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CHEBI:135779 - amrubicin

ChEBI IDCHEBI:135779
ChEBI Nameamrubicin
Stars
DefinitionA synthetic anthracycline antibiotic with molecular formula C25H25NO9. A specific inhibitor of topoisomerase II, it is used (particularly as the hydrochloride salt) in the treatment of cancer, especially lung cancer, where it is a prodrug for the active metabolite, ambrucinol.
Last Modified16 July 2020
DownloadsMolfile
FormulaC25H25NO9
Net Charge0
Average Mass483.473
Monoisotopic Mass483.15293
SMILESCC(=O)[C@]1(N)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](O)[C@H](O)CO2)C1)C(=O)c1ccccc1C3=O
InChIInChI=1S/C25H25NO9/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3/t14-,15+,16-,17-,25-/m0/s1
InChIKeyVJZITPJGSQKZMX-XDPRQOKASA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
topoisomerase II inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase II.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
amrubicin (CHEBI:135779) has role antineoplastic agent (CHEBI:35610)
amrubicin (CHEBI:135779) has role prodrug (CHEBI:50266)
amrubicin (CHEBI:135779) has role topoisomerase II inhibitor (CHEBI:156203)
amrubicin (CHEBI:135779) is a anthracycline antibiotic (CHEBI:49322)
amrubicin (CHEBI:135779) is a methyl ketone (CHEBI:51867)
amrubicin (CHEBI:135779) is a primary amino compound (CHEBI:50994)
amrubicin (CHEBI:135779) is a quinone (CHEBI:36141)
amrubicin (CHEBI:135779) is a tetracenes (CHEBI:51270)
Incoming Relation(s)
amrubicinol (CHEBI:156204) has functional parent amrubicin (CHEBI:135779)
IUPAC Name 
(1S,3S)-3-acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2-deoxy-β-D-erythro-pentopyranoside
INNs  Source
amrubicinChEBI
amrubicinumChEBI
amrubicinaChEBI
amrubicineChEBI
Synonyms  Source
SM-5887ChEBI
(7S,9S)-9-acetyl-9-amino-7-{[(2S,4S,5R)-4,5-dihydroxytetrahydro-2H-pyran-2-yl]oxy}-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dioneIUPAC
Manual XrefsDatabases
202DrugCentral
AmrubicinWikipedia
D08854KEGG DRUG
Registry NumbersSources
CAS:110267-81-7DrugCentral
CAS:110267-81-7ChemIDplus
Citations