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CHEBI:141382 - ekatetrone

ChEBI IDCHEBI:141382
ChEBI Nameekatetrone
Stars
DefinitionAn organic heterotetracyclic compound that is 1,8-dihydroxy-9,10-anthraquinone which is substituted at position 2 and 3 by 3-amino-1-hydroxy-3-oxopropyl and carboxymethyl groups, respectively, in which the hydroxy group β- to the carboxamide has undergone formal condensation with the carboxy group to give the corresponding δ-lactone. Isolated from various strains of Kitasatospora aureofaciens (Streptomyces aureofaciens), it inhibits the growth of Ehrlich ascites carcinoma in vitro.
Last Modified29 March 2023
SubmitterR. Stephan
DownloadsMolfile
FormulaC19H13NO7
Net Charge0
Average Mass367.313
Monoisotopic Mass367.06920
SMILESNC(=O)CC1OC(=O)Cc2cc3c(c(O)c21)C(=O)c1c(O)cccc1C3=O
InChIInChI=1S/C19H13NO7/c20-12(22)6-11-14-7(5-13(23)27-11)4-9-16(18(14)25)19(26)15-8(17(9)24)2-1-3-10(15)21/h1-4,11,21,25H,5-6H2,(H2,20,22)
InChIKeyQZENCFIHIPLZMU-UHFFFAOYSA-N
Species of MetaboliteComponentSourceComments
Streptomyces aureofaciens (ncbitaxon:1894) - PubMed (101502) Strain: various
Roles Classification
Biological Role:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
ekatetrone (CHEBI:141382) has role antineoplastic agent (CHEBI:35610)
ekatetrone (CHEBI:141382) has role bacterial metabolite (CHEBI:76969)
ekatetrone (CHEBI:141382) is a anthraquinone (CHEBI:22580)
ekatetrone (CHEBI:141382) is a organic heterotetracyclic compound (CHEBI:38163)
ekatetrone (CHEBI:141382) is a phenols (CHEBI:33853)
ekatetrone (CHEBI:141382) is a primary carboxamide (CHEBI:140324)
ekatetrone (CHEBI:141382) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(+)-2-(10,12-dihydroxy-3,6,11-trioxo-3,4,6,11-tetrahydro-1H-naphtho[2,3-g]isochromen-1-yl)acetamide
Synonyms  Source
1,8-dihydroxy-2-(1'-hydroxy-2'-carbamoyl)ethyl-9,10-anthraquinone-3-acetic acid lactoneChEBI
(+)-ekatetroneChEBI
(+)-3,4,6,11-tetrahydro-10,12-dihydroxy-3,6,11-trioxo-1H-anthra[2,3-c]pyran-1-acetamideChEBI
ekatetronChEBI
Manual XrefsDatabases
C00018198KNApSAcK
Registry NumbersSources
CAS:12794-19-3ChEBI
Citations