compound that is 5b,7,8,16-tetrahydro-6H,10H-pyrrolo[2,1-c]quinazolino[3,2-a][1,4]benzodiazepine substituted by a methoxy group at position 2 and oxo groups at positions 10 and 16 (the 5bS stereoisomer). An alkaloid isolated from the culture broth of Aspergillus ochraceus, it exhibits potent inhibitory activity towards mitochondrial NADH oxidase.


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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619] > circumdatin H [CHEBI:65634]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 enzyme inhibitor [CHEBI:23924] (825) 
 circumdatin H [CHEBI:65634] (1)
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 circumdatin H [CHEBI:65634] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Fungi, Yeasts, Molds and Mildews (348) 
 Deuteromycotina (255) 
 Hyphomycetes (137) 
 Aspergillus (96) 
 Aspergillus ochraceus (13)
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) 
 circumdatin H [CHEBI:65634] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 circumdatin H [CHEBI:65634] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 circumdatin H [CHEBI:65634] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 aromatic ether [CHEBI:35618] (353) 
 circumdatin H [CHEBI:65634] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 aromatic ether [CHEBI:35618] (353) 
 circumdatin H [CHEBI:65634] (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) 
 circumdatin H [CHEBI:65634] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heteropentacyclic compound [CHEBI:38164] (100) 
 circumdatin H [CHEBI:65634] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 circumdatin H [CHEBI:65634] (1)
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 circumdatin H [CHEBI:65634] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 ether [CHEBI:25698] (876) 
 aromatic ether [CHEBI:35618] (353) 
 circumdatin H [CHEBI:65634] (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) 
 circumdatin H [CHEBI:65634] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heteropentacyclic compound [CHEBI:38164] (100) 
 circumdatin H [CHEBI:65634] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 aromatic ether [CHEBI:35618] (353) 
 circumdatin H [CHEBI:65634] (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 heteropentacyclic compound [CHEBI:38164] (100) 
 circumdatin H [CHEBI:65634] (1)
 aromatic compound [CHEBI:33655] (3799) 
 organic aromatic compound [CHEBI:33659] (3593) 
 aromatic ether [CHEBI:35618] (353) 
 circumdatin H [CHEBI:65634] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 circumdatin H [CHEBI:65634] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heteropentacyclic compound [CHEBI:38164] (100) 
 circumdatin H [CHEBI:65634] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 aromatic ether [CHEBI:35618] (353) 
 circumdatin H [CHEBI:65634] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 lactam [CHEBI:24995] (252) 
 circumdatin H [CHEBI:65634] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heteropentacyclic compound [CHEBI:38164] (100) 
 circumdatin H [CHEBI:65634] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heteropentacyclic compound [CHEBI:38164] (100) 
 circumdatin H [CHEBI:65634] (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) 
 circumdatin H [CHEBI:65634] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heteropentacyclic compound [CHEBI:38164] (100) 
 circumdatin H [CHEBI:65634] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 aromatic ether [CHEBI:35618] (353) 
 circumdatin H [CHEBI:65634] (1)
ChEBI Compound Accession Identifier  [CHEBI:65634]
ChEBI Compound Description  An organic heteropentacyclic compound that is 5b,7,8,16-tetrahydro-6H,10H-pyrrolo[2,1-c]quinazolino[3,2-a][1,4]benzodiazepine substituted by a methoxy group at position 2 and oxo groups at positions 10 and 16 (the 5bS stereoisomer). An alkaloid isolated from the culture broth of Aspergillus ochraceus, it exhibits potent inhibitory activity towards mitochondrial NADH oxidase.
ChEBI Compound Identification Number  65634
ChEBI InChI Value  InChI=1S/C20H17N3O3/c1-26-12-8-9-15-14(11-12)20(25)23-16-6-3-2-5-13(16)19(24)22-10-4-7-17(22)18(23)21-15/h2-3,5-6,8-9,11,17H,4,7,10H2,1H3/t17-/m0/s1
ChEBI InChIKey Value  MLEAYJRUKNTODR-KRWDZBQOSA-N
ChEBI Compound Name  circumdatin H
ChEBI SMILES Value  [H][C@@]12CCCN1C(=O)c1ccccc1-n1c2nc2ccc(OC)cc2c1=O
ChEBI Substance ID  160655797
ChEBI URL  ChEBI:65634
ChemSpider ID  21431235
Ontomatica Chemical Accession Key (OnChAKey)  MLEAYJRUKNTODR_KRWDZBQOSA_N_000_000000
PubChem Compound ID  46184995