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CHEBI:156204 - amrubicinol

ChEBI IDCHEBI:156204
ChEBI Nameamrubicinol
Stars
DefinitionA 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.
Last Modified16 July 2020
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H27NO9
Net Charge0
Average Mass485.489
Monoisotopic Mass485.16858
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/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
InChIKeyHSDGDISMODBEAN-UPOFGPJLSA-N
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
topoisomerase II inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase II.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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
Citations