CHEBI:156204 - amrubicinol

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ChEBI Name amrubicinol
ChEBI ID CHEBI:156204
Definition A diastereoisomeric mixture resulting from the formal reduction of the acetyl group at position 9 of amrubicin to the corresponding 1-hydroxyethyl group. The active metabolite of amrubicin in lung cancer patients.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H27NO9
Net Charge 0
Average Mass 485.489
Monoisotopic Mass 485.16858
InChI InChI=1S/C25H27NO9/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/h2-5,10,14-17,27-29,32-33H,6-9,26H2,1H3/t10?,14-,15+,16-,17-,25-/m0/s1
InChIKey HSDGDISMODBEAN-UPOFGPJLSA-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
Biological Role(s): topoisomerase II inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase II.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing amrubicinol (CHEBI:156204) has functional parent amrubicin (CHEBI:135779)
amrubicinol (CHEBI:156204) has role antineoplastic agent (CHEBI:35610)
amrubicinol (CHEBI:156204) has role apoptosis inducer (CHEBI:68495)
amrubicinol (CHEBI:156204) has role topoisomerase II inhibitor (CHEBI:156203)
amrubicinol (CHEBI:156204) is a diastereoisomeric mixture (CHEBI:60915)
amrubicinol (CHEBI:156204) is a quinone (CHEBI:36141)
amrubicinol (CHEBI:156204) is a secondary alcohol (CHEBI:35681)
amrubicinol (CHEBI:156204) is a tetracenes (CHEBI:51270)
IUPAC Name
(7S,9S)-9-amino-7-{[(2S,4S,5R)-4,5-dihydroxytetrahydro-2H-pyran-2-yl]oxy}-6,11-dihydroxy-9-(1-hydroxyethyl)-7,8,9,10-tetrahydrotetracene-5,12-dione
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Last Modified
16 July 2020