CHEBI:135779 - amrubicin

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ChEBI Name amrubicin
ChEBI ID CHEBI:135779
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H25NO9
Net Charge 0
Average Mass 483.473
Monoisotopic Mass 483.15293
InChI InChI=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
InChIKey VJZITPJGSQKZMX-XDPRQOKASA-N
SMILES O([C@H]1C[C@H](O)[C@@H](CO1)O)[C@@H]2C=3C(=C(O)C4=C(C3O)C(=O)C=5C(C4=O)=CC=CC5)C[C@](C2)(C(C)=O)N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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.
(via anthracycline antibiotic )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via anthracycline )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
amrubicin ChEBI
amrubicina ChEBI
amrubicine ChEBI
amrubicinum ChEBI
Synonyms Sources
(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-dione IUPAC
SM-5887 ChEBI
Manual Xrefs Databases
202 DrugCentral
Amrubicin Wikipedia
D08854 KEGG DRUG
View more database links
Registry Numbers Types Sources
110267-81-7 CAS Registry Number ChemIDplus
110267-81-7 CAS Registry Number DrugCentral
Citations Waiting for Citations Types Sources
31505087 PubMed citation Europe PMC
31557562 PubMed citation Europe PMC
31901017 PubMed citation Europe PMC
32462731 PubMed citation Europe PMC
32569168 PubMed citation Europe PMC
32582522 PubMed citation Europe PMC
32606979 PubMed citation Europe PMC
9849587 PubMed citation Europe PMC
Last Modified
16 July 2020